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Free Radical Research Communications Volume 17, 1992 - Issue 6
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Original Article

Possible Reasons for Differences in Phototoxic Potential of 5 Quinolone Antibacterial Agents: Generation of Toxic Oxygen

Nobuhiko Wagai Developmental Research Laboratories, Daiichi Pharmaceutical Co., Ltd., 16-13, Kitakasai I-chome, Edogawa-ku, Tokyo, 134, Japan
&
Katsuhiko Tawara Developmental Research Laboratories, Daiichi Pharmaceutical Co., Ltd., 16-13, Kitakasai I-chome, Edogawa-ku, Tokyo, 134, Japan
Pages 387-398 | Received 15 Jun 1992, Accepted 21 Aug 1992, Published online: 07 Jul 2009

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Aylin Gürbay, Mireille Osman, Alain Favier & Filiz Hincal. (2005) Ciprofloxacin-Induced Cytotoxicity and Apoptosis in HeLa Cells. Toxicology Mechanisms and Methods 15:5, pages 339-342.
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Articles from other publishers (37)

Khalid Eljaaly, Amina Alkhalaf, Abdullah A. Alhifany & Mohannad Alshibani. (2020) Photosensitivity induced by lomefloxacin versus other fluoroquinolones: A meta-analysis. Journal of Infection and Chemotherapy 26:6, pages 535-539.
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Tao Su, Ming-De Li, Jiani Ma & David Lee Phillips. (2017) Time-Resolved Spectroscopic Study of the Defluorination and Cyclization Reactions of Lomefloxacin in Water. The Journal of Physical Chemistry B 121:17, pages 4512-4520.
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Kyuri Kim, Hyeonji Park & Kyung-Min Lim. (2015) Phototoxicity: Its Mechanism and Animal Alternative Test Methods. Toxicological Research 31:2, pages 97-104.
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Virginia Aiassa, Ana I. Barnes & In?s Albesa. (2013) Macromolecular Oxidation in Planktonic Population and Biofilms of Proteus mirabilis Exposed to Ciprofloxacin. Cell Biochemistry and Biophysics 68:1, pages 49-54.
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Majed M. Masadeh, Nizar M. Mhaidat, Karem H. Alzoubi, Sayer I. Al-Azzam & Ashraf I. Shaweesh. (2012) Ciprofloxacin-Induced Antibacterial Activity is Reversed by Vitamin E and Vitamin C. Current Microbiology 64:5, pages 457-462.
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Klefah A. K. Musa & Leif A. Eriksson. (2009) Theoretical Assessment of Norfloxacin Redox and Photochemistry. The Journal of Physical Chemistry A 113:40, pages 10803-10810.
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Aylin Gürbay, Brigitte Gonthier, Luc Barret, Alain Favier & Filiz Hıncal. (2007) Cytotoxic effect of ciprofloxacin in primary culture of rat astrocytes and protection by Vitamin E. Toxicology 229:1-2, pages 54-61.
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Ichiro Suzuki, Mayuko Takahashi, Akira Shigenaga, Hisao Nemoto & Kei Takeda. (2006) Synthesis and photo DNA-damaging activities of fluoroquinolone analogues. Tetrahedron Letters 47:35, pages 6193-6196.
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P. ReinhardtM. CybulskiS.M. MillerC. FerrarottoR. WilkinsY. Deslauriers. (2006) Broad-spectrum sunscreens prevent the secretion of proinflammatory cytokines in human keratinocytes exposed to ultraviolet A and phototoxic lomefloxacin. Canadian Journal of Physiology and Pharmacology 84:2, pages 221-226.
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Elisa Fasani, Mariella Mella & Angelo Albini. (2004) Photochemistry of the Phototoxic Drug Lomefloxacin: Paths Observed in the Presence of Amines or NaOH and from the Methyl Ester. European Journal of Organic Chemistry 2004:24, pages 5075-5082.
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M Budai, Zs Szab?A Zimmer, M Sz?gyi & P Gr?f. (2004) Studies on molecular interactions between nalidixic acid and liposomes. International Journal of Pharmaceutics 279:1-2, pages 67-79.
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Peter Ball. (2003) Efficacy and safety of levofloxacin in the context of other contemporary fluoroquinolones: a review. Current Therapeutic Research 64:9, pages 646-661.
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Filiz Hincal, Aylin Gürbay & Alain Favier. (2003) Biphasic Response of Ciprofloxacin in Human Fibroblast Cell Cultures. Nonlinearity in Biology, Toxicology, Medicine 1:4, pages 154014203902710.
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A Gürbay, C Garrel, M Osman, M-J Richard, A Favier & F Hincal. (2016) Cytotoxicity in ciprofloxacin-treated human fibroblast cells and protection by vitamin E. Human & Experimental Toxicology 21:12, pages 635-641.
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Satoru Itoh, Michiyuki Katoh & Kazuhisa Furuhama. (2002) In vivo photochemical micronucleus induction due to certain quinolone antimicrobial agents in the skin of hairless mice. Mutation Research/Genetic Toxicology and Environmental Mutagenesis 520:1-2, pages 133-139.
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T Yamamoto, Y Tsurumaki, M Takei, M Hosaka & Y Oomori. (2001) In vitro method for prediction of the phototoxic potentials of fluoroquinolones. Toxicology in Vitro 15:6, pages 721-727.
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Neil K. Gibbs. 2001. Sun Protection in Man. Sun Protection in Man 337 356 .
Suppiah Navaratnam & Jennifer Claridge. (2007) Primary Photophysical Properties of Ofloxacin ¶. Photochemistry and Photobiology 72:3, pages 283-290.
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Laurent Marrot & Catherine Agapakis-Causse. (2000) Differences in the photogenotoxic potential of two fluoroquinolones as shown in diploid yeast strain (Saccharomyces cerevisae) and supercoiled plasmid DNA. Mutation Research/Genetic Toxicology and Environmental Mutagenesis 468:1, pages 1-9.
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Suppiah Navaratnam & Jennifer Claridge. (2000) Primary Photophysical Properties of Ofloxacin¶. Photochemistry and Photobiology 72:3, pages 283.
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Hiroko Hamanaka, Hitoshi Mizutani, Kunihiko Asahig & Masayuki Shimizu. (1999) Melanocyte melanin augments sparfloxacin-induced phototoxicity. Journal of Dermatological Science 21:1, pages 27-33.
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S.J. Bulera, J.C. Theiss, T.A. Festerling & F.A. de la Iglesia. (1999) In VitroPhotogenotoxic Activity of Clinafloxacin: A Paradigm Predicting Photocarcinogenicity. Toxicology and Applied Pharmacology 156:3, pages 222-230.
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Elisa Fasani, Antonella Profumo & Angelo Albini. (2008) Structure and Medium‐Dependent Photodecomposition of Fluoroquinolone Antibiotics. Photochemistry and Photobiology 68:5, pages 666-674.
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S. Sortino, G. Condorelli, G. De Guidi & S. Giuffrida. (2008) Molecular Mechanism of Photosensitization XI. Membrane Damage and DNA Cleavage Photoinduced by Enoxacin. Photochemistry and Photobiology 68:5, pages 652-659.
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Lydia Mart?nez & Colin F. Chignell. (1998) Photocleavage of DNA by the fluoroquinolone antibacterials. Journal of Photochemistry and Photobiology B: Biology 45:1, pages 51-59.
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P. Bilski, L. J. Martinez, E. B. Koker & C. F. Chignell. (2008) Influence of Solvent Polarity and Proticity on the Photochemical Properties of Norfloxacin. Photochemistry and Photobiology 68:1, pages 20-24.
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Michael Engler, Guido Rüsing, Fritz Sörgel & Ulrike Holzgrabe. (1998) Defluorinated Sparfloxacin as a New Photoproduct Identified by Liquid Chromatography Coupled with UV Detection and Tandem Mass Spectrometry. Antimicrobial Agents and Chemotherapy 42:5, pages 1151-1159.
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Lydia J. Martinez, Robert H. Sik & Colin F. Chignell. (1998) Fluoroquinolone Antimicrobials: Singlet Oxygen, Superoxide and Phototoxicity. Photochemistry and Photobiology 67:4, pages 399-403.
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John D. Spikes. (1998) Photosensitizing properties of quinine and synthetic antimalarials. Journal of Photochemistry and Photobiology B: Biology 42:1, pages 1-11.
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Jane E Rosen. (1997) 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 381:1, pages 117-129.
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J.E. Rosen, D. Chen, A.K. Prahalad, T.E. Spratt, G. Schluter & G.M. Williams. (1997) A Fluoroquinolone Antibiotic with a Methoxy Group at the 8 Position Yields Reduced Generation of 8-Oxo-7,8-dihydro- 2′-deoxyguanosine after Ultraviolet-A Irradiation. Toxicology and Applied Pharmacology 145:2, pages 381-387.
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Lydia J. Martinez, Galaxy Li & Colin F. Chignell. (1997) Photogeneration of Fluoride by the Fluoroquinolone Antimicrobial Agents Lomefloxacin and Fleroxacin. Photochemistry and Photobiology 65:3, pages 599-602.
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Lydia Martínez, Piotr Bilski & Colin F. Chignell. (2008) Effect of Magnesium and Calcium Complexation on the Photochemical Properties of Norfloxacin. Photochemistry and Photobiology 64:6, pages 911-917.
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Ernesto Gonz?lez & Salvador Gonz?lez. (1996) Drug photosensitivity, idiopathic photodermatoses, and sunscreens. Journal of the American Academy of Dermatology 35:6, pages 871-885.
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P. Bilski, L. J. Martinez, E. B. Koker & C. F. Chignell. (1996) Photosensitization by Norfloxacin is a Function of pH. Photochemistry and Photobiology 64:3, pages 496-500.
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A.R. Young, T.D. Fakouhi, G.I. Harrison, B. Roniker, E.A. Swabb & J.L.M. Hawk. (1996) The UVR wavelength dependence for lomefloxacin photosensitization of human skin. Journal of Photochemistry and Photobiology B: Biology 32:3, pages 165-170.
Crossref
James Ferguson. (2008) FLUOROQUINOLONE PHOTOSENSITIZATION: A REVIEW OF CLINICAL and LABORATORY STUDIES. Photochemistry and Photobiology 62:6, pages 954-958.
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