Proposed mechanism for the photodynamic generation of 8-oxo-7,8-dihydro-2'-deoxyguanosine produced in cultured cells by exposure to lomefloxacin

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 381, Issue 1, 1997, Pages 117-129

  Rosen, Jane E ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

8 Oxo dG; Antioxidant; Hydroxyl radical; Lomefloxacin; Singlet oxygen; UV light

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; ALPHA TOCOPHEROL; ANTIOXIDANT; BUTYLATED HYDROXYANISOLE; HYDROXYL RADICAL; LOMEFLOXACIN; MANNITOL; QUINOLINE DERIVED ANTIINFECTIVE AGENT; SINGLET OXYGEN; SODIUM AZIDE; SUPEROXIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DNA DAMAGE; DRUG MECHANISM; IRRADIATION; LIVER CELL; NONHUMAN; PHOTOSENSITIZATION; PHOTOTOXICITY; PRIORITY JOURNAL; RAT;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTIOXIDANTS; BUTYLATED HYDROXYANISOLE; CELLS, CULTURED; DEOXYGUANOSINE; FLUOROQUINOLONES; LIVER; MANNITOL; PHOTOSENSITIZING AGENTS; QUINOLONES; RATS; REACTIVE OXYGEN SPECIES; SODIUM AZIDE; ULTRAVIOLET RAYS; VITAMIN E;

ANIMALIA;

EID: 0030834797     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(97)00159-0     Document Type: Article

References (78)

1. Hooper D.C., Wolfson J.S. Mode of action of new quinolones: new data. Eur. J. Clin. Microbiol. Infect. Dis. 10:1991;223-231.
2. Norrby S.R., Lietman P.S. The molecular basis of quinolone action. J. Anitmicrob. Chemother. 30:1993;409-416.
3. Shimoda K., Yoshida M., Wagai N., Takayama S., Kato M. Phototoxic lesions induced by quinolone antibacterial agents in auricular skin and retina of albino mice. Toxicol. Pathol. 21:1993;554-561.
4. Ferguson J., Johnson B.E. Ciprofloxacin-induced photosensitivity: in vitro and in vivo studies. Br. J. Dermatol. 123:1990;9-20.
5. Halkin H. Adverse effects of the fluoroquinolones. Rev. Infect. Dis. 10(suppl.):1988;S258-S261.
6. Robertson D.G., Epling G.A., Kiely J.S., Bailey D.L., Song Bo Mechanistic studies of the phototoxic potential of PD 117596 a quinolone antibacterial compound. Toxicol. Appl. Pharmacol. 111:1991;221-232.
7. Wagai N., Tawara K. Possible direct role of reactive oxygens in the cause of cutaneous phototoxicity induced by five quinolones in mice. Arch. Toxicol. 66:1992;392-397.
8. Fernandez E.B., Cardenas A.M.G., Martinez G.S. Phototoxicity from nalidixic acid: oxygen dependent photohemolysis. Farmaco. Ed. Sci. 42:1987;681-690.
9. Fernandez E.B., Cardenas A.M.G. The mechanism of photohemolysis by photoproducts of nalidixic acid. Photochem. Photobiol. B 4:1990;329-333.
10. Wagai N., Tawara K. Quinolone antibacterial-agent-induced cutaneous phototoxicity: ear swelling reactions in Balb/c mice. Toxicol. Lett. 58:1991;215-223.
11. Wagai N., Tawara K. Possible reasons for the differences in phototoxic potential of 5 quinolone antibacterial agents: generation of toxic oxygen. Free Radic. Res. Commun. 17:1992;387-398.
12. Athar M., Elmets C.A., Bickers D.R., Mukhtar H. A novel mechanism for the generation of superoxide anions in hematoporphyrin derivative-mediated cutaneous photosensitization: activation of the xanthine oxidase pathway. J. Clin. Invest. 83:1989;1137-1143.
13. Wagai N., Tawara K. Important role of oxygen metabolites in quinolone antibacterial agent-induced cutaneous phototoxicity in mice. Arch. Toxicol. 65:1991;495-499.
14. Wada K., Saniabadi A.R., Umemura K., Takiguchi Y., Nakashima M. UV-dependent quinolone-induced human erythrocyte membrane lipid peroxidation: studies on the phototoxicity of Y-26611, a new quinolone derivative. Pharmacol. Toxicol. 74:1994;240-243.
15. Wada K., Saniabadi A.R., Umemura K., Nakano M., Ito T., Nakashima M. Direct measurement of superoxide-dependent chemiluminescence from rat skin following UV-dependent fluoroquinolone-induced dermatitis. Free Radic. Biol. Med. Commun. 18:1995;923-927.
16. A. Forsgren, R. Neringer, C. Hansson, B. Ode, Lomefloxacin versus norfloxacin in the treatment of uncomplicated urinary tract infections: three-day versus seven-day treatment, 30th ICAAC, 1990, Abstract no. 997.
17. Wadworth A.N., Goa K.L. Lomefloxacin, A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 42:1991;1018-1060.
18. Correia O., Delgado L. Bullous photodermatitis after lomefloxacin. Arch. Dermatol. 130:1994;808-809.
19. Rosen J.E., Prahalad A.K., Schluter G., Chen D., William G.M. Quinolone antibiotic photodynamic production of 8-oxo-7,8-dihydro-2′-deoxyguanosine in cultured liver epithelial cells. Photochem. Photobiol. 65:1997;990-996.
20. C.S. Foote, Photosensitized oxidation and singlet oxygen: Consequences in biological systems, in: W.A. Pryor (Ed.), Free Radicals in Biology. Vol. III, Academic Press, New York, 1976, pp. 85-113.
21. Cadet J., Deecarroz C., Wang S.Y., Midden W.R. Mechanisms and products of photosensitized degradation of nucleic acids and related model compounds. Israel J. Chem. 23:1983;420-429.
22. Kessel D. Hematoporphyrin and HPD: photophysic, photochemistry and phototherapy. Photochem. Photobiol. 39:1984;851-859.
23. L.C. Harber, D.R. Bickers, Photosensitivity Diseases: Diagnosis and Treatment. W.B. Saunders, Philadelphia, 1981, 372 pp.
24. Girotti A.W. Mechanism of photosensitization. Photochem. Photobiol. 38:1983;745-751.
25. Ravanat J.-L., Cadet J. Reaction of singlet oxygen with 2′-deoxyguanosine and DNA. Isolation and characterization of the main oxidation product. Chem. Res. Toxicol. 8:1995;379-388.
26. Cadet J., Ravanat J.-L., Buchko G.W., Yeo H.C., Ames B.N. Singlet oxygen DNA damage: chromatographic and mass spectrometry analysis of damage products. Methods Enzymol. 234:1994;79-88.
27. Floyd R.A., West M.S., Eneff K.L., Schneider J.E. Methylene blue plus light mediates 8-hydroxyguanine formation in DNA. Arch. Biochem. Biophys. 273:1989;106-111.
28. Ravanat J.-L., Berger M., Benard F., Langlois R., Ouellet R., van Lier J.E., Cadet J. Phthalcyanine and naphthalocyanine photosensitized oxidation of 2′-deoxyguanosine: distinct type I and type II products. Photochem. Photobiol. 55:1992;809-814.
29. Schneider J.E., Price S., Maidt L., Gutteridge J.M.C., Floyd R.A. Methylene blue plus light mediates 8-hydroxy-2′-deoxyguanosine formation in DNA preferentially over strand breakage. Nucleic Acids Res. 18:1990;631-635.
30. Kasai H., Nishimura S. Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 12:1984;2137-2145.
31. Williams G.M., Gunn J.M. Long-term cell culture of adult rat liver epithelial cells. Exp. Cell Res. 89:1974;139-142.
32. 2 alone or with UVB or UVA irradiation. Photochem. Photobiol. 64:1996;117-122.
33. Marmur J. A procedure for the isolation of deoxyribonucleic acid from micro-organisms. J. Mol. Biol. 3:1961;208-218.
34. Williams G.M. Primary and long-term culture of adult rat liver epithelial cells. Methods Cell Biol. 14:1976;357-364.
35. Floyd R.A., Watson J.J., Wong P.K., Altmiller D.H., Richard G.M. Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanism of formation. Free Radic. Res. Commun. 1:1986;163-172.
36. Fiala E.S., Conaway C.C., Mathis J.E. Oxidative DNA and RNA damage in the livers of Sprague-Dawley rats treated with hepatocarcinogen 2-nitropropane. Cancer Res. 49:1989;5518-5522.
37. E. Cadenas, Oxidative stress and formation of excited species, in: H. Sies (Ed.), Oxidative Stress, Academic Press, London, 1985, pp. 311-330.
38. Stark A.A., Gal Y., Shaulsky G. Involvement of singlet oxygen in photoactivation of aflatoxins B1 and B2 to DNA-binding forms in vitro. Carcinogenesis. 11:1990;529-534.
39. Basu-Modak S., Tyrell R.M. Singlet oxygen: a primary effector in the ultraviolet A/near visible light induction of the human heme oxygenase gene. Cancer Res. 53:1993;4505-4510.
40. Y. Li, M. Trush, Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism, Cancer Res. Suppl. 54 (1994) 1895s-1898s.
41. Foote C.S. Singlet oxygen. Photochem. Photobiol. 28:1978;922-923.
42. C.S. Foote, Quenching of singlet oxygen, in: H.H. Wasserman, R.W. Murray (Eds.), Singlet Oxygen, Academic Press, New York, 1979, pp. 139-171.
43. C.S. Foote, Detection of singlet oxygen in complex systems: a critique, in: W.S. Caughey (Ed.), Biochemical and Clinical Aspects of Oxygen, Academic Press, New York, 1979, pp. 603-626.
44. Singh H., Vadasz J.A. Singlet oxygen: a major reactive species in the furocoumarin photosensitization inactivation of E. coli ribosomes. Photochem. Photobiol. 28:1978;539-545.
45. Singh H., Koroll G.W., Cundall R.B. Pulse radiolysis of aqueous solutions of sodium azide: reactions of azide radical with tryptophan and tyrosine. Radiat. Phys. Chem. 19:1981;137-146.
46. Thompson D., Moldeus P. Cytotoxicity of butylated hydroxyanisole and butylated hydroxytoluene in isolated rat hepatocytes. Biochem. Pharmacol. 37:1988;2201-2207.
47. B. Halliwell, J.M.C. Gutteridge, The chemistry of oxygen radicals and other oxygen-derived species, in: Free Radicals in Biology and Medicine, 2nd ed., Clarendon Press, Oxford, 1989.
48. Knecht K.T., Thurman R.E., Mason R.P. Role of superoxide and trace transition metals in the production of alpha hydroxyethyl radicals from ethanol by microsomes from alcohol dehydrogenase deficient deer mice. Arch. Biochem. Biophys. 303(2):1993;339-348.
49. Maxwell A. The molecular basis of quinolone action. J. Antimicrob. Chemother. 30:1992;409-416.
50. Ames B.N. Endogenous oxidative DNA damage, aging and cancer. Free Radic. Res. Commun. 7:1989;121-128.
51. Floyd R.A. The role of 8-hydroxyguanine in carcinogenesis. Carcinogenesis. 11:1990;1447-1450.
52. Feig D.I., Reid T.M., Loeb L.A. Reactive oxygen species in tumorigenesis. Cancer Res. 54:1994;1890s-1894s.
53. Ferguson J. Fluoroquinolone photosensitization: A review of clinical and laboratory studies. Photochem. Photobiol. 62:1995;954-958.
54. 2 system. Chem. Pharm. Bull. 38:1990;3072-3075.
55. Floyd R.A. Role of oxygen free radicals in carcinogenesis and brain ischemia. FASEB J. 4:1990;2587-2597.
56. Frenkel K., Goldstein M.S., Teebor G.W. Identification of the cis-thymine glycol moiety in chemically oxidized and γ-irradiated deoxyribonucleic acid by high pressure liquid chromatography analysis. Biochemistry. 20:1981;7566-7571.
57. Cathcart R., Schweirs E., Saul R.L., Ames B.N. Thymine glycol and thymidine glycol in human and rat urine: a possible assay for oxidative DNA damage. Proc. Natl. Acad. Sci. USA. 81:1984;3633-3637.
58. Teebor G.W., Frenkel K., Goldstein M.S. Ionizing radiation and tritium transmutation both cause formation of 5-hydroxymethyl-2′-deoxyuridine in cellular DNA. Proc. Natl. Acad. Sci. USA. 81:1984;318-321.
59. Singh A. Chemical and biochemical aspects of superoxide radicals and related species of activated oxygen. Can. J. Physiol. Pharmacol. 60:1982;1330-1345.
60. Farhataziz, Ross A.B. Selected specific rates of reactions of transients from water in aqueous solution. III. Hydroxyl radical and perhydroxyl radical and their radical ions Natl. Stand. Ref. Data Ser. (US Natl. Bur. Stand.). 59:1997;1-113.
61. A. Kornhauser, W. Wamer, A. Giles Jr., Light-induced dermal toxicity: effects on the cellular and molecular level, in: Dermatology, 3rd ed., Hemisphere Publishing, Washington, DC, 1987, pp. 377-412.
62. P.C. Srivastava, R.K. Robins, R.B. Meyer, in: L.B. Townsend (Ed.), Chemistry of Nucleosides and Nucleotides, Plenum, New York, 1988, pp. 113-281.
63. Matsumoto M., Kojima K., Nagano H. S.Ma, Matsubara S., Yokota T. Photostability and biological activity of fluoroquinolones substituted at the 8 position after UV irradiation. Antimicrob. Agents Chemother. 36:1992;1715-1719.
64. Marutani K., Matsumoto M., Otabe Y., Nagamuta M., Tanaka K., Miyoshi A., Hasegawa T., Nagano H., Matsubara S., Kamide R., Yokota T., Matsumoto F., Ueda Y. Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light. Antimicrob. Agents Chemother. 37:1993;2217-2223.
65. Tiefenbacher E.-M., Haen E., Pryzbilla B., Kurz H. Photodegradation of some quinolones used as antimicrobial therapeutics. J. Pharm. Sci. 83:1994;463-467.
66. Chetelat A.A., Albertini S., Gocke E. The photomutagenicity of fluoroquinolones in tests for gene mutation, chromosomal aberration, gene conversion and DNA breakage (Comet assay). Mutagenesis. 11:1996;497-504.
67. Midden W.R., Wang S.Y. Singlet oxygen generation for solution kinetics: clean and simple. J. Am. Chem. Soc. 105:1983;4129-4135.
68. Piette J. Biological consequences associated with DNA oxidation mediated by singlet oxygen. J. Photochem. Photobiol., B: Biol. 11:1991;241-260. (Review).
69. S. Raoul, J.E. Rosen, G.M. Williams, J. Cadet, Photodynamic mechanism for lomefloxacin after UVA exposure in the presence of 2′-deoxyguanosine or ARL-18 cells, Abstracts American Society for Photobiology, 23rd Annual Meeting, Photochem. Photobiol. (1995) 61 Suppl., 108S, ThAM-E5.
70. B.L. Diffey, The need for sunscreens with broad spectrum protection, in: F. Urbach (Ed.), Biological Responses to Ultraviolet A Radiation, Valdenmar, Overland Park, KS, 1992.
71. Schmidt U., Schluter G. Studies on the mechanism of phototoxicity of BAY y 3118 and other quinolones. Adv. Exp. Med. Biol. 387:1996;117-120.
72. Hartman P.E., Dixon W.J., Dahl T.A., Daub M.E. Multiple modes of photodynamic action by cercosporin. Photochem. Photobiol. 47:1988;699-703.
73. Bilski P., Li A.S.W., Chignell C.F. The photo-oxidation of N,N-diethylhydroxylamine by Rose Bengal in acetonitrile and water. Photochem. Photobiol. 54:1991;345-352.
74. Cadet J., Berger M., Buchko G.W., Joshi P.C., Raoul S., Ravanat J.-L. 2,2,-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino]- 5-(2H)-oxazolone: a novel and predominant radical oxidation product of 3′,5′-di-O-acetyl-2′-deoxyguanosine. J. Am. Chem. Soc. 116:1994;7403-7404.
75. Kasai H., Yamaizumi Z., Berger M., Cadet J. Photosensitized formation of 7,8-Dihydro-8-oxo-2′-deoxyguanosine (8-Hydroxy-2′-deoxyguanosine) in DNA by Riboflavin: A non-singlet oxygen mediated reaction. J. Am. Chem. Soc. 114:1992;9692-9694.
76. Camoirano A., DeFlora S., Dahl T.A. Genotoxicity of volatile and secondary reactive oxygen species generated by photosensitization. Environ. Mol. Mutagen. 21:1993;219-228.
77. Loveday K.S. Interrelationship of photocarcinogenicity, photomutagenicity and phototoxicity. Photochem. Photobiol. 63:1996;369-372.
78. R. Osterberg, Consideration for need of photo co-carcinogenesis testing, in: The Toxicology Forum, Toxicology Forum, Washington, DC, 1996, pp. 173-183.