Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange
A series of asymmetric cyanine dyes based on methylenoxy benzothiazole terminal hetero-cycle was synthesized. Absorption and fluorescent properties of these dyes and their complexes with nucleic acids were investigated. The best results were obtained with 2-[(3-methyl-2(3H)-benzothiazolyliden)-methy...
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Інститут молекулярної біології і генетики НАН України
1996
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| Cite this: | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange / S.M. Yarmoluk, V.B. Kovalska, T.V. Smirnova, M.P. Shandura, Y.P. Kovtun, G.K. Matsuka // Биополимеры и клетка. — 1996. — Т. 12, № 6. — С. 74-81. — Бібліогр.: 16 назв. — англ. |
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Digital Library of Periodicals of National Academy of Sciences of Ukraine| _version_ | 1859950439509786624 |
|---|---|
| author | Yarmoluk, S.M. Kovalska, V.B. Smirnova, T.V. Shandura, M.P. Kovtun, Y.P. Matsuka, G.K. |
| author_facet | Yarmoluk, S.M. Kovalska, V.B. Smirnova, T.V. Shandura, M.P. Kovtun, Y.P. Matsuka, G.K. |
| citation_txt | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange / S.M. Yarmoluk, V.B. Kovalska, T.V. Smirnova, M.P. Shandura, Y.P. Kovtun, G.K. Matsuka // Биополимеры и клетка. — 1996. — Т. 12, № 6. — С. 74-81. — Бібліогр.: 16 назв. — англ. |
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| container_title | Биополимеры и клетка |
| description | A series of asymmetric cyanine dyes based on methylenoxy benzothiazole terminal hetero-cycle was synthesized. Absorption and fluorescent properties of these dyes and their complexes with nucleic acids were investigated. The best results were obtained with 2-[(3-methyl-2(3H)-benzothiazolyliden)-methyl]-5,6-dioxymethylene-3-methylbenzothiaz olium p-toluenesulfonate (Cyan 13). A possible model of binding monomethyne benz-thiazole cyanine dyes with double-stranded nucleic acids is proposed.
Синтезовано серію асиметричних монометинових ціанінових барвників з метиленоксибензтіазоловим термінальним гетероциклом. Досліджено їх абсорбційні та флюоресцентні властивості, спектральні властивості їх комплексів з нуклеїновими кислотами. Найкращі результати одержані з n - толулол сул ьфо на том 2-[ ( 3 - метил-2 ( ЗН )-бензотіазоліліден) метил] -5,6-диоксиметилен-3-метил-бензотіазолію. Пропонується гіпотетична модель взаємодії монометинових бензтіазолових барвників з двоспіральними нуклеїновими кислотами.
Синтезирована серия асимметричных монометиновых цианиновых красителей с метиле ноксибензтиазоловым терминальным гетероциклом. Исследованы их абсорбционные и флюоресцентные свойства, спектральные свойства их комплексов с нуклеиновыми кислотами. Наилучшие результаты получены с n-толулолсульфонатом 2-[( 3-метил-2( ЗН )-бензотиазолилиден)метил]-5,6-диоксиметилен-З-метилбензотиазолия. Предлагается гипотетическая модель взаимодействия монометиновых бензтиазоловых красителей с двуспиральными нуклеиновыми кислотами.
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ISSN 0233-7657. Биополимеры и клетка. 1996. Т. 12. № 6
Interaction of cyanine dyes with nucleic acids.
2. Spectroscopic properties of methyleneoxy analogues
of Thiazole Orange
Sergiy M. Yarmoluk*, Vladyslava B. Kovalska, Tetyana V. Smirnova1,
Mykola P. Shandura1, Yuriy P. Kovtun1, Gennadiy Kh. Matsuka
Institute of Molecular Biology and Genetics, National Academy of Sciences of Ukraine
150 Zabolotnogo str., 252143, Kyiv, Ukraine
'institute of Organic Chemistry, National Academy of Sciences of Ukraine
5 Murmanska str., 253660, Kyiv, Ukraine
A series of asymmetric cyanine dyes based on methylenoxy benzothiazole terminal hetero-
cycle was synthesized. Absorption and fluorescent properties of these dyes and their comp-
lexes with nucleic acids were investigated. The best results were obtained with 2-[(3-
methyl-2( 3H )-benzothiazolyliden )-methyl ] -5,6-dioxymethylene-3-methylbenzothiaz
olium p-toluenesulfonate (Cyan 13). A possible model of binding monomethyne benz-
thiazole cyanine dyes with double-stranded nucleic acids is proposed.
Introduction. The use of fluorescent cyanine dyes for the nonradioactive
detection of nucleic acids increased dramatically in recent years because of their
exceptional spectral properties. The polymethyne cyanine dyes have high
extinction coefficients (> 70000 mol-1сm-1), moderate quantum yields (0.08—
0.4) and good photostability [1]. When the polymethyne chain is lengthened
by one vinylene unit, the absorption maximum is shifted to longer wavelength
by about 100 nm. This relationships allows to obtain dyes with fluorescence
emission in the near infrared (IR) region, thus facilitating a significant
improvement of the signal-to-noise ratio, permitting their potential use as
fluorescent probes for the analysis of DNA, lipids, peptides, and proteins [2 ].
Cyanines have relatively narrow emissions bandwidths, making them useful for
multicolour applications in the DNA labelling [3 ].
These cationic dyes have very high binding affinity to double-stranded (ds)
DNA, single-stranded (ss) DNA and RNA [4]. Their fluorescent intensity
magnify an orders when they bound to nucleic acids [5]. Since no separation
step is necessary with this property (homogeneous labelling), determination can
be carried out relatively easy in the presence of unbound dye. This principle
was used by Pitner et al. to design cyanine labelled oligonucleotide probes for
«in-solution» hybridization [6 ].
Unsymmetrical cyanine dyes, thiazole orange dimer TOTO (1,Г-(4,4,7,7-
tetramethyl-4,7-diazaundeca-methylene)-bis-4-[3-methyl-2,3-dihydro-(benzo-
1,3-thiazole)-2-methyl-idene ]-quinolinium tetraiodide) and yellow orange
dimer YOYO (an analogue with a benzo-l,3-oxazole in the place of benzo-1,3-
*Correspondence address.
© S. M. YARMOLUK, V. B. KOVALSKA, Т. V. SMIRNOVA, M. P. SHANDURA, Yu. P. KOVTUN,
G. Kh. MATSUKA, 1996
74
INTERACTION OF CYANINE DYES WITH NUCLEIC ACID
thiazole) are the most sensitive DNA stain dyes currently available. A linear
dependence of fluorescence intensity on DNA concentration over a range from
0.5 to 100 ng/ml allows sensitive quantitation of dsDNA in conventional
spectrofluorymeter [7 ]. Glazer et al. have used these dyes for the detection and
sizing of dsDNA in agarose gels [8 ], investigation of dsDNA binding proteins
[9]. Others have used dimeric cyanines for the examination of static and
dynamic properties of isolated DNA molecules [10] and for the investigation of
DNA migration in capillary solution electrophoresis [11 ].
Interaction of cyanine dyes with nucleic acids occurs by intercalation mode.
Jacobsen at al. have proposed model of binding of TOTO to dsDNA involving
the insertion of a conjugated ring system into the interior of the helix, nestled
between the adjacent base pairs of the DNA. It was shown that the binding of
TOTO to larger oligonucleotides is site selective with CTAG:CTAG as preferred
binding site [12]. Rye and Glazer proposed a partial intercalation model of
TOTO binding to DNA to explain stability and spectroscopic properties of
TOTO-ssDNA complexes [4 ].
This is the second report of our investigation specifying the preparations of
cyanine dyes and their interactions with nucleic acids. Recently we have showed
that monomethyne cyanine dyes with methylenoxy benzothiazole terminal
heterocycle for highly fluorescent complexes with nucleic acids [13 ]. This study
compares the NA-interaction of five new structurally like benzthiazole cyanines
dyes in order to understand possible mode of interaction of cyanine dyes with
dsNA.
Materials and Methods. Spectroscopic measurements. The absorption
spectra were obtained on «SPECORD UV-VIS» spectrophotometer (Germany).
Absorption of free dyes was measured immediately after dissolving of
dimethylsulfoxide (DMSO) dye stock solution in appropriate: 50 mM Tris-HCl,
pH 8 or DMSO. Fluorescence spectra were recorded with a serial fluorescence
spectrophotometer Hitachi Model 850 (Japan). All spectra were corrected by
means of multiplying fluorescence intensities that measured over an interval of
5 nm by suitable correction factor for given wavelengths. In corrected spectra
fluorescence intensity values were proportional to a numbers of photons per unit
of wavelength interval. Fluorescence measurements were carried out in thermo-
statable quartz cell (0.5 * 0.5 cm). Fluorescence was excited with a 150 W
Xe-lamp emission.
Preparation of DNA, RNA and dyes stock solutions. Stock solution of dyes
(2-10-3 M) were prepared by dissolving dyes in DMSO. All dyes were stable
under these conditions for several months, whereas in aqueous solutions some
dyes gradually lost fluorescence properties. Working solutions were prepared
immediately prior to use. For spectral studies total calf thymus DNA («Sigma»)
and yeast RNA («Sigma») were used. Nucleic acids stock solutions were
prepared in ТЕ buffer (Tris-HCl, 50 mM, EDTA, 10 mM, pH 8.0) in
concentration 6.1 • 103 b. p. for DNA and 2.4 • 10-2 b. p. for RNA.
Absorbance and fluorescent emission spectra. For spectral measurements
the complexes of dyes with nucleic acids were obtained by mixing of dye stock
solution with DNA or RNA solution in Tris-HCl (50 mM, pH 8.0) buffer. The
final concentration of DNA an RNA was 1.2 • 104 and 2.0 10 4 mM
respectively. Final dyes concentrations were 0.02 mM. Dye-nucleic acid
complexes were prepared with approximal ratio 1 dye per 10 b. p. of RNA and
per 6 b. p. of DNA. For optical measurement of free cyanines the same dyes
concentrations were used.
Preparation of cyanine dyes. The synthetic scheme for representative dyes
are shown in Fig. 1. Standard procedures were used for the synthesis of
unsymmetrical monomethyne cyanines [14]. The main reaction involved
formation of dyes from quaternized benzothiazole salt with methyl or
75
YARMOLUK S. M. ET AL.
methylthiogroup of unsubstituted benzothiazolium salt. Cyan 15 was obtained
according to [15]. The purity of synthesized dyes were controlled by
UV-spectroscopy and elemental analysis.
Results. Dye structures and specroscopic properties of free dyes. Physical
data for five synthesized cyanine dyes and TO are presented in Table 1. The
fluorescent properties of these dyes have not been previously studied. Dye TO
with well investigated spectral properties was included for the comparison [8 ].
The wavelengths of absorption maxima (absAmax) of benzothiazole cyanines
slightly depend on solvent. Absorption maxima of the dyes showed the red shift
of 5—10 nm after going from aqueous buffer to less polar DMSO. The extinction
coefficients for all dyes are high (3.3—9.06) 104 M 'cmЛ
The fluorescence of free dyes is very low. All of these dyes have Stokes
shift between 53 and 81 nm.
NA-interaction properties of dyes. The data on the absorbance and
fluorescence emission spectra of the NA-bound form of dyes are presented in
Table 2. All dyes had short Stokes shifts (26.0—84.0 nm). Fluorescence spectra
profile of DNA-bounded of symmetrical Cyan 45 is distinctive from the another
dye-NA complexes (Fig. 2). Absorption and emission spectra of dye-nucleic
acids complexes were measured at approximate ratio 1 dye per 6 base pairs for
DNA and 1 dye per 10 bases for RNA.
Titration of cyan 13 and TO with DNA and RNA. Fluorescence titration
of Cyan 13 and TO were carried out in 0.05 M Tris buffer (pH 8) with total
calf thymus DNA and yeast RNA at 490 nm (for Cyan 13) and at 534 nm (for
TO). Fixed concentration of nucleic acid was used for the titration of fixed
concentration of dye (Fig. 3). The dye concentration was 2 -Ю 5 M. The DNA
and RNA concentration was changed from 2.9-10 ъ to 4.1 • 10 4 and from 1.1 • 10 5
to 9.1 10 4 respectively. For the Cyan 13-DNA complexes fluorescence plateau
is reached at 4 base pairs per dye (A). Titration of RNA showed that the
fluorescence emission per bound Cyan 13 reaches a maximum at 15 base/dye
(B). Fluorescence intensity of Cvan 13 is 2—3 fold greater than that for TO.
Fig. 2. Emission spectra of Cyan 45 complexes
with DNA (7) and RNA (2)
76
INTERACTION OF CYANINE D Y E S WITH NUCLEIC A C I D
Table I
Chemical structures and spectroscopic properties of cyanines dyes
•The absAraax values for dyes in buffer are subject to some error because of the tendency to form dye
associates even at the low concentration; **Arbitrary units
77
YARMOLUK S. M. ET AL.
Table 2
SDectvoscooic DroDerties ofcvanine dves conwlexes with nucleic acids
Relative fluorescence intensity ( R r I x o ) is the ratio of fluorescence intensities at the peak emission
for the bound cyanine dye and the bound TO.
Fig. 3. Fluores-
cence titration
of Cyan 13 (1)
and TO (2)
with DNA 04)
and RNA (В)
Discussion. In 1986, Lee et al. reported the use of some new dyes with
structures like thioflavin T as fluorescent probes in nucleic acids analysis. All
of these dyes had a thiazolium or oxazolium moiety which were bridged with
an aromatic amine nucleus (quinolinium, propidium or p-dimethylaminostyryl).
TO, YO and PRO (propidium iodide) were found to have excellent properties
for detection and quantitation of RNA and DNA. They have large molar
absorbtivities (70 ООЮ—100 000 M 1 cm"1), are virtually nonfluorescent in free
78
INTERACTION OF CYANINE DYES WITH NUCLEIC ACID
form but show strong fluorescence when bound with RNA (1000—3000 fold
enhancement [6]) and DNA (1000—1500 fold enhancement [5]).
We have previously showed that methylenoxybenzothiazole is perspective
heterocycle for the development of new cyanine dyes for the nucleic acids
detection. Cyan 3 formed highly fluorescent complexes with RNA and DNA
with 600-fold fluorescent enhancement [13]. Here we present the series of new
monomethyne cyanine dyes with methylenoxybenzothiazole terminal
heterocycle like Cyan 3. Their fluorescence intensity is 1.2—3-fold greater than
that TO. Cyan 13 has the most promising characteristics for the nucleic acid
analysis. Besides it has sufficiently low fluorescence in free state (0.48).
The nature of interaction and the relative affinities of the cyanine dyes for
various nucleic acid targets are unknown [4 ]. An understanding of the
molecular mechanism by which monomethyne cyanines interact with nucleic
acids is important, for several reasons. Such knowledge will be useful for
designing probes that are more sensitive to structural distinctions of nucleic
acids. Information concerning the mechanism of enhancement of fluorescence of
bound dyes is likely to be useful for development of homogeneous detection
methods of nucleic acids. With these thoughts in mind, we have focused our
attention on the investigation of monomethyne benzothiazole cyanines which are
structurally similar.
Jacobsen et al. used classical intercalation model of Lerman [16 ] to explain
possible mode of interaction of TOTO with oligonucleotide duplexes. Their
model demonstrated that TOTO bis-intercalates with the benzothiazole ring
above the cytosin ring and the quinolinium ring system on the top of an
adenosine base. Moreover it was emphasised that only proposed model of
complex was in agreement with NMR data [12]. The data presented here do
not suggest «classical» intercalation-full insertion of conjugated ring system into
the interior of the NA-helix (compare Cyan 15 and Cyan 13).
Recently Rye and Glazer reported that polycationic dyes, such as TOTO
and EtD (Ethidium bromide), capable of bis-intercalation, interact with dsDNA
and ssDNA with very similar high affinity. In order to explain the extensive
and stable association TOTO with homopolymers and ssDNA authors proposed
the model of partially intercalated both thiazole head groups between the bases
of a single DNA strand. This model was named a «partial intercalation-like»
complex [4 ].
However this model of intercalation badly agrees with hypothesis of
enhancement fluorescence intensity of dye upon binding with nucleic acids. It
is considered that the enhancement is the result of decreased rotational mobility
around the internuclear bridge between the two aromatic ring system of TO
chromophore [5, 16]. For dimeric dyes like TOTO the intercalation of thiazole
head could led to the increased rigidity of dye system. But for monomelic dyes
of only of thiazole head groups can not stabilise relative orientation of two
heterocycles of TO.
We propose model of «half intercalation» monomethyne cyanine dye into
the double-stranded helix. Benzothiazole terminal heterocycle «classically»
intercalates, nestled between the adjacent base pairs just when second
heterocycle is spatially fixed by groove of nucleic acid.
It is possible that electronic asymmetry of cyanine serves only for correct
orientation of dye before intercalation. We consider that heterocycle with high
basicity hits in the more nucleophilic groove whereas heterocycle with low
basicity insert (i. e. intercalates) in more electrophilic interbase space.
All dyes presented here have less basic unsubstituted benzothiazole
heterocycle as compared with second substituted one of cyanine. Increase of
asymmetry of positive charge distribution results in increase of fluorescent
intensity of NA-dye complexes (Fig. 4). Introduction of nucleophilic groups
79
YARMOLUK S. M. ET AL.
Fig. 4. Influence of basicity of second terminal heterocycle on the fluorescence intensity of NA-dye
complexes. Basicity of heterocycle increases from Cyan 45 to Cyan 13
Fig. 5. Influence of length of alkyl chain attached to the nitrogen atom of benzothiazole nuclei on the
fluorescence intensity of NA-dye complexes
(S03 , COO ) in the intercalating benzthiazole heterocycle sharply decreases the
intensity thiazole head of fluorescence (see Cyan 1, Cyan 4, Cyan 5 [13]).
Fluorescent intensity of NA-dye complexes, presented in Figure 4 depends
upon structure of groove binding heterocycle. However Cyan 14 and Cyan 15
have similar fluorescence properties. Increase of length of N-alkyl substituent
decreases fluorescence intensity of NA-dye complex too (Fig. 5).
Apparently, structure changes of groove binding heterocycle do not sharply
influence on intensity of fluorescence.
As indicated in the above discussion, the studies presented here have led
to the development new monomethyne cyanine dyes for the high sensitivity
detection of nucleic acids.
Acknowledgements. We are grateful to Drs A. Ishchenko and I. Dubey for
valuable discussions. Author express their gratitude to Dr. Yu. Slominsky for
the providing us with Cyan 13. The project is supported by National Academy
of Sciences of Ukraine.
С. M. Ярмолюк, В. Б. Ковальська, Т. В. Смирнова, М. П. Шандура, Ю. Л. Ковтун, Г. X. Мацука
Взаємодія ціанінових барвників та нуклеїнових кислот. 2. Синтез та спектроскопічні властивості
метиленоксианалогів тіазолового оранжевого
Резюме
Синтезовано серію асиметричних монометинових ціанінових барвників з метиленоксибензтіа-
золовим термінальним гетероциклом. Досліджено їх абсорбційні та флюоресцентні властиво-
сті, спектральні властивості їх комплексів з нуклеїновими кислотами. Найкращі результати
одержані з п - толулол сул ьфо на том 2-[ ( 3 - метил-2 ( ЗН )-бензотіазоліліден) метил] -5,6-диокси-
метилен-3-метил-бензотіазолію. Пропонується гіпотетична модель взаємодії монометино-
вих бензтіазолових барвників з двоспіральними нуклеїновими кислотами.
80
INTERACTION O F CYANINE DYES WITH NUCLEIC ACID
C. H. Ярмолюк, В. Б. Ковальская, Т. В. Смирнова, Н. П. Шандура, Ю. Я Ковтун, Г. X. Мацука
Взаимодействие цианиновых красителей и нуклеиновых кислот. 2. Синтез и
спектроскопические свойства метиленоксианалогов тиазолового оранжевого
Резюме
Синтезирована серия асимметричных монометиновых цианиновых красителей с метиле нокси-
бензтиазоловым терминальным гетероциклом. Исследованы их абсорбционные и флюоресцент-
ные свойства, спектральные свойства их комплексов с нуклеиновыми кислотами. Наилучшие
результаты получены с п-толулолсульфонатом 2-[( 3-метил-2( ЗН )-бензотиазолилиден)ме-
тил]-5,6-диоксиметилен-З-метилбензотиазолия. Предлагается гипотетическая модель
взаимодействия монометиновых бензтиазоловых красителей с двуспиральными нуклеиновыми
кислотами.
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| id | nasplib_isofts_kiev_ua-123456789-154270 |
| institution | Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| issn | 0233-7657 |
| language | English |
| last_indexed | 2025-12-07T16:16:55Z |
| publishDate | 1996 |
| publisher | Інститут молекулярної біології і генетики НАН України |
| record_format | dspace |
| spelling | Yarmoluk, S.M. Kovalska, V.B. Smirnova, T.V. Shandura, M.P. Kovtun, Y.P. Matsuka, G.K. 2019-06-15T12:11:17Z 2019-06-15T12:11:17Z 1996 Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange / S.M. Yarmoluk, V.B. Kovalska, T.V. Smirnova, M.P. Shandura, Y.P. Kovtun, G.K. Matsuka // Биополимеры и клетка. — 1996. — Т. 12, № 6. — С. 74-81. — Бібліогр.: 16 назв. — англ. 0233-7657 DOI: http://dx.doi.org/10.7124/bc.000458 https://nasplib.isofts.kiev.ua/handle/123456789/154270 542 95 A series of asymmetric cyanine dyes based on methylenoxy benzothiazole terminal hetero-cycle was synthesized. Absorption and fluorescent properties of these dyes and their complexes with nucleic acids were investigated. The best results were obtained with 2-[(3-methyl-2(3H)-benzothiazolyliden)-methyl]-5,6-dioxymethylene-3-methylbenzothiaz olium p-toluenesulfonate (Cyan 13). A possible model of binding monomethyne benz-thiazole cyanine dyes with double-stranded nucleic acids is proposed. Синтезовано серію асиметричних монометинових ціанінових барвників з метиленоксибензтіазоловим термінальним гетероциклом. Досліджено їх абсорбційні та флюоресцентні властивості, спектральні властивості їх комплексів з нуклеїновими кислотами. Найкращі результати одержані з n - толулол сул ьфо на том 2-[ ( 3 - метил-2 ( ЗН )-бензотіазоліліден) метил] -5,6-диоксиметилен-3-метил-бензотіазолію. Пропонується гіпотетична модель взаємодії монометинових бензтіазолових барвників з двоспіральними нуклеїновими кислотами. Синтезирована серия асимметричных монометиновых цианиновых красителей с метиле ноксибензтиазоловым терминальным гетероциклом. Исследованы их абсорбционные и флюоресцентные свойства, спектральные свойства их комплексов с нуклеиновыми кислотами. Наилучшие результаты получены с n-толулолсульфонатом 2-[( 3-метил-2( ЗН )-бензотиазолилиден)метил]-5,6-диоксиметилен-З-метилбензотиазолия. Предлагается гипотетическая модель взаимодействия монометиновых бензтиазоловых красителей с двуспиральными нуклеиновыми кислотами. We are grateful to Drs A. Ishchenko and I. Dubey for valuable discussions. Author express their gratitude to Dr. Yu. Slominsky for the providing us with Cyan 13. The project is supported by National Academy of Sciences of Ukraine. en Інститут молекулярної біології і генетики НАН України Биополимеры и клетка Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange Взаємодія ціанінових барвників та нуклеїнових кислот. 2. Синтез та спектроскопічні властивості метиленоксианалогів тіазолового оранжевого Взаимодействие цианиновых красителей и нуклеиновых кислот. 2. Синтез и спектроскопические свойства метиленоксианалогов тиазолового оранжевого Article published earlier |
| spellingShingle | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange Yarmoluk, S.M. Kovalska, V.B. Smirnova, T.V. Shandura, M.P. Kovtun, Y.P. Matsuka, G.K. |
| title | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange |
| title_alt | Взаємодія ціанінових барвників та нуклеїнових кислот. 2. Синтез та спектроскопічні властивості метиленоксианалогів тіазолового оранжевого Взаимодействие цианиновых красителей и нуклеиновых кислот. 2. Синтез и спектроскопические свойства метиленоксианалогов тиазолового оранжевого |
| title_full | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange |
| title_fullStr | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange |
| title_full_unstemmed | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange |
| title_short | Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange |
| title_sort | interaction of cyanine dyes with nucleic acids. 2. spectroscopic properties of methyleneoxy analogues of thiazole orange |
| url | https://nasplib.isofts.kiev.ua/handle/123456789/154270 |
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