메뉴 건너뛰기




Volumn 114, Issue 36, 2010, Pages 11909-11919

Photophysics and photochemistry of the UV filter kynurenine covalently attached to amino acids and to a model protein

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ENZYMES; FLUORESCENCE; ORGANIC ACIDS; PHOSPHATASES; QUANTUM YIELD;

EID: 77956539375     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp104485k     Document Type: Article
Times cited : (27)

References (48)
  • 1
    • 0015216149 scopus 로고
    • Fluorescent Glucoside in the Human Lens
    • van Heyningen, R. Fluorescent Glucoside in the Human Lens Nature 1971, 230, 393-394
    • (1971) Nature , vol.230 , pp. 393-394
    • Van Heyningen, R.1
  • 3
    • 0027453250 scopus 로고
    • UV Filters in Human Lenses: Tryptophan Catabolism
    • Wood, A. M.; Truscott, R. J. W. UV Filters in Human Lenses: Tryptophan Catabolism Exp. Eye Res. 1993, 56, 317-325
    • (1993) Exp. Eye Res. , vol.56 , pp. 317-325
    • Wood, A.M.1    Truscott, R.J.W.2
  • 5
    • 0025410113 scopus 로고
    • Time Resolved Spectroscopic Studies of the Intact Human Lenses
    • Dillon, J.; Atherton, S. J. Time Resolved Spectroscopic Studies of the Intact Human Lenses Photochem. Photobiol. 1990, 51, 465-468
    • (1990) Photochem. Photobiol. , vol.51 , pp. 465-468
    • Dillon, J.1    Atherton, S.J.2
  • 7
    • 0030040917 scopus 로고    scopus 로고
    • Free Radical Reactions Photosensitized by the Human Lens Component, Kynurenine: an ESR and Spin Trapping Investigation
    • Reszka, K. J.; Bilski, P.; Chignell, C. F.; Dillon, J. Free Radical Reactions Photosensitized by the Human Lens Component, Kynurenine: an ESR and Spin Trapping Investigation Free Radical Biol. Med. 1996, 20, 23-34
    • (1996) Free Radical Biol. Med. , vol.20 , pp. 23-34
    • Reszka, K.J.1    Bilski, P.2    Chignell, C.F.3    Dillon, J.4
  • 8
    • 18444410751 scopus 로고    scopus 로고
    • Photochemistry of Kynurenine, a Tryptophan Metabolite: Properties of the Triplet State
    • Tsentalovich, Yu.P.; Snytnikova, O. A.; Sherin, P. S.; Forbes, M. D. E. Photochemistry of Kynurenine, a Tryptophan Metabolite: Properties of the Triplet State J. Phys. Chem. A 2005, 109, 3565-3568
    • (2005) J. Phys. Chem. A , vol.109 , pp. 3565-3568
    • Tsentalovich, Yu.P.1    Snytnikova, O.A.2    Sherin, P.S.3    Forbes, M.D.E.4
  • 9
    • 0032726186 scopus 로고    scopus 로고
    • UV Filter Compounds in Human Lenses: The Origin of 4-(2-amino-3- hydroxyphenyl)-4-oxobutanoic Acid O-beta-D-Glucoside
    • Bova, L. M.; Wood, A. M.; Jamie, J. F.; Truscott, R. J. W. UV Filter Compounds in Human Lenses: the Origin of 4-(2-amino-3-hydroxyphenyl)-4- oxobutanoic Acid O-beta-D-Glucoside Invest. Ophthalmol. Visual Sci. 1999, 40, 3237-3244
    • (1999) Invest. Ophthalmol. Visual Sci. , vol.40 , pp. 3237-3244
    • Bova, L.M.1    Wood, A.M.2    Jamie, J.F.3    Truscott, R.J.W.4
  • 10
    • 34447646160 scopus 로고    scopus 로고
    • Tsentalovich, UV Filter Decomposition. A Study of Reactions of 4-(2-amino-3-aminophenyl)-4-oxocrotonic Acid with Amino Acids and Antioxidants Present in the Human Lens
    • Kopylova, L. V.; Snytnikova, O. A.; Chernyak, E. I.; Morozov, S. V. Tsentalovich, UV Filter Decomposition. A Study of Reactions of 4-(2-amino-3-aminophenyl)-4-oxocrotonic Acid with Amino Acids and Antioxidants Present in the Human Lens Exp. Eye Res. 2007, 85, 242-249
    • (2007) Exp. Eye Res. , vol.85 , pp. 242-249
    • Kopylova, L.V.1    Snytnikova, O.A.2    Chernyak, E.I.3    Morozov, S.V.4
  • 13
    • 0032731157 scopus 로고    scopus 로고
    • Evidence for Crystalline Modification by the Major Ultraviolet Filter, 3-Hydroxy-kynurenine O -β-D-Glucoside
    • Hood, B. D.; Garner, B.; Truscott, R. J. W. Evidence for Crystalline Modification by the Major Ultraviolet Filter, 3-Hydroxy-kynurenine O -β-D-Glucoside J. Biol. Chem. 1999, 274, 32547-32550
    • (1999) J. Biol. Chem. , vol.274 , pp. 32547-32550
    • Hood, B.D.1    Garner, B.2    Truscott, R.J.W.3
  • 14
    • 0036315485 scopus 로고    scopus 로고
    • Glutathione and NADH, but not Ascorbate, Protect Lens Proteins from Modification by UV Filters
    • Taylor, L. M.; Aquilina, J. A.; Jamie, J. F.; Truscott, R. J. W. Glutathione and NADH, but not Ascorbate, Protect Lens Proteins from Modification by UV Filters Exp. Eye Res. 2002, 74, 503-511
    • (2002) Exp. Eye Res. , vol.74 , pp. 503-511
    • Taylor, L.M.1    Aquilina, J.A.2    Jamie, J.F.3    Truscott, R.J.W.4
  • 16
    • 32344431712 scopus 로고    scopus 로고
    • Identification of 3-Hydroxykynurenine Bound to Protein in the Human Lens. A Possible Role in Age-Related Nuclear Cataract
    • Korlimbinis, A.; Truscott, R. J. W. Identification of 3-Hydroxykynurenine Bound to Protein in the Human Lens. A Possible Role in Age-Related Nuclear Cataract Biochemistry 2006, 45, 1950-1960
    • (2006) Biochemistry , vol.45 , pp. 1950-1960
    • Korlimbinis, A.1    Truscott, R.J.W.2
  • 17
    • 0033597823 scopus 로고    scopus 로고
    • Identification of Glutathionyl-3-hydroxykynurenine Glucoside as a Novel Fluorophore Associated with Aging of the Human Lens
    • Garner, B.; Vazquez, S.; Griffith, R.; Lindner, R. A.; Carver, J. A.; Truscott, R. J. W. Identification of Glutathionyl-3-hydroxykynurenine Glucoside as a Novel Fluorophore Associated with Aging of the Human Lens J. Biol. Chem. 1999, 274, 20847-20854
    • (1999) J. Biol. Chem. , vol.274 , pp. 20847-20854
    • Garner, B.1    Vazquez, S.2    Griffith, R.3    Lindner, R.A.4    Carver, J.A.5    Truscott, R.J.W.6
  • 19
    • 0034675384 scopus 로고    scopus 로고
    • Cysteine is the Initial Site of Modification of Alpha-Crystallin by Kynurenine
    • Aquilina, J. A.; Truscott, R. J. W. Cysteine is the Initial Site of Modification of Alpha-Crystallin by Kynurenine Biochem. Biophys. Res. Commun. 2000, 276, 216-223
    • (2000) Biochem. Biophys. Res. Commun. , vol.276 , pp. 216-223
    • Aquilina, J.A.1    Truscott, R.J.W.2
  • 22
    • 39949085602 scopus 로고    scopus 로고
    • Tryptophan-derived Ultraviolet Filter Compounds Covalently Bound to Lens Proteins are Photosensitizers of Oxidative Damage
    • Mizdrak, J.; Hains, P. G.; Truscott, R. J. W.; Jamie, J. F.; Davies, M. J. Tryptophan-derived Ultraviolet Filter Compounds Covalently Bound to Lens Proteins are Photosensitizers of Oxidative Damage Free Radical Biol. Med. 2008, 44, 1108-1119
    • (2008) Free Radical Biol. Med. , vol.44 , pp. 1108-1119
    • Mizdrak, J.1    Hains, P.G.2    Truscott, R.J.W.3    Jamie, J.F.4    Davies, M.J.5
  • 23
    • 65249187863 scopus 로고    scopus 로고
    • Ultrafast Excited-State Dynamics of Kynurenine - A UV Filter of the Human Eye
    • Sherin, P. S.; Grilj, J.; Tsentalovich, Yu.P.; Vauthey, E. Ultrafast Excited-State Dynamics of Kynurenine-a UV Filter of the Human Eye J. Phys. Chem. B 2009, 113, 4953-4962
    • (2009) J. Phys. Chem. B , vol.113 , pp. 4953-4962
    • Sherin, P.S.1    Grilj, J.2    Tsentalovich, Yu.P.3    Vauthey, E.4
  • 24
    • 35148854558 scopus 로고    scopus 로고
    • Kinetics and Mechanism of Reactions of Photoexcited Kynurenine with Molecules of Some Natural Compounds
    • Snytnikova, O. A.; Sherin, P. S.; Kopylova, L. V.; Tsentalovich, Yu.P. Kinetics and Mechanism of Reactions of Photoexcited Kynurenine with Molecules of Some Natural Compounds Rus. Chem. Bull. 2007, 56, 732-738
    • (2007) Rus. Chem. Bull. , vol.56 , pp. 732-738
    • Snytnikova, O.A.1    Sherin, P.S.2    Kopylova, L.V.3    Tsentalovich, Yu.P.4
  • 25
    • 0036538689 scopus 로고    scopus 로고
    • Identifying Sites of Attachment of UV Filters to Proteins in Older Human Lenses
    • Aquilina, J. A.; Truscott, R. J. W. Identifying Sites of Attachment of UV Filters to Proteins in Older Human Lenses Biochim. Biophys. Acta 2002, 1596, 6-15
    • (2002) Biochim. Biophys. Acta , vol.1596 , pp. 6-15
    • Aquilina, J.A.1    Truscott, R.J.W.2
  • 26
    • 0024238047 scopus 로고
    • Reference Materials for Fluorescence Measurement
    • Eaton, D. F. Reference Materials for Fluorescence Measurement J. Photochem. Photobiol., B 1988, 2, 523-531
    • (1988) J. Photochem. Photobiol., B , vol.2 , pp. 523-531
    • Eaton, D.F.1
  • 27
    • 0037118385 scopus 로고    scopus 로고
    • Ultrafast Charge Recombination of Photogenerated Ion Pairs to an Electronic Excited State
    • Morandeira, A.; Engeli, L.; Vauthey, E. Ultrafast Charge Recombination of Photogenerated Ion Pairs to an Electronic Excited State J. Phys. Chem. A 2002, 106, 4833-4837
    • (2002) J. Phys. Chem. A , vol.106 , pp. 4833-4837
    • Morandeira, A.1    Engeli, L.2    Vauthey, E.3
  • 28
    • 33745054090 scopus 로고    scopus 로고
    • Ultrafast Excited-State Dynamics of DNA Fluorescent Intercalators: New Insight Into the Fluorescence Enhancement Mechanism
    • Fürstenberg, A.; Julliard, M. D.; Deligeorgiev, T. G.; Gadjev, N. I.; Vasilev, A. A.; Vauthey, E. Ultrafast Excited-State Dynamics of DNA Fluorescent Intercalators: New Insight Into the Fluorescence Enhancement Mechanism J. Am. Chem. Soc. 2006, 128, 7661-7669
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 7661-7669
    • Fürstenberg, A.1    Julliard, M.D.2    Deligeorgiev, T.G.3    Gadjev, N.I.4    Vasilev, A.A.5    Vauthey, E.6
  • 29
    • 34547273974 scopus 로고    scopus 로고
    • Excited-State Dynamics of Donor-Acceptor Bridged Systems Containing a Boron-Dipyrromethene Chromophore: Interplay Between Charge Separation and Reorientational Motion
    • Duvanel, G.; Banerji, N.; Vauthey, E. Excited-State Dynamics of Donor-Acceptor Bridged Systems Containing a Boron-Dipyrromethene Chromophore: Interplay Between Charge Separation and Reorientational Motion J. Phys. Chem. A 2005, 111, 5361-5369
    • (2005) J. Phys. Chem. A , vol.111 , pp. 5361-5369
    • Duvanel, G.1    Banerji, N.2    Vauthey, E.3
  • 32
    • 0017184389 scopus 로고
    • A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding
    • Bradford, M. M. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding Anal. Biochem. 1976, 72, 248-254
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 33
    • 33745476940 scopus 로고    scopus 로고
    • Ultrafast Solvation Dynamics of Coumarin 153 in Imidazolium-Based Ionic Liquids
    • Lang, B.; Angulo, G.; Vauthey, E. Ultrafast Solvation Dynamics of Coumarin 153 in Imidazolium-Based Ionic Liquids J. Phys. Chem. A 2006, 110, 7028-7034
    • (2006) J. Phys. Chem. A , vol.110 , pp. 7028-7034
    • Lang, B.1    Angulo, G.2    Vauthey, E.3
  • 34
    • 36048934998 scopus 로고    scopus 로고
    • Ultrafast Excited-State Dynamics of Oxazole Yellow DNA Intercalators
    • Fürstenberg, A.; Vauthey, E. Ultrafast Excited-State Dynamics of Oxazole Yellow DNA Intercalators J. Phys. Chem. B 2007, 111, 12610-12620
    • (2007) J. Phys. Chem. B , vol.111 , pp. 12610-12620
    • Fürstenberg, A.1    Vauthey, E.2
  • 35
    • 33847797571 scopus 로고
    • The Solvatochromic Comparison Method. 2. The α-scale of Hydrogen-Bond Donor (HBD) Acidities
    • Taft, R. W.; Kamlet, M. J. The Solvatochromic Comparison Method. 2. The α-scale of Hydrogen-Bond Donor (HBD) Acidities J. Am. Chem. Soc. 1976, 98, 2886-2894
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2886-2894
    • Taft, R.W.1    Kamlet, M.J.2
  • 36
    • 0041573625 scopus 로고
    • Linear Solvation Relationships. 23. A Comprehensive Collection of the Solvatochromic Parameters, π*,α and β, and Some Methods for Simplifying the Generalized Solvatochromic Equation
    • Kamlet, M. J.; Abboud, J-L.M.; Abraham, M. H.; Taft, R. W. Linear Solvation Relationships. 23. A Comprehensive Collection of the Solvatochromic Parameters, π*,α and β, and Some Methods for Simplifying the Generalized Solvatochromic Equation J. Org. Chem. 1983, 48, 2877-2887
    • (1983) J. Org. Chem. , vol.48 , pp. 2877-2887
    • Kamlet, M.J.1    Abboud, J.-L.M.2    Abraham, M.H.3    Taft, R.W.4
  • 38
    • 0016851391 scopus 로고
    • Excited State Chemistry of Aromatic Amino Acids and Related Peptides. III. Tryptophan
    • Bent, D. V.; Hayon, E. Excited State Chemistry of Aromatic Amino Acids and Related Peptides. III. Tryptophan J. Am. Chem. Soc. 1975, 97, 2612-2619
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 2612-2619
    • Bent, D.V.1    Hayon, E.2
  • 39
    • 33847800381 scopus 로고
    • Laser Flash Photolysis of Aqueous Tryptophan
    • Bryant, F. D.; Santus, R.; Grossweiner, L. I. Laser Flash Photolysis of Aqueous Tryptophan J. Phys. Chem. 1975, 79, 2711-2716
    • (1975) J. Phys. Chem. , vol.79 , pp. 2711-2716
    • Bryant, F.D.1    Santus, R.2    Grossweiner, L.I.3
  • 40
    • 0010250930 scopus 로고
    • Flash Photolysis of Tryptophan and N-acetyl-L-tryptophanamide; the Effect of Bromide on Transient Yields
    • Volkert, W. A.; Kuntz, R. R.; Ghiron, C. A.; Evans, R. F. Flash Photolysis of Tryptophan and N-acetyl-L-tryptophanamide; the Effect of Bromide on Transient Yields Photochem. Photobiol. 1977, 26, 3-9
    • (1977) Photochem. Photobiol. , vol.26 , pp. 3-9
    • Volkert, W.A.1    Kuntz, R.R.2    Ghiron, C.A.3    Evans, R.F.4
  • 41
    • 37049104108 scopus 로고
    • Mechanism of Tryptophan Oxidation by Some Inorganic Radical-Anions: A Pulse Radiolysis Study
    • Posener, M. L.; Adams, G. E.; Wardman, P.; Cundall, R. B. Mechanism of Tryptophan Oxidation by Some Inorganic Radical-Anions: a Pulse Radiolysis Study J. Chem. Soc., Faraday Trans. 2 1976, 72, 2231-2239
    • (1976) J. Chem. Soc., Faraday Trans. 2 , vol.72 , pp. 2231-2239
    • Posener, M.L.1    Adams, G.E.2    Wardman, P.3    Cundall, R.B.4
  • 42
    • 33947085617 scopus 로고
    • Electron Ejection and Electron Capture by Phenolic Compounds
    • Feitelson, J.; Hayon, E. Electron Ejection and Electron Capture by Phenolic Compounds J. Phys. Chem. 1973, 77, 10-15
    • (1973) J. Phys. Chem. , vol.77 , pp. 10-15
    • Feitelson, J.1    Hayon, E.2
  • 43
    • 0016851422 scopus 로고
    • Excited State Chemistry of Aromatic Amino Acids and Related Peptides. I. Tyrosine
    • Bent, D. V.; Hayon, E. Excited State Chemistry of Aromatic Amino Acids and Related Peptides. I. Tyrosine J. Am. Chem. Soc. 1975, 97, 2599-2606
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 2599-2606
    • Bent, D.V.1    Hayon, E.2
  • 44
    • 71049139434 scopus 로고    scopus 로고
    • Experimental and Quantum Chemical Study of Photochemical Properties of 4-Hydroxyquinoline
    • Sherin, P. S.; Gritsan, N. P.; Tsentalovich, Yu. P. Experimental and Quantum Chemical Study of Photochemical Properties of 4-Hydroxyquinoline Photochem. Photobiol. Sci. 2009, 8, 1550-1557
    • (2009) Photochem. Photobiol. Sci. , vol.8 , pp. 1550-1557
    • Sherin, P.S.1    Gritsan, N.P.2    Tsentalovich, Yu.P.3
  • 47
    • 0029403121 scopus 로고
    • Subpicosecond Measurements of Polar Solvation Dynamics: Coumarin 153 Revisited
    • Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. Subpicosecond Measurements of Polar Solvation Dynamics: Coumarin 153 Revisited J. Phys. Chem. 1995, 99, 17311-17337
    • (1995) J. Phys. Chem. , vol.99 , pp. 17311-17337
    • Horng, M.L.1    Gardecki, J.A.2    Papazyan, A.3    Maroncelli, M.4
  • 48
    • 0000695363 scopus 로고    scopus 로고
    • High-Resolution Structure (1.33 Å) of a HEW Lysozyme Tetragonal Crystal Grown in the APCF Apparatus. Data and Structural Comparison with a Crystal Grown Under Microgravity from SpaceHab-01 Mission
    • Vaney, M. C.; Maignan, S.; Riés-Kautt, M.; Ducruix, A. High-Resolution Structure (1.33 Å) of a HEW Lysozyme Tetragonal Crystal Grown in the APCF Apparatus. Data and Structural Comparison with a Crystal Grown Under Microgravity from SpaceHab-01 Mission Acta Crystallogr. 1996, D52, 505-517
    • (1996) Acta Crystallogr. , vol.52 , pp. 505-517
    • Vaney, M.C.1    Maignan, S.2    Riés-Kautt, M.3    Ducruix, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.