Fluorescence Quenching of 10‐methylacrjdinium Chloride by Nucleotides

Kubota, Yukio; Motosa, Yuko; Shigemune, Yoko; Fujisaki, Yasuo

doi:10.1111/j.1751-1097.1979.tb07826.x

Cited by 49 publications

(24 citation statements)

References 33 publications

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“…All three nucleotides cause a small (10-15 nm) red shift in the 664 nm absorption of MB. Similar changes have been reported in the absorption spectra of other dyes such as proflavine (Georghiou, 1975), 10methylacridinium (Kubota et al, 1979), and dimethyldiazaperopyrenium (Slama-Schwok et al, 1989). Since we expect no ground state chemical reaction between MB and the nucleotides, the absorption changes indicate the formation of ground state complexes.…”

Section: Discussionsupporting

confidence: 83%

“…( 5 ) ] where we assume the formation of non-fluorescent binary and ternary complexes. Ground state complexation with nucleotides has also been found to cause quenching of the fluorescence of the acridine dyes, proflavine (Badea and Georghiou, 1976) 10-methylacridinium, acridine orange and 9-amino-acridine (Kubota et al, 1979). In the case of proflavine, the quenching was shown to result from the formation of binary complexes.…”

Section: Discussionmentioning

confidence: 99%

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The Role of Ground State Complexation in the Electron Transfer Quenching of Methylene Blue Fluorescence by Purine Nucleotides

Dunn

Lin

Kochevar

1991

Photochem & Photobiology

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The effect of three purine nucleotides on the fluorescence of methylene blue in aqueous buffer has been investigated. Guanosine-5'-monophosphate (GMP) and xanthosine-5'-monophosphate cause fluorescence quenching while adenosine-5'-monophosphate causes a red shift in the fluorescence maximum. All three nucleotides form ground state complexes with the nucleotides as indicated by absorption spectroscopy. The fluorescence changes at nucleotide concentrations less than 30 mM are best described by a static mechanism involving the formation of non-fluorescent binary and ternary complexes in competition with dimerization of the dye. Quenching of the fluorescence decay (tau = 368 ps) at high GMP concentrations (10-100 mM) occurs at the rate of diffusion. The mechanism of fluorescence quenching may involve electron transfer within the singlet excited dye-nucleotide complex although published values of the oxidation potentials of various purine derivatives would suggest that all three nucleotides should cause quenching. Evidence for electron transfer was obtained from flash photolysis experiments in which 100 mM GMP was found to cause the appearance of a long lived transient species absorbing in the region expected for semimethylene blue.

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Section: Discussionsupporting

confidence: 83%

Section: Discussionmentioning

confidence: 99%

The Role of Ground State Complexation in the Electron Transfer Quenching of Methylene Blue Fluorescence by Purine Nucleotides

Dunn

Lin

Kochevar

1991

Photochem & Photobiology

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“…Taking into account that static quenching is frequently observed in fluorophores that engage in stacking interactions with purine and pyrimidine nucleotides [9], one can assume that the above order of increasing K S values reflects the increasing tendency of the nucleotides to display ground-state stacking interactions with 3. The calculated k q values, which reflect the quenching efficiencies, fall into the range expected for the diffusion-controlled rates and increase in the order that coincides with the sequence of decreasing oxidation potentials of the bases in nucleotides (U > C > A > G) [10].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Fluorescence Quenching Study of the Novel Cationic Probe Derived from Luminarosine

Wenska

Skalski

Tomska-Foralewska

et al. 2001

HCA

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Dedicated to Professor Andre¬ M. Braun on the occasion of his 60th birthday A simple and efficient transformation of the zwitterionic luminarosine into a brightly fluorescent cationic analogue, namely 1-amino-9-methoxy-2,4,10-triaza-4b-azoniaphenanthrene (3), is reported. The fluorescence quenching of 3 by common nucleotides, calf-thymus (CT) DNA, and halide ions was investigated by means of spectrophotometric and spectrofluorometric methods. Intermolecular static and dynamic fluorescencequenching constants for quenching of 3 by nucleotides and halide ions were determined in aqueous solution. Evidence for formation of nonfluorescent ground-state complexes of 3 with nucleotides and CT-DNA is presented. Scatchard analysis of the CT-DNA quenching data resulted in a binding constant of 2.8 Â 10 4 m À1 and a number of binding sites per base pair of 0.049., which has excitation and emission maxima at 430 and 530 nm in aqueous solution, belongs to a rather limited number of modified nucleosides that absorb and emit light in the visible region. The attractive photophysical properties of this compound [2], as well as its chemical stability under oligonucleotide-synthesis conditions, make it an excellent candidate for a fluorescent probe of nucleic acids and other biological systems. Sequence-specific introduction of this fluorophore into oligodeoxynucleotides has already been achieved [3]. Recent studies on fluorescence quenching of the parent de-O-acetylated nucleoside (luminarosine) and the aglycone (luminarine) by I À ions in living cells revealed the great potential of the former as a long-wavelength iodidesensitive fluorescent indicator for measurements of the cystic fibrosis transmembraneconductance regulator (CFTR) gene expression in cells [4]. The high intracellular fluorescence of the luminarosine, combined with its red-shifted emission and I À selectivity, make it superior to quinolinium-based halide indicators and indicates its possible application in the high-throughput screening of compounds for correction of the cystic fibrosis phenotype. Encouraged by these findings, we have undertaken the synthesis and detailed photophysical studies of some analogues of the luminarosine modified within the chromophoric part in the hope of obtaining fluorophores of different and possibly improved photophysical properties. In this communication, we present the simple and efficient transformation of the zwitterionic luminarosine into another very bright fluorophore, namely its cationic analog, 1-amino-9-methoxy-2,4,10-triaza-4b-azoniaphenanthrene (3). The spectral properties as well as the results of a fluorescence-quenching study of 3 by common nucleotides and halide ions is discussed.

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“…Each one of them obeys the following equations pyridinium salts. Relations of this kind have been found in numerous studies of distribution of organic molecules between micellar and aqueous phases (27)(28)(29)(30)(31). In those cases Ap,* represents the Gibbs free energy change due to the transfer of the organic molecule from the aqueous phase to the micellar phase, and the coefficient of n, is the contribution of each methylene group to this change.…”

Section: Association Constantsmentioning

confidence: 91%

“…5). According to Kubota et al (27), a reasonable value of K was obtained with a slope that is 44 times higher than the intercept. In the present work, this ratio is many times larger than that, and a real value was obtained only for CsPd where the ratio was equal to 350.…”

Section: Association Constantsmentioning

confidence: 94%

Thermodynamic and Kinetic Study of the Interaction between Alkylpyridinium Ions and Pyrene Derivatives in Aqueous Solution

Rosenbluth

Weiss-López

Olea

1997

Photochem & Photobiology

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The kinetics of fluorescence quenching of pyrene and three of its derivatives by a series of n-alkylpyridinium ions has been studied. The quenching process is diffusion controlled for all the systems studied, independent of the charge in the aromatic molecule and the size of the alkyl chain in the pyridinium ions. Pyrensulfonate, PS, and pyranine form ground-state complexes with these quenchers. The association constants were determined by using a kinetic scheme where both dynamic and static quenching were included. A linear relationship between the free energy change and number of carbon atoms was found for PS, and a methylene contribution equal to -1.1 kJ/mol was determined from the slope. A similar correlation was established for pyranine, but a slope change was observed when the alkyl chain has more than 10 carbon atoms. From the initial slope, an incremental free energy of -0.35 kJ/mol was obtained. The ground-state complex formation is determined mainly by an electrostatic interaction, but there is a hydrophobic effect on the value of the measured association constants.

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Fluorescence Quenching of 10‐methylacrjdinium Chloride by Nucleotides

Cited by 49 publications

References 33 publications

The Role of Ground State Complexation in the Electron Transfer Quenching of Methylene Blue Fluorescence by Purine Nucleotides

The Role of Ground State Complexation in the Electron Transfer Quenching of Methylene Blue Fluorescence by Purine Nucleotides

Synthesis and Fluorescence Quenching Study of the Novel Cationic Probe Derived from Luminarosine

Thermodynamic and Kinetic Study of the Interaction between Alkylpyridinium Ions and Pyrene Derivatives in Aqueous Solution

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