NOVEL FLUORESCENT PYRIMIDINE NUCLEOSIDES CONTAINING 2,1,3-BENZOXADIAZOLE AND NAPHTHO-[1,2,3-CD] INDOLE-6 (2H)-ONE FRAGMENTS

作者：Vasilyeva Svetlana V^*; Kuznetsova Anastasya S; Khalyavina Juliya G; Glazunova Valeria A; Shtil Alexander A; Gornostaev Leonid M; Silnikov Vladimir N

来源：Nucleosides Nucleotides & Nucleic Acids, 2014, 33(9): 615-625.

DOI：10.1080/15257770.2014.913064

• Fluorescent base analogues
• anticancer nucleosides
• base modification
• labeled DNA/RNA
• modified nucleosides

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.

• 出版日期2014