Premium
Structural Identification of DNA Adducts Derived from 3‐Nitrobenzanthrone, a Potent Carcinogen Present in the Atmosphere
Author(s) -
TakamuraEnya Takeji,
Kawanishi Masanobu,
Yagi Takashi,
Hisamatsu Yoshiharu
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700061
Subject(s) - adduct , deoxyguanosine , chemistry , dna , carcinogen , deoxyadenosine , nucleoside , mutagen , stereochemistry , biochemistry , organic chemistry
3‐Nitrobenzanthrone is a powerful bacterial mutagen and carcinogen to mammals. To obtain precise information on DNA‐adduct formation by 3‐nitrobenzanthrone, a number of DNA adducts, including N ‐(2′‐deoxyguanosin‐8‐yl)‐3‐aminobenzanthrone ( 13 a ), 2‐(2′‐deoxyguanosin‐ N 2 ‐yl)‐3‐aminobenzanthrone ( 14 a ), N ‐(2′‐deoxyadenosin‐8‐yl)‐3‐aminobenzanthrone ( 15 a ), 2‐(2′‐deoxyadenosin‐ N 6 ‐yl)‐3‐aminobenzanthrone ( 16 a ), and their N ‐acetylated counterparts 13 b , 14 b , 15 b , and 16 b were synthesized by palladium‐catalyzed aryl amination of the corresponding nucleoside and bromobenzanthrone derivatives. Among these DNA adducts, DNA adducts 13 a , 13 b , 14 a , 14 b , and 16 a were identified in the reaction mixture of nucleosides (2′‐deoxyguanosine, 2′‐deoxyadenosine, or DNA) with N ‐acetoxy‐3‐aminobenzanthrone or N‐ acetyl ‐N ‐acetoxy‐3‐aminobenzanthrone, both of which are recognized as activated metabolites of 3‐nitrobenzanthrone. The formation of these multiple DNA adducts may help explain the potent mutacarcinogenicity of 3‐nitrobenzanthrone.