Mechanisms of photosensitization induced by drugs: A general survey

Autores/as

  • B QUINTERO Dpt. Química Física. Facultad de Farmacia. Campus de Cartuja. Universidad de Granada. 18071 Granada. Spain.
  • MA MIRANDA Instituto de Tecnología Química. Universidad Politécnica. Valencia. Spain.

Palabras clave:

Phototoxicity, Drugs, Mechanisms, Photosensitization, Fluoroquinolones, Non-Steroidal Antiinflammatory drugs, Arenediazonium ions

Resumen

This paper presents a general survey of the mechanisms involved in drug phototoxicity. Moreover, a list of 174currently used clinical drugs inducing photosensitization is provided in addition to some others from which phototoxiceffects are suspected. Likewise, some aspects related to the mechanisms involved in the phototoxicity of fluoroquinolonesand non steroidal-antiinflammatory drugs have been reviewed. Finally, a possible role of the arenediazonium ionsas photosensitisers is discussed.

Descargas

Los datos de descargas todavía no están disponibles.

Citas

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. And references therein

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

Descargas

Publicado

1999-12-20

Cómo citar

1.
QUINTERO B, MIRANDA M. Mechanisms of photosensitization induced by drugs: A general survey. Ars Pharm [Internet]. 20 de diciembre de 1999 [citado 4 de mayo de 2024];41(1):27-46. Disponible en: https://revistaseug.ugr.es/index.php/ars/article/view/5732

Número

Vol. 41 Núm. 1 (2000)

Sección

Artículos de revisión

Licencia

Los artículos que se publican en esta revista están sujetos a los siguientes términos en relación a los derechos patrimoniales o de explotación:

  1. Los autores/as conservarán sus derechos de autor y garantizarán a la revista el derecho de primera publicación de su obra, la cual se distribuirá con una licencia Creative Commons BY-NC-SA  4.0 que permite a terceros reutilizar  la obra siempre que se indique su autor, se cite la fuente original y no se haga un uso comercial de la misma.
  2. Los autores/as podrán adoptar otros acuerdos de licencia no exclusiva de distribución de la versión de la obra publicada (p. ej.: depositarla en un archivo telemático institucional o publicarla en un volumen monográfico) siempre que se indique la fuente original de su publicación.
  3. Se permite y recomienda a los autores/as difundir su obra a través de Internet (p. ej.: en repositorios  institucionales o en su página web) antes y durante el proceso de envío, lo cual puede producir intercambios interesantes y aumentar las citas de la obra publicada. (Véase El efecto del acceso abierto).