Novel fluorescent pyrimidine nucleosides containing 2,1,3-benzoxadiazole and naphtho-[1,2,3-CD] indole-6 (2H)-One fragments

Nucleosides, Nucleotides and Nucleic Acids, Taylor & Francis, UK. 2014. Vol. 33. No. 9. P. 615–625.

Vasilyeva S. V., Kuznetsova A. S., Khalyavina J. G., Glazunova V.A., Shtil A. A., Gornostaev L. M., Sylnikov V. N.

A series of novel fluorescent pyrimidine nucleosides containing 2,1,3-benzoxadiazole or naphtho[1,2,3-cd]indole-6 (2h)-one fragments was designed and synthesized. Introduction of fluorescent fragments into the position 5 of the uridine or cytidine heterocycle was carried out in two ways: by Sonogashira Coupling Reaction and CuI-catalyzed cycloaddition ("click" reaction). The obtained nucleoside derivatives became fluorescent due to the inserted fragments. The excitation wavelength (440-450 nm) was outside the absorption band of many biomolecules and significantly differed from the emission wavelength (560-600 nm). In addition, the intended nucleoside analogs were shown to kill cultured human tumor cells at submicromolar concentrations

Keywords: anticancer nucleosides, base modification, Fluorescent base analogues, labeled DNA/RNA, modified nucleosides