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Azo-dye carcinogenesis. The reactions of 4-hydroxymethylaminoazobenzene with cytosine derivatives

✍ Scribed by J. J. Roberts; G. P. Warwick


Publisher
John Wiley and Sons
Year
1966
Tongue
French
Weight
834 KB
Volume
1
Category
Article
ISSN
0020-7136

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✦ Synopsis


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-I 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 p H values greater than 7, while those derived from cytosine nuczeosides and nucleotides opened at the N-I position at p H 9. At higher p H 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-3H]-benzene with R N A in vivo with respect to their stability at diflerent p H values.


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