Mechanisms of photosensitization induced by drugsA general survey

Referencias bibliográficas

• Ames, B.N.; Magaw, R.; Gold, L.S. (1987), Ranking possible carcinogenic hazards. Science. 236, 271-280
• Ando, W. (1978). In The Chemistry of Functional Groups: Diazonium and Diazo. S.Patai Ed., Wiley.New York. Pp 341.
• Andriole, V.T. (1999). The Future of the Quinolones. Drugs. 58, 1-5
• Artuso, T.; Bernadou, J.; Meunier, B.; Paillous, N. (1990). DNA strand breaks photosensitized by benoxaprofen and other non steroidal anti-inflammatory agents. Biochem.Pharmacol. 39, 407-413
• Artuso, T.; Bernadou, J.; Meunier, B.; Piette, J.; Paillous, N. (1991). Mechanism of DNA cleavage mediated by photoexcited non-steroidal anti-inflammatory drugs. Photochem.Photobiol. 54, 205-213
• Aveline, B.; Redmond, R.W. (1998). Exclusive free radical mechanisms of cellular photosensitization. Photochem.Photobiol. 68, 266-275
• Aveline, B.; Redmond, R.W. (1999). Can cellular phototoxicity be accurately predicted on the basis of sensitizer photophysics?. Photochem.Photobiol. 69, 306-316
• Ayra, D.P.; Warner, P.M.; Jebaratnam, D.J. (1993). Development of a new DNA-binding and cleaving molecules: Design, synthesis and activity of a bisdiazonium salt. Tetr.Lett., 34, 7823-7826
• Baird, G.M.; Willoughby, M.L.N. (1978) Photodegradation of dacarbazine [Letter]. Lancet. 2, 681
• Ball, P.; Tillotson, G.S. (1995) Tolerability of fluoroquinone antibiotics: past present and future. Drug Saf. 13, 343-358
• Ball, P.; Mandell, L.; Niki, Y.; Tillotson, G. (1999). Comparative tolerability of the newer fluoroquinolone antibacterials. Drug Saf. 21, 407-421
• Becker, L; Eberlein K. B.; Przybilla, B. (1996). Phototoxicity of non-steroidal anti-inflammatory drugs: in vitro studies with visible light. Acta Derm.Venereol. 76, 337-40
• Berh, J.P. (1989). Photohydrolysis of DNA by polyaminobenzenediazonium salts. J.Chem.Soc.,Chem.Commun. 101-103
• Beijersbergen van Henegouwen, G.M.J. (1981). The interference of light in pharmacotherapy. Pharmaceutisch Weeklab, Sci.Ed. 3, 85-95
• Beijersbergen van Henegouwen, G.M.J. (1997). Medicinal photochemistry: Phototoxic and phototherapeutic aspects of drugs. Advances in Drug Research. 29, 79-170
• Bilski, P.; Martínez, L.J.; Koker, E.B.; Chignell, F. (1996) Photosensitization by norfloxacin is a function of pH. Photochem.Photobiol. 64, 496-500
• Bilski, P.; Martínez, L.J.; Koker, E.B.; Chignell, F. (1998) Influence of solvent polarity and proticity on the photochemical properties of norfloxacin. Photochem.Photobiol. 68, 20-24
• Boscá, F.; Miranda, M.A.; Vaño, L.; Vargas, F. (1990). New photodegradation pathways for naproxen, a phototoxic nonsteroidal antiinflammatoty drug. J.Photochem.Photobiol., A:Chem. 54, 131-134
• Boscá, F.; Miranda, M.A.; Vargas, F. (1992). Photochemistry of tiaprofenic acid, a nonsteroidal anti-inflammatory drug with phototoxic side effects. J.Pharm.Sci. 81, 181-182
• Boscá, F.; Miranda, M.A.; Carganico, G.; Mauleón, D. (1994). Photochemical and Photobiological properties of ketoprofen associated with the benzophenone chromophore.Photochem.Photobiol. 60, 96-101
• Boscá, F.; Garganico, G.; Castell, J.V. (1995). Evaluation of ketoprofen (R, S and R/S) phototoxicity by a battery of in vitro assays. J.Photochem.Photobiol.B. 99, 1-6
• Boscá, F.; Encinas, S.; Heelis, P.F.; Miranda, M.A. (1997). Photophysical and photochemical characterization of a photosensitizing drug: A combined steady-state photolysis and laser flash photolysis study on carprofen. Chem.Res.Toxicol. 10, 820-827
• Boscá, F.; Miranda, M.A. (1998). Photosensitizing drugs containing the benzophenone chromophore. J.Photochem.Photobiol. B: Biol. 43, 1-26
• Castell, J.V.; Gómez-L., M.J.; Miranda, M.A.; Morera, I.M. (1992). Phototoxicity of non-steroidal anti-inflammatory drugs: In vitro testing of the photoproducts of butibufen and flurbiprofen. J.Photochem.Photobiol. B: Biol. 13, 71-81
• Castell, J.V.; Gómez-L., M.J.; Grassa, C.; Martínez, L.A.; Miranda, M.A.; Tárrega, P. (1993). Involvement of drug-derived peroxides in the phototoxicity of naproxen and tiaprofenic acid. Photochem.Photobiol. 57, 486-490
• Castell, J.V.; Gómez-L., M.J.; Grassa, C.; Martínez, L.A.; Miranda, M.A.; Tarrega, P. (1994a). Photodynamic lipid peroxidation by the photosensitising non-steroidal anti-inflammatory drugs suprofen and tiaprofenic acid. Photochem.Photobiol. 59, 35-39
• Castell, J.V.; Gómez-L., M.J.; Hernández, D.; Martínez, L.A.; Miranda, M.A. (1994b). Molecular basis of drug toxicity: Photosensitized cell damage by the major photoproduct of tiaprofenic acid. Photochem.Photobiol., 60, 586-590
• Castell, J.V.; Hernández, D.; Gómez-L., M.J.; Lahoz, A.; Miranda. M.A.; Morera, I.; Pérez-P., J.; Sarabia, Z. (1998). Photobinding of tiaprofenic acid and suprofen to proteins and cells; A combined study using radiolabelling, antibodies and laser flash photolysis of model bicromophores. Photochem.Photobiol., 68, 660-665
• Chauhan, Y.S.; Toth, B. (1984). Synthesis of N2-[g-L-(+)-glutamyl]-4-carboxyphenylhydrazine, a postulated presucrsor of agaritine of Agaricus bisporus. J.Agric.Food Chem. 32, 676-678
• Chetalat, A.; Albertini, S.; Gocke, E. (1996). The photomutagenicity of fluoroquinolones in tests for gene mutation, chromosomal aberration, gene conversion and DNA breakage (Comet assay). Mutagenesis. 11, 497-504
• Chin, A.; Hung, M.H.; Stock, L.M. (1981). Reactions of benzenediazonium ions with adenine and its derivatives. J.Org.Chem. , 2203-2207
• Chung, K.T.; Cerniglia, C.E. (1992). Mutagenicity of azo dyes: structure-activity relationships. Mutat-Res. 277, 201-20.
• Condorelli, G.; Costanzo, L.L.; De Guidi, G.; Giuffrida, S.; Sortino, S. (1995) Molecular Mechanism of drug photosensitization Part 7. Photocleavage of DNA sensitized by suprofen. Photochem.Photobiol. 62, 155-161
• Condorelli, G.; Costanzo, L.L.; De Guidi, G.; Giuffrida, S.; Miano, P.; Sortino, S.; Velardita, A. (1996a). Photosensitisation induced by non steroidal anti inflammatory drugs: An overview of molecular mechanisms in biological systems. EPA Newsletter. 60-77.
• Condorelli, G.; De Guidi, G.; Giuffrida, S.; Miano, P.; Sortino, S.; Velardita, A. (1996). Membrane and DNA damage photosensitised by fluoroquinolone antimicrobial agents: a comparative screening. Med.Biol.Environ. 24, 103-110
• Condorelli, G.; De Guidi, G.; Giuffrida, S.; Sortino, S.; Chimelli, R.; Sciuto, S. (1999). Molecular mechanisms of photosensitization induced by drugs XII. Photochemistry and photosensitization of rufloxacin: An unusual photodegradation path for the antibacterials containing a fluoroquinolone-like chromophore. Photochem.Photobiol., 70, 280-286
• Costanzo, L.L.; De Guidi, G.; Condorelli, G.; Cambria, A.; Fama, M. (1989a). Molecular mechanism of naproxen photosensitization in red blood cells. J.Photochem.Photobiol. B: Biol. 3, 223-235
• Costanzo, L.L.; De Guidi, G.; Condorelli, G.; Cambria, A.; Fama, M. (1989b). Molecular mechanism of drug photosensitization-II. Photohemolysis sensitized by ketoprofen. Photochem.Photobiol. 50, 359-365
• Curtis, R.E.; Hankey, B.F.; Myers, M.H.; Young, J.L.Jr. (1984). Risk of leukemia associated with the first course of cancer treatment: An analysis of the surveillance, epidemiology and end results program experience. J.Natl.Cancer Int. 72, 531-544
• De Guidi, G.; Chillemi, R.; Costanzo, L.L.; Giuffrida, S.; Condorelli, G. (1993). Molecular mechanism of drug photosensitization Part 4. Photohemolysis sensitized by carprofen. J.Photochem.Photobiol. B: Biol. 17, 239-246
• De Guidi, Chillemi, R.; Costanzo, L.L.; Giuffrida, S.; Sortino, S.; Condorelli, G. (1994). Molecular mechanism of drug photosensitization 5. Photohemolysis sensitized by suprofen. J.Photochem.Photobiol. B: Biol. 23, 125-133
• De Vries, H.; Beijesbergen van Henegouwen, G.M.J. (1995). Photodegradation of nifedipine under in vivo-related circumstances. Photochem.Photobiol. 62, 959-963
• De Vries, H.; Encinas, S.; Miranda, M.A.; Castell, J.V.; Beijesbergen van Henegouwen, G.M.J. (1997). Photodegradation and photobinding of tiaprofenic acid: in vitro versus in vivo. Photochem.Photobiol. 66, 432-435
• De Vries, H.; Beijesbergen van Henegouwen, G.M.J. (1998). Photoreactivity of nifedipine in vitro and in vivo. J.Photochem.Photobiol.B. 43, 217-221
• Diffey, B.L.; Daymond, T.J.; Fairgraves, H. (1983). Photosensitivity studies on non-steroidal anti-inflammatory drugs. Br.J.Dermatol.. 113, 537-549
• Domagala, J.M.; Hann, L.D.; Heifetz, C.L.; Hutt, M.P.; Mich, T.F.; Sánchez, J.P.; Solomon, M. (1986). New structureactivity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay. J.Med.Chem. 29, 394-404
• Domagala, J.M. (1994). Structure-activity and structure-side effect relationships for the quinolone antibacterials. J.Antimicrobiol.Chemother. 33, 685-706
• Dougherty, T.J. and Marcus, S.L. (1992). Photodynamic Therapy. Eur.J.Cancer. 28A, 1734-1742
• Eberlein-König, B.; Bindl, A.; Przybilla, B. (1997) Phototoxic properties of neuroleptic drugs. Dermatology.194, 131-135
• Einsele, H.; Clemens, M.R.; Wegner, U.; Waller, H.D. (1987). Effect of free radical scavengers and metal ion chelators on hydrogen peroxide and phenylhydrazine induced red blood cell lipid peroxidation. Free Radic Res Commun. 3, 257-263
• Ellis, A.L. (1998). Regulatory perspective on in vitro assays as predictors of phototoxicity and co-photocarcinogenicity. Int.J.Toxicol. 17, 571-575
• Encinas, S.; Bosca, F.; Miranda, M.A. (1998a). Phototoxicity associated with diclofenac: A photophysical, photochemical, and photobiological study on the drug and its photoproducts. Chem.Res.Toxicol. 11, 946-952
• Encinas, S.; Miranda, M.A.; Marconi, G.; Monti, S. (1998b). Transient species in the photochemistry of tiaprofenic acid and its decarboxylated photoproduct. Photochem.Photobiol. 68, 633-639
• Encinas, S.; Bosca, F.; Miranda, M.A. (1998c). Photochemistry of 2,6-dichlorodiphenylamine and 1-chlorocarbazole, the photoactive chromophores of diclofenac, meclofenamic acid and their major photoproducts. Photochem.Photobiol. 68, 640-645
• Epe, B. (1993). DNA damage induced by photosensitization. In DNA and Free Radicals. B.Halliwell; O.I.Aruoma. Eds., pp 41-65. New York. Ellis Horwood
• Epstein, J.H. (1989). Photomedicine. In The Science of Photobiology. Second Edition .K.C.Smith Ed., pp. 155-192. New York.Plenum Press
• Fasani, E.; Profumo, A.; Albini, A. (1998). Structure and medium-dependent photodecomposition of fluoroquinolone antibiotics. Photochem.Photobiol., 68, 666-674
• Ferguson, J. (1995). Fluoroquinolone photosensitization: a review of clinical and laboratory studies. Photochem. Photobiol. 62, 954-958
• Fernández-Liencres, M.P.; Carazo, F.; Cabeza, M.C.; Quintero, B.; Thomas, J.; Alvarez, J.M. (1993). Simultaneous C- and N-nitrosation of synephrine. A kinetic study. J. Chem. Soc. Perkin Trans. 2. 2265-2273
• Foote, C.S. (1976). Photosensitised oxidation and singlet oxygen: consequences in biological systems. In Free Radicals in Biology, Vol. 2 W.A. Prior. Ed., pp. 2541-2606. San Diego. Academic Press
• Foote, C.S.; (1991). Definition of type I and type II photosensitized oxidation.[editorial] Photochem.Photobiol. 54, 659
• Foster, B.J.; Newell D.R.; Carmichael, J.; Harris, A.L.; Gumbrell, L.A.; Jones, M.; Goodard, P.M.; Calvert, A.H. (1993)
• Preclinical, phase I and pharmacokinetic studies with the dimethyl phenyltriazene CB10-277. Br J Cancer. 67, 362-368
• Foti, C.; Vena, G.A.; Angelini, G. (1992). Occupational contact allergy to benzydamide hydrochloride. Contact Dermatitis. 27, 328-329
• Galli, C. (1988). Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical. Chem. Rev. 88, 765-792
• Gannett, P.M.; Lawson, T.; Miller, M.; Thakkar, D.D.; Lord, J.W.; Yau, W.M.; Toth, B. (1996). 8-Arylguanine adducts from arenediazonium ions and DNA. Chem.-Biol.Interact. 101, 149-164
• Gannett, P.M.; Shi, X.; Lawson, T.; Kolar, C.; Toth, B. (1997). Aryl radical formation during the metabolism of arylhidrazines by microsomes.Chem.Res.Toxicol. 10, 1372-1377
• Gannett, P.M.; Powell, J. H.; Rao, R.; Shi, X.; Lawson, T.; Kolar, C.; Toth, B. (1999) C8-Arylguanine and C8-aryladenine formation in calf thymus DNA from arenediazonium ions. Chem.Res Toxicol. 12, 297-304
• García-Meijide, M.C.; Bravo Díaz, C.; Romsted, L.S. (1998). A new method for monitoring dediazoniation reactions: Simultaneous monitoring of concentration and rates of product formation and loss of starting material for the dediazoniation of p-methylbenzenediazonium tetrafluoroborate Int.J.Chem.Kinet. 30, 31-39
• Gasper, S.M.; Devadoss, C. ; Schuster, G.B. (1995). Photolysis of substituted benzenediazonium salts: Spin selective reactivity of aryl cations. J. Am. Chem. Soc. 117, 5206-5211
• Giuffrida, S.; De Guidi, G.; Sortino, S.; Chillemi, R.; Costanzo, L.L.; Condorelli, G. (1995). Molecular mechanism of drug photosensitization Part 6. Photohemolysis sensitized by tolmetin. J.Photochem.Photobiol. B.: Biol. 29, 125-133
• Giuffrida, S.; De Guidi, G.; Miano, P.; Sortino, S.; Condorelli, G.; Costanzo, L.L.; (1996a). Molecular mechanism of drug photosensitization Part VIII. Effect of inorganic ions on membrane damage photosensitized by naproxen. J.Inorg.Biochem. 63, 253-263
• Giuffrida, S.; De Guidi, G.; Miano, P.; Sortino, S.; Condorelli, G.; Costanzo, L.L.; (1996b). Molecular mechanism of drug photosensitization Part IX. Effect of inorganic ions on DNA cleavage photosensitized by naproxen. Photochem.Photobiol. 63, 445-462
• Glaser, R.; Horan, C.J.; Lewis, M.; Zollinger, H. (1999) s-Dative and p-backdative phenylcation –dinitrogen interactions and opposing sign reaction constants in dual substituent parameter relations J.Org.Chem. 64, 902-913
• Goday, B.J.J.; Ilardia, L.R.; Soloeta, A.R. (1993). Allergic contact dermatitis from benzydamide with probable crossreaction to indomethacin. Contact Dermatitis. 28, 111-112
• Goldstein. E.J. (1996). Possible role for the new fluoroquinolones (levofloxacin, grepafloxacin, trovafloxacin, clinafloxacin, sparfloxacin, and DU-6859a) in the treatment of anaerobic infections: review of current information on efficacy and safety. Clin Infect Dis 23. S25-30
• González, V.M.; Pérez, J.M.; Alonso, C. (1997). The berenil ligand directs the DNA binding of the cytotoxic drug Ptberenil. J.Inorg.Biochem. 68, 283-287
• Gould, J.G.; Mercurio, M.G.; Elmets, C.A. (1995). Cutaneous photosensitivity diseases induced by exogenous agents. J. Am. Acad. Dermatol. 33, 551-573
• Griffiths, J.; Murphy, J.A. (1992). Cleavage of DNA resulting from exposure to phenyl radicals. J.Chem.Soc., Chem.Commun. 24-26
• Hazlewood, C.; Davies, M.J.; Gilbert, B.C.; Packer, J. E. (1995). Electron paramagnetic resonance studies of the reaction of aryl radicals with nucleic acids and their components. J. Chem. Soc.,Perkin Trans. 2. 2167-74
• Heid, E.; Samsoen, M.; Julliard, J. (1977). Eruptions papulovésiculeuses endogènes à la méthyldopa et au clofibrate. Ann.Derm.Venereol. 104, 494-496
• Henderson, B.W.; Dougherty, T.J. (1992). Photodynamic Therapy.Principles and Clinical Applications. Marcel Dekker.New York
• Hiramoto, K.; Kaku, M.; Kato, T.; Kikugawa, K.; (1995). DNA strand breaking by carbon-centered radical generated from 4-(hydroxymethyl) benzenediazonium salt, a carcinogen in mushroom Agaricus bisporus. Chem. Biol. Interact. 94, 21-36
• Hölzle, E.; Neumann, N.; Hausen, B.; Przybilla, B.; Schauder, S.; Hönigsmann, H.; Bircher, A.; Plewig, G. (1991) Photopatch testing: the five-year experience of the German, Austrian, and Swiss photopatch test group. Journal of the American Academy of Dermatology. 25, 59-68
• Horton, J.K.; Stevens, M.F.G. (1979). Search for drug interaction between the antitumour agent DTIC and other cytotoxic agents. J.Pharm.Pharmacol. 31, 64P
• Hung, M.-H.; Stock, L.M. (1982). Reactions of benzenediazonium ions with guanine and its derivatives. J.Org.Chem. 47, 448-453
• Ishikana, T.; Kamide, R.; Niimura, M. (1994). Photoleukomelanodermatitis (Kabori) induced by afloqualone. J.Dermatol. 21, 430-433
• Iwamoto, Y.; Itoyama, T.; Yasuda, K.; Uzuhashi, T.; Tanizawa, I.; Takino, Y.; Oku, T.; Hashizume, H.; Yanihigara, Y. (1992). Photodynamic deoxyribonucleic acid (DNA) strand breaking avtivity of enoxacin and aflaqualone. Chem.Pharm.Bull. 40, 1868-1870
• Jiménez, M.C.; Miranda, M.A.; Tormos, R. (1997). Photochemistry of naproxen in the presence of b-cyclodextrin. J.Photochem.Photobiol.A Chem. 104, 119-121
• Johnson, B.E.; Gibbs, N.K.; Fegurson, J. (1997). Quinolone antibiotic with potential to photosensitise skin tumorogenesis. J.Photochem.Photobiol.B Biol. 37, 171-173
• Kang, J.S.; Kim, T.H.; Park, K.B.; Chung, B.H.; Youn, J.I. (1993). Enoxacin photosensitivity. Photodermatol. Photoinmunol. Photomed. 9, 159-161
• Kato, T.; Kojima, K.; Hiramoto, K.; Kikugawa, K. (1992). DNA strand breakage by hydroxyphenyl radicals generated from mutagenic diazoquinone compounds. Mutation Res. 268, 105-114
• Kikugawa, K.; Kato, T.; Takeda, Y. (1987). Formation of a highly mutagenic diazo compound from the bamethan-nitrite reaction. Mutation Res. 172, 35-43
• Kikugawa, K.; Kato, T.; Takeda Y. (1989). Formation of a direct mutagen, diazo-N-nitrosoetilefrin, by interaction of etilefrin with nitrite. Chem. Pharm. Bull. 37, 1600-1603
• Kikugawa, K.; Kato, T.; Kojima, K. (1992). Substitution of p- and o-hydroxyphenyl radicals at the 8 position of purine nucleosides by reaction with mutagenic p- and o-diazoquinones. Mutation Res. 268, 65-75.
• Klecak, G.; Urbach, F.; Urwyler, H. (1997) Fluoroquinolone antibacterials enhance UVA-induced skin tumors. J.Photochem.Photobiol.B Biol. 37, 174-181
• Kochevar, I.E.; Hoover, K.W.; Gawienowski, M. (1984). Benoxaprofen photosensitization of cell membrane disruption. J.Invest.Dermatol. 82, 214-218
• Kochevar, I.E. (1989). Phototoxicity of non steroidal anti inflammatory drugs. Arch.Dermatol., 125, 824-826
• Kurumaji, Y.; Ohshiro, Y.; Miyamoto, C.; Keong, C.H.; Katoh, T.; Nishioka, K. (1991). Allergic photocontact dermatitis due to suprofen photopatch testing and cross reaction study. Contact Dermatitis. 25, 218-223
• Lassiani, L.; Ebert, C.; Nisi, C.; Varnavas, A.; Zorzet, S.; Sava, G.; Boccu, E. (1990). Kinetic investigation of the aqueous stability and antitumor activity of a hydrosoluble diaryltriazene, AVIS, related to the antimetastatic agent DMCOOK. Pharmazie. 45, 743-745
• Lawson, T.; Chauhan, Y. (1985) Metabolism of arylhysrazines by mouse liver mixed-function oxidases in vitro. J.Agr.Food Chem. 33, 218-219
• Lawson, T.; Gannett, P.M.; Yau, W.M.; Dalal, N.S.; Toth, B. (1995). Different patterns of mutagenicity of arenediazonium ions in V79 cells and Salmonella typhimurium TA102: Evidence for different mechanisms of actions. J. Agric. Food Chem. 43, 2627-2635
• Leroy, D.; Dompmartin, A.; Szczurko, C. (1996). Flutamide photosensitivity. Photodermatol.Photoinmunol.Photomed. 12, 216-218
• Levenberg, B. (1962). An aromatic diazonium compound in the mushroom Agaricus bisporus Biochim.Biophys.Act. 63, 212-214
• Lietman, P.S. (1995). Fluoroquinone toxicities. An update. Drugs. 49, 794-850
• Lipsky, B.A.; Baker, S.A. (1999) Fluoroquinolone toxicity profiles: a review focusing on newer agents. Clin.Infect.Dis. 28, 352-364
• Ljunggren, B.; Moller, H. (1978). Drug phototoxicity in mice. Acta Dermatologica. 58, 125-130
• Ljunggren, B. (1984). The mouse tail phototoxicity test. Photodermatol.. 1, 96-100
• Ljunggren, B. (1985a). Propionic acid-derived non-steroidal anti-inflammatory drugs are phototoxic in vitro. Photodermatol., 2, 3-9
• Ljunggren, B.; Lundberg, K. (1985b). In vivo phototoxicity of non-steroidal anti-inflammatory drugs evaluated by the mouse tail technique. Photodermatol.. 2, 377-382
• Loveday, K.S. (1996). Interrelationship of photocarcinogenicity, photomutagenicity and phototoxicity. Photochem.Photobiol., 63, 369-72
• Lovell, W.W. (1993). A scheme for in vitro screening of substance for photoallergic potential. Toxicol.In Vitro. 7, 95-102
• Lown J.W.; Singh, R. (1982). Mechanism of action of antitumor 3-(2-haloethyl) aryltriazenes on deoxyribonucleic acid. Biochem Pharmacol. 31, 1257-1266
• Maekinen, M.; Forbes, P.D.; Stenbaek, F. (1997). Quinolone antibacterials: a new class of photochemical carcinogens. J. Photochem. Photobiol. B Biol. 37, 182-187
• Malaveille, C.; Brun, G.; Kolar, G.; Bartsch, H. (1982). Mutagenic and alkylating activities of 3-methyl-1-phenyltriazenes and their possible role as carcinogenic metabolites of the parent dimethyl compounds. Cancer Res. 42, 1446-1453
• Margolis-Nunno, H.; Ben-Hur, E.; Gottlieb, P.; Robinson, R.; Oetjen, J.; Horowitz, B. (1996). Inactivation by phtalocyanine photosensitation of multiple forms of human inmunodeficiency virus in red cell concentrates. Transfusion. 36, 743-750
• Martindale. The Extra Pharmacopeia.(1996). 31 Edition. J.E.F. Reynolds Ed. Royal Pharmaceutical Society
• Martínez, L.J.; Li, G.; Chignell, C.F. (1997). Photogeneration of fluoride by the fluoroquinolone antimicrobial agents lomefloxacin and fleroxacin. Photochem.Photobiol. 65, 599-602
• Martínez, L.J.; Sik, R.H.; Chignell, C.F. (1998). Fluoroquinolone antimicrobials: singlet oxygen, superoxide and phototoxicity. Photochem. Photobiol. 67, 399-403
• Marutani, K.; Matsumoto, M.; Otabe, Y.; Nagamura, M.; Tanaka, K.; Miyoshi, A.; Hasagawa, T.; Nagano, H.; Matsubara, S.; Kamide, R.; Yokota, E.; Matsumoto, F.; Ueda, Y. (1993). 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, 2217-2223
• Marutani K.; Otabe, Y.; Nagamuta, M.; Matsubara, S.; Otani, H. (1998). Photoallergenicity of a Fluoroquinolone Antibacterial Agent with a Fluorine Substituent at the 8-Position in Guinea Pigs Exposed to Long-Wavelength UV Light. Skin Pharmacology and Applied Skin Physiology. 11, 232-240.
• Miranda, M.A.; Morera, I.; Vargas, F.; Gómez-L., M.J.; Castell, J.V. (1991). In vitro assessment of the phototoxicity of anti-inflammatory 2-arylpropionic acids. Toxicol.in Vitro. 5, 451-455
• Miranda, M.A. (1992). Phototoxicity of drugs. In In vitro alternatives to animal pharmaco-toxicology. J.V.Castell & M.J.Gómez-Lechón Eds., pp. 239-270. Farmaindustria. Madrid.Spain
• Miranda, M.A.; Castell, J.V.; Gómez-L.; M.J.; Hernández, D.; Martínez, L.A. (1995). Photobinding of drugs to cells as an indicator of potential photoallergy. Toxicol.in Vitro. 9, 499-503
• Miranda, M.A. (1997). Phototoxicity of drugs. In In vitro Methods in Pharmaceutical Research. J.V. Castell Ed. pp. 289-315. Academic Press. London
• Miranda, M.A.; Pérez-P, J.; Lahoz, A.; Morera, I.M.; Sarabia, Z.; Martínez-M., R.; Castell, J.V.; (1999). Isolation of crosscoupling products in model studies on the photochemical modification of proteins by tiaprofenic acid. Eur.J.Org.Chem. 497-502
• Moore, D.E.; Chappuis, P.P. (1988). A comparative study on the non-steroidal anti-inflammatory drugs, naproxen, benoxaprofen and indomethacin. Photochem.Photobiol. 47, 173-180
• Moore, D.E. (1998). Mechanisms of photosensitization by phototoxic drugs. Mutat.Res. 422, 165-173
• Moore, D.E.; Wang, J. (1998). Electron-transfer mechanisms in photosensitization by the anti-inflammatory drug benzydamine. J. Photochem. Photobiol. B. 43, 175-80
• Morimura, T.; Kohno, K.; Nobuhara, Y.; Matsukura, H. (1997) Photoreaction and active oxygen generation by photosensitization of a new antibacterial fluoroquinolone derivative, orbitofloxacin, in the presence of chloride ion. Chem.Pharm.Bull., 45, 1828-1832
• Mozzanica, N.; Pigatto, P.D. (1990). Contact and photocontact allergy to ketoprofen, clinical and experimental-study. Contact Dermat. 23, 336-340
• Nabeya, R.T.; Kojima, T.; Fujita, M. (1995). Photocontact dermatitis from ketoprofen with an unusual clinical feature. Contact Dermat. 32, 52-53
• Neorodost, S.T.; Dijkstra, J.W.E. (1989) Drug induced photosensitivity reaction. Arch.Dermatol. 125, 433-434
• Neu, H.C. (1990). Quinolones as broad-spectrum agents. In The 4-Quinolones. G.C.Crumplin Ed. Pp 1-13. Springer-Verlag. London
• Norrby, S.R. (1997). New fluoroquinolones: towards expanded indications? Current Opinion in Infectious Diseases. 10, 440-443.
• Ochiai, M.; Wakabayashi, K.; Nagao, M.; Sugimura, T. (1984). Tyramine is a major mutagen precursor in soy sauce, being convertible to a mutagen by nitrite. Gann. 75, 1-3
• Ophaswongse, S.; Maibach, H. (1993). Topical non steroidal antiinflammatory drugs: allergic and photoallergic contac dermatitis and phototoxicity. Contact Dermatitis. 29, 57-64
• Ohshima, H.; Friesen, M.; Malaveille, C.; Brouet, I.; Hautefeuille, A.; Bartsch, H. (1989). Formation of direct acting genotoxic substances in nitrosated smoked fish and meat products: identification of simple phenolic precursors and phenyldiazonium ions as reactive products. Food Chem.Toxicol. 27, 193-203
• Ohta, T.; Oribe, H.; Kameyama, T.; Goto, Y.; Takitani, S. (1988). Formation of diazoquinona-type mutagen from acetaminophen treated with nitrite under acidic conditions. Mutation Res. 209, 95-98
• Ouedraogo, G.; Morlière, P.; Bazin, M.; Santus, R.; Kratzer, B.; Miranda, M.A.; Castell, J.V. (1999). Lysosomes are sites of fluoroquinolone photosensitization in human skin fibroblasts: A microspectrofluorometric approach. Photochem.Photobiol. 70, 123-129
• Palù, G.; Valissena, S.; Ciarrochi, G. ;Gatto, B.; Palumbo, M. (1992). Quinolone binding to DNA is mediated by magnesium ions. Proc.Natl.Acad.Sci.USA. 89, 9671-9675
• Parodi, S.; de Flora, S.; Cavanna, M.; Pino, A.; Robbiano, L.; Bennicelli, C.; Brambilla, G. (1981). DNA-damaging activity in vitro and bacterial mutagenicity of sixteen hydrazine derivatives as related quantitatively to their carcinogenicity. Cancer Res. 41, 1469-1482
• Pazo Llorente, R.; Sarabia Rodríguez, M.J.; Bravo Díaz, C.; González Romero, E. (1999). Hydroxy- and chloro- dediazoniation of 2- and 3- methylbenzenediazonium tetrafluorborate in aqueous solution. Int.J.Chem.Kinet. 31, 73-82
• Pazzagli, L.; Baufi, R.; Borselli, G.; Semmola, M.V. (1998). Photosensitivity reaction to fluoxetine and alprazolam. Pharm. World Sci. 20, 136
• Pendlington, R.U.; Barratt, K.R. (1990). Molecular basis of photocontact allergy. International Journal of Cosmetic Science. 12, 91-103
• Preece; N.E.; Timbrell; J.A. .(1989). Investigation of lipid peroxidation induced by hydrazine compounds in vivo in the rat. Pharmacol Toxicol. 64, 282-285
• Przybilla, B.; Schwab-Przybilla, U.; Ruzicka, T.; Ring, J. (1987a). Phototoxicity of nonsteroidal antiinflammatory drugs demonstrated in vitro by a photo-basophil-histamine-release test. Photodermatology, 4, 73-78
• Przybilla, B.; Ring, J.; Schwab, U.; Galosi, A.; Dorn, M.; Braun-Falco, O. (1987b). Photosensitising properties of nonsteroidal antirheumatic agents determined by the photopatch test. Hautarzt. 38, 18-25
• Quintero, B.; Morales, J.J.; Quirós, M.; Martínez-Puentedura, M.I.;Cabeza, M.C. Dediazoniation of p-hydroxybenzenediazonium ion in a neutral aqueous medium (Submitted for publication)
• Reavy, H.J.; Traynor, N.J.; Gibbs, N.K. (1997). Photogenotoxicity of skin phototumorigenic fluoroquinolone antibiotics detect using the Comet assay. Photochem.Photobiol. 66, 368-373
• Rehse, K.; Shahrouri, T. (1998). New NO donors with antithrombotic and vasodilating activities Part 24. Hydrazyne derivatives. Arch.Pharm. (Weinheim). 331, 308-312
• Rosen, J.E.; Chen, D.; Prahalad, A.K.; Spratt, T.E.; Schluter, G.; Williams, G.M. (1997a). A fluoroquinolone antibiotic with a methoxy group at the 8 position yields reduced generation of 8-oxo-7,8-dihydro-2’-deoxyguonosine after ultraviolet-A irradiation. Toxicol. Appl. Pharmacol., 145, 381-387
• Rosen, J.E.; Prahalad, A.K.; Schluter, G.; Chen, D.; G.; Williams, G.M. (1997b). Quinolone antibiotic photodynamic production of 8-oxo-7,8-dihydro-2’-deoxyguonosine in cultured liver epithelial cells. Photochem. Photobiol. 65, 990-996
• Rosen, J.E. (1997c). Proposed mechanism for the photodynamic production of 8-oxo-7,8-dihydro-2’-deoxyguonosine produced in cultured cells by lomefloxacin. Mutat.Res. 381, 117-129
• Ross, A.E.; Nagel, D.; Toth, B. (1982). Evidence for the occurrence and formation of diazoniumions in Agaricus bisporus. J.Agric.Food Chem. 30, 521-525
• Sanderson, B.J. ; Shield, A.J. (1996). Mutagenic damage to mammalian cells by therapeutic alkylating agents. Mutat.Res. 355, 41-57
• Sik, R.H.; Paschall, C.S.; Chignell, C.F. (1983). The phototoxic effect of benoxaprofen and its analogs on human erythrocytes and rat peritoneal mast cells. Photochem.Photobiol. 38, 411-415
• Smith Jr., R.H.; Mehl, A.F.; Shantz, D.L.; Chmurny, G.N.; Michejda, C.J. (1988). Novel cross linking alkylating agents, 1-(2-chloroethyl)-3-methyl-3-acyltriazenes J.Org.Chem., 53, 1467
• Smith, M.B.; Schmidt, B.F.; Czerwinski, G.; Taneyhill, L.A.; Snyder, E.J.; Kline, A.M.; Michejda, C.J.; Smith, R.H. Jr. (1996). Specificity of DNA alkylation by 1-(2-chloroethyl)-3-alkyl-3-acyltriazenes depends on the structure of the acyl group: kinetic and product studies. Chem. Res. Toxicol. 9, 466-475
• Snyder, R.D.; Cooper, C.S. (1999). Photogenotoxicity of fluoroquinolones in Chinese hamster V79 cells: Dependency on active topoisomerase II. Photochem.Photobiol. 69, 288-293
• Sortino, S.; Condorelli, G.; De Guidi, G.; Giuffrida, S. (1998). Molecular mechanism of photosensitization XI. Membrane and DNA cleavage photoinduced by enoxacin. Photochem. Photobiol. 68, 652-659
• Spielmann, H.; Lovell, W.W.; Hölzle, E.; Johnson, B.E.; Maurer, T.; Miranda, M.A.; Pape, W.J.W.; Sapora, O.; Sladowski, D. (1994) In Vitro Phototoxicity testing. The report and recommendations of ECVAM workshop 2. ATLA 22, 314-348.
• Spikes, J.D. (1989) Photosensitization. In The Science of Photobiology, Second Edition. K.C.Smith Ed., pp 79-110 New York.Plenum Press
• Spikes, J.D. (1998) Photosensitizing propperties of quinine and synthetic antimalarials. J.Photochem.Photobiol.B Biol. 42, 1-11
• Stahlmann, R.; Lode, H. (1998). Safety overview.Toxicity, adverse effects, and drug interactions. In The Quinolones. V.T.Andriole Ed. Pp 369-415. Academic Press. San Diego. USA
• Stahlmann, R.; Lode, H. (1999). Toxicity of quinolones. Drugs. 58, 37-42
• Steeken, S.; Ashokkumar, M.; Maruthamuthu, P.; McClelland, R.A. (1998). Making Photochemically generated phenyl cations visible by addition to aromatics: Production of phenylcyclohexadienyl cations and their reactions with bases/ nucleophiles. J.Am.Chem.Soc., 120, 11925-11931
• Stevens, M.F.G.; Peatey, L. (1978). Photodegradation of solutions of the antitumour drug DTIC. J.Pharm.Pharmacol. 30, 47P
• Stiborova, M.; Asfaw, B.; Anzenbacher, L.; Leseticky, L.; Hodek, P. (1988a). The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphtalene (Sudan I) by microsomes of rat livers. Cancer Lett., 40, 319-326
• Stiborova, M.; Asfaw, B.; Anzenbacher, L.; Hodek, P. (1988b). A new way to carcinogenicity of azo dyes: the benzenediazonium ion formed from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphtalene (Sudan I) by microsomal enzymes binds to deoxyguanosine residues of DNA. Cancer Lett., 40, 327-333
• Stiborova, M.; Frei, E.; Schmeiser, H.H.; Wiessler, M.; Hradec, J. (1990). Mechanism of formation and 32P-postlabelling of DNA adducts derived from peroxidative activation of carcinogenic non-aminoazo dye , 1-phenylazo-2-hydroxynaphtalene. Carcinogenesis. 11, 1843-1848
• Stiborova, M.; Schmeiser, H.H.; Wiessler, M.; Frei, E. (1999). Direct evidence for the formation of deoxyribonucleotide adducts from carcinogenic N-nitroso-N-methylaniline revealed by the 32P-postlabeling technique. Cancer Lett. 138, 61-66
• Szeimies, R.M.; Calzavara-Pinton, M.P.; Karrer, S.; Ortel, B.; Landthaler, M. (1996). Topical photodynamic therapy in dermatology. J.Photochem.Photobiol. B Biol. 36, 213-219
• The Index Merck. (1983). M.Windholz; S.Budavari; R.F.Blumetti; E.S.Otterbein Eds. Merck & Co.Inc. Rahway. New Jersey. USA
• Tokura, Y.; Ogai, M.; Yagi, H.; Takigawa, M. (1994) Afloqualone photosensitivity: inmunogenicity of aloqualone-photomodified epidermal cells. Photochem.Photobiol. 60, 262-267
• Toth, B. (1975). Synthetic and naturally occurring hydrazines as possible cancer causative agents. Cancer Res. 35, 3963-3967
• Toth, N.; Tompa, A; Patil, K. (1977). Tumogenic effect of 4-methylphenylhydrazyne hydrochloride in Swiss mice. Z.Krebsforsch. 89, 245-252
• Toth, B.; Patil, K.; Jae, H. (1981). Carcinogenesis of 4-(hydroxymethyl) benzenediazonium ion (tetrafluoroborate) of Agaricus bisporus. Cancer Res. 41, 2444-2449
• Toth, B.; Nagel, D.; Ross, A. (1982). Gastric tumorigenesis by a single dose of 4-( hydroxymethyl)benzenediazonium ion of Agaricus bisporus. Br.J.Cancer. 46, 417-422
• Toth, B.; Taylor, J.; Mattson, B.; Gannett, P. (1989). Tumor induction by 4-(methyl)benzene-diazonium sulfate in mice. In Vivo. 3, 17-22
• Toth, B.; Gannett, P.; Rogan, E.; Williamson, J. (1992). Bacterial mutagenicity of extracts of the baked and raw Agaricus bisporus mushroom. In vivo. 6, 487-490
• Toth, B.; Gannett, P. (1993). Agaricus bisporus: An assessment of its carcinogenic potency. Mycopathologia. 124, 73-77
• Toth, B.; Patil, K.; Erickson, J.; Gannett, P. (1998). Carcinogenesis by benzenediazonium sulfate in mice. In Vivo. 12, 379-382
• Tracey, B.M.; Shuker, D.E.G. (1997). Characterization of azo coupling adducts of benzene-diazonium ions with aromatic aminoacids in peptides and proteins. Chem.Res.Toxicol. 10, 1378-1386
• Thust, R.; Schneider, M.; Wagner, U.; Schreiber, D. (1991). Structure/activity investigations in eight arylalkyltriazenes comparison of chemical stability, mode of decomposition, and SCE induction in Chinese hamster V79-E cells. Cell Biol Toxicol. 7, 145-165
• Umezawa, N.K.; Arakane, K.; Ryu, A.; Mashiko, S.; S.; Hirobe, M.; Nagano, T. (1997). Participation of reactive oxygen species in phototoxicity induced by quinolone antibacterial agents. Arch. Biochem. Biophys. 342, 275-281
• Urbach, F. (1997). Phototoxicity and possible enhancement of photocarcinogenesis by fluorinated quinolone antibiotics J. Photochem. Photobiol. B Biol. 37, 169-171
• Vargas, F.; Canudas, N.; Miranda, M.A.; Boscá, F. (1993). In vitro phototoxicity of clofibrate. Photochemical and photohemolytic studies on its metabolite clofibric acid. J.Photochem.Photobiol.B Biol. 21, 61-67
• Vargas, F.; Rivas, C.; Canudas, N.; Torrealba, A.; Sarabia, Z. (1996). Mechanism of phototoxicity induced by drugs Acta Cient.Venez. 47, 223-230
• Vazzana, I.; Sparatore, F.; Fadda, G.; Manca, -C. (1993) N-[4-(R’,R”-phenylazo)aryl]amino-lupinanes with antitubercular activity. Farmaco. 48, 737-747.
• Vilaplana, J.; Romaguera, C.; Azon, A.; Lecha, M. (1998). Flutamide photosensitivity-residual vitiliginous lesions. Contact Dermatitis. 38, 68-70
• Wagai, N.; Tawara, K. (1991). Important role of oxygen metabolites in quinolone antibacterial agent-induced cutaneous phototoxicity in mice. Arch.Toxicol. 65, 495-499
• Wagai, N.; Tawara, K. (1992a). Possible role of reactive oxygens in the cause of cutaneous phototoxicity induced by five quinolones in mice. Arch.Toxicol. 66, 392-397
• Wagai, N.; Tawara, K. (1992b). Possible reasons for differences in phototoxic potential of 5 quinolone antibacterial agents: generation of toxic oxygen. Free Radical Res.Commun. 17, 387-398
• Walton, K.; Coombs, M.M.; Caterall, F.S.; Walter, R.; Ioannides, C. (1997). Bioactivation of the mushroom hydrazine, agaritine, to intermediates that bind covalently to proteins and induce mutations in the Ames test. Carcinogenesis. 18, 1603-1608
• Wakabayashi, K.; Nagao, M.; Sugimura, T. (1989) Mutagens and carcinogens produced by the reaction of environmental aromatic compounds with nitrite. Cancer Survey. 8, 385-399
• Yoshida, T.; Yamamoto, Y.; Orita, H.; Kakiuchi, M.; Takahashi, Y.; Itakura, M.; Kado, N.; Yasuda, S.; Kato, H.; Ito, Y. (1996). Studies on quinolones antibacterials.V. Synthesis antibacterial activity of chiral 5-amino-7-(4-subtituted-3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acids and derivatives. Chem. Pharm. Bull. 44, 1376-1386
• Zollinger, H.(1994). Diazo Chemistry Vol.I: Aromatic and Heteroaromatic Compounds. Wiley & Sons: New York. USA