• 1
    Mäkinen, M., P. D. Forbes and F. Stenbäck (1997) Quinolone antibacterials: A new class of photochemical carcinogens. J. Photochem. Photobiol. B, Biol. 37, 182187.
  • 2
    Klecak, G., F. Urbach and H. Urwyler (1997) Fluoroquinolone antibacterials enhance UVA-induced skin tumors. J. Photochem. Photobiol. B, Biol. 37, 174181.
  • 3
    Johnson, B. E., N. K. Gibbs and J. Ferguson (1997) Quinolone antibiotic with potential to photosensitize skin tumorigenesis. J. Photochem. Photobiol. B, Biol. 37, 171173.
  • 4
    Sauvaigo, S., T. Douki, F. Odin, S. Caillat, J. L. Ravanat and J. Cadet (2001) Analysis of fluoroquinolone-mediated photosensitization of 2′-deoxyguanosine, calf thymus and cellular DNA: Determination of Type-I, Type-II and triplet–triplet energy transfer mechanism contribution. Photochem. Photobiol. 73, 230237.
  • 5
    Sanchez, G., M. E. Hidalgo, J. M. Vivanco and J. Escobar (2005) Induced and photoinduced DNA damage by quinolones: Ciprofloxacin, ofloxacin and nalidixic acid determined by comet assay. Photochem. Photobiol. 81, 819822.
  • 6
    Wirnitzer, U., N. Gross-Tholl, B. Herbold and E. Von Keutz (2006) Photo-chemically induced DNA effects in the comet assay with epidermal cells of SKH-1 mice after a single oral administration of different fluoroquinolones and 8-methoxypsoralen in combination with exposure to UVA. Mutat. Res. 609, 110.
  • 7
    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, 171175.
  • 8
    Reavy, H. J., N. J. Traynor and N. K. Gibbs (1997) Photogenotoxicity of skin phototumorigenic fluoroquinolone antibiotics detected using the comet assay. Photochem. Photobiol. 66, 368373.
  • 9
    Struwe, M., K. O. Greulich, W. Suter and U. Plappert-Helbig (2007) The photo comet assay—A fast screening assay for the determination of photogenotoxicity in vitro. Mutat. Res. 632, 4457.
  • 10
    Marrot, L., J. P. Belaidi, C. Jones, P. Perez, L. Riou, A. Sarasin and J. R. Meunier (2003) Molecular responses to photogenotoxic stress induced by the antibiotic lomefloxacin in human skin cells: From DNA damage to apoptosis. J. Invest. Dermatol. 121, 596606.
  • 11
    Marrot, L., J. P. Belaidi, C. Chaubo, J. R. Meunier, P. Perez and C. Agapakis-Causse (2001) Fluoroquinolones as chemical tools to define a strategy for photogenotoxicity in vitro assessment. Toxicol. In Vitro 15, 131142.
  • 12
    Traynor, N. J. and N. K. Gibbs (1999) The phototumorigenic fluoroquinolone lomefloxacin photosensitizes pyrimidine dimer formation in human keratinocytes in vitro. Photochem. Photobiol. 70, 957959.
  • 13
    Catalfo, A., M. L. Calandra, M. Renis, M. E. Serrentino and G. De Guidi (2007) Rufloxacin-induced photosensitization in yeast. Photochem. Photobiol. Sci. 6, 181189.
  • 14
    Catalfo, A., C. Scifo, S. Stella, A. Belvedere, M. Renis and G. De Guidi (2005) Rufloxacin induced photosensitization in bio-models of increasing complexity. Photochem. Photobiol. Sci. 4, 304314.
  • 15
    Struwe, M., K. O. Greulich, U. Junker, C. Jean, D. Zimmer, W. Suter and U. Plappert-Helbig (2008) Detection of photogenotoxicity in skin and eye in rat with the photo comet assay. Photochem. Photobiol. Sci. 7, 240249.
  • 16
    Condorelli, G., G. De Guidi, S. Giuffrida, P. Miano, S. Sortino and A. Velardita (1996) Membrane and DNA damage photosensitized by fluoroquinolone antimicrobials agents: A comparative screening. Med. Biol. Environ. 24, 103110.
  • 17
    De Guidi, G., S. Giuffrida, S. Monti, P. S. Pisu, S. Sortino and L. L. Costanzo (1999) Molecular mechanisms of photosensitization induced by drugs XIV: Two different behaviours in the photochemistry and photosensitization of antibacterials containing a fluoroquinolone like chromophore. Int. J. Photoenergy 1, 16.
  • 18
    Iwamoto, Y., T. Itoyama, K. Yasuda, T. Uzuhashi, H. Tanizawa, Y. Takino, T. Oku, H. Hashizume and Y. Yanagihara (1992) Photodynamic deoxyribonucleic acid (DNA) strand breaking activities of enoxacin and afloqualone. Chem. Pharm. Bull. 40, 18681870.
  • 19
    Iwamoto, Y., A. Kurita, T. Shimizu, T. Masuzawa, K. Uno, M. Yagi, T. Kitagawa, T. Oku and Y. Yanagihara (1994) DNA strand-breaking activities of quinolone antimicrobial agents under visible-light irradiation. Biol. Pharm. Bull. 17, 654657.
  • 20
    Martinez, L. and C. F. Chignell (1998) Photocleavage of DNA by the fluoroquinolone antibacterials. J. Photochem. Photobiol. B, Biol. 45, 5159.
  • 21
    Sortino, S., G. Condorelli, G. De Guidi and S. Giuffrida (1998) Molecular mechanism of photosensitization—XI. Membrane damage and DNA cleavage photoinduced by enoxacin. Photochem. Photobiol. 68, 652659.
  • 22
    Umezawa, N., K. Arakane, A. Ryu, S. Mashiko, M. Hirobe and T. Nagano (1997) Participation of reactive oxygen species in phototoxicity induced by quinolone antibacterial agents. Arch. Biochem. Biophys. 342, 275281.
  • 23
    Yamamoto, T., Y. Tsurumaki, M. Takei, M. Hosaka and Y. Oomori (2001) In vitro method for prediction of the phototoxic potentials of fluoroquinolones. Toxicol. In Vitro 15, 721727.
  • 24
    Lhiaubet-Vallet, V., M. C. Cuquerella, J. V. Castell, F. Bosca and M. A. Miranda (2007) Triplet excited fluoroquinolones as mediators for thymine cyclobutane dimer formation in DNA. J. Phys. Chem. B 111, 74097414.
  • 25
    Miolo, G., G. Viola, D. Vedaldi, F. Dall’Acqua, A. Fravolini, O. Tabarrini and V. Cecchetti (2002) In vitro phototoxic properties of new 6-desfluoro and 6-fluoro-8-methylquinolones. Toxicol. In Vitro 16, 683693.
  • 26
    Spratt, T. E., S. S. Schultz, D. E. Levy, D. Chen, G. Schluter and G. M. Williams (1999) Different mechanisms for the photoinduced production of oxidative DNA damage by fluoroquinolones differing in photostability. Chem. Res. Toxicol. 12, 809815.
  • 27
    Marrot, L. and C. Agapakis-Causse (2000) Differences in the photogenotoxic potential of two fluoroquinolones as shown in diploid yeast strain (Saccharomyces cerevisiae) and supercoiled plasmid DNA. Mutat. Res. 468, 19.
  • 28
    Bosca, F., V. Lhiaubet-Vallet, M. C. Cuquerella, J. V. Castell and M. A. Miranda (2006) The triplet energy of thymine in DNA. J. Am. Chem. Soc. 128, 63186319.
  • 29
    Lhiaubet-Vallet, V., Z. Sarabia, D. Hernandez, J. V. Castell and M. A. Miranda (2003) In vitro studies on DNA-photo sensitization by different drug stereoisomers. Toxicol. In Vitro 17, 651656.
  • 30
    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, 782801.
  • 31
    Sayama, K., Y. Kobayashi, H. Fujita, A. Ito, Y. Tokura and M. Sasaki (2005) Determination of action spectrum for sparfloxacin-photosensitized single-strand breaks in plasmid pBR322 DNA. Photodermatol. Photoimmunol. Photomed. 21, 287292.
  • 32
    Sayama, K., K. Ishikawa, R. Yamada, H. Fujita, A. Ito and M. Sasaki (2002) In vitro evaluation of preventive ability of commercial sunscreens against induction of photosensitivity with sparfloxacin. Photomed. Photobiol. 24, 4346.
  • 33
    Hiraku, Y. and S. Kawanishi (2000) Distinct mechanisms of guanine-specific DNA photodamage induced by nalidixic acid and fluoroquinolone antibacterials. Arch. Biochem. Biophys. 382, 211218.
  • 34
    Saito, I., T. Nakamura, K. Nakatani, Y. Yoshioka, K. Yamaguchi and H. Sugiyama (1998) Mapping of the hot spots for DNA damage by one-electron oxidation: Efficacy of GG doublets and GGG triplets as a trap in long-range hole migration. J. Am. Chem. Soc. 120, 1268612687.
  • 35
    Rosen, J. E., D. Chen, A. K. Prahalad, T. E. Spratt, G. Schluter and 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. Toxicol. Appl. Pharmacol. 145, 381387.
  • 36
    Verna, L. K., D. Chen, G. Schluter and G. M. Williams (1998) Inhibition by singlet oxygen quenchers of oxidative damage to DNA produced in cultured cells by exposure to a quinolone antibiotic and ultraviolet A irradiation. Cell Biol. Toxicol. 14, 237242.
  • 37
    Rosen, J. E. (1997) Proposed mechanism for the photodynamic generation of 8-oxo-7,8-dihydro-2′-deoxyguanosine produced in cultured cells by exposure to lomefloxacin. Mutat. Res. 381, 117129.
  • 38
    Rosen, J. E., A. K. Prahalad, G. Schluter, D. Chen and G. M. Williams (1997) Quinolone antibiotic photodynamic production of 8-oxo-7,8-dihydro-2′-deoxyguanosine in cultured liver epithelial cells. Photochem. Photobiol. 65, 990996.
  • 39
    Belvedere, A., F. Bosca, A. Catalfo, M. C. Cuquerella, G. De Guidi and M. A. Miranda (2002) Type II guanine oxidation photoinduced by the antibacterial fluoroquinolone rufloxacin in isolated DNA and in 2′-deoxyguanosine. Chem. Res. Toxicol. 15, 11421149.
  • 40
    Cuquerella, M. C., F. Bosca, M. A. Miranda, A. Belvedere, A. Catalfo and G. De Guidi (2003) Photochemical properties of ofloxacin involved in oxidative DNA damage: A comparison with rufloxacin. Chem. Res. Toxicol. 16, 562570.
  • 41
    Hiraku, Y., K. Ito, K. Hirakawa and S. Kawanishi (2007) Photosensitized DNA damage and its protection via a novel mechanism. Photochem. Photobiol. 83, 205212.
  • 42
    Jeffrey, A. M., L. Shao, S. Y. Brendler-Schwaab, G. Schluter and G. M. Williams (2000) Photochemical mutagenicity of phototoxic and photochemically carcinogenic fluoroquinolones in comparison with the photostable moxifloxacin. Arch. Toxicol. 74, 555559.
  • 43
    Martinez, L. J., G. Li and C. F. Chignell (1997) Photogeneration of fluoride by the fluoroquinolone antimicrobial agents lomefloxacin and fleroxacin. Photochem. Photobiol. 65, 599602.
  • 44
    Cuquerella, M. C., M. A. Miranda and F. Bosca (2006) Generation of detectable singlet aryl cations by photodehalogenation of fluoroquinolones. J. Phys. Chem. B 110, 64416443.
  • 45
    Lovdahl, M. J. and R. S. Priebe (2000) Characterization of clinafloxacin photodegradation products by LC-MS/MS and NMR. J. Pharm. Biomed. 23, 521534.
  • 46
    Morimura, T., K. Kohno, Y. Nobuhara and H. Matsukura (1997) Photoreaction and active oxygen generation by photosensitization of a new antibacterial fluoroquinolone derivative, orbifloxacin, in the presence of chloride ion. Chem. Pharm. Bull. 45, 18281832.
  • 47
    Cuquerella, M. C., F. Bosca and M. A. Miranda (2004) Photonucleophilic aromatic substitution of 6-fluoroquinolones in basic media: Triplet quenching by hydroxide anion. J. Org. Chem. 69, 72567261.
  • 48
    Fasani, E., F. F. Barberis Negra, M. Mella, S. Monti and A. Albini (1999) Photoinduced C-F bond cleavage in some fluorinated 7-amino-4-quinolone-3-carboxylic acids. J. Org. Chem. 64, 53885395.
  • 49
    Albini, A. and S. Monti (2003) Photophysics and photochemistry of fluoroquinolones. Chem. Soc. Rev. 32, 238250.
  • 50
    Lorenzo, F., S. Navaratnam, R. Edge and N. S. Allen (2008) Primary photophysical properties of moxifloxacin—A fluoroquinolone antibiotic. Photochem. Photobiol. 84, 11181125.
  • 51
    Sortino, S. and G. Condorelli (2002) Complexes between fluoroquinolones and calf thymus DNA: Binding mode and photochemical reactivity. New J. Chem. 26, 250258.