An amine ed formed by bacteria during sulfonamide bacteriostasis

Stetten, M.R.; Fox, C.L.

Journal of Biological Chemistry 161: 333-349


ISSN/ISBN: 0021-9258
PMID: 21005740
Accession: 030004079

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When the normal growth of certain bacteria, such as Escherichia coli, is inhibited by bacterio-static concentration of sulfonamide drugs, a diazotizable amine is found to accumulate in the medium. The action is not confined to any one kind of bacteria or to any specific sulfonamide drug as shown by the tabulated results. The best results were obtained with sulfadiazine. p-Aminoben-zoic acid, in proportion sufficient to block action of the drugs, prevented the formation of the amine. From cultures of E. coli when growth was inhibited by either sulfadiazine or sulfa-pyridine, the amine was isolated as a picrate and samples of the free amine and a number of derivatives were prepd. This amine is a heterocyclic orthodiamine with an empirical formula of C4H6N4O. It is not a pyrimidine and its properties indicate that it is probably 2-hydroxy-5,6-diamino-pyrazine.