Effect of the microenvironment on the efficiency of singlet oxygen (O2(1Δ(g))) production by photosensitizing anti-inflammatory drugs

Journal of Photochemistry and Photobiology B: Biology

Volumn 45, Issue 2-3, 1998, Pages 103-112

  Martïnez, Luis A ^a   Braun, André M ^a   Oliveros, Esther ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

2 Arylpropionic acids; Microemulsions; Non steroidal anti inflammatory drugs; Photosensitizing drugs; Quantum yields; Singlet oxygen luminescence

Indexed keywords

ANIONIC SURFACTANT; ARYLPROPIONIC ACID DERIVATIVE; BENOXAPROFEN; CARPROFEN; CATIONIC SURFACTANT; INDOPROFEN; KETOPROFEN; NONSTEROID ANTIINFLAMMATORY AGENT; SINGLET OXYGEN; SUPROFEN; TIAPROFENIC ACID;

ARTICLE; CONTROLLED STUDY; LUMINESCENCE; MICROEMULSION; PHOTODYNAMICS; PHOTOSENSITIZATION; PRIORITY JOURNAL;

ABSORPTION; ANIONS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CATIONS; MICELLES; MOLECULAR STRUCTURE; OXYGEN; PHOTOSENSITIZING AGENTS; PROPIONIC ACIDS; SINGLET OXYGEN; SOLUTIONS;

EID: 0032170339     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(98)00168-7     Document Type: Article

References (60)

1. [1] G. Condorelli, L.L. Costanzo, G. De Guidi, S. Giuffrida, P. Miano, S. Sortino, A. Velardita, Photosensitization induced by non steroidal anti-inflammatory drugs: an overview of molecular mechanisms in biological systems, EPA Newsletter 58 (1996) 60-77.
2. [2] I.E. Kochevar, Phototoxicity of nonsteroidal anti-inflammatory drugs: coincidence or specific mechanism?, Arch. Dermatol. 125 (1989) 824-826.
3. [3] B. Ljunggren, K. Lundberg, In vivo phototoxicity of non-steroidal anti-inflammatory drugs evaluated by the mouse tail technique, Photodermatology 2 (1985) 377-382.
4. [4] B. Ljunggren, Propionic acid-derived non-steroidal anti-inflammatory drugs are phototoxic in vitro, Photodermatology 2 (1985) 3-9.
5. [5] D.E. Moore, P.P. Chappuis, A comparative study on the photochemistry of the non-steroidal anti-inflammatory drugs naproxen, benoxaprofen and indomethacin, Photochem. Photobiol. 47 (1988) 173-180.
6. [6] J.V. Castell, M.J. Gómez-Lechón, C. Grassa, L.A. Martínez, M.A. Miranda, P. Tárrega, Photodynamic lipid peroxidation by the photosensitizing nonsteroidal anti-inflammatory drugs suprofen and tiaprofenic acid, Photochem. Photobiol. 59 (1994) 35-39.
7. [7] M.A. Miranda, J.V. Castell, M.J. Gómez-Lechón, D. Hernández, L.A. Martínez, Photobinding of drugs to cells as an indicator of potential photoallergy, Toxicol. in Vitro 9 (1995) 499-503.
8. [8] M.A. Miranda, Phototoxicity of drugs, in J.V. Castell, M.J. Gómez-Lechón (Eds.), Alternative in Vitro Models to Animal Experimentation in Pharmacotoxicology, Farmaindustria, Madrid, 1992, and refs. therein.
9. [9] F. Vargas, C. Rivas, M.A. Miranda, F. Boscá, Photochemistry of the non-steroidal anti-inflammatory drugs, propionic acid derived, Pharmazie 46 (1991) 767-771.
10. [10] F. Boscá, S. Encinas, P.F. Heelis, M.A. Miranda, Photophysical and photochemical characterization of a photosensitizing drug: a combined steady state photolysis and laser flash photolysis study on carprofen, Chem. Res. Toxicol. 10 (1997) 820-827.
11. [11] S. Monti, S. Sortino, G. De Guidi, G. Marconi, Photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen). Part 1. A picosecond and nanosecond time resolved study in aqueous solution, J. Chem. Soc., Faraday Trans. 93 (13) (1997) 2269-2275.
12. [12] E. Hölzle, N. Neumann, B. Hausen, B. Przybilla, S. Schauder, H. Hönigsmann, A. Bircher, G. Plewig, Photopatch testing: the 5-year experience of the German, Austrian and Swiss photopatch test group, J. Am. Acad. Dermatol. 25 (1991) 59-68.
13. [13] I.E. Kochevar, K.W. Hoover, M. Gawienowski, Benoxaprofen photosensitization of cell membrane disruption, J. Invest. Dermatol. 82 (1984) 214-218.
14. [14] J.V. Castell, D. Hernández, M.J. Gómez-Lechón, L.A. Martínez, M.A. Miranda, Molecular basis of drug phototoxicity: photosensitized cell damage by the major photoproduct of tiaprofenic acid, Photochem. Photobiol. 60 (1994) 586-590.
15. [15] L.L. Costanzo, G. De Guidi, G. Condorelli, A. Cambria, M. Famà, Molecular mechanism of naproxen photosensitization in red blood cells, J. Photochem. Photobiol. B: Biol. 3 (1989) 223-235.
16. [16] G. De Guidi, L.L. Costanzo, R. Chillemi, S. Giuffrida, G. Condorelli, Molecular mechanism of drug photosensitization 4. Photohemolysis sensitized by carprofen, J. Photochem. Photobiol. B: Biol. 17 (1993) 239-246.
17. [17] G. De Guidi, L.L. Costanzo, R. Chillemi, 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.
18. [18] A. Figueiredo, C.A. Fontes Ribeiro, M. Gonçalo, A. Poiares Baptista, F. Teixeira, Experimental studies on the mechanisms of tiaprofenic acid photosensitization, J. Photochem. Photobiol. B: Biol. 18 (1993) 161-168.
19. [19] D. de la Peña, C. Martí, S. Nonell, L.A. Martínez, M.A. Miranda, Time-resolved near infrared studies on singlet oxygen production by the photosensitizing 2-arylpropionic acids, Photochem. Photobiol. 65 (1997) 828-832.
20. [20] L.M. Prince (Ed.), Microemulsions, Theory, Practice, Academic Press, New York, 1977.
21. [21] R. Leung, M.J. Hou, D.O. Shah, Microemulsions: formation, structure, properties and novel applications, Surfactant Sci. Ser. (Surfactant Chem. Process Eng.) 28 (1988) 315-367.
22. [22] D. Langevin, Microemulsions, liquid crystals, Mol. Cryst. Liq. Cryst. 138 (1986) 259-305.
23. [23] P.G. De Gennes, C. Taupin, Microemulsions and the flexibility of oil/ water interfaces, J. Phys. Chem. 86 (1982) 2294-2304.
24. [24] J.H. Fendler, Microemulsions, micelles and vesicles as media for membrane mimetic photochemistry, J. Phys. Chem. 84 (1980) 1485-1491.
25. [25] D. Balasubramarian, C. Kumar, Water-in-oil microemulsions: structural features and application as biological models, in: K.L. Mittal, J.H. Fendler (Eds.), Solution Behaviour of Surfactants, vol. 2, Plenum, New York, 1982, pp. 1207-1223.
26. [26] R. Sakellariou-Fargues, M.-T. Maurette, E. Oliveros, M. Rivière, A. Lattes, Chemical and photochemical reactivity in micellar media and microemulsions. IV: concentration effects on isophorone dimerization, J. Photochem. 18 (1982) 101-107.
27. [27] F.M. Menger, A.R. Ellington, Organic reactivity in microemulsion systems, J. Am. Chem. Soc. 113 (1991) 9621-9624 and refs. therein.
28. [28] E. Oliveros, P. Pheulpin, A.M. Braun, Comparative study of the sensitized photooxidation of N-methyl phenothiazine in homogeneous and microheterogeneous media, Tetrahedron 43 (1987) 1713-1723.
29. [29] A.M. Braun, E. Oliveros, Local concentration effects on oxidation reactions in microheterogeneous media, in: H.-J. Schneider, H. Dürr (Eds.), Frontiers in Supramolecular Organic Chemistry and Photochemistry, VCH, Weinheim, 1991, pp. 393-419.
30. g) bimolecular processes. Solvent and compartmentalization effects, Chem. Rev. 93 (1993) 699-723 and refs. therein.
31. [31] J.V. Castell, M.J. Gómez-Lechón, C. Grassa, L.A. Martínez, M.A. Miranda, P. Tárrega, Involvement of drug derived peroxides in the phototoxicity of naproxen and tiaprofenic acid, Photochem. Photobiol. 57 (1993) 35-39.
32. [32] L.A. Martínez, Desarrollo de un modelo in vitro para el estudio del potencial fotosensibilizador de nuevos fármacos en humanos. Los ácidos 2-arilpropiónicos antiinflamatorios como grupo modelo, Ph.D. Thesis, Universitat de Valencia, Spain, 1995.
33. [33] E. Oliveros, P. Murasecco-Suardi, T. Aminian-Saghafi, A.M. Braun, 1H-Phenalen-1-one: photophysical properties and singlet oxygen production, Helv. Chim. Acta 74 (1991) 79-90.
34. [34] K. Kalyanasundaran, Photochemistry in Microheterogeneous Systems, Academic Press, New York, 1987.
35. [35] S. Navaratnam, B.J. Parsons, J.L. Hughes, Laser-flash photolysis studies of benoxaprofen and its analogues. 1. Yields of triplet states and singlet oxygen in acetonitrile solutions, J. Photochem. Photobiol. A: Chem. 73 (1993) 97-103.
36. [36] E. Oliveros, P. Murasecco-Suardi, A.M. Braun, H.J. Hansen, Efficiency of singlet oxygen quenching by carotenoids measured by near-infrared steady-state luminescence, in: L. Parker (Eds.), Carotenoids, Methods in Enzymology, Part A, Chemistry, Separation, Quantitation and Antioxidation, Academic Press, San Diego, CA, 1992, pp. 420-429.
37. [37] T. Aminian-Saghafi, G. Nasini, T. Caronna, A.M. Braun, E. Oliveros, Quantum yields of singlet oxygen production by some natural quinoid fungal metabolites and derivatives, Helv. Chim. Acta 75 (1992) 531-538.
38. g), J. Phys. Chem. 94 (1990) 4377-4378.
39. [39] A.M. Braun, E. Oliveros, Applications of singlet oxygen reactions: mechanistic and kinetic investigations, Pure Appl. Chem. 62 (1990) 1467-1476.
40. [40] K. Gollnick, G.O. Schenck, Mechanisms and stereoselectivity of photochemical oxygen transfer reactions, Pure Appl. Chem. 9 (1964) 507-525.
41. [41] E. Gassmann, Die Quantenausbeute der Singulett-Sauerstoff-Sensibilisierung in heterogener Phase, Ph.D. Thesis, Ecole Polytechnique Fédérale de Lausanne, Switzerland, 1984.
42. [42] P. Murasecco-Suardi, E. Gassmann, A.M. Braun, E. Oliveros, Determination of the quantum yield of intersystem crossing of rose bengal, Helv. Chim. Acta 70 (1987) 1760-1773.
43. [43] D.C. Neckers, U.M. Valdes-Aguilera, Photochemistry of the xanthene dyes, in: D. Volman, G.S. Hammond, D.C. Neckers (Eds.), Adv. Photochem., vol. 18, John Wiley, New York, 1993, pp. 315-394.
44. [44] E. Gandin, Y. Lion, A. Van der Vost, Quantum yields of singlet oxygen production by xanthene derivatives, Photochem. Photobiol. 37 (1983) 271-278.
45. g) sensitization, J. Photochem. Photobiol. A: Chem. 79 (1994) 11-18.
46. [46] C. Martí, O. Jürgens, O. Cuenca, M. Casals, S. Nonell, Aromatic ketones as standards for singlet molecular oxygen photosensitization. Time-resolved photoacoustic and NIR emission studies, J. Photochem. Photobiol. A: Chem. 97 (1996) 11-18.
47. [47] P. Murasecco-Suardi, Etude des methodes de caracterisation de sensibilisateurs d'oxygene singulet, Ph.D. Thesis, Ecole Polytechnique Fédérale de Lausanne, Switzerland, 1988.
48. g) luminescence in solution folowing pulsed laser excitation. Solvent deuterium isotope effects on the lifetime of singlet oxygen, J. Am. Chem. Soc. 104 (1982) 2069-2070.
49. g) in liquid water as determined by time-resolved infrared luminescence measurements, J. Am. Chem. Soc. 104 (1982) 5541-5543.
50. [50] S.Y. Egorov, V.F. Kamalov, N.I. Koroteev, A.A. Krasnovsky, Jr., B.N. Tolentaev, S.V. Zinukov, Interpretation of the atmospheric oxygen bands; electronic levels of oxygen molecule, Chem. Phys. Lett. 163 (1989) 421-424 and refs. therein.
51. [51] M. Boneva, S.K. Ivanov, E. Oliveros, A.M. Braun, Singlet oxygen quenching by tertiary alkyl ethers, J. Photochem. Photobiol. A: Chem. 68 (1992) 343-351.
52. g)) deactivation in microemulsions and micellar media, in preparation.
53. [53] P. Bilski, R. Dabestani, C.F. Chignell, Influence of cationic surfactants on the photoprocesses of eosine and rose bengal in aqueous solution, J. Phys. Chem. 95 (1991) 5784-5791.
54. [54] P. Bilski, C.F. Chignell, Properties of differently charged micelles containing rose bengal: application in photosensitization studies, J. Photochem. Photobiol., A: Chem. 77 (1994) 49-58.
55. [55] M. Hoebeke, E. Gandin, J. Decuyper, A. van de Vorst, Effects of micellar adsorption on the photosensitizing properties of xanthene dyes, J. Photochem. 35 (1986) 245-250.
56. [56] F. Lelièvre, P. Gareil, Chiral separations of underivatized arylpropionic acids by capillary zone electrophoresis with various cyclodextrins. Acidity and inclusion constant determination, J. Chromatogr. A 735 (1996) 311-320.
57. a values of several non-steroidal anti-inflammatory drugs, Anal. China. Acta 338 (1997) 127-137.
58. [58] C.D. Burt, Photosensitization by drugs in surfactant solution, Photochem. Photobiol. 34 (1981) 431-439.
59. [59] M.C. Jiménez, M.A. Miranda, R. Tormos, Photochemistry of naproxen in the presence of β-cyclodextrin, J. Photochem. Photobiol. A: Chem. 104 (1997) 119-121.
60. [60] S. Navaratnam, J.L. Hughes, B.J. Parsons, G.O. Philiphs, Laser flash and steady-state photolysis of benoxaprofen in aqueous solution, Photochem. Photobiol. 41 (1985) 375-380.