Theoretical Investigation of NSAID Photodegradation Mechanisms

Quantum Biochemistry

Volumn , Issue , 2010, Pages 805-834

  Musa, Klefah A K ^a   Eriksson, Leif A ^b  

^a ÖREBRO UNIVERSITY   (Sweden)

^b NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

Biocomputational chemistry; Drug photosensitivity; Non steroid anti inflammatory drugs (NSAIDs); Photodegradation; Reactive oxygen species

Indexed keywords

EID: 84860417480     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527629213.ch30     Document Type: Chapter

References (138)

1. Tilstone, C., Report by the Medicines and Healthcare products Regulatary Agency (MHRA), Commission on Human Medicines (CHM), Drug safety update, August 2008, 2, 1-10.
2. Bednar, B. (2009) Nephrol New Issues, 23, 38-40.
3. Yusuff, K. B. and Yusuf, A. (2009) Journal of the American Pharmacists Association, 49, 432-435.
4. The Pharmacovigilance Unit; Irish Medicines Board. (2000) Drug Safety Newslatter, 9th edn., 1.
5. Bond, C.A. and Raehl, C.L. (2006) Pharmacotherapy, 26, 601.
6. Chan, F.K.L. (2006) Nat. Clin. Pract. Gastroenterol. Hepatol., 3, 563.
7. Aldenkamp, A.P. (2004) Epilepsia, 45, 47.
8. Gronroos, M., Chen, M., Jahnukainen, T., Capitanio, A. et al.. (2006) Pediatr. Blood & Cancer, 46, 624.
9. Vargas, F., Rivas, C., Diaz, Y., and Fuentes, A. (2003) J. Photochem. Photobiol. B, 72, 87.
10. Kao, Y.H., Chong, C.H., Ng, W.T., and Lim, D. (2007) Occupational Med. - Oxford, 57, 535.
11. Musshoff, F., Gerschlauer, A., and Madea, B. (2003) Forensic Sci. Int., 134, 234.
12. Werner, J.J., McNeill, K., and Arnold, W.A. (2005) Chemosphere, 58, 1339.
13. Uwai, K., Tani, M., Ohtake, Y., Abe, S. et al.. (2005) Life Sci., 78, 357.
14. Di Paola, A., Addamo, M., Augugliaro, V., Garcia-Lopez, E., Loddo, V., Marci, G., and Palmisano, L. (2006) Int. J. Photoenergy, 2006 6.
15. Han, K.D., Bark, K.M., Heo, E.P., Lee, J.K. et al.. (2000) Photodermatol. Photoimmunol. Photomed., 16, 121.
16. Thoma, K. and Holzmann, C. (1998) Eur. J. Pharm. Biopharm., 46, 201.
17. Andrisano, V., Gotti, R., Leoni, A., and Cavrini, V. (1999) J. Pharm. Biomed. Anal., 21, 851.
18. Brisaert, M. and Plaizier-Vercammen, J. (2000) Int.J. Pharm., 199, 49.
19. Andrisano, V., Ballardini, R., Hrelia, P., Cameli, N. et al.. (2001) Eur. J. Pharm. Sci., 12, 495.
20. Andrisano, V., Hrelia, P., Gotti, R., Leoni, A., and Cavrini, V. (2001) J. Pharm. Biomed. Anal., 25, 589.
21. Stott, C.W., Stasse, J., Bonomo, R., and Campbell, A.H. (1970) J. Invest. Dermatol., 55, 335.
22. Spielmann, H., Lovell, W.W., Holzle, E., Johnson, B.E. et al.. (1994) Alternatives Lab. Animals, 22, 314.
23. DeRosa, M.C., Crutchley, R.J.,. (2002) Coordination Chemistry Reviews 233-234, 351-71.
24. Doll, T.E. and Frimmel, F.H. (2003) Chemosphere, 52, 1757.
25. Ray, R.S., Misra, R.B., Farooq, M., and Hans, R.K. (2002) Toxicol. In Vitro, 16, 123.
26. Quintero, B. and Miranda, M.A. (2000) Ars Pharm., 41, 27.
27. Mroz, P., Pawlak, A., Satti, M., Lee, H., Wharton, T., Gali, H., Sarna, T., and Hamblin, M.R. (2007) Functionalized fullerenes mediate photodynamic killing of cancer cells: Type I versus Type II photochemical mechanism. Free Radical Biology and Medicine, 43, 711-719.
28. Bosca, F. and Miranda, M.A. (1998) J. Photochem. Photobiol. B, 43, 1.
29. Miranda, M.A. (2001) PureApp. Chem., 73, 481.
30. Reid, C.D., Chemical Photosensitivity Another Reason to Be Careful in the Sun. Published by the U.S. Food and Drug Administration. FDA Consumer magazine (May 1996). http://sun1.awardspace.com/Causes_Photosensitivity/chemical_photosensitivity.htm.
31. Zambre, A.P., Ganure, A.L., Shinde, D.B., and Kulkarni, V.M. (2007) J. Chem. Inf. Mod., 47, 635.
32. Penning, T.D., Talley, J.J., Bertenshaw, S.R., Carter, J.S. et al.. (1997) J. Med. Chem., 40, 1347.
33. Prasit, P., Wang, Z., Brideau, C., Chan, C.C. et al.. (1999) Bioorg. Med. Chem. Lett., 9, 1773.
34. Talley, J.J., Brown, D.L., Carter, J.S., Graneto, M.J. et al.. (2000) J. Med. Chem., 43, 775.
35. Talley, J.J., Bertenshaw, S.R., Brown, D.L., Carter, J.S. et al.. (2000) J. Med. Chem., 43, 1661.
36. Frolich, J.C. (1997) Trends Pharmacol. Sci., 18, 30.
37. Frolich, J.C. (1997) Trends Pharmacol. Sci., 18, 312.
38. Jose, V.M. and Antony, T.T. (2003) Indian J. Pharmacol., 35, 318.
39. Cardenas, S., Gallego, M., Valcarcel, M., Ventura, R., and Segura, J. (1996) Anal. Chem., 68, 118.
40. Meloun, M., Bordovska, S., and Galla, L. (2007) J. Pharm. Biomed. Anal., 45, 552.
41. Smith, W.L., DeWitt, D.L., and Garavito, R.M. (2000) Annu. Rev. Biochem., 69, 145.
42. Herschman, H.R., Xie, W.L., and Reddy, S. (1999) Eicosanoids and other Bioactive Lipids in Cancer, Inflammation and Radiation Injury, 469, 3.
43. Griswold, D.E. and Adams, J.L. (1996) Med. Res. Rev., 16, 181.
44. Liu, H., Huang, X.Q., Shen, J.H., Luo, X.M. et al.. (2002) J. Med. Chem., 45, 4816.
45. Marnett, L.J. and Kalgutkar, A.S. (1999) Trends Pharm. Sci., 20, 465.
46. Allison, M.C., Howatson, A.G., Torrance, C.J., Lee, F.D., and Russell, R.I. (1992) New England J. Med, 327, 749.
47. Lucio, M., Bringezu, F., Reis, S., Lima, J., and Brezesinski, G. (2008) Langmuir, 24, 4132.
48. Price, M.L.P. and Jorgensen, W.L. (2000) J. Am. Chem. Soc., 122, 9455.
49. Shao, J.Y., Sheng, H.M., Aramandla, R., Pereira, M.A. et al.. (1999) Carcinogen., 20, 185.
50. Williams, C.S., Luongo, C., Radhika, A., Zhang, T. et al.. (1996) Gastroenterology, 111, 1134.
51. Eberhart, C.E., Coffey, R.J., Radhika, A., Giardiello, F.M. et al.. (1994) Gastroenterology, 107, 1183.
52. Murphy, J.F.,. (2008) Clinical Medicine: Cardiology, 2, 257-262.
53. Llorens, O., Perez, J.J., Palomer, A., and Mauleon, D. (2002) J. Mol. Graphics Mod., 20, 359.
54. Llorens, O., Perez, J.J., Palomer, A., and Mauleon, D. (1999) Bioorg. Med. Chem. Lett., 9, 2779.
55. Xie, W.L., Robertson, D.L., and Simmons, D.L. (1992) Drug Develop. Res., 25, 249.
56. Breitner, J.C.S. (2003) Lancet Neurol., 2, 527.
57. Etminan, M. (2003) Br. Med.J., 327, 751.
58. Price, D. (2003) Br. Med.J., 327, 752.
59. Robertson, M. (2003) Br. Med.J., 327, 751.
60. Aisen, P.S., Schafer, K.A., Grundman, M., Pfeiffer, E. et al.. (2003) J. Am. Med. Assoc., 289, 2819.
61. Trujillo-Murillo, K., Rincon-Sanchez, A.R., Martinez-Rodriguez, H., Bosques-Padilla F. et al.. (2008) Hepatology (Philadelphia), 47, 1462.
62. Marjanovic, M., Zorc, B., Pejnovic, L., Zovko, M., and Kralj, M. (2007) Chem. Biol. Drug Des., 69, 222.
63. Yamazaki, T., Muramoto, M., Oe, T., Morikawa, N. et al.. (2006) Neuropharmacology, 50, 558-567.
64. Munroe, D.G. and Lau, C.Y. (1995) Chem. Biol., 2, 343.
65. Herschman, H.R. (1996) Biochim. Biophys. Acta - Lipids Lipid Metabolism, 1299, 125.
66. Langford, R.M. (2006) Clin. Rheumatol., 25, S2.
67. Jones, R., Rubin, G., Berenbaum, F., and Scheiman, J. (2008) Am.J. Med., 121, 464.
68. Hasan, J., Beharry, K.D., Gharraee, Z., Stavitsky, Y. et al.. (2008) Prostaglandins Lipid Mediators, 85, 81.
69. Chemtob, S., Laudignon, N., Beharry, K., Rex, J. et al.. (1990) Develop. Pharmacol. Therapeut., 14, 1.
70. House, A.A., Oliveira, S.S., and Ronco, C. (2007) Int. J. Artificial Organs, 30, 1042.
71. Hinz, B., Renner, B., and Brune, K. (2007) Nat. Clin. Pract. Rheumatol., 3, 552.
72. Marret, E. and Bonnet, F. (2007) Ann. Fr. d'Anésthesie Reanimation, 26, 535.
73. Suleyman, H., Demircan, B., and Karagoz, Y. (2007) Pharmacol. Rep., 59, 247.
74. Yorgason, J.G., Fayad, J.N., and Kalinec, F. (2006) Expert Opin. Drug Safety, 5, 383.
75. Diaz, R.L., Gardeazabal, J., Manrique, P., Raton, J.A. et al.. (2006) Contact Dermatitis, 54, 239.
76. Bagheri, H., Lhiaubet, V., Montastruc, J.L., and Chouini-Lalanne, N. (2000) Drug Safety, 22, 339.
77. Sugiura, M., Hayakawa, R., Xie, Z.L., Sugiura, K. et al.. (2002) Photodermatol. Photoimmunol. Photomed., 18, 82.
78. Nakajima, A., Tahara, M., Yoshimura, Y., and Nakazawa, H. (2005) J. Photochem. Photobiol. A, 174, 89.
79. Nakazawa, T., Shimo, T., Chikamatsu, N., Igarashi, T. et al.. (2006) Arch. Toxicol., 80, 442.
80. Liu, S., Mizu, H., and Yamauchi, H. (2007) Biochem. Biophys. Res. Commun., 364, 650.
81. Castell, J.V., Gomez, M.J., Miranda, M.A., and Morera, I.M. (1987) Photochem. Photobiol., 46, 991.
82. Miranda, M.A., Morera, I., Vargas, F., Gomezlechon, M.J., and Castell, J.V. (1991) Toxicol. In Vitro, 5, 451.
83. Bergner, T. and Przybilla, B. (1992) J. Am. Acad. Dermatol., 26, 114.
84. Miranda, M.A., Castell, J.V., Gomezlechon, M.J., and Martinez, L.A. (1993) Toxicol. In Vitro, 7, 523.
85. Packer, J.L., Werner, J.J., Latch, D.E., McNeill, K., and Arnold, W.A. (2003) Aquatic Sci., 65, 342.
86. Chouini-Lalanne, N., Defais, M., and Paillous, N. (1998) Biochem. Pharmacol., 55, 441.
87. Artuso, T., Bernadou, J., Meunier, B., and Paillous, N. (1990) Biochem. Pharmacol., 39, 407.
88. Castell, J.V., Gomezlechon, M.J., Grassa, C., Martinez, L.A. et al.. (1993) Photochem. Photobiol., 57, 486.
89. Jimenez, M.C., Miranda, M.A., and Tormos, R. (1997) J. Photochem. Photobiol. A, 104, 119.
90. Partyka, M., Au, B.H., and Evans, C.H. (2001) J. Photochem. Photobiol. A, 140, 67.
91. Martinez, L.J. and Scaiano, J.C. (1998) Photochem. Photobiol., 68, 646.
92. Canudas, N., Moulinier, J., Zamora, D., and Sanchez, A. (2000) Pharmazie, 55, 282.
93. Canudas, N., Zamora, D., Villamizar, J.E., Fuentes, J. et al.. (2005) Pharmazie, 60, 604.
94. Bosca, F., Canudas, N., Marin, M.L., and Miranda, M.A. (2000) Photochem. Photobiol., 71, 173.
95. Castell, J.V., Gomezlechon, M.J., Grassa, C., Martinez, L.A. et al.. (1994) Photochem. Photobiol., 59, 35.
96. Condorelli, G., Costanzo, L.L., Deguidi, G., Giuffrida, S., and Sortino, S. (1995) Photochem. Photobiol., 62, 155.
97. Starrs, S.M. and Davies, R.J.H. (2000) Photochem. Photobiol., 72, 291.
98. Castell, J.V., Gomezlechon, M.J., Miranda, M.A., and Morera, I.M. (1992) J. Photochem. Photobiol. B, 13, 71.
99. Cuk, A., Skerlj, M., Palka, E., and Murn, M. (1991) Z. Vestnik, 60, 267.
100. Encinas, S., Bosca, F., and Miranda, M.A. (1998) Chem. Res. Toxicol., 11, 946.
101. Encinas, S., Bosca, F., and Miranda, M.A. (1998) Photochem. Photobiol., 68, 640.
102. Moore, D.E. (1998) Mutat. Res.-Fundamental Mol. Mechanisms Mutagen., 422, 165.
103. Musa, K.A.K., Matxain, J.M., and Eriksson, L.A. (2007) J. Med. Chem., 50, 1735.
104. Musa, K.A.K. and Eriksson, L.A. (2007) J. Phys. Chem. B, 111, 13345.
105. Musa, K.A.K. and Eriksson, L.A. (2008) J. Photochem. Photobiol. A, 1, 200, 48.
106. Musa, K.A.K. and Eriksson, L.A. (2009) J. Phys. Chem. B, 113, 11306.
107. Musa, K.A.K. and Eriksson, L.A. (2008) J. Phys. Chem. A, 112 (43) 10921.
108. Musa, K.A.K. and Eriksson, L.A. (2008) Phys. Chem. Chem. Phys., 11, 4601.
109. Becke, A.D. (1993) J. Chem. Phys., 98, 5648.
110. Lee, C.T., Yang, W.T., and Parr, R.G. (1988) Phys. Rev. B, 37, 785.
111. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J. (1994) J. Phys. Chem., 98, 11623.
112. Cossi, M., Scalmani, G., Rega, N., and Barone, V. (2002) J. Chem. Phys., 117, 43.
113. Mennucci, B. and Tomasi, J. (1997) J. Chem. Phys., 106, 5151.
114. Cances, E., Mennucci, B., and Tomasi, J. (1997) J. Chem. Phys., 107, 3032.
115. Bauernschmitt, R. and Ahlrichs, R. (1996) Chem. Phys. Lett., 256, 454.
116. Casida, M.E., Jamorski, C., Casida, K.C., and Salahub, D.R. (1998) J. Chem. Phys., 108, 4439.
117. Stratmann, R.E., Scuseria, G.E., and Frisch, M.J. (1998) J. Chem. Phys., 109, 8218.
118. Frisch, M.J.T., Trucks, G.W., Schlegel, H.B., Scuseria, G.E. et al.. (2004) Gaussian 03, Gaussian, Inc., Wallingford CT.
119. Ristila, M., Matxain, J.M., Strid, A., and Eriksson, L.A. (2006) J. Phys. Chem. B, 110, 16774.
120. Lhiaubet, V., Gutierrez, F., Penaud-Berruyer, F., Amouyal, E. et al.. (2000) New J. Chem., 24, 403.
121. Monti, S., Sortino, S., DeGuidi, G., and Marconi, G. (1997) J. Chem. Soc., Faraday Trans., 93, 2269.
122. Du, L.W., Liu, X.H., Huang, W.M., and Wang, E.K. (2006) Electrochim. Acta, 51, 5754.
123. Charoo, N.A., Shamsher, A.A.A., Kohli, K., Pillai, K.K., and Rahman, Z. (2005) Chromatographia, 62, 493.
124. Martinez-Pla, J.J., Martin-Biosca, Y., Sagrado, S., Villanueva-Camanas, R.M., and Medina-Hernandez, M.J. (1047) J. Chromatogr. A, 2004, 255.
125. Sortino, S., De Guidi, G., Marconi, G., and Monti, S. (1998) Photochem. Photobiol., 67, 603.
126. de Micalizzi, Y.C., Pappano, N.B., and Debattista, N.B. (1998) Talanta, 47, 525.
127. Mehta, S.K., Bala, N., and Sharma, S. (2005) Colloids Surfaces A - Physicochem. Eng. Aspects, 268, 90.
128. de Cordova, M.L.F., Barrales, P.O., and Diaz, A.M. (1998) Anal. Chim. Acta, 369, 263.
129. Kenawi, I.M., Barsoum, B.N., and Youssef, M.A. (2005) J. Pharmaceut. Biomed. Anal., 37, 655.
130. Jimenez, M.C., Miranda, M.A., Tormos, R., and Vaya, I. (2004) Photochem. Photobiol. Sci., 3, 1038.
131. Lissi, E.A., Encinas, M.V., Lemp, E., and Rubio, M.A. (1993) Chem. Rev., 93, 699.
132. Ravanat, J.L., Berger, M., Buchko, G.W., Bénard, J.F. et al.. (1991) J. Chim. Phys. Phys.-Chim. Biol., 88, 1069.
133. Geiger, P.G., Korytowski, W., Lin, F.B., and Girotti, A.W. (1997) Free Radical Biol. Med., 23, 57.
134. Ali, H. and vanLier,J.E. (1999) Chem. Rev., 99, 2379.
135. Llano, J., Raber, J., and Eriksson, L.A. (2003) J. Photochem. Photobiol. A, 154, 235.
136. Sarabia, Z., Hernandez, D., Castell, J.V., and van Henegouwen, G. (2000) J. Photochem. Photobiol. B, 58, 32.
137. Moser, J., Hye, A., Lovell, W.W., Earl, L.K. et al. (2001) Toxicol. In Vitro, 15, 333.
138. Paul, B.J. (2004) Calicut Med. J., 2, e8.