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Azo‐dye carcinogenesis. The reactions of 4‐hydroxymethylaminoazobenzene with cytosine derivatives
Author(s) -
Roberts J. J.,
Warwick G. P.
Publication year - 1966
Publication title -
international journal of cancer
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.475
H-Index - 234
eISSN - 1097-0215
pISSN - 0020-7136
DOI - 10.1002/ijc.2910010113
Subject(s) - cytosine , chemistry , pyrimidine , formaldehyde , nucleotide , hydrolysis , guanine , covalent bond , triazine , purine metabolism , stereochemistry , organic chemistry , medicinal chemistry , dna , biochemistry , enzyme , gene
A mixture of formaldehyde and aminoazobenzene condensed readily under physiological conditions to form covalently bound products with purines or pyrimidines and their corresponding nucleosides and nucleotides bearing amino groups. In the case of cytosine derivatives it was established that Mannich type condensations occurred with the pyrimidine amino group and the N‐1 position to form substituted triazines, derived from two molecules of formaldehyde, one of aminoazobenzene and one of the corresponding pyrimidine. The triazine ring structure derived from cytosine was stable at pH values greater than 7, while those derived from cytosine nucleosides and nucleotides opened at the N‐1 position at pH 9. At higher pH values decomposition of these substituted cytosine rings occurred, accompanied by hydrolysis of both methylene bonds. All compounds were hydrolysed by dilute mineral acid into the original constituents. The properties of these in vitro condensation products were compared to those formed by reaction of metabolites of 4‐dimethylaminoazo [G‐ 3 H]‐benzene with RNA in vivo with respect to their stability at different pH values.