Synthesis of new derivatives of 8-oxoG-clamp for better understanding the recognition mode and improvement of selective affinity

Bioorg Med Chem. 2010 Jun 1;18(11):3992-8. doi: 10.1016/j.bmc.2010.04.025. Epub 2010 Apr 18.

Abstract

8-Oxoguanosine (8-oxoG) is a representative metabolite derived by the oxidation of guanosine (G) and is regarded as a marker of oxidative stress in the cells. We previously reported the 8-oxoG-clamp as the first fluorescent probe for detection of 8-oxoG. In this study, new 8-oxoG-clamp derivatives having a variety of N-functional groups were synthesized and their recognition properties were investigated. The sp(3) oxygen atom of the carbamate unit was revealed to play a significant role in the hydrogen bonding interactions, and the pyrene group produced higher stability with 8-oxoG compared with the original 8-oxoG-clamp.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Biomarkers
  • Fluorescent Dyes / chemical synthesis*
  • Guanosine / analogs & derivatives*
  • Guanosine / chemical synthesis
  • Hydrogen Bonding
  • Oxidative Stress
  • Pyrenes

Substances

  • Biomarkers
  • Fluorescent Dyes
  • Pyrenes
  • Guanosine
  • 8-hydroxyguanosine
  • pyrene