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

Zhichun Li, Osamu Nakagawa, Yohei Koga, Yosuke Taniguchi, Shigeki Sasaki

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 sp3 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.

Original languageEnglish
Pages (from-to)3992-3998
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number11
DOIs
Publication statusPublished - Jun 1 2010

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Clamping devices
Derivatives
Oxidative stress
Carbamates
Guanosine
Hydrogen Bonding
Metabolites
Fluorescent Dyes
Functional groups
8-hydroxyguanosine
Hydrogen bonds
Oxidative Stress
Oxygen
Atoms
Oxidation

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Synthesis of new derivatives of 8-oxoG-Clamp for better understanding the recognition mode and improvement of selective affinity. / Li, Zhichun; Nakagawa, Osamu; Koga, Yohei; Taniguchi, Yosuke; Sasaki, Shigeki.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 11, 01.06.2010, p. 3992-3998.

Research output: Contribution to journalArticle

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