Novel 18-crown-6-ether containing mono- and bisstyryl dyes derived from pyridine moiety as fluorescent dyes for non-covalent interaction with DNA. (October 2018)

• Record Type: Journal Article
• Authors: Lebedeva, Anna Y.; Fedorova, Olga A.; Tsvetkov, Vladimir B.; Grinberg, Valerij Y.; Grinberg, Natalia V.; Burova, Tatiana V.; Dubovik, Alexander S.; Babievsky, Kirill K.; Fedorov, Yury V.
• Is Part Of: Dyes and pigments. Volume 157(2018)
• Page Start: 80
• Page End: 92
• Publication Date: 2018-10
• Subjects: Fluorescent dyes -- Styrylpyridine -- Bisstyrylpyridine -- DNA -- Crown ether; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2018.04.038
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Bisstyrylpyridine dyes1 and2, in which two styrylpyridine moieties are connected to each other through the oxo- or azacrown ether unit, and their monomer analogues3 and4 have been synthesized and spectroscopically characterized. The prepared bisstyryl dyes1 and2 are the rare example of bisstyryls constructed in tail-to-tail mode. The binding of dyes1 –4 with salmon DNA has been evaluated using the UV–vis, CD, fluorescence, high-sensitivity differential scanning calorimetry, viscometric data and molecular modeling. The dyes were found to have negligible fluorescence in a buffer solution, but exhibited a significant emission increase upon binding to DNA. The results obtained are consistent with a groove binding mode between mono- and bisstyryls and DNA. Graphical abstract: Highlights: Oxo- and azacrown ethers containing two styrylpyridine units were designed and synthesized. Dyes demonstrate interaction with salmon DNA through the groove binding. Fluorescence intensity enhancement was observed up to 33 times on DNA-dye interaction.