Characterisation of estrone-nucleic acid adducts formed by reaction of 3,4-estrone-o-quinone with 2'-deoxynucleosides/deoxynucleotides using capillary liquid chromatography/electrospray ionization mass spectrometry

Rapid Communications in Mass Spectrometry : RCM
Crispina BorgesEddy L Esmans

Abstract

Xenobiotic and endobiotic molecules can react with DNA leading to formation of so-called DNA adducts. This modified DNA can be repaired enzymatically, but, if not, these modifications are believed to be responsible for the initiation of carcinogenic processes. Hence, we studied the interaction of 2'-deoxynucleosides and 2'-deoxynucleotides with 3,4-estronequinone (3,4-E(1)Q), a metabolite of estrone (E(1)) and a supposed carcinogen. These estrone-nucleic acid adducts were analysed by capillary liquid chromatography (CapLC) coupled to electrospray ionization mass spectrometry (ESI-MS). Knowledge of their behaviour from in vitro studies is a prerequisite for detecting adducts in in vivo studies. Our initial attempts to synthesise nucleos(t)ide adducts of 3,4-E(1)Q in an aprotic solvent (dimethylformamide) yielded no adducts. However, under acidic aqueous conditions, adducts were obtained. With dGuo, a dGuo adduct was found in addition to a Gua adduct. Earlier publications on adduct formation in protic solvents failed to report formation of any adduct with dAdo. A N(3)-Ade adduct was reported upon reaction of 3,4-E(1)Q with Ade base and with DNA. With dAdo, we obtained two nucleoside adducts and six Ade adducts due to loss of 2'-d...Continue Reading

References

Nov 1, 1976·Steroids·G Stubenrauch, R Knuppen
Nov 1, 1984·Journal of Steroid Biochemistry·Y J Abul-Hajj
Feb 1, 1993·Pharmacology & Therapeutics·C P Martucci, J Fishman
Jan 1, 1996·Annual Review of Pharmacology and Toxicology·J D Yager, J G Liehr
Jul 1, 1996·Chemical Research in Toxicology·D E StackE L Cavalieri
Apr 1, 1997·Chemical Research in Toxicology·A AkanniY J Abul-Hajj
Oct 6, 1997·Proceedings of the National Academy of Sciences of the United States of America·E L CavalieriE G Rogan
Oct 20, 1998·Chemical Research in Toxicology·J L BoltonS Qiu
Mar 5, 1999·Mutation Research·D Roy, J G Liehr
Aug 30, 2000·Journal of the National Cancer Institute. Monographs·J D Yager
Aug 30, 2000·Journal of the National Cancer Institute. Monographs·E CavalieriD Roy
Aug 30, 2000·Journal of the National Cancer Institute. Monographs·C R JefcoateL Berstein
Aug 30, 2000·Journal of the National Cancer Institute. Monographs·R RaftogianisJ Weisz
Jan 17, 2003·Journal of the National Cancer Institute·Katharine Miller
May 24, 2003·Best Practice & Research. Clinical Endocrinology & Metabolism·P Kenemans, A Bosman
Nov 19, 2003·The Journal of Steroid Biochemistry and Molecular Biology·W YueE L Cavalieri

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Citations

Jul 29, 2006·Journal of the American Society for Mass Spectrometry·Courtney L ShermanSean M Kerwin
Mar 24, 2016·Analytical and Bioanalytical Chemistry·Maria RajaSonia Sentellas

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