Chemical and structural characterization of interstrand cross-links formed between abasic sites and adenine residues in duplex DNA

Nucleic Acids Research
Nathan E PriceKent S Gates

Abstract

A new type of interstrand DNA-DNA cross-link between abasic (Ap) sites and 2'-deoxyadenosine (dA) residues was recently reported, but the chemical structure and properties of this lesion were not rigorously established. Here we characterized the nucleoside cross-link remnant released by enzymatic digestion of duplex DNA containing the dA-Ap cross-link. A synthetic standard was prepared for the putative nucleoside cross-link remnant 6 in which the anomeric carbon of the 2-deoxyribose residue was connected to the exocyclic N(6)-amino group of dA. Liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis showed that the synthetic material 6: matched the authentic cross-link remnant released by enzymatic digestion of cross-linked DNA. These findings establish the chemical structure of the dA-Ap cross-link released from duplex DNA and may provide methods for the detection of this lesion in cellular DNA. Both the nucleoside cross-link remnant 6: and the cross-link in duplex DNA were quite stable at pH 7 and 37°C, suggesting that the dA-Ap cross-link could be a persistent lesion with the potential to block the action of various DNA processing enzymes.

References

May 1, 1977·Proceedings of the National Academy of Sciences of the United States of America·J M EssigmannG N Wogan
Nov 23, 2000·Chemical Research in Toxicology·M WangS S Hecht
Dec 16, 2000·Carbohydrate Research·J P Dworkin, S L Miller
May 7, 2002·Nature Reviews. Cancer·Laurence H Hurley
Jan 8, 2003·Journal of the American Chemical Society·Ivan D KozekovThomas M Harris
Jul 2, 2003·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Marcus S CookeJoseph Lunec
Dec 3, 2003·Organic & Biomolecular Chemistry·Stéphane Mons, George W J Fleet
Apr 28, 2004·Current Opinion in Genetics & Development·Errol C FriedbergRoger A Schultz
Aug 3, 2005·The Journal of Antibiotics·Yasuhiro IgarashiTamotsu Furumai
Feb 20, 2007·Chemical Research in Toxicology·Natalia TretyakovaMelissa Goggin
Oct 8, 2009·Journal of the American Chemical Society·Lirui Guan, Marc M Greenberg
Oct 9, 2009·The New England Journal of Medicine·Jan H J Hoeijmakers
Oct 31, 2009·Carcinogenesis·Nidhi ShrivastavJohn M Essigmann
Dec 16, 2010·Chemical Research in Toxicology·Kun LuJames A Swenberg
Feb 28, 2013·Chemical Reviews·Natalia TretyakovaSrikanth Kotapati
May 28, 2013·Chemistry & Biology·Kahlin Cheung-OngCorey Nislow
Feb 11, 2014·Journal of the American Chemical Society·Nathan E PriceKent S Gates

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Citations

Apr 28, 2016·Bioorganic & Medicinal Chemistry Letters·Michael J CatalanoKent S Gates
Jun 17, 2016·Acta Crystallographica. Section E, Crystallographic Communications·Michael J CatalanoKent S Gates
Dec 3, 2016·PloS One·Konstantin OkonechnikovFernando Garcia-Alcalde
May 10, 2017·Chemical Research in Toxicology·Suzanne J Admiraal, Patrick J O'Brien
Apr 20, 2017·Chembiochem : a European Journal of Chemical Biology·Maryam Imani NejadKent S Gates
May 23, 2017·Nucleic Acids Research·Zhiyu YangKent S Gates
Nov 9, 2017·Scientific Reports·Raffaele SaladinoErnesto Di Mauro
Mar 8, 2019·Nature·R Alex WuJohannes C Walter
Sep 4, 2020·The Journal of Biological Chemistry·Alyssa A RodriguezBrandt F Eichman
Mar 31, 2021·Chemical Research in Toxicology·Jacqueline Gamboa VarelaKent S Gates
Jun 13, 2018·Biochemistry·Ruixiang WangMarc M Greenberg
Jul 2, 2019·ACS Chemical Biology·Maryam Imani NejadKent S Gates

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Methods Mentioned

BETA
column chromatography
deamination
NMR
electrophoresis

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