Photocleavage of DNA by the fluoroquinolone antibacterials

Journal of Photochemistry and Photobiology B: Biology

Volumn 45, Issue 1, 1998, Pages 51-59

  Martínez, Lydia ^a,b   Chignell, Colin F ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

DNA; Enoxacin; Fleroxacin; Fluoroquinolones; Lomefloxacin; Nalidixic acid; Norfloxacin; Photocleavage

Indexed keywords

DNA; ENOXACIN; FLEROXACIN; FLUORINE; LOMEFLOXACIN; NALIDIXIC ACID; NAPHTHYRIDINE DERIVATIVE; NORFLOXACIN; OXYGEN; PLASMID DNA; QUINOLINE DERIVED ANTIINFECTIVE AGENT;

ARTICLE; CONTROLLED STUDY; DECARBOXYLATION; DNA STRAND BREAKAGE; DRUG DNA INTERACTION; DRUG MECHANISM; DRUG STRUCTURE; NONHUMAN; PHOTOREACTIVITY; PHOTOTOXICITY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET A RADIATION;

ANTI-INFECTIVE AGENTS; DNA DAMAGE; ENOXACIN; FLEROXACIN; FLUOROQUINOLONES; NALIDIXIC ACID; NORFLOXACIN; PHOTOLYSIS; PLASMIDS; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP; ULTRAVIOLET RAYS;

EID: 0032555475     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(98)00160-2     Document Type: Article

References (22)

1. [1] J.M. Domagala, Structure-activity and structure-side-effect relationships for the quinolone antibacterials, J. Antimicrob. Chemother. 33 (1994) 685-706.
2. [2] N. Wagai, K. Tawara, Possible reasons for differences in phototoxic potential of 5 quinolone antibacterial agents: generation of toxic oxygen, Free Rad. Res. Commun. 17 (1992) 387-398.
3. [3] T. Horio, H. Miyauchi, Y. Asada, Y. Aoki, M. Harada, Phototoxicity and photoallergenicity of quinolones in guinea pigs, J. Dermatological Sci. 7 (1994) 130-135.
4. [4] G. Klecak, F. Urbach, H. Urwyler, Fluoroquinolone antibacterials enhance UVA-induced skin tumors, J. Photochem. Photobiol. B: Biol. 37 (1997) 174-181.
5. [5] M. Maekinen, P.D. Forbes, F. Stenbaeck, Quinolone antibacterials: a new class of photochemical carcinogens, J. Photochem. Photobiol. B: Biol. 37 (1997) 182-187.
6. [6] A.-A. Chételat, S. Albertini, E. Gocke, The photomutagenicity of fluoroquinolones in tests for gene mutation, chromosomal aberration, gene conversion and DNA breakage (Comet assay), Mutagenesis 11 (5) (1996) 497-504.
7. [7] G. Condorelli, G. de Guidi, S. Giuffrida, P. Miano, S. Sortino, A. Velardita, Membrane and DNA damage photosensitized by fluoroquinolone antimicrobial agents: a comparative screening, Med. Environ. 24 (1996) 103-110.
8. [8] H.J. Reavy, N.J. Traynor, N.K. Gibbs, Photogenotoxicity of skin phototumorigenic fluoroquinolone antibiotics detected using the Comet assay, Photochem. Photobiol. 66 (1997) 368-373.
9. [9] Y. Iwamoto, T. Itoyama, K. Yasuda, T. Uzuhashi, I. Tanizawa, Y. Takino, T. Oku, H. Hashizume, Y. Yanagihara, Photodynamic deoxyribonucleic acid (DNA) strand breaking activities of enoxacin and afloqualone, Chem. Pharm. Bull. 40 (1992) 1868-1870.
10. [10] Y. Iwamoto, A. Kurita, T. Shimizu, T. Masuzawa, K. Uno, M. Yagi, T. Kitagawa, T. Oku, Y. Yanagihara, DNA strand-breaking activities of quinolone antimicrobial agents under visible light irradiation, Biol. Pharm. Bull. 17 (1994) 654-657.
11. [11] J.E. Rosen, A.K. Prahalad, G. Schluter, D. Chen, G.M. Williams, Quinolone antibiotic photodynamic production of 8-oxo-7,8-dihydro-2′-deoxyguanosine in cultured liver epithelial cells, Photochem. Photobiol. 65 (1997) 990-996.
12. [12] L.J. Martínez, R.H. Sik, C.F. Chignell, Fluoroquinolone antimicrobials: singlet oxygen, superoxide and phototoxicity. Photochem. Photobiol. 67 (1998) 399-403.
13. [13] L. Martínez, G. Li, C.F. Chignell, Photogeneration of fluoride by fluoroquinolone antimicrobial agents LMFX and fleroxacin, Photochem. Photobiol. 65 (1997) 599-602.
14. [14] K. Nakatani, S. Maekawa, K. Tnabe, I. Saito, Alpha diazo ketones as photochemical cleavers: a mimic for the radical generating system of neocarzinostarin, J. Amer. Chem. Soc. 117 (1995) 10635-10644.
15. [15] G. Grabner, C. Richard, G. Kohler, Formation and reactivity of 4-oxocyclohexa-2,5-dienylidene in the photolysis of 4-chlorophenol in aqueous solution at ambient temperature, J. Amer. Chem. Soc. 116 (1994) 11470-11480.
16. [16] Y.M. Li, A.J. Dunipace, G.K. Stookey, Genotoxic effects of fluoride: a controversial issue, Mutat. Res. 195 (1988) 127-136.
17. [17] R.A. Aitken, Carbenes and nitrenes, in: A.C. Knipe, W.E. Watts (Eds.), Organic Reaction Mechanisms, John Wiley, Chichester, UK, 1993, pp. 207-227.
18. [18] M. Matsumoto, K. Kojima, H. Nagano, F. Matsubara, T. Yokota, Photostability and biological activity of fluoroquinolones substituted at the 8 position after UV irradiation, Antimicrobial Agents Chemother. 36 (1992) 1715-1719.
19. [19] B.R. Arnold, J.C. Scaiano, G.F. Bucher, W.W. Sander, Laser flash photolysis studies of 4-oxocyclohexa-2,5-dienylidenes, J. Org. Chem. 57 (1992) 6469-6474.
20. [20] F. Vargas, C. Rivas, N. Canudas, Photosensitized lipid peroxidation by cinoxacin and its photoproducts: involvement of a derived peroxide in its phototoxicity, Pharmazie 49 (1994) 742-745.
21. [21] N. Detzer, B. Huber, Photochemie heterozyklischer Enone I: Photolyse und Thermolyse von Nalidixinsäure, Tetrahedron 31 (1975) 1937-1941.
22. [22] E. Fasani, M. Mella, D. Caccia, S. Tassi, M. Fagnoni, A. Albini, The photochemistry of lomefloxacin. An aromatic carbene as the key intermediate in photodecomposition, Chem. Commun. (1997) 1329-1330.