Photosensitizing mechanism and identification of levofloxacin photoproducts at ambient UV radiation

Photochemistry and Photobiology

Volumn 88, Issue 2, 2012, Pages 344-355

  Dwivedi, Ashish ^a   Mujtaba, Syed F ^a   Kushwaha, Hari N ^b   Ali, Daoud ^a   Yadav, Neera ^a   Singh, S K ^b   Ray, Ratan S ^a  

^a CSIR INDIAN INSTITUTE OF TOXICOLOGY RESEARCH   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

OFLOXACIN; P21 ACTIVATED KINASE; PROTEIN BAX; PROTEIN BCL 2; REACTIVE OXYGEN METABOLITE; SCAVENGER; SUPEROXIDE DISMUTASE;

ANIMAL; APOPTOSIS; ARTICLE; CELL CYCLE CHECKPOINT; CELL LINE; CELL SURVIVAL; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; FIBROBLAST; GENETICS; HUMAN; KERATINOCYTE; LIPID PEROXIDATION; METABOLISM; MOUSE; RADIATION EXPOSURE; SUNLIGHT; ULTRAVIOLET RADIATION; UPREGULATION;

ANIMALS; APOPTOSIS; BCL-2-ASSOCIATED X PROTEIN; CELL CYCLE CHECKPOINTS; CELL LINE; CELL SURVIVAL; FIBROBLASTS; FREE RADICAL SCAVENGERS; HUMANS; KERATINOCYTES; LIPID PEROXIDATION; MICE; OFLOXACIN; P21-ACTIVATED KINASES; PROTO-ONCOGENE PROTEINS C-BCL-2; REACTIVE OXYGEN SPECIES; SUNLIGHT; SUPEROXIDE DISMUTASE; ULTRAVIOLET RAYS; UP-REGULATION;

BACTERIA (MICROORGANISMS);

EID: 84862815943     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2011.01068.x     Document Type: Article

References (57)

1. Solomon, K. R., (2008) Effects of ozone depletion and UV-B radiation on humans and the environment. Atmos. Ocean 46, 185-202.
2. De Fabo, E. C., (2005) Arctic stratospheric ozone depletion and increased UVB radiation: Potential impacts to human health. Int. J. Circumpolar Health 64, 509-522.
3. Bachelet, D., P. W. Barnes, D. Brown, and, M. Brown, (1991) Latitudinal and seasonal variation in calculated ultraviolet-B irradiance for rice growing regions of Asia. Photochem. Photobiol. 54, 411-422.
4. Davidson, A. T., and, H. J. Marchant, (1994) Comparative impact of in situ UV exposure on productivity, growth and survival of Antarctic phaeocystis and diatoms. Proc. NIPR Symp. Polar Biol. 7, 53-69.
5. World Health Organization (1994) Environmental health criteria, ultraviolet radiations, report number, 160.
6. Melhus, A., (2005) Fluoroquinolones and tendon disorders. Expert. Opin. Drug Safety 4, 299-309.
7. Liu, H., and, S. G. Mulholland, (2005) Appropriate antibiotic treatment of genitourinary infections in hospitalized patients. Am. J. Med. 118 (Suppl 7A), 14S-20S. (Pubitemid 40941654)
8. Fish, D. N., and, A. T. Chow, (1997) The clinical pharmacokinetics of levofloxacin. Clin. Pharmacokinet. 32 (2), 101-119. (Pubitemid 27104410)
9. Nakashima, M., T. Uematsu, M. Kanamaru, O. Okazaki, and, H. Hakusui, (1992) Phase I study of levofloxacin, (S)-(-)-ofloxacin. Jpn. J. Clin. Pharmacol. Ther. 23, 515-520.
10. Wagai, N., and, K. Tawara, (1992) Possible direct role of reactive oxygens in the cause of cutaneous phototoxicity induced by five quinolones in mice. Arch. Toxicol. 66, 392-397.
11. Martinez, L. J., R. H. Sik, and, C. F. Chignell, (1998) Fluoroquinolone antimicrobials: Singlet oxygen, superoxide and phototoxicity. Photochem. Photobiol. 67, 399-403. (Pubitemid 128472692)
12. Ferguson, J., and, R. Dawe, (1997) Phototoxicity in quinolones: Comparison of ciprofloxacin and grepafloxacin. J. Antimicrob. Chemother. 40 (Suppl A), 93-98. (Pubitemid 28041172)
13. Sun, Y. W., E. P. Heo, Y. H. Cho, K. M. Bark, T. J. Yoon, and, T. H. Kim, (2001) Pefloxacin and ciprofloxacin increase UV-A-induced edema and immune suppression. Photodermatol. Photoimmunol. Photomed. 17, 172-177. (Pubitemid 32677598)
14. Fujita, H., and, I. Matsuo, (1994) In vitro phototoxic activities of new quinolone antibacterial agents: Lipid peroxidative potentials. Photodermatol. Photoimmunol. Photomed. 10, 202-205. (Pubitemid 24357436)
15. Nishigori, A., Y. Hattori, and, S. Toyokuni, (2004) Role of ROS in skin carcinogenesis. Anitoxid. Redox Signal. 6, 561-570.
16. Ferguson, J., (2002) Photosensitivity due to drugs. Photodermatol. Photoimmunol. Photomed. 18, 262-269. (Pubitemid 35331395)
17. Nilsson, R., T. Maurer, and, N. A. Redmont, (1993) Standard protocol for phototoxicity testing. Results from an inter-laboratory study. Contact Dermatitis 28, 285-290. (Pubitemid 23196983)
18. Martinez, L. J., G. Li, and, C. F. Chignell, (1997) Photogeneration of fluoride by fluoroquinolone antimicrobial agents lomefloxacin and fleroxacin. Photochem. Photobiol. 65 (3), 599-602. (Pubitemid 27159004)
19. Wyllie, A. H., (1993) Apoptosis (the Frank Rose memorial lecture). Br. J. Cancer 67, 205-208. (Pubitemid 23049537)
20. Young, A. R., (1987) The sunburn cell. Photodermatology 4, 127-134. (Pubitemid 17151700)
21. Gniadecki, R., M. Hansen, and, H. C. Wulf, (1997) Two pathways for induction of apoptosis by ultraviolet radiation in cultured human keratinocytes. J. Invest. Dermatol. 109, 163-169. (Pubitemid 27337330)
22. Pourzand, C., G. Rossier, O. Reelfs, C. Borner, and, R. M. Tyrrell, (1997) Overxpression of Bcl-2 inhibits UVA-mediated immediate apoptosis in rat 6 fibroblasts: Evidence for the involvement of Bcl-2 as an antioxidant. Cancer Res. 57, 1405-1411. (Pubitemid 27175550)
23. Oltvai, Z. N., C. L. Milliman, and, S. J. Korsmeyer, (1993) Bcl-2 heterodimerizes in vivo with a conserved homolog, Bax, that accelerates programmed cell death. Cell 74, 609-619. (Pubitemid 23259742)
24. Maisch, T., C. Bosl, R. M. Szeimies, N. Lehn, and, C. Abels, (2005) Photodynamic effects of noval XF porphyrin derivatives on prokaryotic and eukaryotic cells. Antimicrob. Agents Chemother. 49, 1542-1552. (Pubitemid 40463386)
25. Bastianon, C., R. Zanoni, G. Miolo, S. Caffieri, and, E. Reddi, (2005) Mitochondria and plasma membrane as targets of UV-A induced toxicity of neuroleptic drugs fluphenazine, perphenazine and thioridazine. Int. J. Biochem. Cell Biol. 37, 901-908. (Pubitemid 40203010)
26. Ray, R. S., R. B. Misra, M. Farooq, and, R. K. Hans, (2002) Effect of UV-B radiation on some common antibiotics. Toxicol. In Vitro 16, 123-127. (Pubitemid 34182836)
27. Ray, R. S., N. Agrawal, R. B. Misra, M. Farooq, and, R. K. Hans, (2006) Radiation-induced in vitro phototoxic potential of some fluoroquinolones. Drug Chem. Toxicol. 29, 25-38. (Pubitemid 43286712)
28. Agrawal, N., R. S. Ray, M. Farooq, A. B. Pant, and, R. K. Hans, (2007) Photosensitizing potential of ciprofloxacin at ambient level of UV radiation. Photochem. Photobiol. 83, 1226-1236. (Pubitemid 47438522)
29. Valencia, A., and, I. E. Kochevar, (2006) UV-A induces apoptosis via reactive oxygen species in a model for Smith Lemli Opitz syndrome. Free Radic. Biol. Med. 40, 641-650. (Pubitemid 43170816)
30. Shah, P. P., K. Saurabh, M. C. Pant, N. Mathur, and, D. Parmar, (2009) Evidence for increased cytochrome P450 1A1 expression in blood lymphocytes of lung cancer patients. Mutant Res. 670, 74-78.
31. T) method. Methods 25, 402-408. (Pubitemid 34164012)
32. Ribble, D., N. B. Goldstein, D. A. Norris, and, Y. G. Shellman, (2005) A simple technique for quantifying apoptosis in 96-well plates. BMC Biotechnol. 10, 5-12.
33. Lhiaubet, V., N. Paillous, and, N. Chouini-Lalanne, (2001) Comparison of DNA damage photoinduced by ketoprofen, fenofibric acid and benzophenone via electron and energy transfer. Photochem. Photobiol. 74, 670-678.
34. Huselton, C. A., and, H. Z. Hill, (1990) Melanin photosensitizes ultraviolet light (UV-C) DNA damage in pigmented cells. Environ. Mol. Mutagen. 16, 37-43. (Pubitemid 20229515)
35. Bamane, V. S., P. N. Trivedi, S. S. Ranade, and, V. J. Daoo, (1992) Solar UV irradiance and some biological consequences: Bombay, India. Sci. Total Environ. 121, 195-201.
36. Lietman, P. S., (1995) Fluoroquinolone toxicities. An update. Drugs 49, 794-850.
37. Marrot, L., and, C. Agapakis-Causse, (2000) Differences in the photogenotoxic potential of two fluoroquinolones as shown in diploid yeast strain (Saccharomyces cerevisae) and supercoiled DNA. Mutat. Res. 468, 1-9. (Pubitemid 30345556)
38. Oliveira, H. S., M. Goncalo, and, A. C. Figueiredo, (2000) Photo-sensitivity to lomefloxacin. A clinical and photobiological study. Photodermatol. Photoimmunol. Photomed. 16, 116-120. (Pubitemid 30367086)
39. Shimoda, K., (1998) Mechanisms of quinolone phototoxicity. Toxicol. Lett. 28, 369-373. (Pubitemid 29021248)
40. Traynor, N. J., M. D. Barratt, W. W. Lovell, J. Ferguson, and, N. K. Gibbs, (2000) Comparison of an in vitro cellular phototoxicity model against controlled clinical trails of fluoroquinolones skin phototoxicity. Toxicol. In Vitro 14 (3), 275-283. (Pubitemid 30235125)
41. Bagheri, H., V. Lhiaubet, J. L. Montastruc, and, N. Chouini-Lalanne, (2000) Photosensitivity to ketoprofen: Mechanisms and pharmacoepidemiological data. Drug Safety 22, 339-349. (Pubitemid 30261078)
42. Ge, L. K., J. W. Chen, S. Y. Zhang, X. Y. Cai, Z. Wang, and, C. L. Wang, (2010) Photodegradation of fluoroquinolone antibiotic gatifloxacin in aqueous solutions. Environ. Chem. 55 (15), 1495-1500.
43. Castell, J. V., M. J. Gomez-Lechon, C. Grassa, L. A. Martinez, M. A. Miranda, and, P. Tarrega, (1994) Photodynamic lipid peroxidation by the photosensitizing nonsteroidal anti-inflammatory drugs suprofen and tiaprofenic acid. Photochem. Photobiol. 59, 35-39. (Pubitemid 2042994)
44. Ravanat, J. L., S. Sauvaigo, S. Caillat, G. R. Martinez, M. H. Medeiros, P. D. Mascio, A. Favier, and, J. Cadet, (2004) Singlet oxygen-mediated damage to cellular DNA determined by the comet assay associated with DNA repair enzymes. Biol. Chem. 385, 17-20. (Pubitemid 38240290)
45. Zhang, T., J. L. Li, J. Xin, X. C. Ma, and, Z. H. Tu, (2004) Compare two methods of measuring DNA damage induced by photogenotoxicity of fluoroquinolones. Acta Pharmacol. Sin. 25, 171-175. (Pubitemid 38186165)
46. Itoh, S., S. Nakayama, and, H. Shimada, (2002) In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation. Mutat. Res. 517, 113-121. (Pubitemid 34597011)
47. Viola, G., L. Facciolo, M. Canton, D. Vedaldi, F. Dall'Acqua, G. G. Aloisi, M. Amelia, A. Barbafina, F. Elisei, and, L. Latterini, (2004) Photophysical and phototoxic properties of the antibacterial fluoroquinolones levofloxacin and moxifloxacin. Chem. Biodivers. 1, 782-801.
48. Spielmann, H., M. Balls, J. Dupuis, W. J. Papa, G. Pechovitch, O. deSilva, H. G. Holzhutter, R. Clothier, P. Desolle, F. Gerberick, M. Liebsch, W. W. Lovell, T. Maurer, U. Pfannenbecker, J. M. Ptthast, M. Csato, D. Slodowski, W. Steiling, and, P. Brantom, (1998) The International EU/COLIPA in vitro phototoxicity validation study: Results of phase II (blind trial). Part I: The 3T3 NRU phototoxicity test. Toxicol. In Vitro 12, 305-327. (Pubitemid 28331394)
49. Recknagel, R. O., and, E. A. Clende, (1984) Spectrophotometric detection of lipid conjugated dienes. In Oxygen Radicals in Biological Systems, Methods in Enzymology, Vol. 105 (Edited by, L. Pakcer,), pp. 331-337. Academic Press, New York. (Pubitemid 14165395)
50. Kawada, A., K. Hatanaka, H. Gomi, and, I. Matsuo, (1999) In vitro phototoxicity of new quinolones: Production of active oxygen species and photosensitized lipid peroxidation. Photodermatol. Photoimmunol. Photomed. 15, 226-230.
51. Zhan, Q., M. J. Antinore, X. W. Wang, F. Carrier, M. L. Smith, C. C. Harris, and, A. J. Fornace Jr., (1999) Association with Cdc2 and inhibition of Cdc2/Cyclin B1 kinase activity by the p53-regulated protein Gadd45. Oncogene 18, 2892-2900. (Pubitemid 29250879)
52. Shicheng, L., M. Hideo, and, Y. Hitoshi, (2007) Molecular response to phototoxic stress of UVB-irradiated ketoprofen through arresting cell cycle in G2/M phase and inducing apoptosis. Biochem. Biophys. Res. Commun. 3, 650-655.
53. Charrier-Savournin, F. B., M. T. Chateau, V. Gire, J. Sedivy, J. Piette, and, V. Dulic, (2004) p21-Mediated nuclear retention of cyclin B1-Cdk1 in response to genotoxic stress. Mol. Biol. Cell 15, 3965-3976. (Pubitemid 39122002)
54. Cory, S., and, J. M. Adams, (2002) The bcl-2 family: Regulators of the cellular life-or-death switch. Nature Rev. Cancer 2, 647-656. (Pubitemid 37328916)
55. Zhang, L., J. Yu, B. H. Park, K. W. Kinzler, and, B. Vogelstein, (2000) Role of BAX in the apoptotic response to anticancer agents. Science 290, 989-992.
56. Isoherranen, K., I. Sauroja, J. Christer, and, K. Punnonen, (1999) UV irradiation induces downregulation of bcl-2 expression in vitro and in vivo. Arch. Dermatol. Res. 291, 212-216. (Pubitemid 29191829)
57. Gillardon, F., C. Eschenfelder, E. Uhlmann, W. Hartschuh, and, M. Zimmermann, (1994) Differential regulation of c-fos, fosB, c-jun, bcl-2 and bax expression in rat skin following single or chronic ultraviolet irradiation and in vivo modulation by antisense oligodeoxynucleotide superfusion. Oncogene 9, 3219-3225.