Reactions of beta-propiolactone, beta-butyrolactone and gamma-butyrolactone with nucleic acids

Chemico-biological Interactions
K Hemminki

Abstract

Reactivity of beta-propiolactone, beta-butyrolactone and gamma-butyrolactone with guanosine, RNA, DNA and 4-(p-nitrobenzyl)pyridine was studied. beta-Propiolactone was 50--100 times more reactive with all the nucleophiles than beta-butyrolactone whereas gamma-butyrolactone was completely inactive. The rate of alkylation by the lactones was guanosine greater than RNA = denatured DNA greater than double-stranded DNA. The type of the adducts formed were characterized by fluorescence and ultraviolet spectroscopy. Similar alkylation products were formed by the two lactones. The main sites alkylated were N-1 at adenosine, N-3 at cytidine and N-7 at guanosine. The results suggest that the carcinogenic potency of the lactones correlates with their reactivity rather than with specificity of the adducts formed.

Citations

Apr 1, 1983·Archives of Toxicology·K Hemminki
Feb 26, 1982·Biochemical and Biophysical Research Communications·E J Hunt, R C Shank
Apr 5, 2014·SAR and QSAR in Environmental Research·C A CarrasquerS L Cunningham
Apr 7, 2012·Chemical Research in Toxicology·Rafael Gómez-BombarelliJulio Casado
Aug 21, 2010·Critical Reviews in Toxicology·S J Enoch, M T D Cronin
Sep 18, 2010·Chemical Research in Toxicology·Ovanes MekenyanE Maria Donner
Feb 15, 2020·Chemical Research in Toxicology·Eva Španinger, Urban Bren

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