title: Synthesis and photophysical properties of 7-deaza-2'-deoxyadenosines bearing bipyridine ligands and their Ru(II)-complexes in position 7.
abstract: The synthesis of the title 7-deazaadenine 2'-deoxyribonucleosides bearing bipyridine, phenanthroline or terpyridine ligands linked to position 7 via an acetylene or phenylene spacer is reported based on aqueous cross-coupling reactions of unprotected 7-iodo-7-deaza-2'-deoxyadenosine with ligand-functionalized acetylenes or boronic acids. The aqueous cross-coupling with acetylene or boronate building blocks containing the Ru(bpy)(3)-type of complex gave the corresponding Ru-containing nucleosides. Photophysical and electrochemical properties were studied and the most efficient type of complex was selected for future luminescent and redox labelling of DNA. The title nucleosides also showed some cytostatic and anti-HCV activities.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, Flemingovo nam. 2, CZ-16610, Prague 6, Czech Republic.
authors.forename: Milan
authors.initials: M
authors.lastname: Vrábel
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Ivan
authors.initials: I
authors.lastname: Votruba
authors.forename: Mohsen
authors.initials: M
authors.lastname: Sajadi
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Kovalenko
authors.forename: Nikolaus P
authors.initials: NP
authors.lastname: Ernsting
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D015082:2,2'-Dipyridyl / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000494:pharmacology*; D000998:Antiviral Agents / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D004354:Drug Screening Assays, Antitumor; D016174:Hepacivirus / Q000187:drug effects*; D006801:Humans; D008024:Ligands; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010777:Photochemistry; D012428:Ruthenium / Q000737:chemistry*; D014372:Tubercidin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D008024:Ligands; D009942:Organometallic Compounds; D015082:2,2'-Dipyridyl; C053222:2'-deoxytubercidin; D012428:Ruthenium; D014372:Tubercidin