This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via Google Scholar Google Scholar Articles by Miller, E. C. Articles by Miller, J. A. Search for Related Content PubMed PubMed Citation Articles by Miller, E. C. Articles by Miller, J. A.

Methylmercapto-4-acetylaminostilbenes as Products of the Reaction of N-Acetoxy-4-acetylaminostilbene with Methionine and as Degradation Products of Liver Protein from Rats Given N-Hydroxy-4-acetylaminostilbene¹

McArdle Laboratory for Cancer Research, University of Wisconsin Medical Center, Madison, Wisconsin 53706 [E. C. M., B. W. B., J. A. M.], and The Fred Hutchinson Cancer Research Center, Seattle, Washington 98104 [T. L. F.]

The reaction of the carcinogenic electrophile N-acetoxy-4-acetylaminostilbene with methionine at neutral pH yielded ß-methylmercapto-4-acetylaminostilbene as the major product and 3-methylmercapto-4-acetylaminostilbene as a minor product. Two other products were also formed. One of these had the apparent molecular weight (283) of a methylmercapto-4-acetylaminostilbene; it was not identical with 2-, 2', 3'-, or 4'-methylmercapto-4-acetylaminostilbene. The second product had an apparent molecular weight of 301 and appeared to be a methylmercapto derivative. It was formed in larger amounts at slightly acidic pH's, and its yield was inversely related to that of ß-methylmercapto-4-acetylaminostilbene. 3- and ß-methylmercapto-4-acetylaminostilbene were also obtained on alkaline degradation of the liver protein from rats that had received i.p. injections of N-hydroxy-4-acetylaminostilbene. These data provide evidence that an ester of N-hydroxy-4-acetylaminostilbene or a derivative with similar electrophilic reactivity is formed from N-hydroxy-4-acetylaminostilbene in the rat liver.

¹ Supported at the University of Wisconsin by Grant CA-07175 of the National Cancer Institute, USPHS, and at The Fred Hutchinson Cancer Research Center by Grant CA-14500.

Received 2/19/74. Accepted 5/15/74.