DNA alkylation by vinyl chloride metabolites: etheno derivatives or 7-alkylation of guanine?

Chemico-biological Interactions
R J LaibH M Bolt

Abstract

The state of the literature led to a re-investigation of the alkylation products caused by vinyl chloride metabolites in DNA. When rat liver microsomes, an NADPH-regenerating system, DNA and [14C]vinyl chloride were incubated and, when the DNA was subsequently re-isolated and (enzymatically) hydrolyzed, chromatograms (on Aminex A-6) showed the presence of 1,N6-ethenodeoxyadenosine, 3,N4-ethenodeoxycytidine and 7-N-(2-oxoethyl)guanine (the product of hydrolysis of 7-N-(2-oxoethyl)-deoxyguanosine). By contrast, when rats were exposed to [1,2-14C]vinyl chloride and when the liver DNA of these rats was subjected to similar procedures, no radioactive 'etheno' derivatives could be detected, but a radioactive peak was eluted with 7-N-(2-oxoethyl)guanine. This peak could be transformed into 7-N-(2-hydroxyethyl)guanine; the chromatographic behaviour of which was identical to the reference compound used by Ostermann-Golkar et al. (Biochem. biophys. Res. Commun., 76 (1977) 259). Thus, it is concluded that the compound described by these authors, 7-N-(2-oxoethyl)guanine is in fact the major product of base alkylation in DNA after exposure to vinyl chloride.

References

Jul 1, 1977·Journal of Toxicology and Environmental Health·B Singer
Sep 1, 1978·Chemico-biological Interactions·T Green, D E Hathway
Jun 8, 1976·Archives of Toxicology·H M BoltW Bolt
May 23, 1976·Biochemical and Biophysical Research Communications·S Osterman-GolkarC A Wachtmeister
Jul 1, 1967·The Biochemical Journal·K S Kirby, E A Cook
Jan 1, 1981·Carcinogenesis·E SchererP Emmelot
Oct 1, 1963·The Biochemical Journal·P D LAWLEY, P BROOKES

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Citations

Apr 1, 1983·Archives of Toxicology·K Hemminki
Jan 1, 1986·Journal of Cancer Research and Clinical Oncology·H M BoltH Ottenwälder
Sep 1, 1993·Chemico-biological Interactions·J J SolomonA Segal
Jan 1, 1985·Pharmacology & Therapeutics·A M Jeffrey
Jan 1, 1992·Pharmacology & Therapeutics·F P Guengerich
Jan 1, 1985·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·N J van Sittert, G de Jong
Mar 1, 1990·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·J Schlatter, W K Lutz
Sep 1, 1985·Toxicology Letters·P SimonH M Bolt
Aug 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·R W WisemanJ A Miller
Nov 15, 1991·Proceedings of the National Academy of Sciences of the United States of America·K C ChengL A Loeb
Feb 1, 1994·Proceedings of the National Academy of Sciences of the United States of America·M K DosanjhB Singer
Sep 1, 1985·Environmental Health Perspectives·P PolitzerK Jayasuriya
Dec 1, 1996·Environmental Health Perspectives·C BleasdaleB T Golding
Jan 1, 1982·Quarterly Reviews on Drug Metabolism and Drug Interactions·R J Laib
Sep 1, 1989·Drug and Chemical Toxicology·K DillS F Hallowell
Jan 1, 1994·Drug Metabolism Reviews·H BartschY Guichard
Jan 1, 1984·CRC Critical Reviews in Biochemistry·N J Leonard
Jan 1, 1983·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·H PeterH M Bolt
Jan 1, 1990·Toxicology and Industrial Health·R E Sotomayor, T F Collins
Jul 2, 2005·Critical Reviews in Toxicology·Hermann M Bolt
Jan 1, 1988·Critical Reviews in Toxicology·H M Bolt
Feb 1, 1990·Journal of Applied Toxicology : JAT·L JowaG F Kalf
Jun 17, 2021·Genes and Environment : the Official Journal of the Japanese Environmental Mutagen Society·F Peter Guengerich, Pratibha P Ghodke
May 1, 1985·Toxicology and Applied Pharmacology·E L LinM A Pereira
Jun 13, 2020·Chemical Research in Toxicology·Vernon E WalkerJames A Swenberg

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