METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS
The review describes modern physicochemical systems based on complex compounds with organic ligands, which may have fluorescent properties when interacting with metal ions or proteins. Modern methods of synthesis of these compounds and their use in physical-chemical methods of analysis are given. Ap...
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| Дата: | 2021 |
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2021
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Ukrainian Chemistry Journal| _version_ | 1871465757911547904 |
|---|---|
| author | Asieieva, Dasha |
| author_facet | Asieieva, Dasha |
| author_institution_txt_mv | [
{
"author": "Dasha Asieieva",
"institution": "Université Toulouse III - Paul Sabatier, 118 route de Narbonne, Toulouse Cedex, 9, 31062, France"
}
] |
| author_sort | Asieieva, Dasha |
| baseUrl_str | https://ucj.org.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-22T08:23:47Z |
| description | The review describes modern physicochemical systems based on complex compounds with organic ligands, which may have fluorescent properties when interacting with metal ions or proteins. Modern methods of synthesis of these compounds and their use in physical-chemical methods of analysis are given. Approaches to detecting the content of metals and proteins using the fluorescent properties of morin complex compounds are considered. Areas of use of the effects of amplification and quenching of fluorescence for the determination of organic compounds and metal ions, especially in the presence of DNA and RNA of different biological origin are described. The influence of surfactants on the fluorescence intensity of complexes with morin was analyzed separately. |
| doi_str_mv | 10.33609/2708-129X.87.10.2021.74-89 |
| first_indexed | 2025-09-24T17:43:41Z |
| format | Article |
| fulltext |
74 ISSN 2708-129X. Укр. хім. журн., 2020
UDC 546.05+546.06 doi: 10.33609/2708-129X.87.10.2021.74-89
METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS
BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT
ANALYSIS METHODS
Asieieva D.A.1,2
1Université Toulouse III - Paul Sabatier, 118 route de Narbonne, Toulouse Cedex, 9, 31062, France
2Taras Shevchenko National University of Kyiv, Volodymyrska St, 60, Kyiv 01033, Ukraine
email: dasha.aseeva@gmail.com
The review describes modern physicochemical systems based on complex compounds
with organic ligands, which may have fluorescent properties when interacting with metal
ions or proteins. Modern methods of synthesis of these compounds and their use in physi-
cal-chemical methods of analysis are given. Approaches to detecting the content of metals and
proteins using the fluorescent properties of morin complex compounds are considered. Areas
of use of the effects of amplification and quenching of fluorescence for the determination of
organic compounds and metal ions, especially in the presence of DNA and RNA of different
biological origin are described. The influence of surfactants on the fluorescence intensity of
complexes with morin was analyzed separately.
Key words: morin, complex compounds, fluorescence, analysis, metal ions, protein.
INTRODUCTION. Physical-chemical me
thods using fluorescent materials make it pos-
sible to solve various scientific and applied
problems in the field of chemistry, physics, bio
logy, environmental monitoring and medical
diagnostics due to high sensitivity, selectivity
and expressiveness [1]. It is noteworthy that in
many cases the use of micellar systems leads
to an increase in the intensity of fluorescence
and quantum yields by more than two orders
of magnitude, and, accordingly, to a decrease
in the detection limits of analytes. Surfactants
have specific and sometimes unique proper-
ties. They are not only analytical reagents, but
also able to effectively affect the physicochemi-
cal properties of other substances in solutions,
such as proteins [2, 3], which are involved
in building muscle tissue, as well as parts of
the hair, nails and internal bodies. Therefore,
qualitative and quantitative analysis of pro-
teins is important in clinical trials and appli-
cations [4–6]. Therefore, the development of
new physical-chemical methods and selection
of conditions for the rapid determination of
microquantities of protein is very relevant to-
day. In addition, fluorescent properties can be
Asieieva D.A.
75https://ucj.org.ua
UCJ № 10 / Vol. 87
used in the development of labeling reagents
for the further development of such methods
as: high performance liquid chromatogra-
phy, spectrophotometry and selective sensors
[7–9]. For the development of these methods,
the conditions for the synthesis of reagents and
their organic component are of great impor-
tance, which in many cases is the key to the
substance's acquisition of selective properties
in reactions with organic compounds. Flavo-
noids are of particular interest, which are the
most numerous class of natural phenolic com-
pounds, characterized by structural diversity,
high chemical activity and low toxicity. They
have a wide range of biological activity, which
is associated with many structures that lead to
changes in the physicochemical properties of
systems based on them [10,11].
Synthesis and use of organic reagents with
fluorescent properties in physical-chemical
methods of analysis. In recent years, the deve
lopment of new organic fluorescent reagents,
which are further used in various fields of ana
lysis, is becoming more widespread. Thus, in
[12] an organic reagent was obtained through
the reaction of selenoic acid with three aro-
matic orthodiamines. Selenoic acid reacted
with 2,3-diaminonaphthalene in an acidic
solution to form 4,5-benzopiaselenol, which
has fluorescent properties. It was found that
this compound can then be extracted from the
acidic phase with organic solvents and used to
determine selenium with a detection limit of
0.002 μg. 2,3-diaminonaphthalene has been
found to be significantly more sensitive than
the previously recommended 3,3'-diamino
benzidine as a fluorescent reagent.
In [13], new bipyridyl receptors for rutheni-
um (II) imidazole were synthesized, which can
recognize anions of chloride, bromide, dihydro-
gen phosphate, and ATP in mixed polar aque-
ous-organic solutions by fluorescence. Inte
restingly, the combined amidimidazole receptor
Ruthenium (II) exhibits selectivity for the deter-
mination of anhydrous chloride in a solution of
acetonitrile – water with a ratio of 90:10. Also,
this receptor is selective for the determination of
ATP in the acetonitrile – water (50:50) solvent.
The aim of [14] was to develop a new fluores-
cent labeling reagent 9-anthryldiazomethane
(ADAM), for carboxylic acids. 9-anthraldehyde
hydrazone was first oxidized with N-chlorosuc-
cinimide in an organic solvent such as ethyl ace
tate to obtain 9-anthryldiazomethane and then
used directly as a reagent for the derivatization
of carboxylic acids. Both the oxidation reaction
and the derivatization reaction were performed
at room temperature, and an aliquot of the de-
rivative mixture was introduced directly into the
chromatograph. Derivatives of 9-anthrylmethyl
esters formed from ADAM and various carbo
xylic acids were separated on a reversed-phase
column by fluorometric detection. This me
thod can be used for the high performance li
quid chromatographic determination of long
and short chains of fatty acids, keto acids and
hydroxy acids.
Also, in [15] the use of fluorescent reagents
such as 4-bromomethyl-7-acetoxycomarin
(Br-Mac) in high performance liquid chro-
matography is described. It was found that
Br-Mac reacts with carboxylic acids to form
esters, which are then separated by liquid
phase chromatography. Next, the column elu-
ate was mixed with an alkaline solution, where
the labeled carboxylic acids were hydrolyzed
to fluorescent coumarin derivatives, which
were then passed through a fluorimeter. Thus,
a fluorescent hydrolyzate equimolar to a car-
boxylic acid was determined, the fluorophore
METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES
IN FLUORESCENT ANALYSIS METHODS
76 ISSN 2708-129X. Укр. хім. журн., 2021
PHYSICAL CHEMISTRY
of which is common to each carboxylic acid.
There are only slight peak differences for dif-
ferent carboxylic acids. It is established that
this method can detect low levels of femto-
mol in carboxylic acids. 6-oxy-(N-succinimyl
acetate)-9-(2'-methoxycarbonyl) fluorescein
(SAMF) is a new fluorescein-based fluorescent
probe that was developed in [16] as a deriva
tizing reagent for the determination of aliphat-
ic amines. Stable fluorescence intensity was
observed at pH 4–9. Derivatization took place
at room temperature for 6 minutes. Separation
was performed on a C18 column, where SAMF
derivatives with eight aliphatic amines were
separated after 28 min with a mobile metha-
nol-water phase (57:43) containing 10 mmol/l
H3Cit3-NaOH buffer (pH 5.0). In fluorescent
detection at λex/λem = 484/516 nm, the detec-
tion limit reached 2–320 fmol (signal-to-noise
ratio = 3), which is better than the detection
limits obtained in other analytical methods
for the determination of aliphatic amines (Ta-
ble 1). The proposed method has been success-
fully used to determine aliphatic amines in en-
vironmental samples and food products such
as lake water, red wine, white wine and cheese.
In [17] morin was studied (Fig. 1) and its in-
teraction with organotin compounds (chemical
compounds with tin and carbon substitutes),
which is accompanied by green fluorescence.
Fig. 1 Structural formula of morin (3,5,7,2',4'-
pentahydroxyflavone).
The sensitivity of the reagent for the deter-
mination of dialkyltin compounds was espe-
cially noted. The excitation and luminescence
wavelengths were 415 nm and 495 nm for
alkyltin-morin complexes and approximately
405 nm and 520 nm for triphenyltin-morin
complexes, respectively. The maximum fluo-
rescence intensity was achieved with the ra-
tio of reagents: from 3 to 9 mol of morin per
1 mol of dialkyl and triphenyltin and from
6 to 12 mol of morin to 1 mol for trialkyltin.
The authors set the following limits for the de-
tection of organotin compounds: for dialkyl
tins 1·10-9 mol/l, for monoalkyltins 1·10-7 mol/l,
for trialkyltins 5·10-7 mol/l and 5·10-7 mol/l for
triphenyltins (Table 1).
The authors [18] investigated the formation
of fluorescent compounds of o-phthaldialde-
hyde with amino acids in an alkaline medium
in the presence of a reducing agent. The excita-
tion and emission wavelengths were 340 nm
and 455 nm, respectively. The technique allows
to perform fluometric analysis of amino acids
to the nanomolar range. It was found that the
sensitivity of the method using o-phthaldial-
dehyde is much higher than that of the method
of determination of amino acids by ninhydrin,
which was used previously (Table 1).
The phenomenon of fluorescence quench-
ing of rhodamine B due to its interaction with
hydroxyl radicals formed by the Fenton rea-
gent was studied in [19]. The inhibitory effect
of pentachlorophenol on this interaction has
been established. The obtained data allowed the
determination of pentachlorophenol with a de-
tection limit of 3.0 ng/ml and a linear range of
determination of 4.0–240 ng/ml. The method
was used to determine pentachlorophenol in
synthetic samples and natural water samples
with satisfactory results. A rapid method for
OH
OH
OH
O OH
OH
Fig. 1 Structural formula of morin (3,5,7,2',4'- pentahydroxyflavone).
The sensitivity of the reagent for the determination of dialkyltin compounds was
especially noted. The excitation and luminescence wavelengths were 415 nm and 495 nm for
alkyltin-morin complexes and approximately 405 nm and 520 nm for triphenyltin-morin
complexes, respectively. The maximum fluorescence intensity was achieved with the ratio of
reagents: from 3 to 9 mol of morin per 1 mol of dialkyl and triphenyltin and from 6 to 12 mol of
morin to 1 mol for trialkyltin. The authors set the following limits for the detection of organotin
compounds: for dialkyltins 1·10-9 mol/l, for monoalkyltins 1·10-7 mol/l, for trialkyltins 5·10-7
mol/l and 5·10-7 mol/l for triphenyltins (Table 1).
The authors [18] investigated the formation of fluorescent compounds of o-
phthaldialdehyde with amino acids in an alkaline medium in the presence of a reducing agent.
The excitation and emission wavelengths were 340 nm and 455 nm, respectively. The technique
allows to perform fluometric analysis of amino acids to the nanomolar range. It was found that
the sensitivity of the method using o-phthaldialdehyde is much higher than that of the method of
determination of amino acids by ninhydrin, which was used previously (Table 1).
The phenomenon of fluorescence quenching of rhodamine B due to its interaction with
hydroxyl radicals formed by the Fenton reagent was studied in [19]. The inhibitory effect of
pentachlorophenol on this interaction has been established. The obtained data allowed the
determination of pentachlorophenol with a detection limit of 3.0 ng/ml and a linear range of
determination of 4.0-240 ng/ml. The method was used to determine pentachlorophenol in
synthetic samples and natural water samples with satisfactory results. A rapid method for the
fluorescence determination of uranium using the interaction between a uranylbenzoic acid
complex and Rhodamine B was developed. It was found that the fluorescence intensity depends
on the concentration of benzoic acid, the concentration of rhodamine B, pH and the volume of the
aqueous phase, and that the increase in fluorescence intensity is proportional to the increase in the
concentration of uranium. The detection limit of uranium was 5·10-8 mol/l [20] (Table 1).
A new fluorescent reagent 2-amino-5,7-dimethyl-1,8-naphthyridine was synthesized [21],
which was further used to determine trace amounts of nitrites. The authors found that the
fluorescence quenching of the reagent by nitrite ion has a linear relationship in the range of nitrite
concentrations from 1·10−7 to 2.5·10−6 mol/l with a detection limit of 4.06·10−8 mol/l (Table. 1).
Asieieva D.A.
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UCJ № 10 / Vol. 87
the fluorescence determination of uranium
using the interaction between a uranylben-
zoic acid complex and Rhodamine B was de-
veloped. It was found that the fluorescence
intensity depends on the concentration of
benzoic acid, the concentration of rhodamine
B, pH and the volume of the aqueous phase,
and that the increase in fluorescence intensi-
ty is proportional to the increase in the con-
centration of uranium. The detection limit
of uranium was 5·10-8 mol/l [20] (Table 1).
A new fluorescent reagent 2-amino-5,7-
dimethyl-1,8-naphthyridine was synthesized
[21], which was further used to determine
trace amounts of nitrites. The authors found
that the fluorescence quenching of the reagent
by nitrite ion has a linear relationship in the
range of nitrite concentrations from 1·10−7 to
2.5·10−6 mol/l with a detection limit of 4.06·10−8
mol/l (Table. 1).
Fig. 2. Enhancement of fluorescent properties in a Co-salen complex
in the presence of cyanide ions [22].
A sensor based on a Co (II) complex [22]
was developed to determine cyanide ani-
ons, which are able to form a 1:2 complex in
comparison with other anions. The complex
was synthesized by adding 2,2-dihydroxy-
phenyl ethylenediamine to two equivalents of
7-di-ethylaminocoumarin-3-carboxaldehyde.
The resulting compound was then mixed with
cobalt (II) acetate in the presence of triethyl-
amine (TEA) followed by recrystallization of
the complex in methanol and dichlorometh-
ane. With increasing cyanide concentration,
the authors observed an increase in the fluo-
rescence intensity of the complex due to the
cessation of the process of photoinduced elec-
tron transfer from coumarin fluorophore to
cobalt (II) ion (Fig. 2).
Analysis of literature shows that increas-
ing the fluorescent properties of complexes in
the presence of anions is possible by stopping
the process of photoinduced electron transfer
from the organic fluorophore to metal ion, and
that determination of organotin compounds is
possible using complexes with morin. Other
complexing agents are ineffective.
METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES
IN FLUORESCENT ANALYSIS METHODS
78 ISSN 2708-129X. Укр. хім. журн., 2021
PHYSICAL CHEMISTRY
Table 1
Detection limits and linear ranges of fluometric methods using organic reagents.
Organic reagent Analytes Determination
limit
Linear range of con-
centration change Reference
2,3-diaminonaphtalene Selenium 0,002 мкг – [12]
(3,5,7,2',4'- pentahydroxyflavone)
Morin
Organotin
compounds
1·10-7 - 1·10-9
mol/l – [16]
6-oxy-(N- succinimilacetate)-9-(2'-
methoxycarbonyl) fluorescein
Aliphatic
amines 2–320 fmol – [17]
[9-(2- carboxyphenyl)-6-diethyl
amino-3- xanthenyliden]-diethyl
ammonium cloride) Rhodamine B
Pentachloro
phenol 3,0 ng/ml 4,0-240 ng/ml [19]
Rhodamine B Uranium 5·10-8 mol/l – [20]
2-amino-5,7-dimethyl-1,8-
naphthyridine Nitrites 4,06·10−8 mol/l 1·10−7 - 5·10−6 mol/l [21]
Approaches to detecting the content of me
tals and proteins using the fluorescent properties
of morin complex compounds. Flavonoids are
most often used in modern methods of analysis
to determine metals. Morin, which belongs to
this class of compounds (Fig. 1), can form stable
complexes with metal cations, which in some
cases have fluorescent properties in the presence
of protein structures in solutions. Also, these
complexes are quite stable when interacting
with protein molecules in a wide pH range (ta-
ble 2). In [23], the interaction of a Bi (III)-morin
complex with DNA using methyl blue dye was
studied using fluorescence, spectrophotometry
and voltammetry. A Bi (III)-morin (2:1) com-
plex was used in the work, the composition of
which was calculated from the results of UV-
Vis spectroscopy. It was found experimentally
that the fluorescence signal of the Bi (III)-morin
complex increases with the addition of DNA,
while the fluorescence signal of pure morin de-
creases accordingly. Addition of methyl blue to
the Bi (III)–morin–DNA complex reduces the
emission signal and causes a hypochromic shift
of 2 nm, which confirms the intercalation of the
complex into the DNA molecule. The stability
constant of the Bi (III)–morine complex with
DNA, which is 2,8⋅104, was found in the work.
Table 2
Stability constants of metal complexes with morin [24].
Metal ion Stability constant, logβ рН
Cu (II) 4,94 5,8
Zn (II) 6,74 5,5
WO4
2- 11,6 3,0
Pd(II) 4,55 4,0
Ti(C2O4)2
2- 7,35 8,0
Ba (II) 4,55 4,2
Asieieva D.A.
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UCJ № 10 / Vol. 87
During extraction into isopropyl alcohol
from acid solutions at different pH values, the
duration of fluorescence of morin complexes
was established [25]. Complexes of Al (III), Ga
(III) and In (III) change their composition in
accordance with the change in the acidity of
the medium and form complexes with molar
ratios of 1:1 or 1:2 (metal:morin). The lifetime
of fluorescence or the average lifetime of the
molecule in the excited state also changed ac-
cording to the change in the composition of
the complex. Such properties have made it
possible to develop optical sensors for detect-
ing ions of these metals. The sensor was based
on the formation of a complex between specific
metal ions and the complexing ligand. Several
chelate systems and several mechanisms of
their immobilization are proposed. Morin and
its complexes with AI3+, Ga3+ and In3+ at a con-
centration of 5 μmol are markedly fluorescent
when exposed to normal indoor lighting. Mo
rin complexes with AI3+, Ga3+ and In3+ were ex-
cited at a wavelength of 457.9 nm, the emission
wavelength was 525 nm. These spectra overlap
strongly, and therefore morin complexes are
difficult or impossible to distinguish by con-
ventional fluometric methods. Immobilization
did not lead to significant changes in the dura-
tion of luminescence of metal-morin complex-
es. Thus, the sensor based on morin and the
formation of its complexes with AI3+, Ga3+ and
In3+ was not suitable for multi-element deter-
minations using spectrofluorometry [26].
The aim of [27] was to determine Aluminum
using three different methods based on an Al
(III)-morin complex. The methods of spectro-
photometry, spectrofluorometry and differen
tial pulse adsorption stripping voltammetry
were compared under optimized experimental
conditions. Fluorescence spectra were mea
sured in acetoacetate at pH = 5, the concen-
tration of morin was 10 μmol. The maximum
excitation wavelength was set to λex = 350 nm,
and the emmition spectra were recorded in the
range from 400 to 650 nm. The maximum fluo-
rescence intensity was reached at λem = 505 nm.
The authors found that the emission intensity
is influenced by many factors, including the
acidity of the solutions and the concentration
of morin. A calibration graph for the determi-
nation of Al (III) from 0.1 to 1.0 μmol was also
obtained. The method showed good reprodu
cibility and a detection limit of 110 nmol.
In [28], complexes of Al (III) with morin
and quercetin were studied by fluorescence.
The stoichiometry of the complexes was eva
luated by the Job method, the number of flu-
orescent forms in the solution was calculated
by the TRES method. It was found that Al (III)
with morin is able to form two complexes with
stoichiometries of morin:Al (III) either 1:1 or
2:1 with lifetimes of 4.3 and 2.0 ns, respective-
ly. Morin, which was immobilized on cellulose
powder and attached to the end of bifurcated
optical fiber, was used to determine Al3+ based
on their fluorescent complex [29]. When im-
mobilized morin was placed in a solution con-
taining Al3+, the authors observed the fluores-
cence of the Al (III)-morin complex. A linear
dependence of the fluorescence intensity on
the wavelength in the range of Al (III) con-
centrations from 1·10-6 to 1·10-4 mol/l with
the detection limit of 1·10-6 mol/l was estab-
lished. The study of the effect of pH on the flu-
orescence of the complex showed that at a low
acidity of solutions, the stability constant of the
complex decreases due to the destruction of
the complex due to Al3+ protonation, and that
at high pH, most of aluminum is in the form
of hydroxides. Based on this, the most optimal
METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES
IN FLUORESCENT ANALYSIS METHODS
80 ISSN 2708-129X. Укр. хім. журн., 2021
PHYSICAL CHEMISTRY
pH value of 4.8 was established, at which all
measurements were performed. The stability
constant of the Al (III)–immobilized morin
complex of 1.7⋅104 was determined.
The fluorescent activity of the Lanthanum
(III)–quercetin–nucleic acid ternary complex
was established in [30]. The authors chose na
tural calf thymus DNA and thermally denatured
yeast DNA and RNA as nucleic acids. The fluo
rescence intensity of the complexes increased
with the formation of ternary complexes in the
pH range of 7.8-8.3, NH3 - NH4Cl was used as a
buffer mixture. The maximum fluorescence in-
tensity of the ternary complexes was observed
at an emission wavelength of 470 nm and at
an excitation wavelength of 280 nm. Based
on these observations, a technique for the de-
termination of nucleic acids was developed.
The concentrations of La (III) (2.2·10-5 mol/l)
and quercetin (5.0·10-5 mol/l) were selected to
establish the optimal conditions. The authors
obtained calibration graphs with linear rang-
es of 0.5-3.0 μg/ml for calf thymus DNA and
0.5-4.0 μg/ml for yeast DNA and RNA. The
limits of detection were calculated by the 3σ
test and were 0.072 μg/ml, 0.142 μg/ml and
0.307 μg/ml for calf thymus DNA, yeast DNA
and RNA, respectively.
It is also possible to determine the content
of nitric oxide in aqueous and methanolic
solutions based on fluorescence using a copper
complex with tridentate N-donor ligand, in
which with increasing amount of nitric oxide
there is an increase in the fluorescence intensi-
ty of copper with fluorescent ligand in degassed
methanol and aqueous solution (pH=7.2) [31].
Thus, this complex can function as a sensor of
nitric oxide based on fluorescence. It is note-
worthy that it is possible to determine nano-
molar amounts of nitric oxide.
The effect of room temperature ionic li
quid on the formation of the fluorescent ter-
nary oxalate-sodium morine-5-Aluminum
sulfonate complex was studied [32]. In the
presence of 1-butyl-3-methylimidazole hexa
fluorophosphate (BMIM-PF6) the formation
of a complex with better fluorescent charac-
teristics is achieved and as a result a sensitive
method for the determination of oxalate ions
has been developed. The maximum excitation
wavelength was set λex = 420 nm, and emission
λem = 513 nm. The detection limit of oxalate is
0.57 ng/ml. The method showed satisfactory
results in determining the content of oxalate in
plant tissue (spinach leaves).
Using the effects of amplification and quench-
ing of fluorescence to determine organic com-
pounds and metal ions. In [33], the enhance-
ment of fluorescence of a Eu3+ tetracycline com-
plex due to DNA or RNA was studied. It was
found that double-stranded and single-strand-
ed DNA can strongly enhance the fluorescence
of the Eu3+ tetracycline complex, in contrast
to RNA, which showed a very small amplifi-
cation effect, based on which a method of se-
lective determination of DNA in the presence
of RNA was developed. The most optimal pH
conditions, when the maximum fluorescence
intensity was reached at an acidity of solutions
of 8.0–9.7. The excitation wavelength at which
the complex was excited was 398 nm, and the
fluorescence wavelength was 615 nm. Calibra-
tion graphs with linearity ranging from 0.02 to
1.0 μg for single-stranded and double-stranded
DNA were obtained. The relative standard de-
viation (at n = 7) was in the range of 3.0%.
In [34], a new spectrofluometric method for
the determination of lysozyme in the forma-
tion of its triple complex with Eu3+-metacyc
line was developed. Due to the intramolecular
Asieieva D.A.
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UCJ № 10 / Vol. 87
energy transfer from the ligands to the central
Eu3+ atom, the fluorescence intensity increases
threefold at an emission wavelength of 612 nm.
The excitation wavelength is 285 nm. Opti-
mal conditions were also established: pH 9.6,
metacycline concentration 2.0·10-5 mol/l and
Eu3+ concentration 2.4·10-5 mol/l The increase
in fluorescence intensity is proportional to
the lyozyme concentration, the linear range is
from 0 to 3.5·10-5 mol/l with a detection limit
of 4.74·10-7 mol/l. The mechanism by which
an increase in fluorescence between the Eu3+
metacycline complex and lysozyme occurred
was also investigated. The developed method
is simple, sensitive and has been successfully
used to determine lysozyme in urine.
In [35], another approach was used to de-
termine cysteine and glutathione with quench-
ing of the fluorescence of the complex. It was
found that the addition of thiol compounds
to the fluorescent system Zn (II)-8-hydroxy
quinoline-5-sulfonic acid Zn (II)-HQS in a
buffer mixture of H3BO3-Na2B4O7 (pH 8.50)
leads to quenching of the fluorescence of the
complex. Based on these studies, a linear de-
pendency was obtained between the amount of
cysteine or glutathione and the corresponding
decrease in the relative fluorescence intensi-
ty of the Zn (II)-HQS system. The complexes
were excited at a wavelength of 365 nm, and
the emission wavelength was 512 nm. For op-
timal conditions, HQS and Zn (II) concentra-
tions of 4.44·10-6 mol/l and 4.59·10-6 mol/l were
taken. In the analysis of cysteine in the protein
hydrolyzate and reduced glutathione in blood
serum, the detection limits were 17 ng/ml and
0.6 μg/ml, respectively. The removal degree
was 95.6-104.5%.
The effect of protein on the fluorescence of
zinc complexes with morin and fluorescein was
studied [36]. The introduction of protein into
the Zn-morin complex causes the quenching
of fluorescence, which is proportional to the
amount of protein. Under optimal conditions,
the limits of detection for the determination of
bovine serum albumin and human serum al-
bumin are 0.22 g/ml and 0.18 g/ml, respecti
vely.
Based on the fluorescence of DNA-plati-
num complexes, new methods for the deter-
mination of platinum have been developed
[37]. The authors found that cis- or trans-bi-
dentate complexes are formed between DNA
and platinum. DNA with ethidium bromide
forms fluorescent complexes, and the addition
of platinum inhibits the intercalation of ethi
dium bromide, and as a result there is a line-
ar decrease in fluorescence intensity. The me
thod was tested in different ionic media and in
a wide range of ionic strength. The detection
limit of platinum is 5·10-8 g/ml.
The aim of the study [38] was to develop
a sensor for mercury ions based on the fluo-
rescence of iodide anion with the complex
T-HgII-T (T = thymine). The authors synthe-
sized a fluorescent anthracene-thymine (An-T)
dyad, which forms with the Mercury ion an
An-T-HgII-T-An complex, and it was found
that the addition of mercury reduces the fluo-
rescence intensity. In this case, the dyad A-T is
a sensor for mercury (II) ions in aqueous me-
dia based on fluorescence quenching. However,
with the addition of iodide, the fluorescence of
the An-T-HgII-T-An complex is restored due
to the binding of mercury to the iodide ion.
The detection limit for iodine is 126 nmol.
The sensor has shown high selectivity over
other common anions and can be used to de-
tect iodide in drinking water and biological
fluids such as urine.
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PHYSICAL CHEMISTRY
Influence of surfactants on the fluorescence
intensity of complexes with morin. The use of
micellar systems in spectrophotometric me
thods of analysis is the most popular and old-
est field of application of surfactants in analyti-
cal chemistry. In recent years, surfactants have
been successfully used in fluorometric deter-
minations. In many cases, there is a multiple
increase in fluorescence intensity, which leads
to increased interest in these systems due to
high sensitivity and selectivity.
In [39] the effect of cationic surfactants on
the fluorescence of the zirconium (IV)-morine
system is described. It was found that in a sul-
furic acid medium the fluorescence intensity of
this complex can be greatly enhanced by the
cationic surfactant cetyltrimethylammonium
bromide (CTAB). However, the addition of a
nonionic surfactant TritonX-100 only slightly
enhanced fluorescence, and the introduction
of anionic surfactants such as sodium lauryl
sulfate (SLS) and sodium dodecyl sulfonate
(SDS) did not increase the fluorescence inten-
sity. It was found that the determinant factor is
the change of the composition of the analyzed
complex in the presence of CTAB. When the
concentration of CTAB reaches the critical
concentration of micelle formation, a complex
is formed with the ratio Zr (IV):morin = 1:3.
As the concentration of CTAB increases, a
mixed complex with the composition Zr (IV):
morin:SO4
2- = 1:1:2 is formed, and the fluores-
cence intensity sharply increases. It was found
that the formation of mixed-ligand complexes
of zirconium with several anions in the pres-
ence of cationic surfactants increase the fluo-
rescence intensity of the system.
The effect of different surfactants on the sys-
tems Hf-quercetin, Zr-quercetin, Sn-morin,
Mg-oxine-5-sulfonic acid (HIQS), Zn-HzQS,
Cd-HZQS and Tb-EDTA-sulfosalicylic acid
(SSA) was studied in [40]. Increase in fluores-
cence occurs due to the formation of complex-
es such as ionic associates with a rigid struc-
ture, which leads to a significant increase in
fluorescence intensity. Not only traditional no-
nionic and cationic surfactants were used, but
also zwitterionic and anionic one. It is estab-
lished that the fluorescence intensity of each
investigated complex strongly increases in the
presence of the corresponding surfactant. The
authors also determined the optimal condi-
tions for the formation of ternary complex-
es, their structure and quantum yield. It was
found that the fluorescence intensity of the
complexes changes little when surfactants are
added at concentrations lower than the critical
micelle concentration (CMC). With a further
increase in the surfactant content, the fluo-
rescence intensity begins to increase sharply.
Thus, the addition of anionic sodium dodecyl
sulfonate (SDS) to the Sn-morin complex in-
creases the fluorescent properties of the system
by a factor of 4, and a ternary complex with
Sn:morin:SDS = 1:2:2. stoichiometry is formed.
In [41], a simple and sensitive spectrofluori-
metric method for the determination of Al (III)
based on the formation of the ternary complex
Al (III) - morin - Triton X-100 is described. The
effects of other nonionic surfactants, such as
Tween 80, Tween 20 and octyl glucoside (OG),
have also been studied. The addition of Triton
X-100 increases the sensitivity fivefold in the
fluorometric determination of Al (III) using
morin. The complex was excited at a wave-
length of 410 nm, and the fluorescence signal
was measured at a wavelength of 495 nm. The
maximum fluorescence signal was observed at
pH 4.0 (acetate buffer), with 0.6% TX-100 and
at a morin concentration of 1.35·10-3 mol/l. The
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UCJ № 10 / Vol. 87
authors also obtained a calibration graph that
is linear up to 7 mg/l, and the detection limit is
0.022 mg/l. The use of Triton X-100 eliminates
the need to use additional extraction steps for
the sensitive and selective determination of
Al (III).
The effect of the anionic surfactant sodi-
um dodecylbenzenesulfonate (SDBS) on the
fluorescence intensity of the Al (III) – morin
complex and the mechanism of their inter-
action were studied in [42]. It was found that
the luminescence increases and, on this basis,
a fluometric method for the determination of
proteins was developed. The highest fluores-
cence intensity was achieved at pH 6.84, and
it was also shown that the fluorescence inten-
sity is influenced by the type of buffer mixture,
among which the most effective was HMTA –
HCl. The maximum fluorescence intensity was
reached at concentrations of morin and Al (III)
of 1.0·10−6 mol/l and 1.0·10−5 mol/l, respective-
ly. Regarding the anionic surfactant SDBS, its
concentration was 2.0·10–4 mol/l, which is lower
than the critical micelle concentration, which is
3.3·10–4 mol/l for SDBS. Under optimal condi-
tions, the increased fluorescence intensity was
proportional to the protein concentration in
the range of 1.0·10−8–1.3·10−5 g/ml for bovine
serum albumin (BSA), 4.0·10–8–1,2·10–5 g/ml
for egg albumin (EA) and 5.0·10–8–1.2·10–5 g/ml
for human serum albumin (HSA). The limits
of their detection were 5.0·10−9, 1.8·10−8 and
1.6·10−8 g/ml, respectively. Thus, the authors
obtained a highly sensitive, stable and rapid
method for the determination of proteins.
An increased fluorescence intensity of the
aluminum (III)-morin complex was observed
in [43] in the presence of the nonionic sur-
factant Tween-20. The fluorescence of the
complex was measured at an excitation wave-
length of 425 nm and an emission wavelength
of 495 nm. The authors also established opti-
mal conditions: pH = 4.5, the concentration of
morin 20 mmol, and 0.8% Tween-20. A linear
calibration graph from 50 to 100 μg/l was also
obtained, and the detection limit was 3 μg/l.
In [44], a highly sensitive method of fluo-
rometric determination of Fe (III) by reaction
with 5-(4-methoxyphenylazo)-8-(4-toluene
sulfonamido) quinoline in the presence of the
cationic surfactant cetyltrimethylammoni-
um bromide (CTAB) is described. As a result,
a linear fluorescence intensity (λex = 317 nm,
λem = 534 nm) of up to 3 mmol (170 ng/ml) of
Iron (III) in an aqueous solution was observed.
A similar experiment was also performed in the
presence of the anionic surfactant sodium do-
decyl sulfate. The introduction of anionic sur-
factants led to a decrease in fluorescence intensi-
ty. In contrast to this, the introduction of the no-
nionic surfactants Tween-80 and TritonX-100
into the studied system as well as cationic sur-
factants (CTAB) increased the fluorescence
intensity but gave larger background signals.
The most optimal concentration of CTAB was
determined, which was 1.7·10-3 mol/l, which is
higher than the critical concentration of micelle
formation (CMC (CTAB) = 1.3·10-3 mol/l). This
method can also be used to determine the trace
amounts of Fe (III) and Fe (II) without the need
for prior concentration.
In [45], the authors determined how the
addition of nonionic surfactants affects the
fluorescence intensity of Al (III)-morin com-
plexes in order to improve the analytical cha
racteristics of the complex. Morin is one of
the reagents most often used for the qualita-
tive and quantitative determination of Al (III).
The authors found that the addition of cationic
surfactants such as cetyltrimethylammonium
METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES
IN FLUORESCENT ANALYSIS METHODS
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PHYSICAL CHEMISTRY
bromide (CTAB) and nonionic surfactants
such as: polyoxyethylene noniphenols, poly-
oxyethylene higher alcohols, fatty carboxylic
acid esters and alkanolamides do not increase
the fluorescence intensity, but on the contrary,
cause its significant decrease contrary to the
expectations of the authors. Only in some cases
there were an initial increase in luminescence
intensity at high surfactant concentrations and
subsequent quenching with increasing content
of nonionic surfactant in the system. In con-
trast, the authors found that the addition of
GenapolPF-20 (ethylene oxide – condensate
of epoxypropane) to the metal-morin complex
causes an increase in fluorescence intensity,
so the sensitivity of the determination can be
increased tenfold, as well as the selectivity of
the method compared to other methods. The
optimal conditions for increasing the fluores-
cence intensity were: the concentration of no-
nionic surfactant 3%, morin 0.005%, pH 3.8
in an acetate buffer at a temperature of 25 °C.
The excitation and emission wavelength maxi
ma were λex = 430 nm and λem = 495 nm, re-
spectively. The maximum fluorescence intensi-
ty was observed after 1.5 hours and remained
stable for another 5 hours, the detection limit
was 0.2 µg/l. The introduction of surfactants
did not lead to either bathochromic or hypso
chromic shift, which indicates a slight effect of
surfactants on the ground and excited states of
the complex. It was also shown that other de-
rivatives of polyoxyethyl compounds resulted
in increased sensitivity in the same order, but
with a different surfactant concentration.
In [46], the fluorometric determination of
samarium and gadolinium by increasing the
fluorescence of the samarium-tenoyltrifluoro
acetone-gadolinium 1,10-phenanthrolinate
complex (Sm (III) – TTA – Phen – Gd (III))
was investigated, which increases the fluores-
cence intensity almost twofold. To increase
the stability of the Sm (III) – TTA – Phen –
Gd (III) system, surfactants were added, and
their effects were investigated. Thus, the cationic
surfactant CTAB and nonionic surfactant
Tween-80 caused a decrease in fluorescence
intensity. In contrast, the nonionic surfactants
TX-100 and PVA caused a sharp increase in
the fluorescence intensity of the complex.
Therefore, TX-100 was used for further ex-
periments. An increase in the fluorescence in-
tensity at the concentration of TX-100 at the
level of the critical micelle concentration was
shown. The most optimal concentration range
of TX-100 was 0.018–0.064% (fivefold increase
in emissions). A further increase in the con-
centration of TX-100 led to a decrease in emis-
sion intensity. It is noteworthy that the excess
of TX-100 caused a bathochromic shift of the
maximum excitation wavelength. The maxi-
mum fluorescence intensity was obtained in
a pH range of 5.3–6.0 at a wavelength of ex-
citation and emission of 349 nm and 648 nm,
respectively. Thus, the system Sm (III) – TTA –
Phen – Gd (III) – TritonX-100 can be used to
determine trace amounts of samarium in lan-
thanide oxides.
The aim of [47] was to determine tetra-
cyclines (TC) in aqueous solutions based on
the formation of fluorescent chelates with
europium using EDTA as a coligand and cet-
yltrimethylammonium chloride (CTAC) as
a surfactant. The method involves the for-
mation of a chelate, where the lanthanide ion
will be associated with the β-diketone group.
Contrary to the authors' expectations, the
addition of the nonionic surfactant TX-100
almost does not change the luminescence in-
tensity in the pH range 5-9, and the addition
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of EDTA has a negative effect and sharply re-
duces the fluorescence intensity. At the same
time, with the addition of CTAC, the emission
intensity increased and reached a maximum
at pH 9. The Eu – TC – CTAC system has a
sensitivity that is 6 times higher than that of
the Eu – TC – TX-100 system, and the detec-
tion limits were 2,5·10-10, 5·10-10, 1,5·10-9 and
2·10-9 mol/l for TC, oxytetracycline, chlortetra-
cycline and doxycycline, respectively.
In [48], the authors found how the mole
cular structure of the anionic surfactant af-
fects the fluorescence of bovine serum albu-
min (BSA). Sodium alkyl sulfates (CnSO3,
n = 8, 10, and 12) and sodium alkyl carbox-
ylates (CnCOONa, n = 9 and 11) were used
as anionic surfactants. It was established that
with the increase of the hydrophobic chain the
ability to quench the fluorescence of BSA in-
creases, and the hypsochromic shift increases.
It is noteworthy that the replacement of acidic
groups of anionic surfactants does not show a
significant effect on the fluorescence of the al-
bumin complex.
The authors of [49] studied the effect of
surfactants on the fluorescence of the beryl-
lium-morin system. It was found that the
addition of the nonionic surfactant TX-100
significantly increases the fluorescence inten-
sity of the complex, as opposed to the anionic
surfactant sodium lauryl sulfate (SLS), zwitte-
rionic surfactant dodecyldimethylaminoacetic
acid (DDMAA), and cationic surfactant cetyl-
trimethylammonium bromide (CTAB), which
cause only a slight increase of fluorescence.
It was also found that when adding all sur-
factants, except for anionic SLS, a bathochro-
mic shift occurs (up to 25 nm). The addition
of Triton X-100 makes it possible to determine
the nanoquantities of beryllium in weakly
acidic solutions (pH 5.8–6.2, hexamine buffer
solution), detection limit 0.06 ng/ml. The rel-
ative standard deviation is 2.2% for beryllium
at a concentration of 0.5 ng/ml and 0.7% for
5.0 ng/ml. The method is used to determine
beryllium in water quality control samples and
therefore the effect of 25 ions that can affect the
fluorescence of the Be-morin-TX-100 com-
plex, among which Zn2+ and F− interfere the
most, was also studied.
In [50], a method of determination of Al (III)
in a luminescent complex with lumogallion is
presented. The addition of the nonionic sur-
factant Triton X-100 increased the fluores-
cence intensity of the Al (III)-morin complex
by a factor of 5–6. Optimal conditions were
also determined: pH 4.7, the concentrations of
lumogallion and TX-100 were 1 µg/l and 0.5%,
respectively. The detection limit of Al (III) is
0.2 μg/l. The sensitivity of the method does not
depend on the salt concentration in water and
can be used to determine aluminum in water.
Therefore, to date, the study of the effect of
surfactants on the fluorescent properties of or-
ganic reagents and their complexes continues,
because the increase or decrease in fluorescent
properties is not systematic and is not always
explainable.
CONCLUSIONS. To date, the complexes
of morin with metals are actively studied and
tend to be widely used in such physicoche
mical methods of analysis as: high perfor-
mance liquid chromatography, spectropho-
tometry and fluorometry. It has been proved
that in complex compounds of cobalt and
salen, the increase of the fluorescent properties
of complexes in the presence of anions is pos-
sible by stopping the process of photoinduced
electron transfer from organic fluorophore to
metal ion, and the determination of organotin
METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES
IN FLUORESCENT ANALYSIS METHODS
86 ISSN 2708-129X. Укр. хім. журн., 2021
PHYSICAL CHEMISTRY
compounds is possible using complexes with
morin. Other complexing agents are less ef-
fective and ineffective. The most studied is the
complex Al (III) - morin in comparison with
complexes of morin with other metals, such as
In (III), Bi (III) and Ga (III). These complexes
can be used to determine metals or to detect
DNA of different biological origin or for the
quantitative analysis of protein. All complexes
with morin are stable in a wide pH range (3-8)
and have a high fluorescence intensity. The
fluorescence intensity can be increased by add-
ing surfactants. For protein systems of morin
with some metals (zinc and mercury), an op-
posite phenomenon is observed – fluorescence
quenching, which can be used for the quantita-
tive determination of proteins and metals.
ACKNOWLEDGMENT.
The work was done under financial
support of Ministry of Education and
Science of Ukraine.
МЕТОДИ СИНТЕЗУ ТА ОСОБЛИВОСТІ ВИКО-
РИСТАННЯ СИСТЕМ НА ОСНОВІ МЕТАЛО-
КОМПЛЕКСІВ МОРІН У МЕТОДАХ ФЛУОРЕС-
ЦЕНТНОГО АНАЛІЗУ
Асєєва Д. А.1,2
1Університет Тулуза ІІІ - Поль Сабатьє, 118
траса Нарбон, Тулуза Сedex, 9, 31062, Фран-
ція
2Київський національний університет імені
Тараса Шевченка, вул. Володимирська, 60,
м. Київ 01033, Україна
email: dasha.aseeva@gmail.com
В огляді описано сучасні фізико-хіміч-
ні системи на основі комплексних сполук
з органічними лігандами, які можуть мати
флуоресцентні властивості при взаємодії
з іонами металів або білками. Наведено
сучасні методи синтезу цих сполук та ви-
користання їх у фізико-хімічних методах
аналізу. Розглянуто підходи до визначення
вмісту металів і білків за флуоресцентними
властивостями комплексних сполук мори-
ну. Описано сфери використання ефектів
ампліфікації та гасіння флуоресценції для
визначення органічних сполук та іонів ме-
талів, особливо за наявності ДНК та РНК
різного біологічного походження. Окремо
проаналізовано вплив поверхнево-актив-
них речовин на інтенсивність флуоресцен-
ції комплексів із морином.
Ключові слова: морін, комплексні спо-
луки, флуоресценція, аналіз, іони металів,
білок.
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Стаття надійшла 09.11.2021.
|
| id | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-370 |
| institution | Ukrainian Chemistry Journal |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-23T01:07:07Z |
| publishDate | 2021 |
| publisher | V.I.Vernadsky Institute of General and Inorganic Chemistry |
| record_format | ojs |
| resource_txt_mv | ucjorgua/3f/aa61fd14333ece3eeceb9bd768051b3f.pdf |
| spelling | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-3702026-07-22T08:23:47Z METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS Asieieva, Dasha morin, complex compounds, fluorescence, analysis, metal ions, protein. The review describes modern physicochemical systems based on complex compounds with organic ligands, which may have fluorescent properties when interacting with metal ions or proteins. Modern methods of synthesis of these compounds and their use in physical-chemical methods of analysis are given. Approaches to detecting the content of metals and proteins using the fluorescent properties of morin complex compounds are considered. Areas of use of the effects of amplification and quenching of fluorescence for the determination of organic compounds and metal ions, especially in the presence of DNA and RNA of different biological origin are described. The influence of surfactants on the fluorescence intensity of complexes with morin was analyzed separately. V.I.Vernadsky Institute of General and Inorganic Chemistry 2021-11-26 Article Article Physical chemistry Физическая xимия Фізична xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/370 10.33609/2708-129X.87.10.2021.74-89 Ukrainian Chemistry Journal; Vol. 87 No. 10 (2021): Ukrainian Chemistry Journal; 74-89 Украинский химический журнал; ##issue.vol## 87 ##issue.no## 10 (2021): Ukrainian Chemistry Journal; 74-89 Український хімічний журнал; Том 87 № 10 (2021): Український хімічний журнал; 74-89 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/370/191 Copyright (c) 2021 Dasha Asieieva https://creativecommons.org/licenses/by-nc/4.0 |
| spellingShingle | Asieieva, Dasha METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS |
| title | METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS |
| title_full | METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS |
| title_fullStr | METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS |
| title_full_unstemmed | METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS |
| title_short | METHODS OF SYNTHESIS AND FEATURES OF USING SYSTEMS BASED ON MORIN-METAL COMPLEXES IN FLUORESCENT ANALYSIS METHODS |
| title_sort | methods of synthesis and features of using systems based on morin-metal complexes in fluorescent analysis methods |
| topic_facet | morin complex compounds fluorescence analysis metal ions protein. |
| url | https://ucj.org.ua/index.php/journal/article/view/370 |
| work_keys_str_mv | AT asieievadasha methodsofsynthesisandfeaturesofusingsystemsbasedonmorinmetalcomplexesinfluorescentanalysismethods |