INFLUENCE OF ARYL GROUP ON REACTION OF GLUCURONIDES OF N-ARYLACETHYDROXAMIC ACIDS WITH POLYNUCLEOTIDES
- 1 January 1977
- journal article
- research article
- Vol. 37 (2) , 524-528
Abstract
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 [yeast] tRNA, rRNA, [rat liver] 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 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. Synthesis of 2 new glucuronide conjugates, those of N-hydroxy-AAS and N-hydroxy-AAP, is described.This publication has 7 references indexed in Scilit:
- REACTIONS IN VITRO OF SOME TISSUE NUCLEOPHILES WITH GLUCURONIDE OF CARCINOGEN N-HYDROXY-2-ACETYLAMINOFLUORENE1968
- Biosynthesis and Studies of the Alkaline Sensitivity of the NO-Glucuronide of the Carcinogen N-2-Fluorenylacethydroxamic Acid*Biochemistry, 1967
- N-HYDROXY METABOLITES OF 2-ACETYLAMINOPHENANTHRENE AND 7-FLUORO-2-ACETYLAMINOFLUORENE AS PROXIMATE CARCINOGENS IN RAT1966
- A fast, simple and reliable method for the microdetermination of phosphorus in biological materialsAnalytical Biochemistry, 1964
- CARCINOGENESIS + INHIBITION OF WALKER 256 TUMOR IN RAT BY TRANS-4-ACETYLAMINOSTILBENE ITS N-HYDROXY METABOLITE + RELATED COMPOUNDS1964
- N- AND RING-HYDROXYLATION OF 2-ACETYLAMINOFLUORENE AND FAILURE TO DETECT N-ACETYLATION OF 2-AMINOFLUORENE IN DOG1963
- Phosphorus Assay in Column ChromatographyJournal of Biological Chemistry, 1959