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Synthesis of O ‐Acetyl‐ N (4‐biphenylyl)hydroxylamine (“NAcetoxy‐4‐aminobiphenyl”), an Ultimate Metabolite of Carcinogenic 4‐Aminobiphenyl, and Its Reaction with Deoxyguanosine
Author(s) -
Famulok Michael,
Bosold Ferdinand,
Boche Gernot
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198903371
Subject(s) - hydroxylamine , carcinogen , metabolite , deoxyguanosine , chemistry , organic chemistry , biochemistry , dna
The carcinogenicity of aromatic amines has been known since 1895. It has now been possible for the first time to convert the hydroxylamine derivative generated from 4‐aminobiphenyl 1 into the crystalline title compound 2 in vitro. 2 reacts with deoxyguanosine to give the same “adducts” which, e.g., are also obtained when 1 is administered to dogs and the DNA is subsequently cleaved enzymatically (Aryl = 4‐biphenylyl).