Photochemistry of aqueous solutions of kynurenic acid and kynurenine yellow

Photochemical and Photobiological Sciences

Volumn 12, Issue 3, 2013, Pages 546-558

  Zelentsova, Ekaterina A ^a,b   Sherin, Peter S ^a,c   Snytnikova, Olga A ^a,b   Kaptein, Robert ^b,d   Vauthey, Eric ^c   Tsentalovich, Yuri P ^a,b  

^a INTERNATIONAL TOMOGRAPHY CENTER   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^c UNIVERSITY OF GENEVA   (Switzerland)

^d UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

KYNURENIC ACID; KYNURENINE YELLOW; QUINOLONE DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOLYSIS; SOLUTION AND SOLUBILITY; SPECTROFLUOROMETRY;

KYNURENIC ACID; OXIDATION-REDUCTION; PHOTOLYSIS; QUINOLONES; SOLUTIONS; SPECTROMETRY, FLUORESCENCE; WATER;

EID: 84876704510     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c2pp25357g     Document Type: Article

References (46)

1. P. S. Sherin J. Grilj Yu. P. Tsentalovich E. Vauthey Ultrafast excited-state dynamics of kynurenine-a UV filter of the human eye J. Phys. Chem. B 2009 113 4953
2. P. S. Sherin J. Grilj L. V. Kopylova V. V. Yanshole Yu. P. Tsentalovich E. Vauthey Photophysics and photochemistry of UV filter kynurenine covalently attached to amino acids and to a model protein J. Phys. Chem. B 2010 114 11909
3. R. van Heyningen Fluorescent glucoside in the human lens Nature 1971 230 393
4. A. M. Wood R. J. W. Truscott UV filters in human lenses: tryptophan catabolism Exp. Eye Res. 1993 56 317
5. A. M. Wood R. J. W. Truscott Ultraviolet filter compounds in human lenses: 3-hydroxykynurenine glucoside formation Vision Res. 1994 34 1369
6. F. Moroni Tryptophan metabolism and brain function: focus on kynurenine and other indole metabolites Eur. J. Pharmacol. 1999 375 87
7. L. M. Taylor J. A. Aquilina J. F. Jamie R. J. W. Truscott UV filter instability: consequences for the human lens Exp. Eye Res. 2002 75 165
8. Yu. 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
9. L. M. Taylor J. A. Aquilina J. F. Jamie R. J. W. Truscott Glutathione and NADH, but not ascorbate, protect lens proteins from modification by UV filters Exp. Eye Res. 2002 74 503
10. L. V. Kopylova O. A. Snytnikova E. I. Chernyak S. V. Morozov Yu. P. Tsentalovich UV filter decomposition. A study of reactions 4-(2-aminophenyl)-4- oxocrotonic acid with amino acids and antioxidants present in the human lens Exp. Eye Res. 2007 85 242
11. L. M. Bova M. H. J. Sweeney J. F. Jamie R. J. W. Truscott Major changes in human ocular UV protection with age Invest. Ophthalmol. Vis. Sci. 2001 42 200
12. H. Z. Malina X. D. Martin Xanthurenic acid derivative formation in the lens is responsible for senile cataract in humans Graefe's Arch. Clin. Exp. Ophthalmol. 1995 233 38
13. H. Z. Malina X. D. Martin Deamination of 3-hydroxykynurenine in bovine lenses: a possible mechanism of cataract formation in general Graefe's Arch. Clin. Exp. Ophthalmol. 1996 234 723
14. B. K. Zsizsik R. Hardeland Formation of kynurenic acid and xanthurenic acid from kynurenine and 3-hydroxykynurenine in the dinoflagellatae Lingulodinum polyedrum: role of a novel, oxidative pathway Comp. Biochem. Physiol., Part C: Toxicol. Pharmacol. 2002 133 383
15. T. Zarnowski R. Rejdak Z. Zagorski A. G. M. Juenemann E. Zrenner T. Kocki E. M. Urbanska W. A. Turski Content of kynurenic acid and activity of kynurenine aminotransferases in mammalian eyes Ophthalmic Res. 2004 36 124
16. P. S. Sherin N. P. Gritsan Yu. P. Tsentalovich Experimental and quantum chemical study of photochemical properties of 4-hydroxyquinoline Photochem. Photobiol. Sci. 2009 8 1550
17. V. V. Yanshole P. S. Sherin N. P. Gritsan O. A. Snytnikova V. I. Mamatyuk J. Grilj E. Vauthey R. Z. Sagdeev Y. P. Tsentalovich Photoinduced tautomeric transformations of xanthurenic acid Phys. Chem. Chem. Phys. 2010 12 9502
18. J. Mizdrak P. G. Hains R. J. W. Truscott J. F. Jamie M. J. Davies Tryptophan-derived ultraviolet filter compounds covalently bound to lens proteins are photosensitizers of oxidative damage Free Radical Biol. Med. 2008 44 1108
19. E. Okuno F. Du T. Ishikawa M. Tsujimoto M. Nakamura R. Schwarcz R. Kido Purification and characterization of kynurenine-pyruvate aminotransferase from rat kidney and brain Brain Res. 1990 534 37
20. R. Rejdak T. Zarnowski W. A. Turski E. Okuno T. Kocki Z. Zagórski K. Kohler E. Guenther E. Zrenner Presence of kynurenic acid and kynurenine aminotransferases in the inner retina NeuroReport 2001 12 3675
21. W. A. Turski M. Nakamura W. P. Todd B. K. Carpenter W. O. Whetsell R. Schwarcz Identification and quantification of kynurenic acid in human brain tissue Brain Res. 1988 454 164
22. P. Milart E. M. Urbanska W. A. Turski T. Paszkowski R. Sikorski Kynurenine aminotransferase I activity in human placenta Placenta 2001 22 259
23. T. Zarnowski R. Rejdak E. Zielinska-Rzecka E. Zrenner P. Grieb Z. Zagórski A. Junemann W. A. Turski Elevated concentrations of kynurenic acid, a tryptophan derivative, in dense nuclear cataracts Curr. Eye Res. 2007 32 27
24. V. R. Kanth K. Lavanya J. Srinivas Elevated expression of indoleamine 2,3-dioxygenase (IDO) and accumulation of kynurenic acid in the pathogenesis of STZ-induced diabetic cataract in wistar rats Curr. Eye Res. 2009 34 274
25. M. P. Pileni M. Giraud R. Santus Kynurenic acid. I. Spectroscopic properties Photochem. Photobiol. 1979 30 251
26. M. P. Pileni M. Giraud R. Santus Kynurenic acid. II. Photosensitizing properties Photochem. Photobiol. 1979 30 257
27. C. M. Krishna S. Uppuluri P. Riesz J. S. Zigler Jr. D. Balasubramanian A study of the photodynamic efficiencies of some eye lens constituents Photochem. Photobiol. 1991 54 51
28. R. Lugo-Huitrón T. Blanco-Ayala P. Ugalde-Muñiz P. Carrillo-Mora J. Pedraza-Chaverrí D. Silva-Adaya P. D. Maldonado I. Torres E. Pinzón E. Ortiz-Islas T. López E. García B. Pineda M. Torres-Ramos A. Santamaría V. Pezez-De La Cruz On the antioxidant properties of kynurenic acid: free radical scavenging activity and inhibition of oxidative stress Neurotoxicol. Teratol. 2011 33 538
29. R. Rusakowicz A. C. Testa 2-Aminopyridine as a standard for low-wavelength spectrofluorimetry J. Phys. Chem. 1968 72 2680
30. B. Gelernt A. Findeisen A. Stein J. A. Poole Absolute measurement of the quantum yield of quinine bisulphate J. Chem. Soc., Faraday Trans. 2 1974 70 939
31. J. R. Calvert and J. N. Pitts, Photochemistry, John Willey, New-York, 1969
32. A. Morandeira L. Engeli E. Vauthey Ultrafast charge recombination of photogenerated ion pairs to an electronic excited state J. Phys. Chem. A 2002 106 4833
33. G. Duvanel J. Grilj H. Chaumeil P. Jacques E. Vauthey Ultrafast excited-state dynamics of a series of zwitterionic pyridinium phenoxides with increasing sterical hindering Photochem. Photobiol. Sci. 2010 9 908 915
34. G. Duvanel N. Banerji E. Vauthey Excited-state dynamics of donoracceptor bridged systems containing a boron-dipyrromethene chromophore: interplay between charge separation and reorientational motion J. Phys. Chem. A 2007 111 5361
35. N. Banerji G. Duvanel A. Perez-Velasco S. Maity N. Sakai S. Matile E. Vauthey Excited-state dynamics of hybrid multichromophoric systems: toward an excitation wavelength control of the charge separation pathways J. Phys. Chem. A 2009 113 8202
36. Yu. P. Tsentalovich P. S. Sherin L. V. Kopylova I. V. Cherepanov J. Grilj E. Vauthey Photochemical properties of UV filter molecules of the human eye Invest. Ophthalmol. Visual Sci. 2011 52 7687
37. Yu. P. Tsentalovich O. A. Snytnikova P. S. Sherin M. D. E. Forbes Photochemistry of kynurenine, a tryptophan metabolite: properties of the triplet state J. Phys. Chem. A 2005 109 3565
38. S. F. Mason The tautomerism of N-heteroaromatic hydroxycompounds. Part I. Infrared spectra J. Chem. Soc. 1957 4874
39. S. F. Mason The tautomerism of N-heteroaromatic hydroxycompounds. Part II. Ultraviolet spectra J. Chem. Soc. 1957 5010
40. S. F. Mason The tautomerism of N-heteroaromatic hydroxycompounds. Part III. Ionization constants J. Chem. Soc. 1958 674
41. S. K. Lower M. A. El-Sayed The triplet state and molecular electronic processes in organic molecules Chem. Rev. 1966 66 199
42. M. A. El-Sayed R. G. Brewer Polarization of the π → π and π → n phosphorescence spectra of N-heterocyclics J. Chem. Phys. 1963 39 1623
43. E. C. Lim J. M. H. Yu Vibronic interaction between (n, π) and (π, π) states and spin - orbit coupling in nitrogen heterocyclic J. Chem. Phys. 1966 45 4742
44. K. Schmidt S. Brovelli V. Coropceanu D. Beljonne J. Cornil C. Bazzini T. Caronna R. Tubino F. Meinardi Z. Shuai J. L. Brédas Intersystem crossing processes in nonplanar aromatic heterocyclic molecules J. Phys. Chem. A 2007 111 10490
45. H. Z. Malina Xanthurenic acid provokes formation of unfolded proteins in endoplasmic reticulum of the lens epithelial cells Biochem. Biophys. Res. Commun. 1999 265 600
46. J. E. Roberts E. L. Finley S. A. Patat K. L. Schey Photo-oxidation of lens protein with xanthurenic acid: a putative chromophore for cataractogenesis Photochem. Photobiol. 2001 74 740