Free-radical-induced formation of an 8,5'-cyclo-2'-deoxyguanosine moiety in deoxyribonucleic acid - PubMed (original) (raw)
Free-radical-induced formation of an 8,5'-cyclo-2'-deoxyguanosine moiety in deoxyribonucleic acid
M Dizdaroglu. Biochem J. 1986.
Abstract
Isolation and identification of a novel .OH-induced product, namely an 8,5'-cyclo-2'-deoxyguanosine moiety, in DNA and 2'-deoxyguanosine are described. .OH radicals were generated in dilute aqueous solutions by gamma-irradiation. Analyses of 2'-deoxyguanosine and enzymic hydrolysates of DNA by gas chromatography-mass spectrometry (g.c.-m.s.) after trimethylsilylation showed the presence of 8,5-cyclo-2'-deoxyguanosine on the basis of its fragment ions. This product was isolated by h.p.l.c. Its u.v. and n.m.r. spectra taken were in agreement with the structure suggested by its mass spectrum. Exact masses of the typical ions from the mass spectrum of the trimethylsilyl derivative of this product were measured by high-resolution m.s. The values found were in excellent agreement with the theoretical mass derived from the suggested fragmentation patterns. Both (5'R)- and (5'S)-epimers of 8,5'-cyclo-2'-deoxyguanosine were observed. These two diastereomers were separated from each other by g.c. as well as by h.p.l.c. The assignment of the epimers was accomplished on the basis of the n.m.r. data. The formation of 8,5'-cyclo-2'-deoxyguanosine was suppressed by the presence of O2 in the solutions. The use of g.c.-m.s. with the selected-ion monitoring technique facilitated the detection of 8,5'-cyclo-2'-deoxyguanosine in DNA at radiation doses as low as 1 Gy. Its mechanism of formation probably involves hydrogen atom abstraction by .OH radicals from the C-5' of the 2'-deoxyguanosine moiety followed by intramolecular cyclization with the formation of a covalent bond between the C-5' and C-8 and subsequent oxidation of the resulting N-7-centred radical.
Similar articles
- Mass spectrometric assays for the tandem lesion 8,5'-cyclo-2'-deoxyguanosine in mammalian DNA.
Jaruga P, Birincioglu M, Rodriguez H, Dizdaroglu M. Jaruga P, et al. Biochemistry. 2002 Mar 19;41(11):3703-11. doi: 10.1021/bi016004d. Biochemistry. 2002. PMID: 11888287 - Formation of an 8-hydroxyguanine moiety in deoxyribonucleic acid on gamma-irradiation in aqueous solution.
Dizdaroglu M. Dizdaroglu M. Biochemistry. 1985 Jul 30;24(16):4476-81. doi: 10.1021/bi00337a032. Biochemistry. 1985. PMID: 4052410 - (5'S)- and (5'R)-5',8-cyclo-2'-deoxyguanosine: mechanistic insights on the 2'-deoxyguanosin-5'-yl radical cyclization.
Chatgilialoglu C, Bazzanini R, Jimenez LB, Miranda MA. Chatgilialoglu C, et al. Chem Res Toxicol. 2007 Dec;20(12):1820-4. doi: 10.1021/tx700282x. Epub 2007 Nov 8. Chem Res Toxicol. 2007. PMID: 17988100 - 8,5'-Cyclopurine-2'-deoxynucleosides in DNA: mechanisms of formation, measurement, repair and biological effects.
Jaruga P, Dizdaroglu M. Jaruga P, et al. DNA Repair (Amst). 2008 Sep 1;7(9):1413-25. doi: 10.1016/j.dnarep.2008.06.005. Epub 2008 Jul 17. DNA Repair (Amst). 2008. PMID: 18603018 Review. - Purine 5',8-cyclonucleoside lesions: chemistry and biology.
Chatgilialoglu C, Ferreri C, Terzidis MA. Chatgilialoglu C, et al. Chem Soc Rev. 2011 Mar;40(3):1368-82. doi: 10.1039/c0cs00061b. Epub 2011 Jan 11. Chem Soc Rev. 2011. PMID: 21221459 Review.
Cited by
- Evolutionary Origins of DNA Repair Pathways: Role of Oxygen Catastrophe in the Emergence of DNA Glycosylases.
Prorok P, Grin IR, Matkarimov BT, Ishchenko AA, Laval J, Zharkov DO, Saparbaev M. Prorok P, et al. Cells. 2021 Jun 24;10(7):1591. doi: 10.3390/cells10071591. Cells. 2021. PMID: 34202661 Free PMC article. Review. - Advances in Nucleic Acid Research: Exploring the Potential of Oligonucleotides for Therapeutic Applications and Biological Studies.
Moccia M, Pascucci B, Saviano M, Cerasa MT, Terzidis MA, Chatgilialoglu C, Masi A. Moccia M, et al. Int J Mol Sci. 2023 Dec 21;25(1):146. doi: 10.3390/ijms25010146. Int J Mol Sci. 2023. PMID: 38203317 Free PMC article. Review. - Oxidatively Generated Guanine(C8)-Thymine(N3) Intrastrand Cross-links in Double-stranded DNA Are Repaired by Base Excision Repair Pathways.
Talhaoui I, Shafirovich V, Liu Z, Saint-Pierre C, Akishev Z, Matkarimov BT, Gasparutto D, Geacintov NE, Saparbaev M. Talhaoui I, et al. J Biol Chem. 2015 Jun 5;290(23):14610-7. doi: 10.1074/jbc.M115.647487. Epub 2015 Apr 22. J Biol Chem. 2015. PMID: 25903131 Free PMC article. - Dual Inhibitors of 8-Oxoguanine Surveillance by OGG1 and NUDT1.
Tahara YK, Kietrys AM, Hebenbrock M, Lee Y, Wilson DL, Kool ET. Tahara YK, et al. ACS Chem Biol. 2019 Dec 20;14(12):2606-2615. doi: 10.1021/acschembio.9b00490. Epub 2019 Oct 29. ACS Chem Biol. 2019. PMID: 31622553 Free PMC article. - The Effect of 8,5'-Cyclo 2'-deoxyadenosine on the Activity of 10-23 DNAzyme: Experimental and Theoretical Study.
Cieślak M, Karwowski BT. Cieślak M, et al. Int J Mol Sci. 2024 Feb 21;25(5):2519. doi: 10.3390/ijms25052519. Int J Mol Sci. 2024. PMID: 38473767 Free PMC article.
References
- Z Naturforsch B. 1968 Aug;23(8):1034-43 - PubMed
- Radiat Res. 1985 Dec;104(3):272-83 - PubMed
- Radiat Res. 1976 Mar;65(3):414-22 - PubMed
- Int J Radiat Biol Relat Stud Phys Chem Med. 1978 Jun;33(6):563-9 - PubMed
- Biochem Biophys Res Commun. 1978 Aug 14;83(3):1061-6 - PubMed
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous