Arylhydroxylamine-induced ribonucleic acid chain cleavage and chromatographic analysis of arylamine-ribonucleic acid adducts

Chemico-biological Interactions
J B VaughtC M King

Abstract

Reaction of N-hydroxy-2-aminofluorene (N-OH-AF) with rRNA at pH 5.0 decreased the molecular weight of the polynucleotide. Toluene-soluble aryl derivatives were released on hydrolysis of fluorenylamine- and biphenylamine-substituted RNA by treatment with venom phosphodiesterase and alkaline phosphatase. These data suggested that arylhydroxylamines, activated by incubation at pH 5.0 or by enzymatic O-acetylation, might react with the phosphate group of RNA to give unstable phosphate triesters. Spontaneous hydrolysis of these triesters would result in cleavage of the polynucleotide chain. Further enzymatic hydrolysis of the phosphate esters would yield nonpolar arylamine derivatives. Enzymatically degraded 4-aminobiphenyl(ABP)-RNA adducts were examined by high performance liquid chromatography (HPLC) for the presence of a putative phosphorylated adduct. Synthetic standards of the C-8-guanosine monophosphate-ABP adduct (ABP-GMP) and o-aminobiphenyl-O-phosphate were used as markers in the analysis of the digested RNA. A phosphate adduct of ABP was undetectable by these methods. The data also indicated that the ABP-GMP formed in the acyltransferase-mediated binding of N-hydroxy-4-acetylaminobiphenyl (N-OH-AABP) to RNA is readily degr...Continue Reading

References

Jul 1, 1977·Journal of Toxicology and Environmental Health·B Singer
Aug 12, 1977·Science·H B GamperM Calvin
Aug 23, 1968·Biochimica Et Biophysica Acta·C C Irving, R A Veazey
Sep 22, 1965·Biochemical and Biophysical Research Communications·E Kriek
Mar 1, 1981·Chemico-biological Interactions·M S Lee, C M King

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Citations

Feb 28, 1983·Biochemical and Biophysical Research Communications·K C MortonL J Marnett
Jan 1, 1982·Drug Metabolism Reviews·B Lindeke

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