Role of aromatic amino acid tryptophan UVA-photoproducts in the determination of drug photosensitization mechanism: A comparison between methylene blue and naproxen

Photochemical and Photobiological Sciences

Volumn 8, Issue 10, 2009, Pages 1467-1475

  Catalfo, Alfio ^a   Bracchitta, Giuseppina ^a   De Guidi, Guido ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

METHYLENE BLUE; NAPROXEN; REACTIVE OXYGEN METABOLITE; TRYPTOPHAN;

ARTICLE; CONTROLLED STUDY; DRUG TARGETING; PHOTODEGRADATION; PHOTOOXIDATION; PHOTOSENSITIZATION; PRIORITY JOURNAL; QUANTUM YIELD; ULTRAVIOLET A RADIATION;

EID: 70349786936     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b9pp00028c     Document Type: Article

References (58)

1. A. Hideki, I. Kenji, H. Junichi and I. Hisami, Methylene blue photosensitization: Mechanisms of virus inactivation and its clinical application. Recent Research Developments in Photochemistry & Photobiology, Transworld Research Network, Trivandrum, India, 2001
2. Y. Usui M. Tsukada H. Nakamura Kinetic studies of photosensitized oxygenation by singlet oxygen in aqueous micellar solutions Bull. Chem. Soc. Jpn. 1978 51 379 384
3. - from excited thionine and methylene blue in aqueous solutions J. Photochem. 1983 23 233 239
4. L. Zhi-Ren A. M. Wilkie M. J. Clemens C. W. J. Smith Detection of double-stranded RNA-protein interactions by methylene blue-mediated photo-crosslinking RNA 1996 2 611 621
5. E. Silva C. De Landea A. M. Edwards E. Lissi Lysozyme photo-oxidation by singlet oxygen: properties of the partially inactivated enzyme J. Photochem. Photobiol., B 2000 55 196 200
6. A. Michaeli J. Feitelson Reactivity of singlet oxygen toward proteins: the effect of structure in basic pancreatic trypsin inhibitor and in ribonuclease A Photochem. Photobiol. 1997 65 309 315
7. S. G. Bertolotti N. A. Garcia G. A. Argüello Effect of the peptide bond on the singlet molecular oxygen-mediated photo-oxidation of tyrosine and tryptophan dipeptides J. Photochem. Photobiol., B 1991 10 57 70
8. G. T. Wondrak M. K. Jacobson E. L. Jacobson Endogenous UVA-photosensitizers: mediators of skin photodamage and novel targets for skin photoprotection Photochem. Photobiol. Sci. 2006 5 215 237
9. N. R. Parker J. F. Jamie M. J. Davies R. J. W. Truscott Protein-bound kynurenine is a photosensitizer of oxidative damage Free Radical Biol. Med. 2004 37 1479 1489
10. U. Khan T. Wilson Reactive oxygen species as cellular messengers Chem. Biol. 1995 2 437 445
11. R. M. Danziger K. H. Bar-Eli K. Weiss The laser photolysis of methylene blue J. Phys. Chem. 1967 71 2633 2640
12. J. G. Lombardino, Nonsteroidal Antiinflammatory Drugs, Wiley, New York, 1985
13. G. Condorelli L. L. Costanzo G. De Guidi S. Giuffrida P. Miano S. Sortino A. Velardita Photosensitization induced by non-steroidal antiinflammatory drugs: An overview of molecular mechanisms in biological systems EPA newsletter 1996 58 60 77
14. F. Boscá M. A. Miranda Photosensitizing drugs containing the benzophenone chromophore J. Photochem. Photobiol., B 1998 43 1 26
15. M. A. Miranda, J. V. Castell and M. J. Gòmez-Lechòn, Phototoxicity of drugs. In vitro methods in pharmaceutical research, Academic Press, San Diego, 1997
16. 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. 1989 3 223 235
17. F. Boscà M. L. Marin M. A. Miranda Photoreactivity of the nonsteroidal anti-inflammatory 2-arylpropionic acids with photosensitizing side effects Photochem. Photobiol. 2001 74 637 655
18. R. V. Bensasson, E. J. Land and T. G. Truscott, Exicited States and Free Radicals in Biology and Medicine: Contributions from Flash Photolysis and Pulse Radiolysis, Oxford University Press, New York, 1993
19. D. Creed The photophysics and photochemistry of the near-uv absorbing amino acids-I. Tryptophan, and its simple derivatives Photochem. Photobiol. 1984 39 537 562
20. E. Silva J. Godoy Riboflavin sensitized photooxidation of tyrosine Int. J. Vitamin. Nutr. Res. 1994 64 253 256
21. Y. P. Tsentalovich O. A. Snytnikova M. D. E. Forbes E. I. Chernyak S. V. Morozov Photochemical and thermal reactivity of kynurenine Exp. Eye Res. 2006 83 1439 1445
22. J. P. McCormick J. R. Fischer J. P. Pachlatko A. Eisenstark Characterization of a cell-lethal product from the photooxidation of tryptophan: hydrogen peroxide Science 1976 191 468 469
23. V. Vorobey S. V. Pinchuk Formation and photosensitizing activity of protein tryptophaniles photochemical destruction products in isolated erythrocyte membranes Biofizika 1995 40 342 346
24. J. M. Dyer S. D. Bringans W. G. Bryson Characterisation of photo-oxidation products within photoyellowed wool proteins: tryptophan and tyrosine derived chromophores Photochem. Photobiol. Sci. 2006 5 698 706
25. H. Robotka J. Toldi L. Vcsei L- kynurenine: metabolism and mechanism of neuroprotection Future Neurol. 2008 3 169 188
26. P. Walrant R. Santus N-Formylkynurenine, a tryptophan photooxidation product, as a photodynamic sensitizer Photochem. Photobiol. 1974 19 411 417
27. P. Walrant R. Santus L. I. Grossweiner Photosensitizing properties of N-formylkynurenine Photochem. Photobiol. 1975 22 63 65
28. M. Spodheim-Maurizot M. Charlier C. Helene Photochemical modifications of lac repressor: effect of effectors binding on tryptophan photooxidation Photochem. Photobiol. 1985 42 353 359
29. G. De Guidi R. Chillemi L. L. Costanzo S. Giuffrida G. Condorelli Molecular mechanism of drug photosensitization. 4. Photohemolysis sensitized by carprofen J. Photochem. Photobiol., B 1993 17 239 246
30. D. Tang P. H. Santschi Sensitive determination of dissolved sulfide in estuarine water by solid-phase extraction and high-performance liquid chromatography of methylene blue J. Chromatogr., A 2000 883 305 309
31. O. Kurnasov L. Jablonski B. Polanuyer P. Dorrestein T. Begley A. Osterman Aerobic tryptophan degradation pathway in bacteria: novel kynurenine formamidase FEMS Microbiol. Lett. 2003 227 219 227
32. M. Valero M. P. Lopez-Cornejo S. M. B. Costa Effect of the structure and concentration of cyclodextrins in the quenching process of naproxen J. Photochem. Photobiol., A 2007 188 5 11
33. A. Blàzquez-Castro J. C. Stockert F. Sanz-Rodrìguez A. Zamarròn A. Juarranz Differential photodynamic response of cultured cells to methylene blueand toluidine blue: role of dark redox processes Photochem. Photobiol. Sci. 2009 8 371 376
34. L. Grajcar N. Ivanoff J. F. Delouis J. Faure Photosensitization of phenylhydrazone derivatives by methylene blue and xanthene dyes J. Chim. Phys. Phys.-Chim. Biol. 1984 81 33 38
35. A. Pirie Formation of N-formylkynurenine in proteins from lens and other sources by exposure to sunlight Biochem. J. 1971 125 203 208
36. M. Wood R. J. W. Truscott Ultraviolet filter coupounds in human lenses: 3-hydroxykynurenine glycoside formation Vision Res. 1994 34 1369 1374
37. Balzer R. Hardeland Action of kynuramine in a dinoflagellate: stimulation of bioluminescence in gonyaulax polyedra Comp. Biochem. Physiol., Part C: Comp. Pharmacol. 1989 94 129 132 (Pubitemid 20047144)
38. W. Wang B. Qiu X. Xu L. Zhang G. Chen Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection Electrophoresis 2005 26 903 910
39. M. Valero C. Carrello Effect of binary and ternary polyethyleneglycol and/or b-cyclodextrin complexes on the photochemical and photosensitizing properties of Naproxen J. Photochem. Photobiol., B 2004 74 151 160 (Pubitemid 38667457)
40. H. Salminen M. Heinonen Plant phenolics affect oxidation of tryptophan J. Agric. Food Chem. 2008 56 7472 7481
41. K. Schafer D. Goddinger H. Hocker Photodegradation of tryptophan in wool J. Soc. Dyers Colourists 1997 113 350 355
42. N. I. Churakova N. A. Kravchenko E. P. Serebryakov E. D. Kaverzneva Nature of tryptophan photooxidation products in lysozyme in the presence of methylene blue Biokhimiya 1976 41 822 826
43. J. Slawinski M. Elbanowski D. Slawinska Spectral characteristics and mechanism of chemiluminescence from tryptophan solutions induced by UV-irradiation Photochem. Photobiol. 1980 32 253 260
44. D.V. Bent E. Hayon Excited state chemistry of aromatic amino acids and related peptides. III. Tryptophan J. Am. Chem. Soc. 1975 97 2612 2619
45. J. Cygler G. R. Freeman Effects of solvent structure on electron reactivity and radiolysis yields: 2-propanol/water mixed solvents Can. J. Chem. 1984 62 1265 1270
46. H. J. Bielski and G. G. Shiue, Oxygen Free Radicals and Tissue Damage, Ciba Foundation Symposium 65 (New Series), Excerpta Medica, New York, 1979
47. G. Navon G. Stein The reactivity of atomic hydrogen with cysteine, cystine, tryptophan and tyrosine in aqueous solution Isr. J. Chem. 1964 2 151 154
48. G. V. Buxton C. L. Greenstock W. P. Helman A. B. J. Ross Critical review of rate constant for reactions with hydrated electrons, hydrogen atoms and hydroxyl radicals (OH/O) in aqueous solutions Phys. Chem. Ref. Data 1988 17 513 886
49. T. Simat K. Meyer H. Steinhart Synthesis and analysis of oxidation and carbonyl condensation compounds of tryptophan J. Chromatogr., A 1994 661 93 99
50. T. V. Birich N. I. Pozniak I. M. Byteva Z. A. Luka I. I. Ugolev Role of singlet oxygen in formation of senile cataract Oftal'mol. Zh. 1985 7 388 391
51. F. Takeuchi R. Tsubouchi S. Izuta Y. Shibata Kynurenine metabolism and xanthurenic acid formation in vitamin B6-deficient rat after tryptophan injection J. Nutr. Sci. Vitaminol. 1989 35 111 122
52. T. J. Simat H. Steinhart Oxidation of free tryptophan and tryptophan residues in peptides and proteins J. Agric. Food Chem. 1998 46 490 498
53. P. G. Hainsa L. Gaoa R. J. W. Truscott The photosensitiser xanthurenic acid is not present in normal human lenses Exp. Eye Res. 2003 77 547 553
54. S. Liang J. Hong-Fang Theorical exploration of the photosensitive properties of xanturenic acid, a tryptophan metabolite in cataractous human lenses Dyes Pigm. 2008 77 646 649
55. S. Gurnani M. Arifuddin K. T. Augusti Effect of visible light on amino acids. I. Tryptophan Photochem. Photobiol. 1966 5 495 505
56. U. Rannug A. Rannug U. Sjöberg H. Li R. Westerholm J. Bergman Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands Chem. Biol. 1995 2 841 845
57. M. Öberg L. Bergander H. Håkansson U. Rannug A. Rannug Identification of the Tryptophan Photoproduct 6-Formylindolo[3,2-b]carbazole, in Cell Culture Medium, as a Factor That Controls the Background Aryl Hydrocarbon Receptor Activity Toxicol. Sci. 2005 85 935 943
58. M. Sun S. Zigman Isolation and identification of tryptophan photoproducts from aqueous solutions of tryptophan exposed to near-UV light Photochem. Photobiol. 1979 29 893 897