title: 5-Bromo-2'-deoxycytidine-a potential DNA photosensitizer.
abstract: A double-stranded oligonucleotide, 80 base pairs in length, was multiply labeled with 5-bromo-2'-deoxycytidine (BrdC) using polymerase chain reaction (PCR). The modified oligonucleotide was irradiated with 300 nm photons and its damage was assayed by employing DHPLC, LC-MS and denaturing polyacrylamide gel electrophoresis (PAGE). Two types of damage were demonstrated, namely, single strand breaks (SSBs) and intrastrand cross-links (ICLs); the ICLs were in the form of d(G^C) and d(C^C) dimers. The former species are probably formed due to photoinduced electron transfer between the photoexcited BrdC and the ground state 2'-deoxyguanosine (dG), whereas the latter is a result of a cycloaddition reaction. Since SSBs and ICLs are potentially lethal to the cell, BrdC could be considered as a nucleoside with possible clinical applications.
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland. janusz.rak@ug.edu.pl.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Zdrowowicz
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland. janusz.rak@ug.edu.pl.
authors.forename: Paweł
authors.initials: P
authors.lastname: Wityk
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland. janusz.rak@ug.edu.pl.
authors.forename: Barbara
authors.initials: B
authors.lastname: Michalska
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland. janusz.rak@ug.edu.pl.
authors.forename: Janusz
authors.initials: J
authors.lastname: Rak
mesh_terms: D001972:Bromodeoxycytidine / Q000737:chemistry* / Q000528:radiation effects; D002851:Chromatography, High Pressure Liquid; D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry* / Q000528:radiation effects; D053904:DNA Breaks, Single-Stranded; D058645:Denaturing Gradient Gel Electrophoresis; D013058:Mass Spectrometry / Q000379:methods; D009841:Oligonucleotides / Q000737:chemistry / Q000528:radiation effects*; D017319:Photosensitizing Agents / Q000737:chemistry*; D016133:Polymerase Chain Reaction; D014466:Ultraviolet Rays
chemical_list: D009841:Oligonucleotides; D017319:Photosensitizing Agents; D001972:Bromodeoxycytidine; D004247:DNA