Photosensitizing effect of some nonsteroidal antiinflammatory drugs on natural and artificial membranes: Dependence on phospholipid composition

Chemical Research in Toxicology

Volumn 18, Issue 2, 2005, Pages 204-212

  De Guidi, Guido ^a   Ragusa, Santa ^a   Cambria, Maria T ^a   Belvedere, Alessandra ^a   Catalfo, Alfio ^a   Cambria, Antonio ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DIFLUNISAL; FATTY ACID ESTER; FREE RADICAL; KETOPROFEN; LIPOSOME; MEMBRANE PHOSPHOLIPID; NAPROXEN; NONSTEROID ANTIINFLAMMATORY AGENT; PEROXIDE; PHOSPHATIDYLCHOLINE; PHOTOSENSITIZING AGENT; REACTIVE OXYGEN METABOLITE; SATURATED FATTY ACID; SPHINGOMYELIN; UNSATURATED FATTY ACID;

ANIMAL CELL; ARTICLE; ARTIFICIAL MEMBRANE; BILAYER MEMBRANE; CAT; CATTLE; COVALENT BOND; DOG; DOUBLE BOND; DRUG STRUCTURE; ERYTHROCYTE; ERYTHROCYTE MEMBRANE; HEMOLYSIS; HORSE; HUMAN; HUMAN CELL; LIPID COMPOSITION; MAMMAL CELL; MEMBRANE FLUIDITY; MEMBRANE RESISTANCE; NONHUMAN; OSMOTIC STRESS; PHOTODEGRADATION; PHOTOHEMOLYSIS; PHOTOSENSITIZATION; PHOTOTOXICITY; STRUCTURE ACTIVITY RELATION; SWINE;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CATTLE; ERYTHROCYTES; HUMANS; MEMBRANES, ARTIFICIAL; MOLECULAR STRUCTURE; PHOSPHOLIPIDS; PHOTOCHEMISTRY; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; TIME FACTORS;

EID: 13844250567     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049824a     Document Type: Article

References (53)

1. Ochroch, E. A., Mardini, I. A., and Gottschalk, A. (2003) What is the role of NSAIDs in pre-emptive analgesia? Drugs 63, 2709-2723.
2. Albes, B., Marguery, M. C., Schwarze, H. P., Journe, F., Loche, F., and Bazex J. (2000) Prolonged photosensitivity following contact photoallergy to ketoprofen. Dermatology 201, 171-174.
3. Lhiaubet-Vallet, V., Sarabia, Z., Hernandez, D., Castell, J. V., and Miranda, M. A. (2003) In vitro studies on DNA-photosensitization by different drug stereoisomers. Toxicol. in Vitro 17, 651-656.
4. He, Y. Y., Ramirez, D. C., Detweiler, C. D., Mason, R. P., and Chignell, C. F. (2003) UVA-ketoprofen induced hemoglobin radicals detected by immuno-spin trapping. Photochem. Photobiol. 77, 585-591.
5. Vinette, A. L., McNamee, J. P., Bellier, P. V., McLean, J. R., and Scaiano, J. C. (2003) Prompt and delayed nonsteroidal antiinflammatory drug photoinduced DNA damage in peripheral blood mononuclear cells measured with the comet assays. Photochem. Photobiol. 77, 390-396.
6. Sugiura, M., Hayakawa, R., Xie, Z., Sugiura, K., Hiramoto, K., and Shamoto, M. (2002) Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs. Photodermatol. Photoimmunol. Photomed. 18, 82-89.
7. Bosca, F., Marin, M. L., and Miranda, M. A. (2001) Photoreactivity of the nonsteroidal antiinflammatory 2-arylpropionic acids with photosensitizing side effects. Photochem. Photobiol. 74, 637-655.
8. Condorelli, G., Costanzo, L. L., De Guidi, G., Giuffrida, S., Miano, P., Sortino, S., and Velardita, A. (1996) Photosensitization induced by non streroidal antiinflammatory drugs: An overview of molecular mechanism in biological systems. EPA Newsl. 58, 60-77.
9. Lhiaubet, V., Paillous, N., and Chouini-Lalanne, N. (2001) Comparison of DNA damage photoinduced by ketoprofen, fenofibric acid and benzophenone via electron and energy transfer. Photochem. Photobiol. 74, 670-678.
10. Chouini-Lalanne, N., Defais, M., and Paillous, N. (1998) Nonsteroidal antiinflammatory drug photosensitized formation of pyrimidine dimer in DNA. Biochem. Pharmacol. 55, 441-446.
11. Lahoz, A., Hernandez, D., Mirando, M. A., Perez-Prieto, J., Morera, I. M., and Castell, J. V. (2001) Antibodies directed to drug epitopes to investigate the structure of drug-protein photoadducts. Recognition of a common photobound substructure in tiaprofenic acid/ketoprofen cross-photoreactivity. Chem. Res. Toxicol. 14, 1486-1491.
12. Bosca, F., Cuquerella, M. C., Marin, M. L., and Miranda, M. A. (2001) Photochemistry of 2-hydroxy-4-trifluoromethylbenzoic acid, major metabolite of the photosensitizing platelet antiaggregant drug triflusal. Photochem. Photobiol. 73, 463-468.
13. Giuffrida, S., De Guidi, G., Miano, P., Sortino, S., Condorelli, G., and Costanzo, L. L. (1996) Molecular mechanism of drug photosensitization: VIII. Effect of inorganic ions on membrane damage photosensitized by naproxen. J. Inorg. Biochem. 63, 253-263.
14. Albini, A., and Fasani, E. (1998) Drugs: Photochemistry and Photostability, The Royal Society of Chemistry, London.
15. Monti, S., Sortino, S., De Guidi, G., and Marconi, G. (1997) 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, 2269-2275.
16. Bosca, F., Mirando, M. A., Cardanico, G., and Mauleon, D. (1993) Photochemical and photobiological properties of ketoprofen associated with the benzophenone chromophores. Photochem. Photobiol. 60, 96-101.
17. Radschuweit, A., Ruttinger, H. H., Nuhn, P., Wohlrab, W., and Huschka, C. (2001) UV-induces formation of hydrogen peroxide based on the photochemistry of Ketoprofen. Photochem. Photobiol. 73, 119-127.
18. Cosa, G., Llauger, L., Scaiano, J. C., and Miranda, M. A. (2002) Absolute rate constants for water protonation of 1-(3-benzoylphenyl)alkyl carbanions. Org. Lett. 4, 3083-3085.
19. Chignell, C. F., and Sik, R. H. (1998) Effect of magnetite particles on photoinduced and nonphotoinduced free radical processes in human erythrocytes. Photochem. Photobiol. 68, 598-601.
20. Chignell, C. F., and Sik, R. H. (1998) The effect of static magnetic fields on the photohemolysis of human erythrocytes by ketoprofen. Photochem. Photobiol. 67, 591-595.
21. Bonomo, R. P., Conte, E., De Guidi, G., Maccarrone, G., Rizzarelli, E., and Vecchio, G. (1996) Characterization and superoxide dismutase activity of copper(II) complexes of 6A,6X-difunctionalized β-cyclodextrins. J. Chem. Soc., Dalton Trans. 23, 4351-4355.
22. Durbize, E., Vigan, M., Puzenat, E., Girardin, P., Adessi, B., Desprez, P. H., Humbert, P. H., Laurent, R., and Aubin, F. (2003) Spectrum of cross-photosensitization in 18 consecutive patients with contact photoallergy to ketoprofen: associated photoallergies to nonbenzophenone-containing molecules. Contact Dermatitis 48, 144-149.
23. Neumann, N. J., and Lehmann, P. (2003) The photopatch test procedure of the German, Austrian, and Swiss photopatch test group. Photodermatol. Photoimmunol. Photomed. 19, 8-10.
24. Matsushita, T., and Kamide, R. (2001) Five cases of photocontact dermatitis due to topical ketoprofen: Photopatch testing and cross-reaction study. Photodermatol. Photoimmunol. Photomed. 17, 26-31.
25. Vigan, M., Girardin, P., Desprez, P., Adessi, B., Aubin, F., and Laurent, R. (2002) Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to fenticlor(R). Ann. Dermatol. Venereol. 129, 1125-1127.
26. Sugiyama, M., Nakada, T., Hosaka, H., Sueki, H., and Iijima, M. (2001) Photocontact dermatitis to ketoprofen. Am. J. Contact Dermatitis 12, 180-181.
27. Kawada, A., Aragane, Y., Asai, M., and Tezuka, T. (2001) Simultaneous photocontact sensitivity to ketoprofen and oxybenzone. Contact Dermatitis 44, 370.
28. Nelson, G. J. (1967) Lipid composition of erythrocytes in various mammalian species. Biochim. Biophys. Acta 144, 221-232.
29. Giammona, G., Pitarresi, G., Tomarchio, V., De Guidi, G., and Giuffrida, S. (1998) Swellable microparticles containing Suprofen: Evaluation of in vitro release and photochemical behaviour. J. Controlled Release 51, 249-257.
30. Bigelow, M. W., Wiessener, J. H., Kleinman, J. G., and Mandel, N. S. (1996) Calcium oxalate-crystal membrane interactions: dependence on membrane lipid composition. J. Urol. 155, 1094-1098.
31. Wade, A. (1986) Clarke's Isolation and Identification of Drugs, Pharmaceutical Press, London.
32. Valenzeno, P., and Trank, J. W. (1985) Measurement of cell lysis by scattering. Photochem. Photobiol. 42, 335-339.
33. Rose, H. G., and Oklander, M. (1965) Improved procedure for the extraction of lipids from human erythrocytes. J. Lipid Res. 6, 428.
34. Bécart, J., Chevalier, C., and Biesse, J. P. (1990) Quantitative analysis of phospholipids by HPLC with a light scattering detector: Application to raw materiels for cosmetic use. J. High Resolut. Chromatogr. 13, 126-129.
35. Kremer, J. M. H., van der Esker, W. M. J., Pathmamanoharan, C., and Wiersema, P. H. (1977) Vesicles of variable diameter prepared by a modified injection method. Biochemistry 16, 3932-3940.
36. Costanzo, L. L., De Guidi, G., Giuffrida, S., Sortino, S., Condorelli, G., and Pappalardo, G. (1995) Antioxidant effect of copper(II) on photosensitized lipid peroxidation. J. Inorg. Biochem. 57, 115-125.
37. Girotti, A. W., and Thomas, J. P. (1984) Damaging effects of oxygen radicals on resealed erythrocyte ghosts. J. Biol. Chem. 2597, 1744-1752.
38. Allain, C. A., Poon, L. S., Chan, C. S. G., Richmond, W., and Fu, P. C. (1974) Enzymatic determination of total serum cholesterol. Clin. Chem. 20, 470.
39. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951) Protein measurement with folin phenol reagent. J. Biol. Chem. 193, 265.
40. Gutteridge, J. M. C. (1995) Lipid peroxidation and antioxidants as biomarkers of tissue damage. Clin. Chem. 41, 1819-1828.
41. Girotti, A. W. (2001) Photosensitized oxidation of membrane lipids: Reaction pathways, cytotoxic effects and cytoprotective mechanism. J. Photochem. Photobiol. B: Biol. 63, 103-113.
42. Watson, A. D., Leitinger, N., Navab, M., Faull, K. F., Horkko, S., Witztum, J. L., Palinski, W., Schwenke, D., Salomon, R. G., and Sha, W. (1997) Structural identifcation by mass spectrometry of oxidized phospholipids in minimally oxidized low-density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo. J. Biol. Chem. 272, 13597-13607.
43. Watson, A. D., Subbanagounder, G., Welsbie, D. S., Faull, K. F., Navab, M., Jung, M. E., Fogelman, A. M., and Berliner, J. A. (1999) Structural identification of a novel pro-infiammatory epoxyisoprostane phospholipid in mildly oxidized low-density lipoprotein. J. Biol. Chem. 274, 24787-24798.
44. Byrdwell, W. C., and Neff, W. E. (2001) Autoxidation products of normal and genetically modified canola oil varieties determined using liquid chromatography with mass spectrometric detection. J. Chromatogr. A 905, 85-102.
45. Spickett, C. M., Rennie, N., Winter, H., Zambonin, L., Landi, L., Jerlich, A., Schaur, R. J., and Pitt, A. R. (2001) Detection of phospholipid oxidation in oxidatively stressed cells by reversed-phase HPLC coupled with positive-ionization electrospray MS. Biochem. J. 355, 449-457.
46. Brouwers, J. F. H. M., Gadella, B. M., van Golde, L. M. G., and Tielens, A. G. M. (1998) Quantitative analysis of phosphatidylcholine molecular species using HPLC and light scattering detection. J. Lipid Res. 39, 344-353.
47. Hall, L. M., and Murphy, R. C. (1998) Analysis of stable oxidized molecular species of glycerophospholipids following treatment of red blood cell ghosts with tert-butylhydroperoxide. Anal. Biochem. 258, 184-194.
48. Brouwers, J. F. H. M., Vernooij, E. A. A. M., Tielens, A. G. M., and van Golde, L. M. G. (1999) Rapid separation and identification of phosphatidylethanolamine molecular species. J. Lipid Res. 40, 164-169.
49. Ekroos, K., Ejsing, C. S., Bahr, U., Karas, M., Simons, K., and Shevchenko, A. (2003) Charting molecular composition of phosphatidylcholines by fatty acid scanning and ion trap MS3 fragmentation. J. Lipid Res. 44, 2181-2192.
50. Hax, W. M. A., and van Kessel, W. S. M. G. (1977) High-performance liquid chromatographic separation and photometric detection of phospholipids. J. Chromatogr. 142, 735-741.
51. Han, X., and Gross, R. W. (1994) Electrospray ionization mass spectroscopic analysis of human erythrocyte plasma membrane phospholipids. Proc. Natl. Acad. Sci. U.S.A. 91, 10635-10639.
52. Van den Berg, J. J. M., Op den Kamp, J. A. F., Lubin, B. H., and Kuypers, F. A. (1993) Conformational changes in oxidized phospholipids and their preferential hydrolysis by phospholipase A2: A monolayer study. Biochemistry 32, 4962-4967.
53. Salgo, M. G., Corongiu, F. P., and Sevanian, A. (1993) Enhanced interfacial catalysis and hydrolytic specificity of phospholipase A2 toward peroxidized phosphatidylcholine vesicles. Arch. Biochem. Biophys. 304, 123-132.