DNA damage in a solution containing copper(II) ions and ascorbic acid
Effect of the presence of sulfite
DOI:
https://doi.org/10.1590/s2175-979020200004181084Keywords:
Gel electrophoresis. DNA damage. copper. ascorbic acid. sulfite.Abstract
Some antioxidant compounds have a pro-oxidant effect in the presence of transition metal ions, due to the reduction of Mn+ to M(n-1)+ with simultaneous formation of free radicals, which then promote DNA damage. In the present study, we evaluated the pUC19 DNA damage in a solution containing Cu(II) and ascorbic acid (AA) or S(IV) saturated with air by agarose gel electrophoresis. Our results showed that this damage decreases if AA and S(IV) are simultaneously added. This study also illustrates the importance of Cu(II) in this process, as no DNA damage was observed when AA or S(IV) were present in the absence of this metallic ion. Our data showed that DNA preservation depends on the concentration of AA and S(IV) and occurs when the [S(IV)]:[AA] ratio ranges from 1:1 to 20:1. Absorbance measurements and thermodynamic data show that no reaction occurs between AA and S(IV) when this mixture (pH 5.5) is added to pUC-19 DNA. The presence of dissolved oxygen may be the cause of AA consumption in the mixture of these two antioxidants, which subsequently decreases DNA damage.
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Aguiar A, Ferraz A, Contreras D, Rodríguez J. Mecanismo e aplicações da reação de Fenton assistida por compostos fenólicos. Quim Nova. 2007;30(3):623-8.
Alipázaga MV, Moreno RGM, Linares E, Medeiros MHG, Coichev N. DNA damage by sulfite autoxidation catalyzed by cobalt complexes. Dalton Trans. 2008;(41):5636-44.
Alipázaga MV, Moya HD, Coichev N. Effect of some antioxidants on oxidative DNA damage induced by autoxidation of microquantities of sulfite in the presence of Ni(II)/Gly-GlyL-His. J. Coord. Chem. 2010;63(14-16):2450-60.
Alipázaga VM, Cerchiaro G, Moya HD, Coichev N. Oxidative DNA damage mediated by Cu2+ and Cu+ complexes in the presence of S(IV). J Braz Chem Soc. 2009;20(7):1302-12.
Aruoma OI, Halliwell B, Gajewski E, Dizdaroglu M. Copper ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem J. 1991;273(Pt 3):601-4.
Asad SF, Singh S, Ahmad A, Hadi SM. Bilirubin/biliverdinCu(II) induced DNA breakage; reaction mechanism and biological significance. Toxicol Lett. 2002;131(3):181-9.
Blanco M, Iturriaga H, Maspoch S, Tarin P. A simple method for spectrophotometric determination of two-components with overlapped spectra. J Chem Educ. 1989;66(2):178-80.
Cerqueira FM, Medeiros MHG, Augusto O. Antioxidantes dietéticos: controvérsias e perspectivas. Quim Nova. 2007;30(2):441-9.
Costa P, Monteiro A. Benefícios dos antioxidantes na alimentação. Revista Saúde e Pesquisa. 2009;2(1):87-90.
Dong-Sheng G, Xiao-Ying Y, Jie-Qing L. Influence of Cu(II) on the interaction of sulfite with DNA. Spectrochim. Acta, Part A. 2006;65(2):459-462.
Favero DM, Ribeiro CSG, Aquino AD. Sulfitos importância na indústria alimentícia e seus possíveis malefícios à população. Segurança Alimentar e Nutricional. 2011;18(1):11-20.
Frelon S, Douki T, Favier A, Cadet J. Hydroxyl radical is not the main reactive species involved in the degradation of DNA bases by copper in the presence of hydrogen peroxide. Chem Res Toxicol. 2003;16(2):191-7.
Hajhashemi V, Vaseghi G, Pourfarzam M, Abdollahi A. Are antioxidants helpful for disease prevention? Res Pharm Sci. 2010;5(1):1-8.
Harris DC. Aplicações da espectrofotometria. In: Harris DC, editor. Análise Química Quantitativa. 6th ed. Rio de Janeiro: LTC. 2005. p. 424-450.
Husain S, Hadi SM. Strand scission in DNA induced by L-DOPA in the presence of Cu(II). FEBS Lett. 1995;364(1):75-8.
Iwamoto T, Hiraku Y, Oikawa S, Mizutanoi H, Kojima M, Kawanishi S. Oxidative DNA damage induced by photodegradation products of 3’-azido-3’-deoxythymidine. Arch Biochem Biophys. 2003;416(2):155-63.
Jameton RA, Muller JG, Burrows CJ. Oxidative DNA damage from sulfite autoxidation catalyzed by manganese(III). C R Chimie. 2002;5(5):461-6.
Kawanishi S, Yamamoto K, Inoue S. Site-specific DNA damage induced by sulfite in the presence of cobalt(II) ion. Role of sulfate radical. Biochem Pharmacol. 1989;38(20):3491-96.
Lee G, Rossi MV, Coichev N, Moya HD. The reduction of Cu(II)/neocuproine complexes by some polyphenols. Analytical application in wine samples. Food Chemistry. 2011;126:679-86.
Lesniak W, Harris WR, Kravitz JY, Schacht J, Pecoraro VL. Solution chemistry of copper(II)-gentamicin complexes: relevance to metal-related aminoglycoside toxicity. Inorg Chem. 2003;42(5):1420-9.
Li Y, Trush MA. Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res. 1994;54(7 Suppl):1895s-8s.
Lurie J. Handbook of Analytical Chemistry. 2nd ed. Moscow: Mir Publishers; 1978. p. 300-313.
Manela-Azulay M, Mandarim-de-Lacerda CA, Perez MA, Filgueira AL, Cuzzi T. Vitamin C. An Bras Dermatol. 2003;78:265-74.
Moreno RGM, Alipázaga MV, Medeiros MHG, Coichev N. DNA damage induced by sulfite autoxidation catalyzed by copper(II)/tetraglycine complexes. Dalton Trans. 2005;(6):1101-7.
Moreno RGM. Estudo da lesão no DNA promovido pela autoxidação de S(IV) na presença de complexos de Cu(II)/ tetraglicina. [tese]. São Paulo: Instituto de Química, USP; 2005.
Ogawa K, Hiraku Y, Oikawa S, Murata M, Sugimura Y, Kawamura J, et al. Molecular mechanisms of DNA damage induced by procarbazine in the presence of Cu(II). Mutat. Res. 2003;539(1-2):145-155.
Oikawa S, Yamada K, Yamashita N, Tada-Oikawa S, Kawanishi S. N-acetylcysteine, a cancer chemopreventive agent, causes oxidative damage to cellular and isolated DNA. Carcinogenesis. 1999;20(8):1485-90.
Pedrosa LFC, Cozzolino SMF. Alterações metabólicas e funcionais do cobre em diabetes mellitus. Rev Nutr. 1999;12(3):213-224.
Rohenkohl C, Carniel A, Colpo E. Consumo de antioxidantes durante tratamento quimioterápico. Arquivos Brasileiros de Cirurgia Digestiva. 2011;24(1):107-12.
Roriz BC, Moya HD. Study of DNA damage caused by dipyrone in presence of some transition metal ions. Saudi Pharm J. 2017;25(7):961-6.
Sakano K, Oikawa S, Hiraku Y, Kawanishi S. Oxidative DNA damage induced by a melatonin metabolite, 6-hydroxymelatonin, via a unique non-o-quinone type of redox cycle. Biochem Pharmacol. 2004;68(9):1869-78.
Sies H, Stahl W. Vitamins E and C, β-carotene, and other carotenoids as antioxidants. Am J Clin Nutr. 1995;2(6):315-21.
Smith RM, Martell AE. Version 8.0. NIST critically selected stability constants of metal complexes database 46. [Computer program]. Gaithersburg: National Institute of Standards Technology; 2004.
Sugiyama M, Tsuzuki K, Ogura R. Effect of ascorbic acid on DNA damage, cytotoxicity, glutathione reductase, and formation of paramagnetic chromium in Chinese hamster V-79 cells treated with sodium chromate(VI). J Biol Chem. 1991;266(6):3383-6.
Win W, Cao Z, Peng X, Trush MA, Li Y. Different effects of genistein and resveratrol on oxidative DNA damage in vitro. Mutat Res. 2002;513(1-2):113-20.
Yamashita N, Murata M, Inoue S, Burkitt MJ, Milne L, Kawanishi S. Alpha-tocopherol induces oxidative damage to DNA in the presence of copper(II) ions. Chem Res Toxicol. 1998;11(8):855-62.
Yoshino M, Haneda M, Naruse M, Murakami K. Prooxidant activity of flavonoids: copper-dependent strand breaks and the formation of 8-hydroxy-2’-deoxyguanosine in DNA. Mol Genet Metab. 1999;68(4):468-72.
Zheng LF, Wei QY, Cai YJ, Fang JG, Zhou B, Yang L, Liu ZL. DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu (II) ions: mechanism and structure-activity relationship. Free Radic Biol Med. 2006;41(12):1807-16.
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