BODIPY-modified 2'-deoxyguanosine as a novel tool to detect DNA damages

Bioorg Med Chem Lett. 2011 Jul 15;21(14):4206-9. doi: 10.1016/j.bmcl.2011.05.084. Epub 2011 May 30.

Abstract

BODIPY-modified 2'-deoxyguanosine was synthesized for use as a detection reagent for genotoxic compounds. BODIPY-FL is a well known fluorescence reagent whose fluorescent light emission diminishes near a guanine base by a photo-induced electron transfer process. We attached BODIPY-Fl to the 5' position of the deoxyribose moiety of 2'-deoxyguanosine. Although this compound has low fluorescence activity, when depurination by the action of alkylating reagents and dG oxidation by singlet oxygen occurred, the emission of strong fluorescence was observed. BODIPY-dG was found, therefore, to be a very useful tool for selectively detecting DNA damaging activity particularly in natural environmental extracts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Boron Compounds / chemistry*
  • DNA / chemistry*
  • DNA Damage*
  • Deoxyguanosine / chemistry*
  • Deoxyguanosine / pharmacology
  • Fluorescent Dyes / chemistry*
  • Oxidation-Reduction
  • Singlet Oxygen / chemistry
  • Singlet Oxygen / metabolism
  • Ultraviolet Rays

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Singlet Oxygen
  • DNA
  • Deoxyguanosine