Generation of guanine-thymine cross-links in human cells by one-electron oxidation mechanisms - PubMed (original) (raw)
. 2013 Jul 15;26(7):1031-3.
doi: 10.1021/tx400158g. Epub 2013 Jun 11.
Affiliations
- PMID: 23734842
- PMCID: PMC3812307
- DOI: 10.1021/tx400158g
Generation of guanine-thymine cross-links in human cells by one-electron oxidation mechanisms
Guru S Madugundu et al. Chem Res Toxicol. 2013.
Abstract
The one-electron oxidation of cellular DNA in cultured human HeLa cells initiated by intense nanosecond 266 nm laser pulse irradiation produces cross-links between guanine and thymine bases (G*-T*), characterized by a covalent bond between C8 guanine (G*) and N3 thymine (T*) atoms. The DNA lesions were quantified by isotope dilution LC-MS/MS methods in the multiple reaction-monitoring mode using isotopically labeled [(15)N, (13)C]-nucleotides as internal standards. Among several known pyrimidine and 8-oxo-7,8-dihydroguanine lesions, the G*-T* cross-linked lesions were detected at levels of ~0.21 and 1.19 d(G*-T*) lesions per 10(6) DNA bases at laser intensities of 50 and 280 mJ/cm(2)/pulse, respectively.
Conflict of interest statement
The authors declare no competing financial interest.
Figures
Chart 1
Structures of DNA lesions.
Similar articles
- Oxidation of single-stranded oligonucleotides by carbonate radical anions: generating intrastrand cross-links between guanine and thymine bases separated by cytosines.
Crean C, Uvaydov Y, Geacintov NE, Shafirovich V. Crean C, et al. Nucleic Acids Res. 2008 Feb;36(3):742-55. doi: 10.1093/nar/gkm1092. Epub 2007 Dec 15. Nucleic Acids Res. 2008. PMID: 18084033 Free PMC article. - Generation of guanine-thymidine cross-links in DNA by peroxynitrite/carbon dioxide.
Yun BH, Geacintov NE, Shafirovich V. Yun BH, et al. Chem Res Toxicol. 2011 Jul 18;24(7):1144-52. doi: 10.1021/tx200139c. Epub 2011 May 4. Chem Res Toxicol. 2011. PMID: 21513308 Free PMC article. - Structural, energetic and dynamic properties of guanine(C8)-thymine(N3) cross-links in DNA provide insights on susceptibility to nucleotide excision repair.
Ding S, Kropachev K, Cai Y, Kolbanovskiy M, Durandina SA, Liu Z, Shafirovich V, Broyde S, Geacintov NE. Ding S, et al. Nucleic Acids Res. 2012 Mar;40(6):2506-17. doi: 10.1093/nar/gkr1087. Epub 2011 Dec 1. Nucleic Acids Res. 2012. PMID: 22135299 Free PMC article. - One-electron oxidation reactions of purine and pyrimidine bases in cellular DNA.
Cadet J, Wagner JR, Shafirovich V, Geacintov NE. Cadet J, et al. Int J Radiat Biol. 2014 Jun;90(6):423-32. doi: 10.3109/09553002.2013.877176. Epub 2014 Apr 3. Int J Radiat Biol. 2014. PMID: 24369822 Free PMC article. Review. - The Two Faces of the Guanyl Radical: Molecular Context and Behavior.
Chatgilialoglu C. Chatgilialoglu C. Molecules. 2021 Jun 9;26(12):3511. doi: 10.3390/molecules26123511. Molecules. 2021. PMID: 34207639 Free PMC article. Review.
Cited by
- Translesion synthesis past guanine(C8)-thymine(N3) intrastrand cross-links catalyzed by selected A- and Y-family polymerases.
Lee YA, Lee YC, Geacintov NE, Shafirovich V. Lee YA, et al. Mol Biosyst. 2016 May 24;12(6):1892-900. doi: 10.1039/c6mb00160b. Mol Biosyst. 2016. PMID: 27102383 Free PMC article. - Traceless Tandem Lesion Formation in DNA from a Nitrogen-Centered Purine Radical.
Zheng L, Greenberg MM. Zheng L, et al. J Am Chem Soc. 2018 May 23;140(20):6400-6407. doi: 10.1021/jacs.8b02828. Epub 2018 May 8. J Am Chem Soc. 2018. PMID: 29738242 Free PMC article. - 5,6-Dihydropyrimidine peroxyl radical reactivity in DNA.
San Pedro JM, Greenberg MM. San Pedro JM, et al. J Am Chem Soc. 2014 Mar 12;136(10):3928-36. doi: 10.1021/ja412562p. Epub 2014 Feb 28. J Am Chem Soc. 2014. PMID: 24579910 Free PMC article. - Radiation-mediated formation of complex damage to DNA: a chemical aspect overview.
Ravanat JL, Breton J, Douki T, Gasparutto D, Grand A, Rachidi W, Sauvaigo S. Ravanat JL, et al. Br J Radiol. 2014 Mar;87(1035):20130715. doi: 10.1259/bjr.20130715. Br J Radiol. 2014. PMID: 24472775 Free PMC article. Review. - Formation and repair of oxidatively generated damage in cellular DNA.
Cadet J, Davies KJA, Medeiros MH, Di Mascio P, Wagner JR. Cadet J, et al. Free Radic Biol Med. 2017 Jun;107:13-34. doi: 10.1016/j.freeradbiomed.2016.12.049. Epub 2017 Jan 2. Free Radic Biol Med. 2017. PMID: 28057600 Free PMC article. Review.
References
- Moraes MC, Neto JB, Menck CF. Front Biosci. 2012;17:1362–1388. - PubMed
- Steenken S, Jovanovic SV. J Am Chem Soc. 1997;119:617–618.
- Cadet J, Carell T, Cellai L, Chatgilialoglu C, Gimisis T, Miranda M, O’Neill P, Ravanat JL, Robert M. Chimia. 2008;62:742–749.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources