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Studies on the N-Hydroxylation and Carcinogenicity of 4-Aminoazobenzene and Related Compounds¹

McArdle Laboratory for Cancer Research, Medical Center, University of Wisconsin, Madison, Wisconsin

N-Hydroxy-N-acetyl-4-aminoazobenzene (N-hydroxy-AAB) was excreted in conjugated form in the urine of rats, mice, or hamsters given injections of 4-aminoazobenzene (AB) or N-acetyl-4-aminoazobenzene (AAB) and in the urine of rats given injections of N,N-dimethyl- or N-methyl-4-aminoazobenzene. AAB and 3- and 4'-hydroxy-AAB were also excreted under these conditions.

Like AAB and AB, neither N-hydroxy-AAB nor N-hydroxy-AB was carcinogenic for rats under the conditions studied. The tests used were long-term feeding of N-hydroxy-AAB in the diet of rats, repeated i.p. injections of N-hydroxy-AB, N-hydroxy-AAB, or N-acetoxy-AAB into young female rats, and repeated s.c. injections of the cupric chelate of N-hydroxy-AAB into young female rats.

The syntheses of the following new compounds are described: N-hydroxy-AB, N-acetoxy-AAB, and N-hydroxy-AAB.

¹ This investigation was supported by a research training grant, CRTY-5002, and by Program-Project Grant CA-07175 of the National Cancer Institute, USPHS; by a grant from the Jane Coffin Childs Memorial Fund for Medical Research; and by the Alexander and Margaret Stewart Trust Fund.

² Dr. Sato's address is Department of Education, Hirosaki University, Hirosaki, Aomori-ken, Japan. Requests for reprints should be sent either to Dr. Sato in Japan or to Dr. J. A. Miller at the McArdle Laboratory for Cancer Research.

Received 1/28/66.