Photoinduced protein modifications by methylene blue and naproxen

Photochemical and Photobiological Sciences

Volumn 11, Issue 12, 2012, Pages 1886-1896

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

^a UNIVERSITY OF CATANIA   (Italy)

^b Consorzio Interuniversitario Chimica per l'Ambiente ^*  (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BOVINE SERUM ALBUMIN; METHYLENE BLUE; NAPROXEN; PHOTOSENSITIZING AGENT; SERUM ALBUMIN; SINGLET OXYGEN; TRYPTOPHAN;

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; HUMAN; METABOLISM; PHOTOLYSIS; QUANTUM THEORY; SPECTROFLUOROMETRY; ULTRAVIOLET RADIATION;

ANIMALS; CATTLE; HUMANS; METHYLENE BLUE; NAPROXEN; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; QUANTUM THEORY; SERUM ALBUMIN; SERUM ALBUMIN, BOVINE; SINGLET OXYGEN; SPECTROMETRY, FLUORESCENCE; TRYPTOPHAN; ULTRAVIOLET RAYS;

EID: 84869987790     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c2pp25067e     Document Type: Article

References (59)

1. B. A. Kerwin R. L. Remmele Jr. Protect from light: photodegradation and protein biologics J. Pharm. Sci. 2007 96 1468 1479
2. A. Kawada K. Hatanaka H. Gomi I. Matsuo In vitro phototoxicity of new quinolones: production of active oxygen species and photosensitized lipid peroxidation Photodermatol., Photoimmunol. Photomed. 1999 15 226 230
3. M. Mauget-Fa M. Quaranta N. Francoz D. BenEzra Incidental retinal phototoxicity associated with ingestion of photosensitizing drugs Graefe's Arch. Clin. Exp. Ophthalmol. 2001 239 501 508
4. 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
5. M. A. Miranda J. V. Castell D. Hernandez M. J. Gomez-Lechon F. Bosca I. M. Morera Z. Sarabia Drug-photosensitized protein modification: identification of the reactive sites and elucidation of the reaction mechanisms with tiaprofenic acid/albumin as model system Chem. Res. Toxicol. 1998 11 172 177
6. A. Hideki, I. Kenji, H. Junichi and I. Hisami, Methylene blue photosensitization: mechanisms of virus inactivation and its clinical application, in Recent Research Developments in Photochemistry and Photobiology, ed. S. G. Pandalai, Transworld Research Network, Trivandrum, India, 2001, vol. 5, pp. 163-173
7. 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
8. - from excited thionine and methylene blue in aqueous solutions J. Photochem. 1983 23 233 239
9. 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
10. 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
11. 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
12. 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
13. 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
14. U. Khan T. Wilson Reactive oxygen species as cellular messengers Chem. Biol. 1995 2 437 445
15. R. M. Danziger K. H. Bar-Eli K. Weiss The laser photolysis of methylene blue J. Phys. Chem. 1967 71 2633 2640
16. J. G. Lombardino, Nonsteroidal Antiinflammatory Drugs, Wiley, New York, 1985
17. 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
18. F. Boscá M. A. Miranda Photosensitizing drugs containing the benzophenone chromophore J. Photochem. Photobiol., B 1998 43 120 123
19. 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
20. C. J. Le Coz A. Bottlaender J.-N. Scrivener F. Santinelli B. J. Cribier E. Heid E. M. Grosshans Photocontact dermatitis from ketoprofen and tiaprofenic acid: cross-reactivity study in 12 consecutive patients Contact Dermatitis 1998 38 245 252
21. J. V. Castell M. J. Gomez-Lechon C. Grassa L. A. Martinez M. A. Miranda P. Tarrega Involvement of drug-derived peroxides in the phototoxicity of naproxen and tiaprofenic acid Photochem. Photobiol. 1993 57 486 490
22. M. A. Miranda I. Morera F. Vargas M. J. Gomez-Lechon J. V. Castell In vitro assessment of the phototoxicity of anti-inflammatory 2-arylpropionic acids Toxicol. in Vitro 1991 5 451 455
23. 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 1989 3 223 235
24. 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
25. A. Catalfo G. Bracchitta G. De Guidi Role of aromatic amino acid tryptophan UVA-photoproducts in the determination of drug photosensitization mechanism: a comparison between methylene blue and naproxen Photochem. Photobiol. Sci. 2009 8 1467 1475
26. 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
27. T. Banerjee S. K. Singh N. Kishore Binding of naproxen and amitriptyline to bovine serum albumin: biophysical aspects J. Phys. Chem. B 2006 110 24147 24156
28. M. Maruthamuthu G. Selvakumar Selective quenching of tryptophanyl fluorescence in bovine serum albumin by the iodide ion J. Chem. Soc. 1995 107 79 86
29. T. Peters Jr. Serum albumin Adv. Protein Chem. 1985 37 161 245
30. R. G. Eckenhoff J. S. Johansson Molecular interactions between inhaled anesthetics and proteins Pharmacol. Rev. 1997 49 343 367
31. Y. J. Hu Y. Liu X. S. Shen X. Y. Fang S. S. J. Qu Studies on the interaction between 1-hexylcarbamoyl-5-fluorouracil and bovine serum albumin J. Mol. Struct. 2005 738 143 147
32. Y. Ping-gui L. Jun-feng S. Zhi-cai Y. Qing-sen Study on the interaction between methylene blue and bovine serum albumin by fluorescence spectroscopy Guangpuxue Yu Guangpu Fenxi 2001 21 826 828
33. D. C. Carter X. M. He Structure of human serum albumin Science 1990 249 302 303
34. P. Miskovsky D. Jancura S. Sanchez-Cortes E. Kocisova L. Chinsky Antiretrovirally active drug hypericin binds the IIA subdomain of human serum albumin: resonance Raman and surface-enhanced Raman spectroscopy study J. Am. Chem. Soc. 1998 120 6374 6379
35. Y.-J. Hu Y. Liu R.-M. Zhao J.-X. Dong S.-S. Qu Spectroscopic studies on the interaction between methylene blue and bovine serum albumin J. Photochem. Photobiol., A 2006 179 324 329
36. Y.-J. Hu W. Li Y. Liu J.-X. Dong S.-S. Qu Short communication Fluorometric investigation of the interaction between methylene blue and human serum albumin J. Pharm. Biomed. Anal. 2005 39 740 745
37. S. Wei L. Zhao X. Cheng J.-M. Lin Determination of naproxen with flow injection chemiluminescence of Ru(bpy)32+-PbO2 system and its application for the binding study of naproxen to protein Anal. Chim. Acta 2005 545 65 73
38. M. M. Rahman M. H. Rahman N. N. Rahaman Competitive binding of Ibuprofen and Naproxen to serum bovine albumin: modified form of drug-drig displacement interaction at the binding site Pak. J. Pharm. Sci. 2005 18 43 47
39. C. B. Murphy Y. Zhang T. Troxler V. Ferry J. J. Martin W. E. Jones Probing förster and dexter energy-transfer mechanisms in fluorescent conjugated polymer chemosensors J. Phys. Chem. B 2004 108 1537 1543
40. 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
41. K. Schafer D. Goddinger H. Hocker Photodegradation of tryptophan in wool J. Soc. Dyers Colour. 1997 113 350 355
42. 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
43. 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
44. M. Wood R. J. W. Truscott Ultraviolet filter coupounds in human lenses: 3-hydroxykynurenine glycoside formation Virus Res. 1994 34 1369 1374
45. I. Balzer R. Hardeland Action of kynuramine in a dinoflagellate: stimulation of bioluminescence in gonyaulax polyedra Comp. Biochem. Physiol., C 1989 94 129 132
46. 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 2004 25 903 910
47. P. Walrant R. Santus N-Formylkynurenine, a tryptophan photooxidation product, as a photodynamic sensitizer Photochem. Photobiol. 1974 19 411 417
48. A. Pirie Formation of N-formylkynurenine in proteins from lens and other sources by exposure to sunlight Biochem. J. 1971 125 203 208
49. H. Salminen M. Heinonen Plant phenolics affect oxidation of tryptophan J. Agric. Food Chem. 2008 56 7472 7481
50. g) J. Am. Chem. Soc. 1983 105 3423 3430
51. E. Skovsen J. W. Snyder J. D. C. Lambert P. R. Ogilby Lifetime and diffusion of singlet oxygen in a cell J. Phys. Chem. B 2005 109 8570 8573
52. J. Davila A. Harriman Photoreactions of macrocyclic dyes bound to human serum albumin Photochem. Photobiol. 1990 51 9 19
53. E. Reddi C. R. Lambert G. Jori M. A. Rodgers Photokinetic and photophysical measurements of the sensitized photooxidation of the tritptophyl residue in N-acetyl tryphophanasmide and in human serum albumine Photochem. Photobiol. 1987 45 345 351
54. A. Michaeli J. Feitelson Reactivity of singlet oxygen toward amino acids and peptides Photochem. Photobiol. 1994 59 284 289
55. W. M. Sharman J. E. van Lier C. M. Allen Targeted photodynamic therapy via receptor mediated delivery systems Adv. Drug Delivery Rev. 2004 56 53 76
56. U. Kragh-Hansen Structure and ligand binding properties of human serum albumin Dan. Med. Bull. 1990 37 57 84
57. A. Siemiarczuk C. E. Petersen C.-E. Ha J. Yang N. V. Bhagavan Analysis of tryptophan fluorescence lifetimes in a series of human serum albumin mutants with substitutions in subdomain 2A Cell Biochem. Biophys. 2004 40 115 122
58. E. Alarcon A. M. Edwards A. Aspee F. E. Moran C. D. Borsarelli E. A. Lissi D. Gonzalez-Nilo H. Poblete J. C. Scaiano Photophysics and photochemistry of dyes bound to human serum albumin are determined by the dye localization Photochem. Photobiol. Sci. 2010 9 93 102
59. V. Lhiaubet-Vallet Z. Sarabia F. Boscá M. A. Miranda Human serum albumin-mediated stereodifferentiation in the triplet state behavior of (S)- and (R)-Carprofen J. Am. Chem. Soc. 2004 126 9538 9539