Photosensitizing drugs containing the benzophenone chromophore

Journal of Photochemistry and Photobiology B: Biology

Volumn 43, Issue 1, 1998, Pages 1-26

  Boscá, Francisco ^a   Miranda, Miguel A ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

Amiodarone; Benzophenone; Fenofibrate; Ketoprofen; Photoallergy; Photodegradation; Photosensitization; Phototoxicity; Suprofen; Tiaprofenic acid; Tolmetin

Indexed keywords

AMIODARONE; ANTIARRHYTHMIC AGENT; BENZOPHENONE; FENOFIBRATE; KETOPROFEN; NONSTEROID ANTIINFLAMMATORY AGENT; PHOTOSENSITIZING AGENT; SUPROFEN; TIAPROFENIC ACID; TOLMETIN;

ARTICLE; CHROMATOPHORE; CONTROLLED STUDY; ELECTRON TRANSPORT; LIPID PEROXIDATION; PHOTOALLERGY; PHOTOCHEMISTRY; PHOTODEGRADATION; PHOTOSENSITIVITY; PHOTOTOXICITY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0032052529     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(98)00062-1     Document Type: Review

References (97)

1. [1] M. A. Miranda, J.V. Castell and M.J. Gómez-Lechón. Phototoxicity of Drugs in In Vitro Methods in Pharmaceutical Research. Academic Press, San Diego, CA. 1997, pp. 289-315.
2. [2] N. Mozzanica, P.D. Pigatto, Contact and photocontact allergy to ketoprofen, clinical and experimental-study. Contact Dermatitis 23 (1990) 336-340.
3. [3] F. Cusano, M. Capozzi, Photocontact dermatitis from ketoprofen with cross-reactivity to ibuproxam. Contact Dermatitis 27 (1992) 50-51.
4. [4] P.D. Pigatto, N. Mozzanica, A.S. Bigardi, A. Legori, R. Valsecchi, F. Cusano. A. Tosti. M. Guarrera. N. Balato, A, Sertoli, Topical NSAID allergic contact dermatitis italian experience. Contact Dermatitis 29 (1993) 39-41.
5. [5] R.T. Nabeya, T. Kojima, M. Fujita. Photocontact dermatitis from ketoprofen with an unusual clinical feature, Contact Dermatitis 32 (1995) 52-53.
6. [6] M. Gebhardt, U. Wollina, Cutaneous side-effects of nonsteroidal anti-inflammatory drugs (NSAID). Zeitschrift fur Rheumatologie 54 (1995) 405-412.
7. [7] J.G. Gould, M.G. Mercurio, C.A. Elmets, Cutaneous photosensitivity diseases induced by exogenous agents, J. Am. Acad. Dermatol. 33 (1995) 551-573.
8. [8] D. Leroy, A. Dompmartin, E. Lorier, Y. Leport, C. Audebert, Photosensitivity induced by fenofibrate. Photodermatol. Photoimmunol. Photomed. 7 (1990) 136-138.
9. [9] F. Vargas, N. Canudas, MA. Miranda, F. Boscá, Photodegradation and in-vitro phototoxicity of fenolibrate, a photosensitizing anti-hyperlipoproteinemic drug, Photochem. Photobiol. 58 (1993) 471-476.
10. [10] M.C. Marguery, F. Elsayed, J. Rakotondrazafy, R. Saqi, G. Samalens, B. Gorguet. J. Bazex. Photoallergy and photoaggravation induced by fenofibrate-cross-photoreaction and transient light reaction, Eur. J. Dermatol. 5 (1995) 204-207.
11. [11] S. Ophaswongse, H. Maibach, Topical nonsteroidal anti-inflammatory drugs: allergic and photoallergic contact dermatitis and phototoxicity, Contact Dermatitis 29 (1993) 57-64.
12. [12] B.L. Diffey, T.J. Daymond, H. Fairgreaves, Phototoxic reactions to piroxicam, naproxen and tiaprofenic acid. Br. J. Rheumatol. 22 (1983) 239-242.
13. [13] Y. Kurumaji, Y. Ohshiro, C. Miyamoto, C.H. Keong, T. Katoh, K. Nishioka, Allergic photocontact dermatitis due to suprofen. photopatch testing and cross-reaction study, Contact Dermatitis 25 (1991) 218-223.
14. [14] S. Giuffrida, G. De Guidi, S. Sortino, S. Chillemi, L.L. Costanzo, G. Condorelli, Molecular mechanism of drug photosensitization. Part 6. Photohemolysis sensitized by tolmetin. J. Photochem. Photobiol. B: Biol. 29 (1995) 125-133.
15. [15] J.L. Blackshear, H.W. Randle, Reversibility of blue-gray cutaneous discoloration from amiodarone, Mayo Clinic Proceedings 66 (1991) 721-726.
16. [16] N. Paillous, M. Verrier, Photolysis of amiodarone, an antiarrhythmic drug, Photochem. Photobiol. 47 (1988) 337-343.
17. [17] E.A. Son, Z.G. Yugai, Case of photodermatosis due to long-term treatment with amiodarone, Klinicheskaya Meditsina 70 (1992) 46.
18. [18] G. Dootson, C. Byatt, Amiodarone-induced vasculitis and a review of the cutaneous side-effects of amiodarone. Clin. Exper. Dermatol. 19 (1994) 422-424.
19. [19] M. Zehender, Amiodarone phototoxic reaction, Circulation 92 (1995) 1665.
20. [20] B. Przybilla, J. Ring, U. Schwab, A. Galosi, M. Dorn, O. Braun-Falco. Photosensibilisierende Eigenschaften nichtsteroidaler Antirheumatika im Photopatch-test, Hautarzt 38 (1987) 18-25.
21. [21] B.L. Diffey, S. Brown, A method for predicting the phototoxicity of non-steroidal anti-inflammatory drugs, Br. J. Clin. Pharmacol. 16 (1983) 633-638.
22. [22] E. Holzle, N. Neumann, B. Hausen, B. Przybilla, S. Schauder, H. Honigsmann, A. Bircher, G. Plewig, Photopatch testing: the five-year experience of the German. Austrian, and Swiss photopatch test group, J. Am. Acad. Dermatol. 25 (1991) 59-68.
23. [23] G. Serrano, J.M. Fortea, J.M. Latasa, F. Millan, C. Janes, F. Boscá, M.A. Miranda, Photosensitivity induced by fibric acid derivatives and its relation to photocontact dermatitis to ketoprofen. J. Am. Acad. Dermatol. 27 (1992) 204-208.
24. [24] M. Jeanmougin, J.R. Manciet. Y. Deprost, P. Reygagne, L. Pinquier, L. Dubertret, Photoallergy induced by fenofibrate, Annales de Dermatologie et de Vénéréologie 120 (1993) 549-554.
25. [25] B. Ljunggren, K. Lundberg, In vivo phototoxicity of non-steroidal anti-inflammatory drugs evaluated by the mouse tail technique, Photodermatol. 2 (1985) 377-382.
26. [26] C.F. Chignell, R.H. Sik, Magnetic-held effects on the photohemolysis of human erythrocytes by ketoprofen and protoporphyrin-JX, Photochem. Photobiol. 62 (1995) 205-207.
27. [27] G. Condorelli, L.L. Costanzo, G. De Guidi, S. Giuffrida, E. Rizzarelli, G. Vecchio, Inhibition of photohemolysis by Copperi (II) complexes with SOD-like activity, J. Inorg. Biochem. 54 (1994) 257-265.
28. [28] G. De Guidi, G. Condorelli, S. Giuffrida, G. Puglisi, G. Giammona. Effect of β-cyclodextrin complexation on the photohacmolytic activity induced by ketoprofen and naproxen sensitization, J. Incl. Phenomena Mol. Recog. Chem. 15 (1993) 43-58.
29. [29] L.L. Costanzo, G. De Guidi, G. Condorelli, A. Cambria, M. Fama, Molecular mechanism of drug photosensitization. II-Photohemolysis sensitized by ketoprofen. Photochem. Photobiol. 50 (1989) 359-365.
30. [30] F. Boscá, G. Carganico, J.V. Castell, M.J. Gómez-Lechón, D. Hernandez, D. Mauleon, L.A. Martinez, M.A. Miranda, Evaluation of ketoprofen (R,S and R/S) phototoxicity by a battery of in vitro assays, J. Photochem. Photobiol. B: Biol. 31 (1995) 133-138.
31. [31] B. Przybilla, U. Schwab-Przybilla, T. Ruzicka, J. Ring, Phototoxicity of non-steroidal anti-inflammatory drugs demonstrated in vitro by a photo-basophil-histamine-release test, Photodermatol. 4 (1987) 73-78.
32. [32] B. Ljunggren, Propionic acid-derived non-steroidal anti-inflammatory drugs are phototoxic in vitro, Photodermatol. 2 (1985) 3-9.
33. [33] T. Artuso, J. Bernadou, B. Meunier, N. Paillous, DNA strand breaks photosensitized by benoxaprofen and other non steroidal anti-inflamatory agents, Biochem. Pharmacol. 39 (1990) 407-413.
34. [34] T. Artuso, J. Bernadou, B. Meunier, J. Piette, N, Paillous, Mechanism of DNA cleavage mediated by photoexcited nonsteroidal anti-inflammatory drugs. Photochem. Photobiol. 54 (1991) 205-213.
35. [35] L.L. Costanzo, G. De Guidi, S. Giuffrida, S. Sortino, G. Condorelli, G. Paalardo, Antioxidant effect of Copper(II) on photosensitized lipid peroxidation, J. Inorg. Biochem. 57 (1995) 115-125.
36. [36] F. Boscá, M.A. Miranda, G. Carganico, D. Mauleon, Photochemical and photobiological properties of ketoprofen associated with the benzophenone chromophore, Photochem. Photobiol. 60 (1994) 96-101.
37. [37] M.A. Miranda. F. Boscá, F. Vargas, N. Canudas, Photosensitization by fenofibrate. II. In vitro phototoxicity of the major metabolites, Photochem. Photobiol. 59 (1994) 171-174.
38. [38] A. Figueiredo, C.A.F. Ribeiro, M. Goncalo, A.P. Baptista, F. Teixeira, Experimental studies on the mechanisms of tiaprofenic acid photosensitization, J. Photochem. Photobiol. B: Biol. 18 (1993) 161-168.
39. [39] J.V. Castell, MJ. Gómez-Lechón, D. Hernandez, L.A. Martinez, M.A. Miranda, Molecular basis of drug phototoxicity: photosensitized cell damage by the major photoproduct of tiaprofenic acid, Photochem Photobiol. 60 (1994) 586-590.
40. [40] M.A. Miranda, J.V. Castell, M.J. Gómez-Lechón, D. Hernandez, L.A. Martinez, Photobinding of drugs to cells as an indicator of potential photoallergy, Toxicology in Vitro 9 (1995) 499-503.
41. [41] J.V. Castell, M.J. Gómez-Lechón, C. Grassa, L.A. Martinez, M.A. Miranda, P. Tarrega, Photodynamic lipid peroxidation by the photosensitizing nonsteroidal anti-inflammatory drugs suprofen and tiaprofenic acid, Photochem. Photobiol. 59 (1994) 35-39.
42. [42] M.A. Miranda, J.V. Castell, D. Hernandez, M.J. Gómez-Lechón, F. Boscá, I.M. Morera and Z. Sarabia, Drug-photosensitized protein modification: Identification of the reactive sites and elucidation of the reaction mechanism with tiaprofenic acid/albumin as a model system Chem. Res. Toxicol., in press.
43. [43] G. De Guidi, R. Chillemi, L.L. Costanzo, S. Giuffrida, S. Sortino, G. Condorelli, Molecular mechanism of drug photosensitization. 5. Photohemolysis sensitized by suprofen, J. Photochem. Photobiol. B: Biol. 23 (1994) 125-133.
44. [44] G. Condorelli, L.L. Costanzo, G. De Guidi, S. Giuffrida, S. Sortino, Molecular mechanism of drug photosensitization. 7. Photocleavage of DNA sensitized by suprofen. Photochem. Photobiol. 62 (1995) 155-161
45. [45] H. Fujita, Y. Matsuo, Type 1 lipid photooxidation by the nonsteroidal anti-inflammatory drug suprofen. A possible key to its photosensitivity, Photodermatol. Photoimmunol. Photomed. 9 (1993) 203-208.
46. [46] T. Hasan, I.E. Kochevar, D. Abdulah, Amiodarone phototoxicity to human erythrocytes and lymphocytes, Photochem. Photobiol. 40 (1984) 715-719.
47. [47] H. Spielmann, W. W. Lovell, E. Hölzle, B.E. Johnson, T. Maurer, M.A. Miranda, W.J.W. Pape, O. Sappora, D. Sladowski, In vitro phototoxicity testing. The report and recommendations of ECVAM Workshop-2, ATLA 22 (1994) 314-348.
48. [48] A.M. Sautereau, C. Tournaire, M. Suares, J.F. Tocanne. N. Paillous. Interactions of amiodarone with model membranes and amiodarone-photoinduced peroxidation of lipids. Biochem. Pharmacol. 43 (1992) 2559-2566.
49. [49] N. Turro, Modern Molecular Photochemistry, Benjamin/Cummings, Menlo Park, CA, 1978.
50. [50] J.C. Scaiano, Handbook of Organic Photochemistry, CRC Press, Boca Raton, FL, 1989.
51. [51] G. Dorman. G.D. Prestwich, Benzophenone photophores in biochemistry. Biochemistry 33 (1994) 5661-5673.
52. [52] D.R. Arnold, R.J. Birtwell, Photochemical reactivity of some benzoylthiophenes. I. Electronic absorption and emission spectra, J. Am. Chem. Soc. 95 (1973) 4599-4605.
53. [53] H. Shimamori, H. Uegaito, K. Houdo, Dipole-moments of excited triplet-states of substituted benzophenones, J. Phys. Chem. 95 (1991) 7664-7667.
54. [54] B. Marciniak, K. Bobrowski, G.L. Hug, Quenching of triplet states of aromatic ketones by sulfur-contnining ammo-acids in solution- evidence for electron transfer, J Phys. Chem. 97 (1993) 11937-11943.
55. [55] M. Barra, J.C. Scaiano, Photoinduced transient phenomena in cyclodextrin solid complexes. Photochemistry of aromatic ketones, Photochem. Photobiol. 62 (1995) 60-64.
56. [56] A.P. Darmanyan, C.S. Foote, Solvent effects on singlet oxygen yield from nπ* and π-π* triplet carbonyl-compounds. J. Phys. Chem. 97 (1993) 5032-5035.
57. [57] A.P. Darmanyan, C.S. Foote, Definition of the nature of ketone triplet states on the basis of singlet oxygen generation efficiency, J. Phys. Chem. 97 (1993) 4573-4576.
58. [58] N. Filipescu, F.L. Minn, On the photoreduction of benzophenone in isopropyl alcohol, J. Am. Chem. Soc. 90 (1968) 1544-1547.
59. [59] A. Albini, P. Bortolus, E. Fasani, S. Monti, E. Negri, G. Orlandi, The photoreduction of 3-benzoylpyridine, An experimental and theoretical study of the formation of the intermediate LAT, J. Chem. Soc., Perkin Trans. 2. (1993) 691-695.
60. [60] K.L. Berger, A.L. Nemecek, C.J. Abelt, Photochemistry of benzophenone-capped beta-cyclodextrin, J. Org. Chem. 56 (1991) 3514-3520.
61. [61] N. Filipescu, F.L. Minn, Photochemical reactions of 4.4′-di-tert-butyl-benzophenone in isopropyl alcohol, J. Chem. Soc. (B) 629 (1969) 84-88.
62. [62] F.L. Minn, C.L. Trichilo, C.R. Hurt, N. Filipescu, Photochemistry of di-[4-pyridyl)ketone in isopropyl alcohol. J Am. Chem. Soc. 92 (1970) 3600-3610.
63. [63] A. Schönberg, G.O. Schenck and O. Neumüller, Preparative Organic Photochemistry. Springer, Heidelberg, Germany, Ch. 41. 1968, pp. 414-433.
64. [64] M.V. Encinas. J.C. Scaiano. Reaction of benzophenone triplets, with allylic hydrogens. A laser flash photolysis study. J. Am. Chem. Soc. 103 (1981) 6393-6397.
65. [65] J.C. Scaiano, E.B. Abuin, L.C. Stewart, Photochemistry of benzophenone in micelles. Formation and decay of radical pairs, J. Am. Chem. Soc. 104 (1982) 5673-5679.
66. [66] Y. Fujiwara, M. Mukai, T. Tamura, Y. Tanimoto, M. Okazaki, A laser flash-photolysis study of the effect of intense magnetic-fields on the photoreaction of benzophenone in SDS micellar solution, Chem. Phys. Lett. 213 (1993) 89-94.
67. [67] S. Monti, L. Flamigni, A. Martelli, P. Bortolus. Photochemistry of benzophenone-cyclodextrin inclusion complexes. J. Phys. Chem. 92 (1988) 4447-4451.
68. [68] A.W. Girotti, Photodynamic lipid peroxidation in biological systems. Photochem. Photobiol. 51 (1990) 497-509.
69. [69] D.Z. Markovic, L.K. Patterson, Benzophenone sensitized lipid peroxidation in linoleate micelles, Photochem. Photobiol. 58 (1993) 329-334.
70. [70] D.Z. Markovic, T. Durand, L.K. Patterson, Hydrogen abstraction from lipids by triplet states of denvatized benzophenone photosensitizers, Photochem. Photobiol. 51 (1990) 389-394.
71. [71] L.R.C. Barclay, K.A. Baskin, S.J. Locke, T.D. Schaefer. Benzophenone photosensitized autooxidation of linoleate in solution and sodium dodecyl sulfate micelles, Can. J. Chem. 65 (1987) 2529-2540.
72. [72] G.D. Pestwich, G. Dorman, J.T. Elliot. D.M. Marecak, A. Chaudhary, Benzophenone photoprobes for phosphoinositides, peptides and drugs, Photochem. Photobiol. 65 (1997) 222-234.
73. [73] K. Bobrowski, B. Marciniak, G.L. Hug, 4-Carboxybenzophenone-sensitized photooxidation of sulfur-containing amino-acids. Nanosecond laser flash-photolysis and pulse-radiolysis studies. J. Am. Chem. Soc. 114 (1992) 10279-10288.
74. [74] B. Marciniak, K. Bobrowski, G.L. Hug, J. Rozwadowski. Photoinduced electron-transfer between sulfur-containing carboxylic acids and the 4-carboxybenzophenone triplet state in aqueous solution, J. Phys. Chem. 98 (1994) 4854-4860.
75. [75] K. Bobrowski, G.L. Hug, B. Marciniak, H. Kozubek, 4-Carboxybenzophenone-sensitized photooxidation of sulfur-containing amino-acids in alkaline aqueous solutions. Secondary photoreactions kinetics, J. Phys. Chem. 98 (1994) 537-544.
76. [76] B. Marciniak, G.L. Hug, K. Bobrowski, H. Kozubek, Mechanism of 4-carboxybenzophenone-sensitized photooxidation of methionine-containing dipeptides and tripeptides in aqueous-solution, J. Phys. Chem. 99 (1995) 13560-13568.
77. [77] B. Morin, J. Cadet, Chemical aspects of the benzophenone-photosensitized formation of 2-lysine-2′-deoxyguanosine cross-links, J. Am. Chem. Soc. 117 (1995) 12408-12415.
78. [78] S. Raoul, J. Cadet, Photosensitized reaction of 8-oxo-7,8-dihydro-2′-deoxyguanosine, Identification of 1 -(2-deoxy-β-d-erythro-pentofuranosyl)cyanuric acid as the major singlet oxygen oxidation-product, J. Am. Chem. Soc. 118 (1996) 1892-1898.
79. [79] P.J. Wagner, J.H. Sedon, A. Gudmundsdottir, Photoinduced radical cleavage of bromophenyl ketones. J. Am. Chem. Soc. 118 (1996) 746-754.
80. [80] P.J. Wagner, C.I. Waite, Photoinduced radical cleavage of iodobenzophenones, J. Phys. Chem. 99 (1995) 7388-7394.
81. [81] G. Favaro, Photochemical and photophysical behaviour of benzoylpiridines. Part I. Triplet-triplet energy transfer to diacetyl, J. Chem. Soc. Perkin Trans. II (1976) 869-874.
82. [82] P. Bortolus, F. Blisei, G. Favaro, S. Monti, F. Ortica, Photocyclization 2-pyridyl phenyl ketone. A reaction driven by hydrogen bonding, J. Chem. Soc.. Faraday Trans. 92 (1496) 1841-1851.
83. [83] S. Monti, N. Camaioni, P. Bortolus, Photochemistry in a cyclodextrin cavity, primary processes in the photoreduction of 3-benzoylpyridine and 4-benzoylpyridine studied by laser flash photolysis. Photochem. Photobiol. 54 (1991) 577-584.
84. [84] F. Ortica, F. Elisei, G. Favaro, Photophysics of 3-phenyl and 4-phenyl pyridyl ketones in submicellar and micellar solutions of ionic and nonionic surfactants, J. Chem. Soc., Faraday Trans. 91 (1995) 3405-3413.
85. [85] D.R. Arnold, R.J. Birtwell. B.M. Clarke. The photochemical reactivity of some benzoylthiophenes. II. Photocycloaddition, Can. J. Chem. 52 (1974) 1681-1689.
86. [86] S. Monti, S. Sortino, G. De Guidi, G. Marconi, Photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen). Part I. A picosecond and nanosecond time resolved study in aqueous solution. J. Chem. Soc. Faraday Trans. 93 (1997) 2269-2275.
87. [87] D. de la Peña, C. Marti, S. Nonell, L.A. Martinez, M.A. Miranda, Time-resolved near infrared studies on singlet oxygen production by the photosensitizing 2-arylpropionic acids, Photochem. Photobiol. 69 (1997) 828-832.
88. 2-scavenger activity. J. Inorg. Biochem. 50 (1993) 273-281.
89. [89] L.J. Martinez and J.C. Scaiano, Transiert intermediates in the laser flash photolysis of ketoprofen in aqueous solution: Absolute rate constants for carbanions in solution. J. Am. Chem. Soc., in press.
90. [90] M.A. Miranda, F. Boscá, F. Vargas, N. Canudas, Unusual (1. 2) Wittig rearrangement of a carbanion generated in neutral aqueous-medium by photodecarboxylation of a phenoxyacetic acid analogue, J. Photochem. Photobiol. A: Chem. 78 (1994) 149-151.
91. [91] F. Vargas, C. Rivas, R. Machado. M.A. Miranda, Photodegradation of nalidixic and tiaprofenic acids and nifedipine in aerobic conditions. Photodermatol. Photoimmunol. Photomed. 8 (1991) 218-221.
92. [92] F. Boscá, M.A. Miranda, F. Vargas, Photochemistry of tiaprofenic acid, a nonsteroidal anti-inflammatory drug with phototoxic side-effects, J. Pharm. Sci. 81 (1992) 181-182.
93. [93] J.V. Castell, M.J. Gómez-Lechón, C. Grassa, L.A. Martinez, M.A. Miranda, P. Tarrega, Involvement of drug-derived peroxides in the phototoxicily of naproxen and tiaprofenic acid, Photochem. Photobiol. 57 (1993) 486-490.
94. [94] S. Encinas, M.A. Miranda, G. Marconi and S. Monti. Triplet photoreactivity of the diaryl ketone tiaprofenic acid and its decarboxylated photoproduct. Photobiological implications, Photochem. Photobiol., in press.
95. [95] F. Boscá, Procesos de transferencia electronica en la fotodegradacion de los acidos 2-arilpropionicos y 1,4-dihidropiridinas, Ph. D. Thesis, Universidad de Valencia, Valencia, Spain, 1992, p. 58.
96. [96] A.S.W. Li, C.F. Chignell, Spectroscopic studies of cutaneous photo-sensitizing agents-IX. A spin trapping study of the photolysis of amiodarone and desethylamiodarone, Photochem. Photobiol, 45 (1987) 191-197.
97. [97] N. Paillous, S. Fery-Forgues. Is there a link between the phototoxic or antioxidant properties of amiodarone, an antiarrhythmic drug, and its lipophilic character, Biochem. Pharmacol. 48 (1994) 851-857.