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Influence of the Aryl Group on the Reaction of Glucuronides of N-Arylacethydroxamic Acids with Polynucleotides¹

Veterans Administration Hospital and Department of Urology, University of Tennessee Center for the Health Sciences, Memphis, Tennessee 38104

The reactions of the glucuronide conjugates of the carcinogens N-hydroxy-2-acetylaminofluorene (N-hydroxy-AAF), N-hydroxy-4-acetylaminostilbene (N-hydroxy-AAS), N-hydroxy-4-acetylaminobiphenyl (N-hydroxy-AABP), and N-hydroxy-2-acetylaminophenanthrene (N-hydroxy-AAP) with transfer RNA, ribosomal RNA, DNA, polyadenylate, polyguanylate, polyuridylate, polycytidylate, poly(adenylate, guanylate), and poly(guanylate, uridylate) were studied. The relative order of reactivity of these glucuronides with nucleic acids, measured by the covalent binding of the aryl group labeled with ³H or ¹⁴C, was glucuronide of N-hydroxy-AAF > glucuronide of N-hydroxy-AAS > glucuronide of N-hydroxy-AABP > glucuronide of N-hydroxy-AAP. The glucuronide of N-hydroxy-AAP showed only marginal or negligible reactivity. The glucuronide of N-hydroxy-AAF showed greater reactivity with polyguanylate than with polyadenylate, but the reverse was true for the glucuronide of N-hydroxy-AAS. Both of these glucuronides had much lower extents of reaction with polyuridylate and polycytidylate. Except for the reaction of the glucuronide of N-hydroxy-AABP with polyadenylate, there was no detectable reaction of this glucuronide or the glucuronide of N-hydroxy-AAP with the homopolynucleotides. Under comparable conditions the glucuronide conjugates of N-hydroxy-AAF, N-hydroxy-AAS, and N-hydroxy-AABP demonstrated greater reactivity with poly(adenylate, guanylate) and poly(guanylate, uridylate) than with the homopolynucleotides. Furthermore, the synthesis of two new glucuronide conjugates, those of N-hydroxy-AAS and N-hydroxy-AAP, is described.

¹ This work was supported by United States Veterans Administration Project 4323-01 and USPHS Research Grant CA-05490 from the National Cancer Institute.

Received 8/12/76. Accepted 10/29/76.

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