A novel method using 8-hydroperoxy-2′-deoxyguanosine formation for evaluating antioxidative potency

Free Radical Research

Volumn 36, Issue 3, 2002, Pages 307-316

  Sakakibara, Hiroyuki ^a   Ashida, Hitoshi ^a   Kanazawa, Kazuki ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

8 Hydroperoxy dG; Antioxidant; Flavonoids; Genetic damage; Oxidative stress; Polyphenols

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2' AZOBIS(2 AMIDINOPROPANE); ANTIOXIDANT; ASCORBIC ACID; DEOXYGUANOSINE DERIVATIVE; DNA BASE; EPIGALLOCATECHIN GALLATE; QUERCETIN; REACTIVE OXYGEN METABOLITE; SCAVENGER;

ANTIOXIDANT ACTIVITY; ARTICLE; CANCER; CONTROLLED STUDY; DEGENERATIVE DISEASE; DIET SUPPLEMENTATION; DNA DAMAGE; DNA DETERMINATION; DRUG POTENCY; GENETIC DAMAGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY;

AMIDINES; ANTIOXIDANTS; DEOXYGUANOSINE; DRUG SYNERGISM; FREE RADICALS; INDICATORS AND REAGENTS; OXIDANTS; PICRATES; REACTIVE OXYGEN SPECIES;

EID: 0036521944     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715760290019336     Document Type: Article

References (50)

1. Guyton, K.Z. and Kensler, T.W. (1993) "Oxidative mechanisms in carcinogenesis", Br. Med, Bull. 49, 523-544.
2. Emerit, I. (1994) "Reactive oxygen species, chromosome mutation, and cancer: possible role of clastogenic factors in carcinogenesis", Free Radic. Biol. Med. 16, 99-109.
3. Marnett, L.J. (2000) "Oxyradicals and DNA damage", Carcinogenesis 21, 361-370.
4. Randerath, K., Zhou, G.-D., Monk, S.A. and Randerath, E. (1997) "Enhanced levels in neonatal rat liver of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxydeoxyguanosine), a major mutagenic oxidative DNA lesion", Carcinogenesis 18, 1419-1421.
5. Boiteux, S. and Radicella, J.P. (1999) "Base excision repair of 8-hydroxyguanosine protects DNA from endogenous oxidative stress", Biochemie 81, 59-67.
6. Nomoto, M., Yamaguchi, R., Kawamura, M., Kohno, K. and Kasai, H. (2000) "Analysis of 8-hydroxyguanine in rat kidney genomic DNA after administration of a renal carcinogen, ferric nitrilotriacetate", Carcinogenesis 20, 837-841.
7. Podmore, I.D., Cooper, D., Evans, M.D., Wood, M. and Lunec, J. (2000) "Simultaneous measurement of 8-oxo-2′deoxyguanosine and 8-oxo-2′-deoxyadenosine by HPLCMS/MS", Biochem. Biophys. Res. Commun. 275, 764-770.
8. Yamamoto, F., Kasai, H., Togashi, Y., Takeichi, N., Hori, T. and Nishimura, S. (1993) "Elevated level of 8-hydroxydeoxyguanosine in DNA of liver, kidneys, and brain of Long-Evans Cinnamon rats", Jpn. J. Cancer Res. 84, 508-511.
9. Kondo, S., Toyokuni, S., Tanaka, T., Hiai, H., Onodera, H., Kasai, H. and Imamura, M. (2000) "Overexpression of the hOGGI gene and high 8-hydroxy-2′-deoxyguanosine (8-OhdG ) lyase activity in human colorectal carcinoma: regulation mechanism of the 8-OHdG level in DNA", Clin. Cancer Res. 6, 1394-1400.
10. Foksinski, M., Kotzbach, R., Szymanski, W. and Olinski, R. (2000) "The level of typical biomarker of oxidative stress 8-hydroxy-2′deoxyguanosine is higher in uterine myomas than in control tissues and correlates with the size of the tumor", Free Radic. Biol. Med. 29, 597-601.
11. Mecocci, P., Fanó, G., Fulle, S., MacGarvey, U., Shinobu, L., Polidori, M.C., Cherubini, A., Vecchiet, J., Senin, U. and Beal, M.F. (1999) "Age-dependent increases in oxidative damage to DNA, lipids, and proteins in human skeletal muscle", Free Radic. Biol. Med. 26, 303-308.
12. Calderón-Garcidueñas, L., Wen-Wang, L., Zhang, Y.-J., Rodriguez-Alcaraz, A., Osnaya, N., Villarreal-Calderón, A. and Santella, R.M. (1999) "8-Hydroxy-2′-deoxyguanosine, a major mutagenic oxidative DNA lesion, and DNA strand breaks in nasal respiratory epithelium of children exposed to urban pollution", Environ. Health Perspect. 107, 469-474.
13. Lodovici, M., Casalini, C., Cariaggi, R., Michelucci, L. and Dolara, P. (2000) "Levels of 8-hydroxydeoxyguanosine as a marker of DNA damage in human leukocytes", Free Radic. Biol. Med. 28, 13-17.
14. Simic, M.G. (1992) "Urinary biomarkers and the rate of DNA damage in carcinogenesis and anticarcinogenesis", Mutat. Res. 267, 277-290.
15. Kasai, H. (1997) "Analysis of a form of oxidative DNA damage, 8-hydroxy-2′-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis", Mutat. Res. 387, 147-163.
16. Halliwell, B. (1998) "Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies", Free Radic. Res. 29, 469-486.
17. de Zwart, L.L., Meerman, J.H.N., Commandeur, J.N.M. and Vermeulen, N.P.E. (1999) "Biomarkers of free radical damage applications in experimental animals and humans", Free Radic. Biol. Med. 26, 202-226.
18. Youdim, K.A. and Joseph, J.A. (2001) "A possible emerging role of phytochemicals in improving age-related neurological dysfunctions: a multiplicity of effects", Free Radic. Biol. Med. 30, 583-594.
19. Floyd, R.A., West, M.S., Eneff, K.L., Hogsett, W.E. and Tingey, D.T. (1988) "Hydroxyl free radical mediated formation of 8-hydroxyguanosine in isolated DNA", Arch. Biochem. Biophys. 262, 266-272.
20. Taylor, D.E., Ghio, A.J. and Piantadosi, C.A. (1995) "Reactive oxygen species produced by liver mitochondria of rats in sepsis", Arch. Biochem. Biophys. 316, 70-76.
21. Abu-Shakra, A. and Zeiger, E. (1997) "Formation of 8-hydroxy-2′-deoxyguanosine following treatment of 2′-deoxyguanosine or DNA by hydrogen peroxide or glutathione", Mutat. Res. 390, 45-50.
22. Lloyd, D.R. and Phillips, D.H. (1999) "Oxidative DNA damage mediated by copper (II), iron (II) and nickel (II) Fenton reactions: evidence for site-specific mechanisms in the formation of double-strand breaks, 8-hydroxydeoxyguanosine and putative intrastrand cross-links", Mutat. Res. 424, 23-36.
23. Goldman, R., Claycamp, G.H., Sweetland, M.A., Sedlov, A.V, Tyurin, V.A., Kisin, E.R., Tyurina, Y.Y., Ritov, V.B., Wenger, S.L., Grant, S.G. and Kagan, V.E. (1999) "Myeloperoxidase-catalyzed redox-cycling of phenol promotes lipid peroxiclation and thiol oxidation in HL-60 cells", Free Radic. Biol. Med. 27, 1050-1063.
24. Kaneko, T. and Tahara, S. (2000) "Formation of 8-oxo-2′-deoxyguanosine in the DNA of human diploid fibroblasts by treatment with linoleic acid hydroperoxide and ferric ion", Lipids 35, 961-965.
25. Kasai, H. and Nishimura, S. (1984) "Hydroxylation of deoxyguanosine a the C-8 position by ascorbic acid and other reducing agents", Nucleic Acids Res. 12, 2137-2145.
26. Nappi, A.H. and Vass, E. (1997) "Comparative studies of enhanced iron-mediated production of hydroxyl radical by glutathione, cysteine, ascorbic acid, and selected catechols", Biochim. Biophys. Acta 1336, 295-301.
27. Yokozawa, T., Dong, E., Liu, Z.W. and Shimuzu, M. (1997) "Antioxidative activity of flavones and flavonols in vitro", Phytother. Res. 11, 446-449.
28. Sugihara, N., Arakawa, T. Ohnishi, M. and Furuno, K. (1999) "Anti- and pro-oxidative effects of flavonoids on metal-induced lipid hydroperoxide-dependent lipid peroxidation in cultured hepatocytes loaded with α-linolenic acid", Free Radic. Biol. Med. 27, 1313-1323.
29. Puppo, A. (1992) "Effect of flavonoids on hydroxyl radical formation by Fenton-type reactions; influence of the iron chelator", Phytochemistry 31, 85-88.
30. Niki, E. (1990) "Free radical initiators as source of water-or lipid-soluble peroxyl radicals", Methods Enzymol. 186, 100-108.
31. Simandan, T., Sun, J. and Dix, T.A. (1998) "Oxidation of DNA bases, deoxyribonucleosides; and homopolymers by peroxyl radicals", Biochem. J. 335, 233-240.
32. Cadenas, E. and Davies, K.J.A. (2000) "Mitochondrial free radical generation, oxidative stress, and aging", Free Radic. Biol. Med. 29, 222-230.
33. Atlante, A., Calissano, P., Bobba, A., Azzariti, A., Marra, E. and Passarella, S. (2000) "Cytochrome c is released from mitochondria in a reactive oxygen species (ROS)-dependent fashion and can operate as a ROS scavenger and as a respiratory substrate in cerebellar neurons undergoing excitotoxic death", J. Biol. Chem. 275, 37159-37166.
34. Blois, M.B. (1958) "Antioxidant determinations by the use of a stable free radical", Nature 181, 1199-1200.
35. Sies, H. (1993) "Damage to plasmid DNA by singlet oxygen and its protection", Mutat. Res. 299, 183-191.
36. Sully, B.D. (1954) "A modified iodimetric determination of organic peroxides", Analysts 79, 86-90.
37. Lin, T.-S., Cheng, J.-C., Ishiguro, K. and Sartorelli, A.C. (1985) "8-Substituted guanosine and 2′-deoxyguanosine derivatives as potential inducers of the differentiation of friend erythroleukemia cells", J. Med. Chem. 28, 1194-1198.
38. Ikehara, M., Uesugi, S. and Yoshida, K. (1972) "Studies on the conformation of purine nucleosides and their 5′-phosphates", Biochemistry 11, 830-836.
39. Culp, S.J., Cho, B.P., Kadlubar, RE and Evans, EE. (1989) "Structural and conformational analyses of 8-hydroxy-2′-deoxygusanosine", Chem. Res. Toxicol. 2, 416-422.
40. Uesugi, S. and Ikehara, M. (1977) "Carbon-13 magnetic resonance spectra of 8-substituted purine nucleosides. Characteristic shifts for the syn conformation", J. Am. Chem. Soc. 99, 3250-3253.
41. Bros, W., Heller, W., Michel, C. and Saran, M. (1990) "Flavonoids as antioxidants: determination of radical-scavenging efficiencies", Methods Enzymol. 186, 343-355.
42. Krinsky, N.I. (1989) "Antioxidant functions of carotenoids", Free Radic. Biol. Med. 7, 617-635.
43. Mascio, P.D., Murphy, M.E. and Sies, H. (1991) "Antioxidant defense systems: the role of carotenoids, tocopherols, and thiols", Am. J. Clin. Nutr. 53, 194S-200S.
44. 4-induced microsomal lipid peroxidation", Experimentia 47, 195-199.
45. Yokozawa, T., Chen, C.P., Dong, E., Tanaka, T., Nonaka, G.-I. and Nishioka, I. (1998) "Study on the inhibitory effect of tannina and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical", Biochem. Pharmacol. 56, 213-222.
46. Levine, M., Conry-Cantilena, C., Wang, Y., Welch, R.W., Washko, P.W., Dhariwal, K.R., Park, J.B., Lazarev, A., Graumlich, J.F., King, J. and Cantilena, L.R. (1996) "Vitamin C pharmacokinetics in healthy volunteers: evidence for a recommended dietary allowance", Proc. Natl Acad. Sci. USA 93, 3704-3709.
47. Mecocci, P., Polidori, M.C., Troiano, L., Cherubini, A., Cecchetti, R., Pimi, G., Straatman, M., Monti, D., Stahl, W., Sies, H., Franceschi, C. and Senin, U. (2000) "Plasma antioxidants and longevity: a study on healthy centenarians", Free Radic. Biol. Med. 28, 1243-1248.
48. Conquer, J.A., Maiani, G., Azzini, E., Raguzzini, A. and Holub, B.J. (1998) "Supplementation with quercetin markedly increases plasma quercetin concentration without effect on selected risk factors for heart disease in healthy subjects", J. Nutr. 128, 593-597.
49. de Vries, J.H.M., Hollman, P.C.H., Meyboom, S., Buysman, M.N.C.P., Zock, P.L., van Staveren, W.A. and Katan, M.B. (1998) "Plasma concentrations and urinary excretion of the antioxidant flavonols quercetin and kaempferol as biomarkers for dietary intake", Am. J. Clin. Nutr. 68, 60-65.
50. Nakagawa, K., Okuda, S. and Miyazawa, T. (1997) "Dose-dependent incorporation of tea catechins, (-)-epigallocatechin-3-gallate and (-)-epigallocatechin, into human plasma", Biosci. Biotechnol. Biochem. 61, 1981-1985.