Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex DNA. Xie, X., Choi, B., Largy, E., Guillot, R., Granzhan, A., & Teulade-Fichou, M. Chemistry - A European Journal, 19:1214–1226, 2013.
doi  abstract   bibtex   
The interactions of three cationic distyryl dyes, namely 2,4-bis(4-dimethylaminostyryl)-1-methylpyridinium (1a), its derivative with a quaternary aminoalkyl chain (1b), and the symmetric 2,6-bis(4-dimethylaminostyryl)-1-methylpyridinium (2a), with several quadruplex and duplex nucleic acids were studied with the aim to establish the influence of the geometry of the dyes on their DNA-binding and DNA-probing properties. The results from spectrofluorimetric titrations and thermal denaturation experiments provide evidence that asymmetric (2,4-disubstituted) dyes 1a and 1b bind to quadruplex DNA structures with a near-micromolar affinity and a fair selectivity with respect to double-stranded (ds) DNA K(a)(G4)/K(a)(ds)=2.5-8.4. At the same time, the fluorescence of both dyes is selectively increased in the presence of quadruplex DNAs (more than 80-100-fold in the case of human telomeric quadruplex), even in the presence of an excess of competing double-stranded DNA. This optical selectivity allows these dyes to be used as quadruplex-DNA-selective probes in solution and stains in polyacrylamide gels. In contrast, the symmetric analogue 2a displays a strong binding preference for double-stranded DNA K(a) (ds)/K(a) (G4)=40-100), presumably due to binding in the minor groove. In addition, 2a is not able to discriminate between quadruplex and duplex DNA, as its fluorescence is increased equally well (20-50-fold) in the presence of both structures. This study emphasizes and rationalizes the strong impact of subtle structural variations on both DNA-recognition properties and fluorimetric response of organic dyes.
@article{xie_asymmetric_2013,
	title = {Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex {DNA}.},
	volume = {19},
	copyright = {All rights reserved},
	doi = {10.1002/chem.201203710},
	abstract = {The interactions of three cationic distyryl dyes, namely 2,4-bis(4-dimethylaminostyryl)-1-methylpyridinium (1a), its derivative with a quaternary aminoalkyl chain (1b), and the symmetric 2,6-bis(4-dimethylaminostyryl)-1-methylpyridinium (2a), with several quadruplex and duplex nucleic acids were studied with the aim to establish the influence of the geometry of the dyes on their DNA-binding and DNA-probing properties. The results from spectrofluorimetric titrations and thermal denaturation experiments provide evidence that asymmetric (2,4-disubstituted) dyes 1a and 1b bind to quadruplex DNA structures with a near-micromolar affinity and a fair selectivity with respect to double-stranded (ds) DNA K(a)(G4)/K(a)(ds)=2.5-8.4. At the same time, the fluorescence of both dyes is selectively increased in the presence of quadruplex DNAs (more than 80-100-fold in the case of human telomeric quadruplex), even in the presence of an excess of competing double-stranded DNA. This optical selectivity allows these dyes to be used as quadruplex-DNA-selective probes in solution and stains in polyacrylamide gels. In contrast, the symmetric analogue 2a displays a strong binding preference for double-stranded DNA K(a) (ds)/K(a) (G4)=40-100), presumably due to binding in the minor groove. In addition, 2a is not able to discriminate between quadruplex and duplex DNA, as its fluorescence is increased equally well (20-50-fold) in the presence of both structures. This study emphasizes and rationalizes the strong impact of subtle structural variations on both DNA-recognition properties and fluorimetric response of organic dyes.},
	journal = {Chemistry - A European Journal},
	author = {Xie, Xiao and Choi, Bina and Largy, Eric and Guillot, Régis and Granzhan, Anton and Teulade-Fichou, Marie-Paule},
	year = {2013},
	pmid = {23292703},
	keywords = {Base Sequence, Crystallography, Fluorescent Dyes, Fluorescent Dyes: chemical synthesis, Fluorescent Dyes: chemistry, Fluorometry, G-Quadruplexes, Kinetics, Molecular Conformation, Pyridinium Compounds, Pyridinium Compounds: chemistry, X-Ray, sumo},
	pages = {1214--1226},
}

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