Synthesis of  O ‐Acetyl‐ N  (4‐biphenylyl)hydroxylamine (“NAcetoxy‐4‐aminobiphenyl”), an Ultimate Metabolite of Carcinogenic 4‐Aminobiphenyl, and Its Reaction with Deoxyguanosine | Zendy

Famulok Michael | Zendy; Bosold Ferdinand | Zendy; Boche Gernot | Zendy

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Synthesis of O ‐Acetyl‐ N (4‐biphenylyl)hydroxylamine (“NAcetoxy‐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).

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