title: Novel fluorescent pyrimidine nucleosides containing 2,1,3-benzoxadiazole and naphtho-[1,2,3-CD] Indole-6 (2H)-one fragments.
abstract: 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.
authors.affiliation: a Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences , Novosibirsk , Russia.
authors.forename: Svetlana V
authors.initials: SV
authors.lastname: Vasilyeva
authors.forename: Anastasya S
authors.initials: AS
authors.lastname: Kuznetsova
authors.forename: Juliya G
authors.initials: JG
authors.lastname: Khalyavina
authors.forename: Valeria A
authors.initials: VA
authors.lastname: Glazunova
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Shtil
authors.forename: Leonid M
authors.initials: LM
authors.lastname: Gornostaev
authors.forename: Vladimir N
authors.initials: VN
authors.lastname: Silnikov
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D057930:Click Chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry / Q000494:pharmacology; D010069:Oxadiazoles / Q000737:chemistry / Q000494:pharmacology; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D005456:Fluorescent Dyes; D007211:Indoles; D009284:Naphthols; D010069:Oxadiazoles; D011741:Pyrimidine Nucleosides
keywords: Fluorescent base analogues; anticancer nucleosides; base modification; labeled DNA/RNA; modified nucleosides