The NSAIDs indomethacin and diflunisal as scavengers of photogenerated reactive oxygen species

Photochemistry and Photobiology

Volumn 89, Issue 6, 2013, Pages 1463-1470

  Purpora, Rebeca ^a   Massad, Walter ^b   Ferrari, Gabriela ^c   Reynoso, Eugenia ^b   Criado, Susana ^b   Miskoski, Sandra ^b   Pajares, Adriana ^a   García, Norman A ^b  

^a UNIVERSIDAD NACIONAL DE LA PATAGONIA SAN JUAN BOSCO   (Argentina)

^b DEPARTAMENTO DE QUÍMICA   (Argentina)

^c UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

DIFLUNISAL; INDOMETACIN; NONSTEROID ANTIINFLAMMATORY AGENT; REACTIVE OXYGEN METABOLITE;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DIFLUNISAL; INDOMETHACIN; REACTIVE OXYGEN SPECIES;

EID: 84887405520     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/php.12114     Document Type: Article

References (45)

1. McGeer, E. G., and, P. L. McGeer, (2003) Inflammatory processes in Alzheimer disease. Prog. Neuro-Psicoph. 27, 741-749.
2. Dumont, M., and, M. Flint Beal, (2011) Neuroprotective strategies involving ROS in Alzheimer disease Free Rad. Biol. Med. 51, 1014-1026.
3. Lovell, M. A., and, W. R. Markesbery, (2007) Oxidative damage in mild cognitive impairment and early Alzheimer's disease. J. Neurosci. Res. 85, 3036-3040.
4. Markesbery, W. R., and, M. A. Lovell, (2007) Damage to lipids, proteins, DNA, and RNA in mild cognitive impairment. Arch. Neurol. 64, 954-956.
5. Choi, W., Y. J. Lee, J. T. Hong, and, H. J. Lee, (2012) Antioxidant properties of natural polyphenols and therapeutic to potentials for Alzheimer disease. Brain Res. Bull. 87, 2-3.
6. Esposito, E., V. Di Matteo, A. Benigno, M. Pierucci, G. Crescimanno, and, G. Di Giovanni, (2007) Non-steroidal anti-inflammatory drugs in Parkinson's disease Exp. Neurol. 205, 295-312.
7. Gund, P., and, N. P. Jensen, (1983) Nonsteroidal antiinflammatory and antiarthritic drugs. Med. Chem. 119, 285-327.
8. Ganguly, K., P. Kundu, A. Banerjee, R. J. Reiter, and, S. Swarnakar, (2006) Hydrogen peroxide-mediated downregulation of matrix metalloprotease-2 in indomethacin-induced acute gastric ulceration is blocked by melatonin and other antioxidants Free Rad. Biol. Med. 41, 911-925.
9. Yadav, S. K., B. Adhikary, S. K. Bandyopadhyay, and, S. Chattopadhyay, (2013) Inhibition of TNF-α, and NF-κB and JNK pathways accounts for the prophylactic action of the natural phenolic, allylpyrocatechol agains t indomethacin gastropathy. Biochim. Biophys. Acta 1830, 3776-3786.
10. Takeiuchi, K., K. Ueshima, Y. Hironaka, Y. Fuyioka, J. Matsumoto, and, S. Okabe, (1991) Oxyen free radicals and lipid peroxidation in the pathogenesis of gastric mucosal lesions induced by indomethacin in rats. Digestion 49, 175-184.
11. Odabasoglu, F., A. Cakir, H. Suleyman, A. Aslan, Y. Bayir, M. Halici, and, C. Kazaz, (2006) Gastroprotective and antioxidant effects of usnic acid on indomethacin-induced gastric ulcer in rats. J. Ethnopharm. 103, 59-65.
12. Evanson, N. K., (2007) Diflunisal. xPharm: The Comprehensive Pharmacology Reference 1-5
13. Heelis, P. F., (1982) The photophysical and photochemical properties of flavins (isoalloxazines). Chem. Soc. Rev. 11, 15-39.
14. Heelis, P. F., (1991) Chemistry and Biochemistry of Flavoenzymes. F. Muller, Vol. 1 Boca Ratõn, FL.
15. Fent, K., A. Weston, and, D. Caminada, (2006) Ecotoxicology of human pharmaceuticals. Aquat. Toxicol. 76, 122-159.
16. Weast, R. C., (1963) Handbook of Chemistry and Physics, 55th edn. CRC Press, USA.
17. Nokhodchi, A., Y. Javadzadeh, M. R. Siahi-Shadbad, and, M. Barzegar-Jalali, (2005) The effect of type and concentration of vehicles on the dissolution rate of a poorly soluble drug (Indomethacin) from liquisolid compacts. J. Pharm. Pharmaceut. Sci. 8, 18-25.
18. T. L. Lemke, and, D. A. Williams, (2008) Foye';s principles of medicinal chemistry. In Chapter 31 Nonsteroidal Anti-inflammatory Drugs. Seventh Edition (Edited by, R. Borne, M. Levi, and, N. Wilson,), pp. 987-1044. Lippincott Williams & Wilkins (LWW), Philadelphia.
19. Scully, F. E., and, J. Hoingé, (1987) Rate constants for the reaction of singlet oxygen with phenols and other compounds in water. Chemosphere 16, 694-699.
20. Criado, S., A. Pajares, J. Gianotti, G. Stettler, J. P. Escalada, S. Bertolotti, F. Amat-Guerri, and, N. A. García, (2003) Kinetic study of the riboflavin-sensitised photooxygenation of two hydroxyquinolines of biological interest. J. Photochem. Photobiol. B: Biol. 71, 19-25.
21. Neumann, M., and, N. A. García, (1992) Kinetics and mechanism of the light-induced deterioration of lemon oil. J. Agric. Food Chem. 40, 957-960.
22. Krishna, C. M., S. Uppuluri, P. Riesz, J. S. Zigler, and, D. Balasubramanian, (1991) A study of the photodynamic efficiencies of some eye lens constituents. Photochem. Photobiol. 54, 51-58.
23. Lu, C., G. Bucher, and, W. Sander, (2004) Photoinduced interaction between oxidized and reduced lipoic acid and riboflavin (Vitamin B2). Phys. Chem. Phys. 5, 47-56.
24. Kanofsky, J. R., (1991) Singlet oxygen production from the reaction of superoxide ion an aprotic solvents: implications for hydrophobic biochemistry. Free Rad. Res. Commun. 87, 12-13.
25. Land, E. J., and, A. J. Swallow, (1969) One-electron reactions in biochemical systems as studied by pulse radiolysis, II Riboflavin. Biochemistry 8, 2117-2125.
26. 2) photosensitised oxidation of 2′-deoxy-guanosine-5′-monophosphate (dGMP) in aqueous solution: A transient intermediates study. Phys. Chem. Phys. 2, 329-334.
27. Lu, C. Y., W. F. Wang, W. Z. Lin, Z. H. Han, S. D. Yao, and, N. Y. Lin, (1999) Generation and photosensitisation properties of the oxidized radicals of riboflavin: A laser flash photolysis study. J. Photochem. Photobiol. B: Biol. 52, 111-116.
28. Redmond, R. W., and, J. N. Gamlin, (1999) A compilation of singlet oxygen yields from biologically relevant molecules. Photochem. Photobiol. 70, 391-475.
29. Criado, S., and, N. A. García, (2004) Vitamin B 2 -sensitised photooxidation of the ophthalmic drugs Timolol and Pindolol: Kinetics and mechanism. Redox Rep. 9, 291-297.
30. Pajares, A., J. Gianotti, G. Stettler, S. Bertolotti, S. Criado, A. Posadaz, F. Amat-Guerri, and, N. A. García, (2001) Modelling the natural photodegradation of water contaminants: A kinetic study on the light-induced aerobic interactions between riboflavin and 4-hydroxypyridine. J. Photochem. Photobiol. A: Chem. 139, 199-204.
31. Escalada, J. P., A. Pajares, J. Gianotti, W. Massad, S. Bertolotti, F. Amat-Guerri, and, N. A. García, (2006) Dye-sensitized photodegradation of the fungicide carbendazim and related benzimidazoles. Chemosphere 65, 237-244.
32. Silva, E., L. Herrera, A. M. Edwards, J. De La Fuente, and, E. Lissi, (2005) Enhancement of riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by uronic acid. Photochem. Photobiol. 81, 206-211.
33. Silva, E., A. M. Edwards, and, D. Pacheco, (1999) Visible light-induced photooxidation of glucose sensitized by riboflavin. J. Nutr. Biochem. 10, 181-185.
34. Wilkinson, F., W. P. Helman, and, A. B. Ross, (1993) Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 22, 133-262.
35. Lambert, C. R., and, I. E. Kochevar, (1996) Does rose bengal generate superoxide anion? J. Am. Chem. Soc. 118, 3297-3298.
36. Posadaz, A., A. Biasutti, C. Casale, J. Sanz, F. Amat-Guerri, and, N. A. García, (2004) Rose bengal-sensitized photooxidation of the dipeptides Trp-Phe, Trp-Tyr and Trp-Trp. kinetics, mechanism and photoproducts. Photochem. Photobiol. 80, 132-138.
37. Wilkinson, F., W. P. Helman, and, A. Ross, (1995) Rate constants for the decay of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data 24, 663-1021.
38. Garcia, J., and, E. Silva, (1997) Flavin-sensitized photooxidation of amino acids present in a parenteral nutrition infusate: Protection by ascorbic acid. J. Nutr. Biochem. 8, 341-5.
39. Rehm, D., and, A. Weller, (1970) Kinetics of fluorescent quenching by electron transfer and H-atom transfer. Israel J. Chem. 8, 259-271.
40. Porcal, G., S. G. Bertolotti, C. M. Previtali, and, M. V. Encinas, (2003) Electron transfer quenching of singlet and triplet excited states of flavins and lumichrome by aromatic and aliphatic electron donors. Phys. Chem. 5, 4123-4128.
41. Sawyer, D. T., A. Sobkowiak, and, J. L. Jr Roberts, (1995) Electrochemistry for Chemists, 2nd edn, p. 192. Wiley, NY.
42. Saỹn, F., and, S. Kõr, (2001) Analysis of diflunisal by electrochemical methods. J. Pharm. Biomed. Anal. 25, 153-163.
43. Tabeshnia, M., H. Heli, A. Jabbari, and, A. A. Moosavi-Movahedi, (2010) Electro-oxidation of some non-steroidal anti-inflammatory drugs on an alumina. nanoparticle-modified glassy carbon electrode. Turk. J. Chem. 34, 35-45.
44. Koizumi, M., S. Kato, N. Mataga, T. Matsuura, and, I. Isui, (1978) Photosensitized Reactions. Kagakudogin Publishing Co., Kyoto, Japan.
45. Benassi, C. A., E. Scoffone, G. Galiazzo, and, G. Jori, (1967) Proflavin-sensitized photooxidation of tryptophan and related peptides. Photochem. Photobiol. 28, 857-862.