PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review)
The review article summarizes and systematizes many years of literature data on possible areas of application of aminocarboxyphosphonic acids and metal complexes based on them. It is shown that aminocarboxyphosphonates, due to their wide range of functional properties, in particular, such as photolu...
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2025
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Ukrainian Chemistry Journal| _version_ | 1871466171714240512 |
|---|---|
| author | Trunova, Olena |
| author_facet | Trunova, Olena |
| author_institution_txt_mv | [
{
"author": "Olena Trunova",
"institution": "V.I. Vernadsky Institute of General and Inorganic Chemistry NAS of Ukraine"
}
] |
| author_sort | Trunova, Olena |
| baseUrl_str | https://ucj.org.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-22T08:23:56Z |
| description | The review article summarizes and systematizes many years of literature data on possible areas of application of aminocarboxyphosphonic acids and metal complexes based on them. It is shown that aminocarboxyphosphonates, due to their wide range of functional properties, in particular, such as photoluminescence, magnetic properties, biological activity, can find application in a wide variety of areas. Both aminocarboxyphosphonic acids themselves and their complexes can serve as the basis for biologically active substances in agronomy - as synthetic growth regulators, as effective preparations for increasing extracted sugar from various plants (sugar cane, sweet potato, sugar beet, melon, etc.) and preparations for accelerating fruit ripening under adverse weather conditions. One of the most interesting areas of use of aminocarboxyphosphonates and nanoparticles based on them for biomedical purposes is the creation of precursors for the development of new antitumor drugs. Due to their high porosity, these materials can be used in ecology for the purification of soil and/or drinking water from heavy metals. The approaches to the modification of the coordination environment, variations in the nature of metals and ligand environment highlighted in the work can be used as a model for the development of new coordination polymers and MOFs structures as environmentally friendly depressants for selective flotation separation of minerals (dolomite, galena, sphalerite). Aminocarboxyphosphonates of metals as a subclass of coordination polymers, due to the presence of such groups in the molecules as POH, COOH, N+-H, demonstrate acidic properties, the combination of which with electrocatalytically active transition metals makes them very attractive in the field of fuel cells and electrolyzers. They can be used as potential proton conductors and/or precursors of electrocatalysts, heterogeneous catalysts in the Knoevenagel condensation with high selectivity. |
| doi_str_mv | 10.33609/2708-129X.91.9.2025.49-79 |
| first_indexed | 2025-12-17T12:07:54Z |
| format | Article |
| fulltext |
49
UDK 541.49:546.30+546.65-54-386 doi: 10.33609/2708-129X.91.9.2025.49-79
PROSPECTS FOR THE PRACTICAL APPLICATION
OF AMINOCARBOXYPHOSPHONATES AND THEIR
METAL COMPLEXES (review).
O.K. Trunova
V.I. Vernadsky Institute of General and Inorganic Chemistry of the National Academy
of Sciences of Ukraine, 32/34 Academic Palladin Avenue, 03142 Kyiv, Ukraine
* e-mail: trunova@ionc.kiev.ua
The review article summarizes and systematizes many years of literature data on possible
areas of application of aminocarboxyphosphonic acids and metal complexes based on them.
It is shown that aminocarboxyphosphonates, due to their wide range of functional properties,
in particular, such as photoluminescence, magnetic properties, biological activity, can find
application in a wide variety of areas. Both aminocarboxyphosphonic acids themselves and
their complexes can serve as the basis for biologically active substances in agronomy - as syn-
thetic growth regulators, as effective preparations for increasing extracted sugar from various
plants (sugar cane, sweet potato, sugar beet, melon, etc.) and preparations for accelerating
fruit ripening under adverse weather conditions. One of the most interesting areas of use of
aminocarboxyphosphonates and nanoparticles based on them for biomedical purposes is the
creation of precursors for the development of new antitumor drugs. Due to their high poro
sity, these materials can be used in ecology for the purification of soil and/or drinking water
from heavy metals. The approaches to the modification of the coordination environment,
variations in the nature of metals and ligand environment highlighted in the work can be
used as a model for the development of new coordination polymers and MOFs structures as
environmentally friendly depressants for selective flotation separation of minerals (dolomite,
galena, sphalerite). Aminocarboxyphosphonates of metals as a subclass of coordination po
lymers, due to the presence of such groups in the molecules as POH, COOH, N+-H, demon-
strate acidic properties, the combination of which with electrocatalytically active transition
metals makes them very attractive in the field of fuel cells and electrolyzers. They can be used
as potential proton conductors and/or precursors of electrocatalysts, heterogeneous catalysts
in the Knoevenagel condensation with high selectivity.
Keywords: complexes, aminocarboxyphosphonates, 3-d, 4-f metals, biological activity,
catalyst, purification from heavy metals, practical application.
50 ISSN 2708-129X. Укр. хім. журн., 2025
PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
INTRODUCTION. Complexones are or-
ganic compounds that contain basic and acidic
centers, the mutual arrangement of which de-
termines the formation of stable chelate cycles
upon coordination with metal ions. The first
representatives of complexones are aminocar-
boxylic acids - nitrilotriacetic acid (H3NTA) and
ethylenediaminetetraacetic acid (H4EDTA),
in the molecules of which there are several
aminoacetate fragments -NHCH2COOH [1, 2].
To solve a wide range of practical problems,
the range of complexones has significant-
ly increased. Today, in addition to classical
polyaminopolycarboxylic acids, this group
also includes aminocarboxyphosphonic acids
(ACPhA), which contain two different types of
acid moieties near the donor nitrogen atom -
carboxyl and phosphonic groups: Н2РО3-
NCH2-R ( R = -H, -CH2COOH, -CH2PO3H2).
The presence of two different acid groups in
the molecules of aminocarboxyphosphonic
acids, which differ significantly in basicity,
charge, electron-donating ability, stereochem-
istry, and size, ensures their high coordina-
tion capacity and selectivity towards metals
of various natures. Aminocarboxyphosphonic
acids, combining the properties of aminocar
boxylic and phosphonic/aminophosphonic
acids, compared to their carboxyl- or phospho-
rus-containing analogues, form a much larger
set of differently protonated metal complexes
in solutions and polynuclear structures of un-
usual structure in the solid state due to the for-
mation of additional chelate cycles. Due to the
presence of different types of coordination sites
in their molecules, aminocarboxyphosphonate
metal complexes have higher solubility, which
facilitates their crystallization compared to
aminocarboxylate and/or phosphonate ana-
logues [3–5].
Earlier, in review articles [6, 7], literature
data on the structure and physicochemical
properties of both aminocarboxyphosphonic
acids themselves and metal complexes (3-d,
4-f metals) based on them were summarized.
Through the analysis of numerous works, in-
cluding those from the last 5 years, this article
examines the prospects for the application of
aminocarboxyphosphonic acids and their me
tal complexes in various industries for the cre-
ation of multifunctional materials.
EXPERIMENT AND DISCUSSION OF
THE RESULTS. Aminocarboxyphosphonates,
unlike their carboxyl- and/or phosphorus-con-
taining analogues, are a relatively poorly stud-
ied class of compounds that are not yet widely
used in industry. But in the last 30 years, this
class of compounds has attracted significant
attention from researchers around the world
due to the wide potential of their practical use
as plant growth regulators and herbicides, as
well as the potential application of their metal
complexes in materials chemistry as functional
materials due to the presence of a number of
useful properties (high porosity, photolumi-
nescence, catalytic, nonlinear optical, magne
tic properties, etc.) [8–11].
Biological activity
of aminocarboxyphosphonates
Aminocarboxyphosphonates exhibit bio-
logical activity, are non-toxic to mammals and,
importantly, are capable of fairly rapid deg-
radation in the environment. The biological
properties of aminocarboxyphosphonic acids
and biometal complexes based on them are
due to the fact that they are structural phos-
phorus-containing analogues of natural ami-
no acids, therefore they can participate in the
mechanisms of many bioprocesses, have low
toxicity and high solubility in the natural en-
51https://ucj.org.ua
O.K. Trunova UCJ № 9 / Vol. 91
vironment [1, 4, 12]. Studies in recent decades
have shown that aminocarboxyphosphonates
exhibit herbicidal and growth-stimulating
properties [5, 13–16]. Among all aminocar-
boxyphosphonates, the most studied organo-
phosphonate, which is widely used in practice,
is N-(phosphonomethyl)glycine (H3PMG) -
a phosphonomethyl derivative of the amino
acid glycine, and is known worldwide as the
non-selective herbicide «Glyphosate» (the
original agricultural product «Roundup»).
It has a strong phyllocid effect, which causes
disruption of enzymatic processes in plants.
In the soil, glyphosate is microbiologically
decomposed and deactivated. This process
is inhibited by the binding of glyphosate to
metal cations present in the soil. N-(phospho-
nomethyl)glycine is able to selectively inhibit
the synthesis of the enzyme 5-enelpyruvoyl-
shikimate-3-phosphate synthase (EPSPhS),
which, although absent in higher organisms, is
necessary for the synthesis of aromatic amino
acids in plants and microorganisms. Glypho-
sate-based preparations exhibit a universal ef-
fect when in contact with green plants at low
rates of application (~0.8–1.7 kg/ha), have low
phytotoxicity and are rapidly decomposed in the
environment under aerobic and anaerobic con-
ditions with the formation of the main metabo-
lite - aminomethylphosphonic acid [17–19].
In [20], the effect of Glyphosate on micro-
bial biomass and soil activity was investigated.
It was shown that it significantly stimulates
soil microbial activity by mineralizing C and
N, but does not affect soil microbial biomass.
C mineralization, as well as the rate of mine
ralization, increases with increasing glypho-
sate application rates (Fig. 1). Moreover, the
rate of C mineralization increases on the first
day after glyphosate addition and continues
for 14 days. It was found that Glyphosate di-
rectly and rapidly decomposes microbes, even
at high rates of application, without negatively
affecting their activity.
Fig. 1. Effect of glyphosate addition rate on soil C mineralization.
(1×−5× are rates of glyphosate addition to soil at doses of 47, 94, 140, and 234 mg, respectively.
Error bars indicate one standard deviation [20]).
52 ISSN 2708-129X. Укр. хім. журн., 2025
PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
An analogue of N-(phosphonomethyl)
glycine – N,N-bis(phosphonomethyl)glycine
(Н5BPMG) – known as the drug «Glyphosin»,
is a synthetic growth regulator and is used
mainly to increase the extracted sugar from
various plants (sugar cane, sweet potato, sugar
beet, melon, etc.) and is effective for accelerat-
ing fruit ripening under adverse weather con-
ditions. Thus, N,N-bis(phosphonomethyl)gly-
cine has been recognized as a chemical ripener
of sugar cane in small replicated field plots and
on a commercial scale to determine optimal
rates and timing of application [176, 177]. It
was shown that the use of Glyphosine at doses
of 2.24, 4.48 and 6.72 kg/ha 6 weeks after appli-
cation contributed to a significant increase in
the percentage (>15%) of sucrose in sugarcane
compared to the untreated control. A greater
increase in sugar was observed for the dose
of 6.72 kg/ha. Trials of Glyphosine on a com-
mercial scale (application rate – 3.36 kg/ha)
showed an increase in sugar from 9 to 15%
compared to the control already 4 weeks after
application.
In [21], aqueous solutions of N,N-bis(phos
phonomethyl)glycine (were tested on canta-
loupe plantings. It was shown that the increase
in melon yield under the influence of BPMG
was 6.6%, and the sugar content increased by
approximately 10%, regardless of the concent
ration of glyphosate.
The biological properties of ACPhA are due
to the presence in their molecule of a cova-
lent C—P bond that is resistant to photolysis,
chemical hydrolysis, and temperature, but ca-
pable of being destroyed by the enzymatic ac-
tion of microorganisms [20, 22–25].
The ability to biodegrade compounds with a
C-P bond has been demonstrated in many bac-
teria of the genera Escherichia, Pseudomonas,
Agrobacterium, Klebsiella, Arthrobacter, Bacil-
lus, Rhizobium, and Rhizobium [26, 27]. Some
strains (e.g., Pseudomonas sp. LBr and Flavobac-
terium sp.) transform most of the N-(phospho-
nomethyl)glycine into aminomethylphospho-
nate or glyphosate oxidoreductase [28, 29]. The
metabolism of N-phosphonomethylglycine by
Pseudomonas sp. LBr, a bacterium isolated from
waste from the glyphosate production process,
was investigated by a combination of 13C NMR
and phosphonate analysis of the culture medi-
um. Pseudomonas sp. LBr is capable of remov-
ing 20 mM glyphosate from the culture me-
dium, which is approximately 20 times more
than any other microorganism. The bacterium
degrades high levels of glyphosate primarily
by converting it to aminomethylphosphonate
with subsequent release into the culture me-
dium. Only a small amount of aminomethyl
phosphonate (about 0.5–0.7 mM), which is
necessary to provide phosphorus for growth,
could be metabolized by the microorganism.
NMR analysis of Pseudomonas sp. LBr grown
on 1 mM glyphosate showed that about 5% of
H3PMG was degraded by a separate pathway
involving its cleavage to glycine.
That is, the main role in the biodegradation
of H3PMG in soils, after its use as a herbicide, is
played by bacteria (Fig. 2) or enzymes of some
microorganisms (for example, glyphosate oxi
doreductase) (Fig. 3) [28–30].
At low concentrations, H3PMG does not
affect the vital activity of soil microorganisms,
but an increase in its concentration up to
100 times causes a decrease in bacterial popu-
lation cultures and diversity [31, 32].
Toxicological studies have shown that H3P-
MG has low toxicity after oral, dermatological
and inhalation administration and does not ex-
hibit genotoxic, carcinogenic, neurotoxic, tera-
53https://ucj.org.ua
O.K. Trunova UCJ № 9 / Vol. 91
togenic effects. The LD50 of N-(phosphonome-
thyl)glycine for mammals is 2100 mg/kg [11,
33]. In the body of laboratory animals, 23–36%
of H3PMG is absorbed, it is well distributed in
tissues with the formation of the main meta
bolite - aminomethylphosphonic acid [34, 35].
Fig. 2. Scheme of biodegradation of N-(phosphonomethyl)glycine in soils.
Fig. 3. Scheme of biodegradation of N-(phosphonomethyl)glycine under the action of enzymes.
54 ISSN 2708-129X. Укр. хім. журн., 2025
PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
Particular attention is drawn to the stimu-
lating effect of aminocarboxyphosphonates on
the growth of microorganisms used in biotech-
nology. It is known that the influence of Pseu-
domonas sp. on the development of agricultural
crops can be both positive and negative. Some
bacterial strains are phytopathogenic, others,
for example, saprophytic pseudomonads,
which widely inhabit the rhizosphere of plants,
play an important role in their protection. Bac-
terial antagonists from the genus Pseudomonas
are used as means of biological control of plant
diseases of bacterial and mycological etiology.
Also, saprophytic representatives of the genus
Pseudomonas are producers of a large number
of biologically active compounds, such as pig-
ments, antibiotics, amino acids, polysaccha-
rides, toxins, vitamins, as well as other organic
substances used in immunology, medicine and
agriculture [36–38].
In studies conducted at the V.I. Vernadsky
Institute of General and Inorganic Chemistry
of the NAS of Ukraine, the growth-stimulating
activity of N-(phosphonomethyl)aminosuc-
cinic and N,N΄-bis(phosphonomethyl)amino-
succinic acids and 3d-metal complexes based
on them was established against non-patho-
genic bacterial strains of Pseudomonas cul-
tures (Pseudomonas fluorescens, Pseudomonas
aureofaciens) and microorganisms Escherichia
coli ATCC 25922 [6, 39]. The interest in the
mentioned Pseudomonas species is connected,
first of all, with manifestation of useful proper-
ties for plants, since these bacteria are able to
stimulate their growth and development, to act
as antagonists of phytopathogenic fungi and
bacteria. Substances, which have the proper-
ty to activate growth of such microorganisms,
in turn, become potential objects for develop-
ment of biological preparations for agrobio-
technology. On the other hand, some species
of microorganisms of the genus Pseudomonas
are able to assimilate organic, including phos-
phorus-containing compounds, to final eco-
logically clean decomposition products, which
becomes actual in practical use of carboxyami
nophosphonates without their accumulation
in the environment [40–44]. It has been pro
ven that N-(phosphonomethyl) aminosucci
nic and bis(phosphonomethyl)aminosuccinic
acids and 3d-metal complexes based on them
exhibit growth-stimulating activity against
strains of gram-negative microorganisms of
the genus Pseudomonas. At the same time,
the growth-stimulating effect of the MIIPMAS
complexes, depending on the 3d-metal ion, in-
creases in the following order: Сu(ІІ) > Zn(ІІ)
> Ni(ІІ) > Со(ІІ). The maximum stimulating
effect on the growth of bacterial cultures is
exhibited by bis(phosphonomethyl)amino-
succinate Co(II), which is able to initiate the
synthesis of one of the most important growth
hormones - heteroauxin.
In addition to agronomy, the use of amino
carboxyphosphonates has been proposed to
reduce the toxicity of heavy metals in soils
during their purification [45, 46], to create a
protective film during steel corrosion [47], to
obtain surface-modified nanoparticles that
have antitumor activity [48, 49], as an additive
to cosmetic compositions [50, 51], etc.
Use of aminocarboxyphosphonates
for the removal of heavy metals.
The variety and quantity of waste discharged
into the environment are the main disadvan-
tages of industrialization. The activities of in-
dustrial enterprises, automobile exhausts and
other attributes of civilization, unfortunately,
negatively affect the state of ecology, the qua
lity of water, air, soil, etc. Heavy metals are
55https://ucj.org.ua
O.K. Trunova UCJ № 9 / Vol. 91
one of the most toxic pollutants of anthro-
pogenic origin. The danger of heavy metals
entering the environment is determined by
the fact that, unlike organic pollutants, they
do not break down, but pass from one form
to another, in particular, they are included in
the composition of salts, oxides, organome-
tallic compounds. The term «heavy metals» is
used for metals whose specific gravity exceeds
5 g/cm3 or atomic number is more than 20.
Among them, the most toxic are metal ions -
Cu, Cd, Pb, Cr, Mn, Hg, Fe, Al, Se, Sn, ra-
re-earth elements (REE), etc.
Water pollution by heavy metal ions is of se-
rious concern due to their toxicity to many life
forms. In order to reduce the impact of heavy
metals on the environment, various water pu-
rification technologies are being studied, such
as: chemical precipitation, ion exchange, re-
dox processes. The trend is to find a universal
and economical method for removing heavy
metals from wastewater. One of the water pu-
rification methods that is effectively used to
remove heavy metal ions from drinking water
and wastewater is adsorption. Adsorption is a
separation process that consists in the adhesion
of metal ions dissolved in aqueous solutions to
the surface of an adsorbent. The mechanisms of
metal ion separation from water by adsorption
are influenced by both their characteristics and
the characteristics of the adsorbent, which are
determined by the interaction between them.
These interactions can be of a physical nature,
caused by low-energy forces (for example, Van
der Waals-type forces). In this case, metal ions
are adsorbed in the pores of the adsorbent
without the participation of electron transfer.
In this case, the process is reversible, and the
metal ion molecules retained on the surface of
the adsorbent can be removed by desorption,
regenerating the adsorbent. If the interaction
between metal ions and adsorbents involves
electron transfer and the formation of chemical
bonds, the process is called chemical adsorp-
tion, or chemisorption. In this case, the metal
ions are not attracted to the entire surface of
the adsorbent materials, but only to the active
zones, which contain functional groups that
react with the metal using more energy than
in physical adsorption, a fact that explains the
greater selectivity of chemical adsorption. In
adsorption processes, the adsorbent material
used is an important element for obtaining an
effective separation. Porous activated carbons,
zeolites, bioadsorbents, carbon nanotubes are
often used to remove heavy metals. However,
these materials have limited practicality due to
low adsorption capacity, low efficiency, or high
cost. The best adsorbents are compounds with
well-ordered structures, such as metal-organic
frameworks (MOFs) and coordination mac-
romolecular compounds (Coordination Pol-
ymers, CPs), which are currently being inten-
sively studied to create new materials. The main
advantages of MOFs and CNs in adsorption
processes over other adsorbent materials are
their large specific surface area, well-organized
unique structures, and stable pores with uni-
form size, which ensure their high adsorption
capacity over a wide pH range for the removal
of heavy metals from wastewater [52–55].
N,N-bis(phosphonomethyl)glycine, which
has excellent chelating ability, was used for
wastewater treatment from heavy metals in [53,
55]. Metallophosphonate organic frameworks
of Ni(II) were synthesized by hydrothermal
method using Ni(CH3COO)2·4H2O and phos-
phonic acids (phosphonoacetic acid, vinylphos-
phonic acid (VP) and N,N-bis(phosphonome-
thyl)glycine (Gly)). The adsorption properties
56 ISSN 2708-129X. Укр. хім. журн., 2025
PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
of these materials in the process of removing
heavy metals (Cr(VI), Cd(II), Pb(II)) from
aqueous solutions at different pH values, con-
tact time and initial adsorbate concentration
were investigated (Fig. 4.).
Fig. 4. Adsorption capacity of metallophos-
phonate organic Ni(II) frameworks in the process
of removing heavy metal ions from aqueous solu-
tions. (Ci=30 mg/l, S:L=2 g/l, t=60 min. [53]).
As can be seen from Fig. 4, metal organ-
ic frameworks based on Ni(II) phosphonates
showed the highest adsorption capacity in the
process of Cr(VI) removal compared to the re-
moval of divalent metal ions. Detailed studies of
the removal of Cr(VI) from aqueous solutions
showed that the highest adsorption capacity of
all materials is at pH 2.5 (Fig. 5), and the ad-
sorption efficiency of the studied materials in
the process of removing Cr(VI) ions from aque-
ous solutions is in the following order:
Ni-CP<Ni-Gly≤Ni-VP.
In [56], two coordination network polymers
based on N,N-bis(phosphonomethyl)glycine
Co–Gly and Ni–Gly were used as adsorbents
for the removal of Cd(II) ions from aqueous
solutions, which contain as the main structural
units [М(HO3PCH2)2N(H)CH2COO)(H2O)2]
(М= Ni, Сo). Adsorption of cadmium on the
studied compounds was carried out in a batch
mode at different pH, initial concentration,
contact time, temperature and mass of the
sorbent. It was found that the Ni–Gly samp
le has a larger specific surface area and pore
volume (45 m2/g, 0.85 cm3/g) compared to the
Co–Gly sample (32 m2/g, 0.25 cm3/g), and ex-
hibits higher adsorption capacity in removing
Cd(II) ions from aqueous solutions.
Fig. 5. Effect of initial pH on the adsorption
capacity of Ni(II) metallophosphonate organic
frameworks in the process of removing Cr(VI) ions
from aqueous solutions [53].
The maximum adsorption capacity for Co-
Gly and Ni-Gly was 51.5 mg/g and 58.1 mg/g,
respectively. The higher specific surface area
and pore volume of Ni–Gly together with the
higher negative partial charges of Ni in the
polymer network increase the electrostatic
attraction between Ni-Gly and the positively
charged Cd2+ ions, which causes a higher ad-
sorption capacity of Ni-Gly. In addition, the
adsorbent materials can be easily regenerated
and recycled without significant loss of cadmi-
um adsorption capacity.
Of no less concern is the contamination of
57https://ucj.org.ua
O.K. Trunova UCJ № 9 / Vol. 91
ground and/or drinking water with high con-
centrations of arsenic. Therefore, the need to
find new appropriate methodologies capable
of removing this pollutant is relevant today. An
important aspect to consider is the possibility
of finding arsenic in different chemical forms,
which may require different approaches for its
removal. To this end, speciation analysis is cru-
cial for a better understanding of the behavior
of arsenic species in aqueous solutions, espe-
cially in the presence of compounds with pro-
nounced chelating properties. In recent years,
the interest of scientists has focused on the in-
creasing use of phosphonates in the industrial
field and on their binding capacity. This class
of ligands is characterized by a stable cova-
lent carbon-phosphorus bond, and the most
used compounds have structures similar to the
known aminopolycarboxylates, such as ethy
lenediaminetetraacetate and nitrilotriacetate.
Italian scientists have studied the interaction of
As(III) with three phosphonic acids: N-(phos
phonomethyl)iminodiacetic (Н4PMIDA),
tri(nitrilotri(methyl)phosphonic (NTA3P)
acids and N,N-bis-(phosphonomethyl)gly-
cine (H5BPMG) [54]. In-depth potentiometric
and calorimetric studies depending on pH al-
lowed the authors to determine the formation
of complexes of the composition ML, MLHi
and ML(OH) in solutions and to propose the
use of aminocarboxyphosphonates for arsenic
removal. Based on the analysis of the values of
the coefficient pL0.5 (the concentration of the
ligand capable of removing 50% of metal ions
present in trace amounts), it was shown that all
ligands demonstrate good sequestering ability
in fresh water conditions, which varies in the
series NTA3P > H5BPMG >H4PMIDA.
Aminocarboxyphosphonate-based metal-
organic frameworks can be used to extract or
separate rare earth elements from solutions.
Rare earth elements are a group of valuable
metals with growing demand and widespread
applications. Mineral ores, traditional sources
of REE, require significant capital investment,
and their processing is a source of environ-
mental pollution. Industrial and natural fluids
containing REE are potential alternative sour
ces of these metals. REE, being toxic in nature,
accumulate in water bodies as their industrial
use increases exponentially, so their effective
separation is of great importance.
In [57], the efficiency of polymer resin beads
functionalized with H5BPMG for the selec-
tive extraction of REE from saline solutions in
fixed-bed adsorption columns was investigated.
Competitive adsorption experiments were per-
formed with different metals (Nd, Gd, Ho, Al,
Fe, Co, Ni, Ba, Pb, Th, and U). BPMG-function-
alized resins showed improved performance af-
ter 1–2 cycles of use or after an acid pre-rinse
cycle, and REE adsorption was consistent for at
least five cycles. At the same time, the adsorbent
materials showed a slight preference for heavier
REEs (qHo > qNd), although the overall adsorp-
tion of REEs on the amine resin was insignifi-
cant. Experiments with multi-element mixtures
containing REEs and competing ions showed
that the absorption of REEs by BPMG-func-
tionalized resins was 137 times higher and more
selective than for unfunctionalized amine re
sins. BPMG resin granules did not experience a
significant decrease in REE adsorption capacity
upon addition of other metals, whereas the per-
formance of the aminated resin granules dete-
riorated at high concentrations. The REE and
Pb removal efficiency was 10 times higher for
BPMG-functionalized resins than for aminated
resins in both REE-only and REE + competing
metal mixtures (Fig. 6a).
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PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY 9
Fig. 6. Improvement of metal extraction for BMPG resins compared to aminated resins (a) and separation
coefficients (αREE/competing metal) for REE (average value for Nd, Gd and Ho) for each competing metal in
the mixture (b) [57].
The average separation coefficients for the BMPG-functionalized resins were highest for
REE/Ba and REE/Th (αREE/competing metal > 1000) and were ≈ 137 times higher than for the
aminated resins (Fig. 6b). A multi-element column test showed that the BMPG resin granules adsorbed
~15 times more REE than the granules of the unfunctionalized aminated resin (1.99 mg-REE/g BMPG
resin vs. 0.137 mg-REE/g Amine resin). The aminated resins adsorbed mainly actinides (Th and U)
with minor uptake of other metals.
Elution with the BMPG column yielded the following order of recovery: Ni > Ho > U/Co > Gd
> Nd > Pb≫Ba/Th. The recovered concentrations were low for Pb, which is related to the low
concentration of HNO3 (0.75 M) used for elution. This study highlights the potential of these new
materials for REE recovery and provides new insights into their performance under a range of
conditions.
For the selective adsorption of La(III) from wastewater, an iron-benzenetricarboxylic acid-
based polyacrylonitrile polymer (Fe-BTC) functionalized with N-(phosphonomethyl)iminodiacetic acid
(PMIDA) was used [58] (Fig. 7).
Fig. 6. Improvement of metal extraction for BMPG resins compared to aminated resins (a)
and separation coefficients (αREE/competing metal) for REE (average value for Nd, Gd and Ho)
for each competing metal in the mixture (b) [57].
a
b
The average separation coefficients for the
BMPG-functionalized resins were highest for
REE/Ba and REE/Th (αREE/competing me
tal > 1000) and were ≈ 137 times higher than
for the aminated resins (Fig. 6b). A multi-ele-
ment column test showed that the BMPG resin
granules adsorbed ~15 times more REE than
the granules of the unfunctionalized aminated
resin (1.99 mg-REE/g BMPG resin vs. 0.137
mg-REE/g Amine resin). The aminated resins
adsorbed mainly actinides (Th and U) with
minor uptake of other metals.
Elution with the BMPG column yielded the
following order of recovery: Ni > Ho > U/Co
> Gd > Nd > Pb≫Ba/Th. The recovered con-
centrations were low for Pb, which is related to
the low concentration of HNO3 (0.75 M) used
for elution. This study highlights the potential
of these new materials for REE recovery and
provides new insights into their performance
under a range of conditions.
For the selective adsorption of La(III) from
wastewater, an iron-benzenetricarboxylic acid-
based polyacrylonitrile polymer (Fe-BTC) func-
tionalized with N-(phosphonomethyl)imino
diacetic acid (PMIDA) was used [58] (Fig. 7).
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Fig. 7. Scheme of the synthesis of functionalized FeBTC with PMIDA molecules [58].
According to the authors, such research is
necessary because La(III) due to its properties
is used for various purposes: for the removal
of phosphates in water purification, for im-
proving special optical properties of glass, as
an automotive catalytic converter, as a cata-
lyst for biodiesel production and oil refining,
etc. [59–61]. And what is more important is
that La has wide application in nuclear tech-
nologies for controlling neutrons in control
rods [62]. In this regard, scientists are mak-
ing great efforts to develop processes for the
extraction of lanthanum from alternative re-
sources (such as acid mine drainage, brines,
wastewater, etc.) to increase the availability
of lanthanum and minimize the pressure on
exhaustible resources. The extraction of La
is also necessary because lanthanum, being
toxic in nature, causes environmental da
mage and contaminates the food chain when
accumulated [63, 64]. Considering these
points, several separation methods, such as
ion exchange, solvent extraction, chemical
precipitation, adsorption and membrane se
paration, are currently used in industry to
remove, separate and preconcentrate La from
waste streams. These processes are successful
but energy-intensive, which affects the scal-
ability, ease of operation and cost-effective-
ness of the process. Adsorption methods for
lanthanum extraction are cost-effective and
user-friendly. The adsorption of lanthanum
from aqueous solutions (sewage, wastewater,
brines, acid mine drainage, etc.) has been in-
vestigated using a wide range of adsorbents,
which are mainly functionalized inorganic,
carbonaceous (including nanoparticles), and
organic-inorganic composites: magnetic si
lica P507 [65], cysteine-modified Fe3O4 nan-
oparticles [66], HESI-SBA15 [67], Cu-Al in-
tercalated with EDTA [68], etc. However, low
adsorption capacity, limited surface-to-mass
ratio, and low selectivity are the main prob-
lems faced by these adsorbents.
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PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
To overcome these difficulties, the authors
[58] proposed the use of polymer beads based
on a functionalized metal-organic framework,
since they have a high specific surface area
and have a great potential for the extraction of
lanthanum from water sources. It was shown
that the functionalization of MOF with PMI-
DA chelate groups leads to an increase in La3+
adsorption (over 95%) compared to FeBTC,
which is due to the formation of bidentate co-
ordination bonds of lanthanum with the sur-
face carboxyl groups of PMIDA, which is con-
firmed by NMR, high-resolution IR spectros-
copy, X-ray photoelectron spectroscopy, etc.
In addition, the interaction of PMIDA with
carboxyl groups changes the effective surface
charge, which also contributes to the improve-
ment of the adsorption characteristics of func-
tionalized MOFs. The adsorption capacity of
the functionalized MOF and composite gran-
ules was 232.5 mg/g and 77.51 mg/g. It was
found that the adsorption characteristics of
PMIDA-FeBTC for La3+ depend on the pH of
the solution and the dosage of the adsorbent.
When the pH increases from 2 to 8, the ad-
sorption capacity increases, but at pH>6, inso
luble hydroxide La(OH)3 can be formed, which
significantly reduces its adsorption. Therefore,
the authors proposed to maintain the pH of the
solutions at ~4.0 for effective extraction of La,
at which the surface potential does not change,
which contributes to faster diffusion of various
forms of La3+ to the surface of the adsorbent.
When the sorbent dosage is increased
from 2.5 g/l to 3 g/l for a La3+ concentration of
750 mg/l, its adsorption increases from 60% to
98.35%, while the adsorption capacity decrea
ses from 302.8 mg/g to 257 mg/g. However,
above 3 g/l, the adsorption percentage remains
unchanged due to the limited amount of ad-
sorbate. Therefore, 3 g/l can be chosen as the
optimal adsorbent dosage at a layer height of
12 cm and a flow rate of 10 ml/min.
Prospects for the use
of aminocarboxyphosphonates
as antitumor agents.
Despite the worldwide success of plati-
num complexes (1-4 cis-diamindichloro-
platinum(II) - cisplatin, carboplatin, cis-di-
amine-(1,1-cyclobutanedicarboxylato)plati-
num(II), oxaliplatin (trans-R,R-cyclohexane-
1,2-diamine)oxalatoplatinum(II)) as some of
the best agents in clinical cancer chemothe
rapy, researchers around the world continue
to make efforts to find new anticancer drugs
to overcome the serious side effects caused
by platinum drugs, improve clinical effica-
cy, and expand the spectrum of use of new-
ly created compounds. For the synthesis of
platinum complexes with selective activity in
primary and secondary malignant bone neo-
plasms (osteosarcoma and bone metastases of
tumors with other primary localizations), a se-
ries of stereoisomeric platinum(II) complexes
based on bis(phosphonomethyl)aminoace
tic acid and cyclohexane-1,2-diamine ligands
(chxn), - [(bis(phosphonomethyl)aminoκN)
acetato-κO(2-)]-platinum(II) with (Fig. 8) was
synthesized in [69], the antitumor activity of
which was studied on human ovarian cancer
cells (CH1) using the colorimetric microcul-
ture assay (MTT assay).
The antitumor activity of the synthesized
complexes in vitro was compared with the
similar action of cisplatin, carboplatin, and
oxaliplatin (Fig. 9, Table 1).
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а b
Fig. 8. Structural formulas of known antitumor Pt(II) complexes (a) and synthesized in [69] (b).
Fig. 9. Concentration-response curves of [(bis(phosphonomethyl)amino-κN)acetato-
κO(2-)]platinum(II) complexes in ovarian cancer cells (CH1) after exposure
for 96 h (T/C - ratio of live cells to tumor cells) [69].
Table 1.
Antiproliferative activity of [(bis(phosphonomethyl)amino-κN)acetato-κO(2-)]plati-
num(II) complexes in comparison with known platinum-based anticancer drugs on the CH1
ovarian cancer cell line [69].
Complex IC50, µM
[Pt(NH3)2BPMAA] 128 ± 22
[Pt(en)BPMAA 532 ± 154
[Pt(cis-R,S-chxn)BPMAA] 169 ± 56
[Pt(trans-S,S-chxn)BPMAA] 52.4 ± 10.9
[Pt(trans-R,R-chxn)BPMAA] 20.6 ± 1.1
cisplatin 0.15 ± 0.01
carboplatin 2.5 ± 0.4
oxaliplatin 0.27 ± 0.07
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PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
Both compounds [Pt(trans-chxn)BPMAA]
demonstrate higher antitumor activity than
the corresponding analogue [Pt(cis-R,Schxn)
BPMAA], and the complex [Pt(trans-R,R-
chxn)BPMAA] is the most active among the
three isomers. This is consistent with the ef-
fectiveness of the oxaliplatin isomers. In addi-
tion, both complexes [Pt(trans-chxn)BPMAA]
demonstrate significantly higher activity
compared to [Pt(NH3)2BPMAA] and [Pt(en)
BPMAA], while the cis-isomer [Pt(cis-R,S-
chxn)BPMAA] has either similar or even
slightly lower activity than [Pt(NH3)2BPMAA].
Thus, the antitumor activity of the studied
complexes decreases in the following order:
[Pt(trans-R,R-chxn)BPMAA] > [Pt(trans-S,S-
chxn)BPMAA] > [Pt(NH3)2BPMAA] ≥ [Pt(-
cis-R,S-chxn)BPMAA] > [Pt(en)BPMAA].
The advantage of [Pt(trans-R,R-chxn)
BPMAA] was also confirmed when studying
the in vivo effect of the synthesized complexes
on white mice infected with murine leukemia
L1210. In this tumor model, the survival of ex-
perimental animals is significantly increased
by the administration of [Pt-(trans-R,R-chxn)
BPMAA], which is reflected in T/C values
>250% at the optimal dosage.
The authors believe that the activity of BP-
MAA complexes with chxn will be preserved
also in these cisplatin-resistant cells and rele-
vant tumor models in vivo.
In recent years, with the development of
modern nanotechnology, interest has arisen in
the synthesis and study of metal nanoparticles
(NPs) with biological activity. The size of na-
noparticles or nanosystems used in chemistry,
medicine, and biotechnology is of great impor-
tance, since it determines the permeability, ac-
tivity, solubility, and toxicity of nanoparticles
[70, 71]. A feature of such particles is that they
easily form complex compounds with organic
ligands, which have new properties compared
to macrocompounds. Thus, nanoparticles
can bind to nucleic acids, proteins, integrate
into membranes, penetrate into cellular orga-
nelles, changing the functions of biostructures.
A number of works have been devoted to the
study of the properties of metals in the ultradis-
perse range in the form of powders, solutions
and suspensions [72, 73]. It has been shown
that non-aggregated metal nanoparticles have
antimicrobial, antiviral, and antioxidant acti
vity [75–76]. A number of authors have shown
that the biological activity of metal nanopar-
ticles is determined not only by their size, but
also by their shape. For example, dendritic and
spindle-shaped nanoparticles have higher cy-
totoxicity than spherical ones [77]. Thus, the
totality of the above facts indicates that metal
nanoparticles have biological activity, the se-
verity of which depends on their size, shape,
surface structure, aggregate state, chemical
composition, solubility and a number of other
factors [66, 78]. Among the various forms of
nanoscale materials, solutions of metal nano
particles are of interest. Their advantage lies
in a relatively narrow size distribution (up to
12 nm) and shape (mostly spherical) and a long
retention time of biological activity. Therefore,
the use of stable metal nanoparticles in aque-
ous solutions is promising in various fields of
biology, veterinary medicine and medicine. In
this regard, the search for new ways to form
monodisperse systems with controlled nano-
particle size is relevant.
One of the most interesting chemical ele-
ments used as nanoparticles for biomedical
purposes is cobalt Co(II) and its oxide. Despite
its physiological role as a cofactor of vitamin
B12, cobalt cannot be considered only as an es-
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sential element. Cobalt-based nanoparticles
in general and cobalt oxide nanoparticles in
particular are currently attracting great inte
rest due to their unique properties, which de-
pend on size, shape and potential applications
in pigments, catalysis, sensors, electrochemist
ry, magnetism, energy storage, etc. [79]. Co-
balt nanoparticles have the ability to penetrate
cells very quickly [80], which has attracted the
attention of researchers to biomedical appli-
cation systems based on cobalt nanoparticles.
However, the use of cobalt nanoparticles is li
mited due to their toxicity, and this problem
can be overcome by coating magnetite/maghe
mite nanoparticles with polymeric organo-
phosphorus compounds [81, 82]. The binding
of organophosphorus molecules to the inor-
ganic phase occurs as a result of the formation
of strong M-O-P bonds through heterocon-
densation and coordination. Homoconden-
sation with the formation of P-O-P bridges is
unlikely, and such bridges are unstable in the
presence of water. Organophosphorus cou-
pling agents react specifically with metal oxide
surfaces and promote only the formation of a
monolayer. The resulting monolayers are high-
ly stable under physiological conditions.
Using this approach, Chattopadhyay and
colleagues [83] investigated the prospects of
using surface-modified cobalt oxide (CoO)
nanoparticles as carriers of cancer antigens in
human macrophages. N-Phosphomethylimi-
nodiacetic acid used to modify the CoO sur-
face in order to overcome the toxic effect of
CoO nanoparticles. In this case, the phospho-
nate group of PMIDA acts as a surface ancho
ring agent, and the two -COOH groups bind
nonspecifically to tumor-associated antigens.
Cytotoxicity studies, flow cytometric analysis,
and scanning electron micrographs showed
that PMIDA-coated nanoparticles significant-
ly enhance the cellular uptake of nanoparticles
and thus promote apoptosis of cancer cells.
The conjugation of PMIDA with CoO nano
particles studied by IR spectroscopy (Fig. 10).
In the IR spectra, a decrease in the intensity
of the ν(OH) band at 3440 cm−1 is observed,
indicating the conjugation of the phosphonic
group of PMIDA on CoO NPs. The presence
of bands at 1750 cm−1 and 1050 cm−1, which
correspond to M–O–P and P–O vibrations, re-
spectively, confirms the conjugation of PMIDA
on the surface of the nanoparticles.
Fig. 10. IR spectra of PMIDA (a), CoO (b) and
CoO nanoparticles coated with PMIDA (c) [83].
The authors carried out a study of the toxicity
of CoO-PMIDA nanoparticles towards normal
human lymphocytes and oral squamous epi-
thelial cells in vitro. The experiments were con-
ducted in comparison with the well-known an-
ticancer drug doxorubicin. The study revealed
no significant difference between the effects of
CoO-PMIDA nanoparticles and doxorubicin:
doxorubicin killed Jurkat cells (lymphoma
T-cell lines) and KB cells (oral carcinoma) by
15.64%, 25.28%, 40.52% and 17.08%, 30.80%,
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PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
42.73%, respectively, at doses of 1, 5 and
10 μg/ml, while CoO-PMIDA nanoparticles
killed Jurkat and KB cells by 14.2%, 21.80%,
34.28% and 12.20%, 23.58%, 35.78%, respec-
tively. However, PMIDA-coated CoO nano-
particles did not have a toxic effect on nor-
mal human lymphocytes and oral epithelial
cells, while doxorubicin had a toxic effect on
normal cells. This selectivity significantly en-
hances the therapeutic potential of nanopar-
ticles by cells, and thus facilitates cancer cell
apoptosis.
The authors proposed a model in which cy-
totoxicity against oral cancer is manifested by
activation of normal human macrophages us-
ing the CL-PMIDA-CoO complex (Fig. 11).
Fig. 11. Proposed pathway of action of CL–PMIDA–CoO nanoparticles as antitumor agents [83].
This model allows for basic studies of tumor
lysate delivery to macrophages and immuno
stimulation mediated by activated macropha
ges against oral cancer cells. To identify factors
involved in anticancer activity, the researchers
used pentoxifylline (POF), a potent TNF-α
blocker, in the experiment (TNF-α – tumor
necrosis factor extracellular protein and mul-
tifunctional pro-inflammatory cytokine syn-
thesized by monocytes and macrophages). It
was found that TNF-α is responsible for the
destruction of KB cells, and in the presence of
aminocarboxyphosphonate, the production of
NO, which is responsible for the destruction
of cancer cells, is increased. From this per-
spective, the authors believe that CL–PMIDA–
CoONPs indirectly stimulate TNF-α and thus
exhibit anticancer immunotherapy (Fig. 12).
Functionalization of the CoO surface with –
COOH and –NH2 groups facilitates the conju-
gation of nanoparticles with anticancer drugs
through amide bonds, which are effectively
taken up by cancer cells. Thus, PMIDA-coated
CoO nanoparticles may have great promise for
cancer treatment due to the lack of lethal to
xicity to normal (living) cells.
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а
b
Fig. 12. Scheme of the synthesis of functionalized paramagnetic magnetite nanoparticles (a) and
a multifunctional nanomedical platform for magnetic resonance/optical imaging of cancer cells (b) [84].
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PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
No less interesting results were obtained in
the study of a nanosystem based on an ultra
small superparamagnetic iron oxide nano-
core (USPIO) modified with a hydrophilic,
biocompatible and biodegradable coating -
N-phosphonomethyliminodiacetic acid to
create a multifunctional nanoprobe that can
selectively target, detect and kill cancer cells
[84]. The synthesis of the nanosystem consists
of 4 stages. First, ultrasmall superparamagne
tic magnetite nanoparticles were synthesized
by alkaline chemical co-precipitation of Fe3+
and Fe2+ in the presence of PMIDA (Fig. 12, a).
PMIDA-coated magnetite nanoparticles
(USPIO-PMIDA, 1) served as the base materi-
al to enable magnetically guided drug delivery
and to enhance magnetic resonance contrast.
Then, a fluorescent dye, rhodamine B isothio-
cyanate (RITC), was linked to the amino-de-
rivative substrate of USPIO-PMIDA (1.1) to
provide optical imaging capabilities. In step 3,
folic acid (FA) was conjugated to 1.1 to target
cancer cells overexpressing the folate receptor
(FR). Finally, the folate analog methotrexate
(MTX) was linked to the nanoparticle surface
via a pH-labile ester linkage to facilitate drug
release within acidic tumor endosomes and to
initiate apoptosis (Fig. 12, b).
The synthesized USPIO–PMIDA–EDBE–
RITC–FA–OH–MTX (1.5) nanoparticles are
biocompatible and biodegradable because they
are composed of biodegradable and biocom-
patible components. These functional nano-
particles are stable in aqueous buffer solutions,
have good cellular targeting ability, and their
relatively simple synthesis process is scalable.
To further demonstrate the anticancer po-
tential of USPIO-PMIDA-EDBE-RITC-FA-
OH-MTX, in vitro cell uptake experiments
were performed. FR-positive human cervical
carcinoma HeLa cells were selected as the tar-
get cell line. Magnetic-activated cell sorting
(MACS) was used to preliminarily quantify the
uptake of nanoparticles into target cells.
Cellular uptake of conjugates containing
folic acid as the targeting molecule was signi
ficantly improved compared to their non-tar-
geted controls, demonstrating active targeting
of magnetite nanoparticles through the inter-
action between folate groups on the surface of
the nanoparticles and receptors of HeLa cells
(Fig. 13).
Fig. 13. Quantitative assessment of the uptake of
USPIO–PMIDA–EDBE–RITC–FA–OH–MTX na-
noparticles by FR-positive HeLa and FR-negative
MG-63 cell lines [84].
To confirm receptor specificity for the con-
jugate, the uptake of 1.5 by HeLa cells was also
compared with that of the FR-negative human
osteosarcoma cell line MG-63. The uptake of
nanoparticles by HeLa cells was much greater
than that of their non-targeted counterparts.
In contrast, the uptake of folate-targeted na-
noparticles by MG-63 cells was significant-
ly lower and similar to that of non-targeted
controls.
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Magnetic resonance phantom imaging was
used to assess the detectability by MRI and to
further confirm the association of these nano
particles with FR-overexpressing HeLa cells.
HeLa cells cultured with FA-functionalized
nanoparticles had a shorter T2 relaxation time
(higher relaxivity) than those cultured with
the unfunctionalized counterpart due to the
enhanced magnetism. The results presented
here show the high potential of the obtained
nanocarriers as a cancer-targeting MRI probe.
In vitro drug release experiments of 1.5 con-
ducted at different pH values (pH = 2.0 - 7.4)
showed that the release rate was much higher
in the lower pH range (pH 2–5) with negligible
drug release at physiological pH. This suggests
that USPIO-PMIDA-EDBE-RITC-FA-OH-
MTX would be released more in acidic tumor
regions than in normal tissues. When particles
accumulate inside cells via FR-mediated endo-
cytosis, reduced pH values may induce further
accelerated release within acidic endosomes of
tumor cells.
When exposed to drug-modified nano-
particles at low concentrations (0.01 mg/ml)
after 24 hours, cancer cells showed a noticea-
ble trend towards decreased viability. To test
whether USPIO–PMIDA–EDBE–RITC–FA–
OH–MTX could induce cell death by initiat-
ing apoptosis, HeLa cells were exposed to 1.0
mg/ml USPIO–PMIDA–EDBE–RITC–FA–
OH–MTX for 0.5 h and incubated at 37°C for
24 h. The results showed intense red fluores-
cence in the cytoplasm of cells treated with
folate-targeted nanoparticles, demonstrating
cellular internalization via receptor-mediated
endocytosis. To examine nuclear morpholo-
gy and identify nuclear alterations associated
with cell death, cells were additionally stained
with 4’-6-diamidino-2-phenylindole (DAPI), a
nuclear dye that exhibits strong blue fluores-
cence upon binding to DNA. Cells treated with
USPIO-PMIDA-EDBE-RITC-FA-OH-MTX
exhibited typical apoptotic morphology, which
included condensed nuclei, membrane blebs,
and the formation of apoptotic bodies.
Other areas of application
of aminocarboxyphosphonates.
Aminocarboxyphosphonates have promi
sing applications for flotation separation of
minerals [85–87]. For example, [86, 87] pro-
posed the use of N,N-bis(phosphonomethyl)
glycine as a highly effective dolomite depres-
sant for the flotation of magnesite from dolo-
mite using sodium oleate (NaOL) as a collector.
Using an optimized reagent system consisting
of 80 mg/L NaOL, 30 mg/L BPMG, and pH
10.0, concentrates with MgO and CaO con-
tents of 42.81% and 4.35%, respectively, were
obtained with their recoveries of 80.85% and
23.67%, respectively. Both single mineral and
binary mixed mineral tests clearly confirm the
exceptional depressant capabilities of BPMG
in dolomite flotation, while demonstrating
negligible impact on magnesite flotation. At
the same time, the depressant effect of BPMG
on dolomite demonstrates excellent selectivity,
ensuring maximum MgO recovery with mini-
mal CaO recovery.
Contact angle measurements demonstrate
hydrophobic limitations inherent to the natu
ral minerals magnesite and dolomite. How
ever, adsorption of NaOL on mineral surfaces
enhances the hydrophobic characteristics of
both minerals. In the presence of BPMG, the
differential adsorption behavior of NaOL on
mineral surfaces gives magnesite and dolo-
mite distinct wetting properties. Zeta potential
measurements showed that both magnesite
and dolomite have negative zeta potentials
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PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
under alkaline conditions (pH≈10.0). Therefore,
BPMG must overcome electrostatic repulsion
during adsorption on mineral surfaces. BPMG
exhibits increased adsorption affinity to the sur-
face of dolomite minerals, which can be attri
buted to the difference in atomic radii of calci-
um and magnesium in the semi-closed state on
the mineral surface. Fourier transform infrared
spectroscopy analysis confirmed that the strong
interaction between BPMG and dolomite can be
attributed to the chemical interaction between
the phosphonic groups in BPMG and the metal
atoms on the surface of the dolomite mineral.
XPS analysis confirmed the specific interaction
of BPMG with calcium rather than magnesium
sites on the dolomite surface. Coordination be-
tween the –PO3 groups in BPMG and the cal-
cium sites leads to the formation of Ca–BPMG
complexes, thereby facilitating selective adsorp-
tion on mineral surfaces.
Based on the conducted studies, the
authors proposed possible adsorption models
for BPMG and NaOL on dolomite and magne-
site (Fig. 14).
Fig. 14. Model of adsorption of BPMG and NaOL on magnesite and dolomite [86].
BPMG is intensively chemisorbed on the
dolomite surface through calcium sites. In ad-
dition, the weak interaction between BPMG
and magnesite has little effect on the adsorp-
tion of NaOL on the magnesite surface, main-
taining the excellent flotation of magnesite. For
dolomite, the high adsorption of BPMG on its
surface and the formation of Ca-BPMG che-
lates, which accumulate on the dolomite sur-
face, possibly due to steric hindrance, signifi-
cantly reduce the adsorption of NaOL.
In [87], the use of N-(phosphonomethyl)
iminodiacetic acid (PMIDA) as an environ-
mentally friendly depressant for the selective
flotation of galena and sphalerite was investi-
gated. PMIDA microflotation tests were per-
formed to evaluate its effectiveness. In addition,
the mechanism of PMIDA depression was ana-
lyzed using solution chemistry calculations,
zeta potential measurements, contact angle de-
termination, X-ray photoelectron spectrosco-
py, and density functional theory calculations.
Solution chemistry calculations showed that
the presence of PMIDA in the pulp (СPMIDA =
69https://ucj.org.ua
O.K. Trunova UCJ № 9 / Vol. 91
120 mg/l, pH = 8) in the form of PMIDA3− ions
optimized the depressive effect on the sphalerite
surface, while galena demonstrated excellent
flotation. The addition of PMIDA increased
the hydrophilicity of the sphalerite surface and
made it difficult for xanthate to adsorb on the
sphalerite surface. However, the introduction
of PMIDA had minimal effect on the surface
hydrophilicity and adsorption of xanthate on
galena, thereby promoting the selective sepa-
ration of sphalerite and galena. Zeta potential
measurements showed that the adsorption ca-
pacity of xanthate on the sphalerite surface was
significantly reduced after PMIDA treatment.
X-ray photoelectron spectroscopy analysis
showed that the adsorption of PMIDA on the
sphalerite surface was associated with the for-
mation of a stable chemical bond between the
oxygen atoms of the phosphonic acid group
and the surface zinc atoms of sphalerite. That
is, PMIDA exhibited a higher adsorption affi
nity for the sphalerite surface compared to the
galena surface, thereby selectively inhibiting
the flotation of sphalerite.
Metal phosphonates, as a subclass of coor-
dination polymers, exhibit acidic properties
due to the presence of groups such as POH,
SO3H, COOH, N+-H in their molecules. The
combination of these properties with electro-
catalytically active transition metals makes
them very attractive in the field of fuel cells
and electrolyzers, as potential proton con-
ductors and/or precursors of electrocatalysts
[88, 89]. The authors [90] obtained a series
of Co2+ and Sn4+ phosphonates based on gly-
cine-N,N-bis(methylene)phosphonic acid (BP-
MGLY) by hydrothermal synthesis. In the case
of the tin derivative, the amorphous compound
Sn(C4H11O8NP2)0,75Cl2,5(H2O)2,5(Sn4+-BPMGLY)
is formed. Its pyrolytic treatment at 700 ºC in
air led to the formation of amorphous pyro
phosphate (Sn4+-BPMGLY-700). As for cobalt
phosphonates, three crystalline phases with the
composition [Co(C4H11O8NP2(H2O)2]·nH2O
(n = 0; 2) were obtained. All synthesized com-
pounds were studied as proton conductors in
a wide range of temperatures and humidity
conditions. Sn4+ derivatives at 95°C and 95%
relative humidity showed the highest conduc-
tivity values of 7.99·10-4 and 6.63·10-3 S·cm-1
for Sn4+-BPMGLY and Sn4+-BPMGLY-700, re-
spectively, and cobalt aminocarboxyphospho-
nates were used as precursors for base metal
catalysts by pyrolysis of the complexes at dif-
ferent temperatures in a 5%-H2/Ar atmosphere
and investigated as electrocatalysts for oxygen
and hydrogen evolution reactions (OER or
HER), and oxygen reduction reactions (ORR).
A group of Indian scientists led by B.V.
Appa Rao first conducted a series of studies
on the protection of carbon steel surfaces
from corrosion using a synergistic mixture of
environmentally friendly N,N-bis(phospho-
nomethyl)glycine and zinc ions [48, 91]. In
[91], published in 2008, a study of an envi-
ronmentally friendly ternary inhibitor com-
position consisting of the binary BPMG-Zn2+
system as the primary synergist and ascorbate
ions as a secondary synergist for protecting
carbon steel from corrosion in a low chloride
environment was presented. The fact is that
N,N-bis(phosphonomethyl)glycine in com-
bination with Zn2+ in almost neutral aqueous
media, although an effective corrosion inhi
bitor, requires relatively high concentrations of
both BPMG and Zn2+ (≥ 80 ppm). Therefore,
to improve the inhibition efficiency of this sys-
tem at lower concentrations, sodium ascor-
bate was added as a second synergist, since the
ascorbate ion contains five hydroxyl and one
70 ISSN 2708-129X. Укр. хім. журн., 2025
PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
carboxyl group and forms strong complexes
with Fe3+. It turned out that the effect of add-
ing ascorbate was quite significant. While the
binary system BPMG-Zn2+ (BPMG:Zn2+ = 1:4,
СBPMG = СZn2+ = 40 ppm) inhibited the corro-
sion of carbon steel with an inhibition efficien-
cy (IE) of 90%, the addition of only 25 ppm of
ascorbate to the above system provided an IE
of 95%. The ternary inhibitor composition was
found to be effective in the pH range of 5–11
and even at pH=11 it had excellent inhibition
efficiency, a condition at which all other phos-
phonate-based systems fail.
Potentiostatic polarization studies of the
ternary inhibitor system showed that the cor-
rosion potential shifts from -350 to -371 mV
in the cathodic direction, and the corrosion
current decreases from 6.16 mA·cm-2, ob-
served in the case of the control solution, to
0.94 mA·cm-2 in the presence of the inhibitor.
Such a significant decrease in the corrosion
current indicates a decrease in the corrosion
rate in the presence of the inhibitor. Compa
rison of the Fourier transform infrared spectra
of pure BPMG and ascorbic acid with the cor-
responding IR spectra of surface films formed
in the presence of the inhibitor showed the for-
mation of Fe(III) complexes with BPMG and
ascorbate on the steel surface (bathochromic
shift of the ν(СОО-) vibration from 1732BPMG
(1676ascorbate) cm-1 to 1623 cm-1 in the film; shift
of ν(PO3) 1181 cm-1 → 1140 cm-1). A small
peak at 1323 cm-1 indicates the formation of
Zn(OH)2 on the film surface.
Based on the results of the research, the au-
thors proposed a plausible mechanism for cor-
rosion inhibition:
1. Carbon steel undergoes initial corrosion
with the formation of Fe2+ ions at the anodic
sites: Fe → Fe2+ + 2e-;
2. Then Fe2+ undergoes oxidation in the
presence of oxygen: Fe2+ + О2 → Fe3+ + e-;
3. A reduction reaction occurs at the ca
thode in a neutral and alkaline environment:
O2 + 2H2O + 4e- → 4OH-;
4. Before the formation of a protective film,
iron oxides, namely γ-Fe2O3 and Fe3O4, are
formed on the metal surface;
5. BPMG and ascorbate ions react with Zn2+
ions present in the bulk of the solution to form
a complex [Zn(II)–BPMG–ascorbate] and
this complex diffuses to the metal surface. The
formed zinc complex then reacts with Fe3+ ions
available at the anode sites to form hetero- and
polynuclear complexes [Fe(III)–BPMG–ascor-
bate];
6. Zn2+ ions released in the previous re-
action combine with OH- ions present at
the cathode, forming a precipitate Zn(OH)2:
Zn2+ + 2ОН- → Zn(OH)2↓;
7. Thus, the ternary inhibitor system sup-
presses corrosion by controlling both the
anodic and cathodic reactions. A protec-
tive film is formed on the metal surface,
which consists of iron oxides, Zn(OH)2 and
[Fe(III)–BPMG–ascorbate].
The effectiveness of this ternary inhibitor
composition at high pH environments is due to
the stability of the [Fe(III)–BPMG–ascorbate]
complex formed on the metal surface and the
presence of optimal amounts of Fe(OH)3 and
Zn(OH)2 in the surface film.
Continuing their research, the authors
found that the binary BPMG-Zn2+ system is an
effective corrosion inhibitor for carbon steel in
low-chloride aqueous media in the pH range
of 5 to 8, which is commonly used for cooling
water systems. The inhibitor mixture acts as a
mixed-type inhibitor, controlling both anodic
and cathodic reactions [48].
71https://ucj.org.ua
O.K. Trunova UCJ № 9 / Vol. 91
In [92], four 3d–4f heterometallic coordina-
tion polymers based on N-(phosphonomethyl)
iminodiacetic acid were synthesized: [LnFeIII-
FeII
6(HPMIDA)6]·2H2O (Ln = Eu, Dy, Ho, Y),
which were investigated as heterogeneous ca
talysts in the Knoevenagel condensation. This
is an important reaction of the C–C coupling
of a carbonyl group with a compound contain-
ing an activated methylene group and is wide-
ly used for the synthesis of fine chemicals and
pharmaceuticals.
The Eu complex was tested as a heteroge
neous catalyst in the Knоevenagel condensa-
tion of benzaldehyde with malononitrile in
1.0 ml of toluene at 60°C (Fig.15).
Fig.15. Scheme of heterogeneous catalysis in the Knoevenagel condensation
of benzaldehyde with iminodiacetic acid [92].
The material showed catalytic activity in this
reaction compared to a control experiment per-
formed using the same conditions but without
the addition of catalyst. After 27 hours of reac-
tion, the conversion of benzaldehyde was 27%,
while in the control experiment the conversion
was only 7%. In this case, the yield of the main
product in the reaction with the catalyst was
98%, while in the condensation reaction with-
out the catalyst the yield was 89%. Benzoic acid
was formed as a minor product. After the re-
action, the heterogeneous catalyst was filtered,
washed with toluene, and used in a second ca
talytic cycle under the same experimental con-
ditions. After 27 hours, the benzaldehyde con-
version was 32%, and in the third and fourth
catalytic cycles using [EuFeIIIFeII
6(HPMIDA)6],
the benzaldehyde conversion was 28% and 8%,
respectively. Thus, the synthesized heterome-
tallic complex can be recycled and reused for at
least two more catalytic cycles without loss of
catalytic activity. The substrate scope was also
extended to o-tolualdehyde and heptaldehyde.
The reaction with o-tolualdehyde and malono
nitrile gave an aldehyde conversion of 20%
in 4.0 mL toluene at 60°C. No side products
were detected, indicating that the reaction
was selective for the Knevenagel condensation
product. The reaction of malononitrile with
heptanoaldehyde in 1.0 mL of toluene at 60 °C
72 ISSN 2708-129X. Укр. хім. журн., 2025
PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES
AND THEIR METAL COMPLEXES (review).INORGANIC CHEMISTRY
gave 57% conversion of the aldehyde, but the
reaction was not selective, as heptanoic acid
was formed as a by-product. Complexes with
Dy, Ho, and Y show similar catalytic activity,
but the europium-containing complex is the
most effective.
The authors proposed a mechanism for the
catalytic activity of the complexes. The synthe-
sized MOFs contain only Lewis acid centers,
and the Knоevenagel condensation is tradi-
tionally catalyzed by basic catalysts. However,
the organometallic framework LnFeIIIFeII
6(H-
PMIDA)6 works as a Brønsted base in the re-
action and deprotonates the active methylene
group of malononitrile. Thus, a defec Brønsted
acid site is formed in the MOF, which, toge
ther with the neighboring Lewis acid (iron
and rare earth ions), facilitates the activation
of both reagents in the Knevenagel condensa-
tion. The deprotonated active methylene group
of malononitrile attacks the aldehyde, and
then, after re-protonation and dehydration
of the adduct, the Knоevenagel condensation
product is formed. The catalytic properties of
heterometallic complexes indicate that these
types of compounds are heterogeneous cata-
lysts for the Knоevenagel condensation with
high selectivity.
CONCLUSIONS. The polydentate nature of
aminocarboxyphosphonate ligands due to their
diverse coordination sites and different affini
ties for different metal centers allows for the
preparation of new compounds with a number
of unique properties. This opens up prospects
for obtaining a large number of highly stable
complexes of various cyclic structures, both in
composition and shape, in particular hetero-
nuclear complexes, the internal coordination
sphere of which includes two or more different
metals simultaneously. In the synthesis of he
teronuclear complexes based on complexones,
the conformational ability of ligands to bind
metals of different natures (for example, d- and
f-elements) into a single coordination site is
used. The effectiveness of such compounds as
materials for new technologies and medicines
is obvious. In recent years, aminocarboxyphos-
phonic acids and their metal complexes have
attracted significant attention from researchers
around the world due to their broad poten-
tial for practical use. Aminocarboxyphospho-
nates of transition metals are currently used in
agronomy as plant growth regulators and her-
bicides. Their potential application in materi-
als chemistry as functional materials has also
been revealed due to the presence of a number
of useful properties: high porosity, photolu-
minescence, catalytic, nonlinear optical, and
magnetic properties, etc. Due to these proper-
ties, aminocarboxyphosphonates can be used
for the removal of heavy metals (Cd, Pb, Cr, La,
As) from wastewater or groundwater, for the
production of surface-modified nanoparticles
with antitumor activity, for flotation separa-
tion of minerals, for the creation of a protec-
tive film during steel corrosion, for chelation
therapy, molecular imaging and catalysis.
ACKNOWLEDGMENTS. The work
was financially supported by the Na-
tional Academy of Sciences of Ukraine
within the framework of the state
budget topic 331E «Hybrid and com-
posite systems based on coordination
compounds of d- and 4f-transition
metals: synthesis, structural features,
and luminescent and biochemical
properties» (state registration number
0125U000479).
73https://ucj.org.ua
O.K. Trunova UCJ № 9 / Vol. 91
ПЕРСПЕКТИВИ ПРАКТИЧНОГО ЗАСТОСУВАННЯ
АМІНОКАРБОКСИФОСФОНАТІВ ТА ЇХНІХ
МАТАЛОКОМПЛЕКСІВ (огляд)
О. К. Трунова
Інститут загальної та неорганічної хімії
ім. В. І. Вернадського НАН України,
просп. Акад. Палладіна, 32/34, Київ 03142,
Україна
е-mail: trelkon@gmail.com
В оглядовій статті узагальнено та сис-
тематизовано багаторічні літературні дані
щодо можливих сфер застосування аміно-
карбоксифосфонових киcлот та метало-
комплексів на їхній основі. Показано, що
амінокарбоксифосфонати з огляду на їхній
широкий спектр функціональних власти-
востей, зокрема таких як фотолюмінес-
ценція, магнітні властивості, біологічна
активність, можуть знайти застосування у
найрізноманітніших сферах. Як самі амі-
нокарбоксифосфонові кислоти, так і їхні
комплекси здатні виступати основою для
біологічно активних речовин в агрономії
– як синтетичні регулятори росту, як ефек-
тивні препарати для збільшення екстраго-
ваного цукру з різних рослин (цукрова тро-
стина, солодка картопля, цукровий буряк,
диня та ін.) та препарати для прискорення
дозрівання плодів за несприятливих по-
годних умов. Однією з найцікавіших сфер
використання амінокарбоксифосфонатів
та наночастинок на їхній основі для біоме-
дичних цілей є створення прекурсорів для
розроблення нових протипухлинних пре-
паратів. Завдяки високій пористості ці ма-
теріали можна використовувати в екології
для очищення ґрунтової та/або питної води
від важких металів. Висвітлені в роботі
підходи щодо модифікації координаційно-
го середовища, варіації природи металів і
лігандного оточення можуть бути викори-
стані як модель для розроблення нових ко-
ординаційних полімерів та MOF-структур
як екологічно чистих депресантів для се-
лективної флотаційної сепарації мінералів
(доломіту, галеніту, сфалериту). Амінокар-
боксифосфонати металів як підклас коор-
динаційних полімерів завдяки наявності
в молекулах таких груп, як POH, COOH,
N+-H демонструють кислотні властивості,
поєднання яких з електрокаталітично-ак-
тивними перехідними металами робить їх
привабливими в області паливних елемен-
тів і електролізерів. Вони можуть бути ви-
користані як потенційні протонопровідни-
ки та/або прекурсори електрокаталізато-
рів, гетерогенні каталізатори у конденсації
Кневенаґеля з високою селективністю.
Ключові слова: комплекси, амінокар-
боксифосфонати, 3d-, 4f-метали, біологічна
активність, каталізатор, очишення від важ-
ких металів, практичне застосування.
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Стаття надійшла 17.08.2025.
|
| id | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-751 |
| institution | Ukrainian Chemistry Journal |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-23T01:13:41Z |
| publishDate | 2025 |
| publisher | V.I.Vernadsky Institute of General and Inorganic Chemistry |
| record_format | ojs |
| resource_txt_mv | ucjorgua/ee/c10ae43af69a4bc2bb909c7d39eb47ee.pdf |
| spelling | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-7512026-07-22T08:23:56Z PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review) Trunova, Olena complexes, aminocarboxyphosphonates, 3-d, 4-f metals, biological activity, catalyst, purification from heavy metals, practical application. The review article summarizes and systematizes many years of literature data on possible areas of application of aminocarboxyphosphonic acids and metal complexes based on them. It is shown that aminocarboxyphosphonates, due to their wide range of functional properties, in particular, such as photoluminescence, magnetic properties, biological activity, can find application in a wide variety of areas. Both aminocarboxyphosphonic acids themselves and their complexes can serve as the basis for biologically active substances in agronomy - as synthetic growth regulators, as effective preparations for increasing extracted sugar from various plants (sugar cane, sweet potato, sugar beet, melon, etc.) and preparations for accelerating fruit ripening under adverse weather conditions. One of the most interesting areas of use of aminocarboxyphosphonates and nanoparticles based on them for biomedical purposes is the creation of precursors for the development of new antitumor drugs. Due to their high porosity, these materials can be used in ecology for the purification of soil and/or drinking water from heavy metals. The approaches to the modification of the coordination environment, variations in the nature of metals and ligand environment highlighted in the work can be used as a model for the development of new coordination polymers and MOFs structures as environmentally friendly depressants for selective flotation separation of minerals (dolomite, galena, sphalerite). Aminocarboxyphosphonates of metals as a subclass of coordination polymers, due to the presence of such groups in the molecules as POH, COOH, N+-H, demonstrate acidic properties, the combination of which with electrocatalytically active transition metals makes them very attractive in the field of fuel cells and electrolyzers. They can be used as potential proton conductors and/or precursors of electrocatalysts, heterogeneous catalysts in the Knoevenagel condensation with high selectivity. V.I.Vernadsky Institute of General and Inorganic Chemistry 2025-10-25 Article Article Inorganic Chemistry Неорганическая химия Неорганічна хімія application/pdf https://ucj.org.ua/index.php/journal/article/view/751 10.33609/2708-129X.91.9.2025.49-79 Ukrainian Chemistry Journal; Vol. 91 No. 9 (2025): Ukrainian Chemistry Journal; 49-79 Украинский химический журнал; ##issue.vol## 91 ##issue.no## 9 (2025): Ukrainian Chemistry Journal; 49-79 Український хімічний журнал; Том 91 № 9 (2025): Ukrainian Chemistry Journal; 49-79 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/751/386 Copyright (c) 2025 Olena Trunova https://creativecommons.org/licenses/by-nc/4.0 |
| spellingShingle | Trunova, Olena PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review) |
| title | PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review) |
| title_full | PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review) |
| title_fullStr | PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review) |
| title_full_unstemmed | PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review) |
| title_short | PROSPECTS FOR THE PRACTICAL APPLICATION OF AMINOCARBOXYPHOSPHONATES AND THEIR METAL COMPLEXES (review) |
| title_sort | prospects for the practical application of aminocarboxyphosphonates and their metal complexes (review) |
| topic_facet | complexes aminocarboxyphosphonates 3-d 4-f metals biological activity catalyst purification from heavy metals practical application. |
| url | https://ucj.org.ua/index.php/journal/article/view/751 |
| work_keys_str_mv | AT trunovaolena prospectsforthepracticalapplicationofaminocarboxyphosphonatesandtheirmetalcomplexesreview |