Development for an efficient synthesis method of 2'-deoxyguanosine-C8 adducts with several amino/nitro-arenes.

Takeji Takamura-Enya, Satoko Ishikawa, Masataka Mochizuki, Keiji Wakabayashi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Heterocyclic amines (HCAs) are mutagenic compounds present in cooked meat and fish, and some of them are known to be carcinogenic. DNA adduct formation is now believed to be the initial critical step for carcinogenesis. HCAs are metabolically activated to form predominantly 2'-deoxyguanosine-C8 adducts (dG-C8 adduct) where the exocyclic N atom of activated compounds are covalently bound to the C8 position of dG. In order to prepare a high yield of dG-C8 adducts with HCAs, we tried to adapt the Buchwald-Hartwig arylamination reaction using 8-bromo-dG derivatives and HCAs. With the combined use of xantphos and Cs2CO3, we successfully obtained coupling compound derived from a carcinogenic HCA, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) at a 97% yield. Subsequent deprotection may lead to authentic dG-C8 adducts of several HCAs.

Original languageEnglish
Pages (from-to)23-24
Number of pages2
JournalNucleic acids research. Supplement (2001)
Issue number3
DOIs
Publication statusPublished - 2003
Externally publishedYes

ASJC Scopus subject areas

  • Medicine(all)

Fingerprint Dive into the research topics of 'Development for an efficient synthesis method of 2'-deoxyguanosine-C8 adducts with several amino/nitro-arenes.'. Together they form a unique fingerprint.

  • Cite this