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Mutagenicity of Hydroxamic Acids and the Probable Involvement of Carbamoylation¹

Department of Nutrition and Food Science, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

A series of hydroxamic acids (aceto-, propiono-, benzo-, and p-nitrobenzo-) and seven derivatives of these were examined for biological activity using Salmonella typhimurium. Acylation to yield O-acetyl and O-benzoyl derivatives markedly enhanced toxic properties and was necessary for mutagenic activity for all but p-nitrobenzohydroxamic acid. The dose necessary to produce a minimum significant mutagenic response varied from 21 µM for O-benzoyl benzohydroxamate to 430 µM for O-acetyl acetohydroxamate. These two compounds were also tested with human lymphoblasts to which they were toxic at 100 µM but not mutagenic. O-Acetyl benzohydroxamate, a mutagen, was prepared with a ¹⁴C label in the carbonyl carbon atom of the benzoyl group and was shown to form an adduct in vitro with DNA and polyguanylic acid. The level of binding was 1 mol of ¹⁴C per 5 x 10⁴ mol of DNA phosphate and 1 mol of ¹⁴C per 10⁵ mol of polyguanylic acid phosphate.

¹ This work was supported by Grant 2-P01-ES00597-09 from the National Institute of Environmental Health Sciences, USPHS.

² To whom requests for reprints should be addressed.

Received 5/ 2/80. Accepted 9/ 2/80.