| Автор | Ahmad, Iqbal |
| Автор | Vaid, Faiyaz H.M. |
| Дата выпуска | 2006 |
| ISBN | 978-0-85404-331-6 |
| dc.description | The photochemical aspects of flavins have been reviewed with reference to the analysis of flavins and photoproducts in degraded solutions, spectral and photophysical properties, photodegradation reactions, photosensitization reactions, and photostability of riboflavin in pharmaceutical preparations. The photochemistry of flavins in aqueous solution involves two major photodegradation reactions, viz intramolecular photoreduction and photoaddition, occurring separately or concomitantly in the presence of phosphate buffer, leading to the formation of lumichrome and cyclodehydroriboflavin, respectively. The photoreduction is catalyzed by H2PO4- ions and the photoaddition by HPO4<sup>2â </sup> ions. Intermolecular photoreduction also takes place in a large number of flavin-substrate interactions involving the flavin triplet state. Knowledge of the spectral and photophysical properties, and photochemical behaviour of flavins is necessary to understand the nature of flavinâ protein interactions, flavin photosensitization reactions, and their role in biological processes. The study of the photochemical behaviour of riboflavin as a function of pH is a prerequisite to achieve optimum stability of the vitamin in pharmaceutical preparations. Technological processes are being developed to utilize riboflavin as a photosensitizer in the pathogenic inactivation of blood components. Riboflavin-sensitized photooxidation of amino acids in protein may have important biological implications to control photoinduced damage in biological systems. The application of femtosecond-resolved fluorescence spectroscopy and transient absorption techniques may provide useful information on the dynamics of flavoproteins. |
| Формат | application.pdf |
| Издатель | Royal Society of Chemistry |
| Название | Chapter 2. Photochemistry of Flavins in Aqueous and Organic Solvents |
| Тип | other |
| DOI | 10.1039/9781847555397-00013 |
| Print ISSN | 2041-9716 |
| Журнал | Flavins Photochemistry and Photobiology: Volume 6 |
| Том | 6 |
| Первая страница | 13 |
| Последняя страница | 40 |
| Аффилиация | Ahmad Iqbal; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Karachi |
| Аффилиация | Vaid Faiyaz H.M.; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Karachi |
| Библиографическая ссылка | D.E. Edmondson, S. Ghisla, Flavoenzyme structure and function: approaches using flavin analogues, Methods Mol. Biol., 1999, 131, 157, 179 |
| Библиографическая ссылка | V. Massey, The chemical and biological versatility of riboflavin, Biochem. Soc. Trans., 2000, 28, 283, 296 |
| Библиографическая ссылка | R. Miura, Versatility and specificity in flavoenzymes: control mechanisms of flavin reactivity, Chem. Rec., 2001, 1, 183, 194 |
| Библиографическая ссылка | G.R. Penzer, G.K. Radda, Photochemistry of flavins, Methods Enzymol., 1971, 18B, 479, 506 |
| Библиографическая ссылка | H.J. Powers, Riboflavin and health, Am. J. Clin. Nutr., 2003, 77, 1352, 1360 |
| Библиографическая ссылка | D.B. McCormick, On becoming a nutritional biochemist, Ann. Rev. Nutr., 2004, 24, 1, 11 |
| Библиографическая ссылка | B. Holmstrom, Mechanism of the photoreduction of riboflavin, Arkiv. Kemi, 1964, 22, 329, 346 |
| Библиографическая ссылка | G.R. Penzer, G.K. Radda, The chemistry and biological function of isoalloxazine (flavines), Q. Rev., 1967, 21, 43, 65 |
| Библиографическая ссылка | P. Hemmerich, The present status of flavin and flavocoenzyme chemistry, Fortsch. Chem. Org. Naturst., 1976, 33, 451, 527 |
| Библиографическая ссылка | F. Muller, Spectroscopy and photochemistry of flavins and flavoproteins, Photochem. Photobiol., 1981, 34, 753, 759 |
| Библиографическая ссылка | P.F. Heelis, The photophysical and photochemical properties of flavins (isoalloxazines), Chem. Soc. Rev., 1982, 11, 15, 39 |
| Библиографическая ссылка | G. Tollin, Use of flavin photochemistry to probe intraprotein and interprotein electron transfer mechanisms, J. Bioenerg. Biomembr., 1995, 27, 303, 309 |
| Библиографическая ссылка | G. Tollin, J.K. Hurley, J.T. Hazzard, T.E. Meyer, Use of laser flash photolysis time-resolved spectrophotometry to investigate interprotein and intraprotein electron transfer mechanisms, Biophys. Chem., 1993, 48, 259, 279 |
| Библиографическая ссылка | R.J. Stanley, Advances in flavin and flavoprotein optical spectroscopy, Antiox. Redox Signal., 2001, 3, 847, 866 |
| Библиографическая ссылка | P.A.W. van den Berg, K.A. Feenstra, A.E. Mark, H.J.C. Berendsen, A.J.W. G. Visser, Dynamic confirmation of flavin adenine dinucleotide: simulated molecular dynamics of the flavin cofactor related to the time-resolved characteristics, J. Phys. Chem. B, 2002, 106, 8858, 8869 |
| Библиографическая ссылка | D. Zhong, A. Zewail, 2, Proc. Natl. Acad. Sci. USA, 2001, 98, 11867, 11872 |
| Библиографическая ссылка | M.B. Tayler, G.K. Radda, Flavins as photosensitizers, Methods Enzymol., 1971, 18, 496, 506 |
| Библиографическая ссылка | E. Silva, Sensitized photooxidation of amino acids in proteins: some important biological implications, Biol. Res., 1996, 29, 57, 67 |
| Библиографическая ссылка | S. Wang, R. Gao, F. Zhou, M. Silke, Nano materials and singlet oxygen photosensitizers: potential applications in photodynamic therapy, J. Mater. Chem., 2004, 14, 487, 493 |
| Библиографическая ссылка | B. Quintero, M.A. Miranda, Mechanisms of photosensitization induced by drugs: a general survey, Ars Pharmaceutica, 2000, 41, 27, 46 |
| Библиографическая ссылка | E.C. Smith, D.E. Metzler, The photochemical degradation of riboflavin, J. Am. Chem. Soc., 1963, 85, 3285, 3288 |
| Библиографическая ссылка | M. Halwer, The photochemistry of riboflavin and related compounds, J. Am. Chem. Soc., 1951, 73, 4870, 4874 |
| Библиографическая ссылка | B. Holmstrom, Spectral studies of the bleaching of riboflavin phosphate, Arkiv. Kemi., 1964, 22, 281, 301 |
| Библиографическая ссылка | C.K. Radda, M. Calvin, Chemical and photochemical reduction of flavin nucleotides and analogues, Biochemistry, 1964, 3, 384, 393 |
| Библиографическая ссылка | P.S. Song, E.C. Smith, D.E. Metzler, Photochemical degradation of flavins. IV. The mechanism of alkaline hydrolysis of 6,7-dimethyl-9-formylmethylisoalloxazine, J. Am. Chem. Soc., 1965, 87, 4181, 4184 |
| Библиографическая ссылка | M.M. McBride, M.W. Moore, The photochemistry of riboflavin. II. Polarographic studies on the hydroxyethyl and formylmethyl analogs of riboflavin, Photochem. Photobiol., 1967, 6, 103, 113 |
| Библиографическая ссылка | Y. Sato, M. Yokoo, S. Takahashi, T. Takahashi, Biphasic photolysis of riboflavin with a low-intensity light source, Chem. Pharm. Bull. (Jpn), 1982, 30, 1803, 1810 |
| Библиографическая ссылка | Y. Sato, S. Yamasato, Y. Suzuki, Biphasic photolysis of riboflavin. II. Effect of gelatin on the photolysis, Chem. Pharm. Bull. (Jpn), 1983, 31, 4167, 4171 |
| Библиографическая ссылка | Y. Sato, H. Chaki, Y. Suzuki, Biphasic photolysis of riboflavin. III. Effect of ionic strength on the photolysis, Chem. Pharm. Bull. (Jpn), 1984, 32, 1232, 1235 |
| Библиографическая ссылка | P. Montana, N. Pappano, N. Debattista, V. Avila, A. Posadaz, S.G. Bertolotti, N.A. Garcia, The activity of 3- and 7-hydroxyflavones as scavengers of superoxide radical anion generated from photo-excited riboflavin, Can. J. Chem., 2003, 81, 909, 914 |
| Библиографическая ссылка | M. Diaz, M. Luiz, S.G. Bertolotti, S. Miskoshi, N.A. Garcia, Scavenging of photogenerated singlet molecular oxygen and superoxide radical anion by sulpha drugs â kinetics and mechanism, Can. J. Chem., 2004, 82, 1752, 1759 |
| Библиографическая ссылка | I. Ahmad, H.D.C. Rapson, Multicomponent spectrophotometric assay of riboflavin and photoproducts, J. Pharm. Biomed. Anal., 1990, 8, 217, 223 |
| Библиографическая ссылка | P.F. Heelis, G.O. Phillips, I. Ahmad, H.D.C. Rapson, The photodegradation of formylmethylflavin â a steady state and laser flash photolysis study, Photobiochem. Photobiophys., 1980, 1, 125, 130 |
| Библиографическая ссылка | I. Ahmad, H.D.C. Rapson, P.F. Heelis, G.O. Phillips, Alkaline hydolysis of 7,8-dimethyl-10-(formylmethyl) isoalloxazine. A kinetic study, J. Org. Chem., 1980, 45, 731, 733 |
| Библиографическая ссылка | I. Ahmad, Q. Fasihullah, A. Noor, I.A. Ansari, Q.N.M. Ali, Photolysis of riboflavin in aqueous solution: a kinetic study, Int. J. Pharm., 2004, 280, 199, 208 |
| Библиографическая ссылка | I. Ahmad, Q. Fasihullah, F.H.M. Vaid, A study of simultaneous photolysis and photoaddition reactions of riboflavin in aqueous solution, J. Photochem. Photobiol. B: Biol., 2004, 75, 13, 20 |
| Библиографическая ссылка | I. Ahmad, Q. Fasihullah, F.H.M. Vaid, Effect of phosphate buffer on photodegradation reactions of riboflavin in aqueous solution, J. Photochem. Photobiol. B: Biol., 2005, 78, 229, 234 |
| Библиографическая ссылка | I. Ahmad, Q. Fasihullah, F.H.M. Vaid, Effect of light intensity and wavelengths on photodegradation reactions of riboflavin in aqueous solution, J. Photochem. Photobiol. B: Biol., 2006, 82, 21, 27 |
| Библиографическая ссылка | C.B. Martin, E. Wilfong, P. Ruane, R. Goodrich, M. Platz, An action spectrum of the riboflavin-photosensitized inactivation of lambda phage, Photochm. Photobiol., 2005, 81, 474, 480 |
| Библиографическая ссылка | G. Weber, Fluorescence of riboflavin and flavin adenine dinucleotide, Biochem. J., 1950, 47, 114, 121 |
| Библиографическая ссылка | A.J.W.G. Visser, F. Muller, Absorption and fluorescence studies on neutral and cationic isoalloxazine, Helv. Chim. Acta, 1979, 62, 593, 608 |
| Библиографическая ссылка | M. Sun, T.A. Moore, P.S. Song, Molecular luminescence studies of flavins. I. The excited states of flavins, J. Am. Chem. Soc., 1972, 94, 1730, 1740 |
| Библиографическая ссылка | E. Sikorska, I. Khmelinskii, A. Komasa, J. Koput, L.F.V. Ferreira, J.R. Herance, J.L. Bourdelande, S.L. Williams, D.R. Worrall, M. Insinska-Rak, M. Sikorski, Spectroscopy and photophysics of flavin related compounds: riboflavin and iso-6,7)-riboflavin, Chem. Phys., 2005, 314, 239, 247 |
| Библиографическая ссылка | E. Sikorska, I.V. Khmelinskii, W. Prukala, S.L. Williams, M. Patel, D.R. Worrall, J.L. Bourdelande, J. Koput, M. Sikorski, Spectroscopy and photophysics of lumiflavins and lumichromes, J. Phys. Chem. A., 2004, 108, 1501, 1508 |
| Библиографическая ссылка | E. Sikorska, I.V. Khmelinskii, D.R. Worrall, J. Koput, M. Sikorski, Spectroscopy and photophysics of iso- and alloxazines: experimental and theoretical study, J. Fluorescence, 2004, 14, 57, 64 |
| Библиографическая ссылка | E. Sikorska, J.R. Herance, J.L. Bourdelande, I.V. Khmelinskii, S.L. Williams, D.R. Worrall, G. Nowacka, A. Komasa, M. Sikorski, Spectroscopy and photophysics of flavin-related compounds: 3-ethyllumiflavin, J. Photochem. Photobiol. A: Chem., 2005, 170, 267, 272 |
| Библиографическая ссылка | M. Insinska-Rak, E. Sikorska, J.R. Herance, J.I. Bourdelande, I.V. Khmelinskii, M. Kubicki, W. Prukala, I.F. Machado, A. Komasa, L.F.V. Ferreira, M. Sikorski, Spectroscopy and photophysics of flavin-related compounds: 3-benzyl-lumiflavin, Photochem. Photobiol. Sci., 2005, 4, 463, 468 |
| Библиографическая ссылка | M. Sikorski, E. Sikorska, A. Koziolowa, R.G. Moreno, J.L. Bourdelande, R.P. Steer, F. Wilkinson, Photophysical properties of lumichrome in water, J. Photochem. Photobiol. B: Biol., 2001, 60, 114, 119 |
| Библиографическая ссылка | E. Sikorska, D.R. Worrall, J.L. Bourdelande, M. Sikorski, Photophysics of lumichrome and its analogs, Polish J. Chem., 2003, 77, 65, 73 |
| Библиографическая ссылка | E. Sikorska, I.V. Khmelinskii, W. Prukala, S.L. Williams, D.R. Worrall, J.L. Bourdelande, A. Bednarek, J. Koput, M. Sikorski, Spectroscopy and photophysics of 9-methylalloxazine. Experimental and theoretical study, J. Mol. Struct., 2004, 689, 121, 126 |
| Библиографическая ссылка | E. Sikorska, I.V. Khmelinskii, S.L. Williams, D.R. Worrell, J.R. Herance, J.L. Bourdelande, J. Koput, M. Sikorski, Spectroscopy and photophysics of 6,7-dimethyl-alloxazine: experimental and theoretical study, J. Mol. Struct., 2004, 697, 199, 205 |
| Библиографическая ссылка | E. Sikorska, I.V. Khmelinskii, J. Koput, J.L. Bourdelande, M. Sikorski, Electronic structure of isoalloxazines in their ground and excited states, J. Mol. Struct., 2004, 697, 137, 141 |
| Библиографическая ссылка | E. Sikorska, M. Sikorski, R. P. Steer, F. Wilkinson, D.R. Worrall, Efficiency of singlet oxygen generation by alloxazines and isoalloxazines, J. Chem. Soc., Faraday Trans., 1998, 94, 2347, 2353 |
| Библиографическая ссылка | M. Mir, E. Sikorska, M. Sikorski, F. Wilkinson, Study of the effect of β-cyclodextrin on the photophysics of alloxazines in the solid state, J. Chem. Soc., Perkin Trans., 1997, 2, 1095, 1098 |
| Библиографическая ссылка | M. Sikorski, E. Sikorska, F. Wilkinson, R.P. Steer, Studies of the photophysics and spectroscopy of alloxazine and related compounds in solution and in the solid state, Can. J. Chem., 1999, 77, 472, 480 |
| Библиографическая ссылка | M. Sikorski, Photophysics of dimethyl-alloxazines and 1-methyllumichrome on cellulose, Phys. Chem. Chem. Phys., 2002, 4, 211, 215 |
| Библиографическая ссылка | M. Sikorski, E. Sikorska, I.V. Khmelinskii, R. Gonzalez-Moreno, J.L. Bourdelande, A. Siemiarczuk, Photophysics of alloxazines on cellulose, Photochem. Photobiol. Sci., 2002, 1, 715, 720 |
| Библиографическая ссылка | J. Wouters, F. Durant, B. Champagne, J.-M. Andre, Molecular structure, dynamics, and function of biological systems. Electronic properties of flavins: implications on the reactivity and absorption properties of flavoproteins, Int. J. Quant. Chem., 1997, 64, 721, 733 |
| Библиографическая ссылка | P. Drossler, W. Holzer, A. Penzkofer, P. Hegemann, pH dependence of the absorption and emission behaviour of riboflavin in aqueous solution, Chem. Phys., 2002, 282, 429, 439 |
| Библиографическая ссылка | Y.-L. Pan, R.G. Pinnick, S.C. Hill, S. Niles, S. Holler, J.R. Bottiger, J.-P. Wolf, R.S. Chang, Dynamics of photon-induced degradation and fluorescence in riboflavin microparticles, Appl. Phys. B: Lasers Optics, 2001, 72, 449, 454 |
| Библиографическая ссылка | E. Sikorska, A. Koziolowa, Excited state proton transfer of methyl- and cyano-substituted alloxazines in the presence of acetic acid, J. Photochem. Photobiol. A: Chem., 1996, 95, 215, 221 |
| Библиографическая ссылка | E. Sikorska, A. Koziolowa, M. Sikorski, A. Siemiarczuk, The solvent effect on the excited-state proton transfer of lumichrome, J. Photochem. Photobiol. A: Chem., 2003, 157, 5, 14 |
| Библиографическая ссылка | R. Leenders, M. Kooijman, A. van Hoek, C. Veeger, A.J.W.G. Visser, Flavin dynamics in reduced flavodoxins. A time-resolved polarized fluorescence study, Eur. J. Biochem., 1993, 211, 37, 45 |
| Библиографическая ссылка | P.A.W. van den Berg, A. van Hoek, C.D. Walentas, R.N. Perham, A.J.W.G. Visser, Escherichia coli, Biophys. J., 1998, 74, 2046, 2058 |
| Библиографическая ссылка | L.J. Kricka, P.E. Stanely, Time-resolved fluorescence: 1996â 1998, Luminescence, 1999, 14, 47, 61 |
| Библиографическая ссылка | P.A.W. van den Berg, J. Widengren, M.A. Hink, R. Rigler, A.J.W.G. Visser, Fluorescence correlation spectroscopy of flavins and flavoenzymes: photochemical and photophysical aspects, Spectrochim. Acta Part A, 2001, 57, 2135, 2144 |
| Библиографическая ссылка | S.D.M. Islam, A. Penzkofer, P. Hegemann, Chlamydomonas reinhardtii, Chem. Phys., 2003, 291, 97, 114 |
| Библиографическая ссылка | M. Sakai, H. Takahashi, One-electron photoreduction of flavin mononucleotide: time-resolved resonance Raman and absorption study, J. Mol. Struct., 1996, 379, 9, 18 |
| Библиографическая ссылка | A.J. Visser, J. Vervoot, D.J. Oâ Kane, J. Lee, L.A. Carreira, Raman spectra of flavin bound in flavodoxins and in other flavoproteins. Evidence for structural variations in the flavin-binding region, Eur. J. Biochem., 1983, 131, 639, 645 |
| Библиографическая ссылка | T. Picaud, A. Desbois, Electrostatic control of the isoalloxazine environment in the two-electron reduced states of yeast glutathione reductase, J. Biol. Chem., 2002, 277, 31715, 31721 |
| Библиографическая ссылка | Y. Zheng, P.R. Carey, Raman spectrum of fully reduced flavin, J. Raman Spectrosc., 2004, 35, 521, 524 |
| Библиографическая ссылка | D.H. Murgida, E. Schieicher, A. Bacher, G. Richter, P. Hildebrandt, Escherichia coli, J. Raman Spectrosc., 2001, 32, 551, 556 |
| Библиографическая ссылка | K.J. Griffin, G.D. Degala, W. Eisenreich, F. Muller, A. Bacher, F. Freeman, Paracoccus denitrificans, Eur. J. Biochem., 1998, 255, 125, 132 |
| Библиографическая ссылка | C.G. Van Schagen, F. Mullar, A comparative <sup>13</sup>C-NMR study on various reduced flavins, Helv. Chim. Acta, 2004, 63, 2187, 2201 |
| Библиографическая ссылка | A. Niemz, V.M. Rotello, Model systems for flavoenzyme activity. The effects of specific hydrogen bonds on the <sup>13</sup>C- and <sup>1</sup>H-NMR of flavins, J. Mol. Recognit., 1999, 9, 158, 162 |
| Библиографическая ссылка | G. Fleischmann, F. Lederer, F. Muller, A. Bacher, H. Ruterjans, 2, Eur. J. Biochem., 2000, 267, 5156, 5167 |
| Библиографическая ссылка | C.E. Lyon, J.J. Lopez, B.-M. Cho, P.J. Hore, Low field CIDNP of amino acids and proteins: characterization of transient radicals and NMR sensitivity enhancement, Mol. Phys., 2002, 100, 1261, 1269 |
| Библиографическая ссылка | M. Schuman Jorns, G. Schollnhammer, P. Hemmerich, Intramolecular addition of the riboflavin side chain. Anion-catalysed neutral photochemistry, Eur. J. Biochem., 1975, 57, 35, 48 |
| Библиографическая ссылка | G.E. Treadwell, W.L. Cairns, D.E. Metzler, Photochemical degradation of flavins. V. Chromatographic studies of the products of photolysis of riboflavin, J. Chromatogr., 1968, 35, 376, 388 |
| Библиографическая ссылка | W.L. Cairns, D.E. Metzler, Photochemical degradation of flavins. VI. A new photoproduct and its use in studying the photolytic mechanism, J. Am. Chem. Soc., 1971, 93, 2772, 2777 |
| Библиографическая ссылка | P.S. Song, D.E. Metzler, Photochemical degradation of flavins. IV. Studies of the anaerobic photolysis of riboflavin, Photochem. Photobiol., 1967, 6, 691, 709 |
| Библиографическая ссылка | P. Drossler, W. Holzer, A. Penzkofer, P. Hegemann, Fluorescence quenching of riboflavin in aqueous solution by methionin and cystein, Chem. Phys., 2003, 286, 409, 420 |
| Библиографическая ссылка | S.G. Bertolotti, C.M. Previtali, A.M. Rufs, M.V. Encinas, Riboflavin/triethanolamine as photoinitiator system of vinyl polymerization. A mechanistic study by laser flash photolysis, Macromolecules, 1999, 32, 2920, 2924 |
| Библиографическая ссылка | P.F. Heelis, G.O. Phillips, A laser flash photolysis study of the triplet states of lumichrome, J. Phys. Chem., 1985, 89, 770, 774 |
| Библиографическая ссылка | M.S. Grodowski, B. Veyret, K. Weiss, Photochemistry of flavins. II. Photophysical properties of alloxazines and isoalloxazines, Photochem. Photobiol., 1977, 26, 341, 352 |
| Библиографическая ссылка | S. Ghisla, V. Massey, Mechanisms of flavoprotein-catalysed reactions, Eur. J. Biochem., 1989, 181, 1, 17 |
| Библиографическая ссылка | S. Bornemann, Flavoenzymes that catalyse reactions with no net change, Nat. Prod. Rep., 2002, 19, 761, 772 |
| Библиографическая ссылка | N. Carrillo, E.A. Ceccarelli, Open questions in ferredoxin-NADP<sup>+</sup> reductase catalytic mechanism, Eur. J. Biochem., 2003, 270, 1900, 1915 |
| Библиографическая ссылка | J.A. Watkins, M.A. Cusanovich, T.E. Meyer, G. Tollin, A â parallel plateâ electrostatic model for bimolecular rate constants applied to electron transfer proteins, Protein Sci., 1994, 3, 2104, 2114 |
| Библиографическая ссылка | I. Ahmad, M.A. Cusanovich, G. Tollin, c, Proc. Natl. Acad. Sci. USA, 1981, 78, 6724, 6728 |
| Библиографическая ссылка | I. Ahmad, M.A. Cusanovich, G. Tollin, c, Biochemistry, 1982, 21, 3122, 3128 |
| Библиографическая ссылка | T.E. Meyer, J.A. Watkins, C.T. Przysiecki, G. Tollin, M.A. Cusanovich, c, Biochemistry, 1984, 23, 4761, 4767 |
| Библиографическая ссылка | J.T. Hazzard, T.A. Poulas, G. Tollin, c, c, Biochemistry, 1987, 26, 2836, 2848 |
| Библиографическая ссылка | J.T. Hazzard, S.J. Moench, J.E. Erman, J.D. Satterlee, G. Tollin, c, c, Biochemistry, 1988, 27, 2002, 2008 |
| Библиографическая ссылка | L. Quin, N.M. Kostic, f, Biochemistry, 1992, 31, 5145, 5150 |
| Библиографическая ссылка | I. Sevrioukova, C. Shaffer, D.P. Ballou, J.A. Paterson, Equlibrium and transient state spectrophotometric studies of the mechanism of reduction of the flavoprotein domain of P450BM-3, Biochemistry, 1996, 35, 7058, 7068 |
| Библиографическая ссылка | S.G. Mayhew, The effect of pH and semiquinone formation on the oxidationâ reduction potentials of flavin mononucleotides. A reappraisal, Eur. J. Biochem., 1999, 265, 698, 702 |
| Библиографическая ссылка | J.T. Hazzard, A.G. Mauk, G. Tollin, c, c, Arch. Biochem. Biophys., 1992, 298, 91, 95 |
| Библиографическая ссылка | C.T. Przysiecki, G. Tollin, T.E. Meyer, J.E. Staggers, M.A. Cusanovich, Effect of pH and exocyclic substitution on flavosemiquinone reactivity with redox proteins and inorganic oxidants, Arch. Biochem. Biophys., 1985, 238, 334, 343 |
| Библиографическая ссылка | J.D. Walsh, A.-F. Miller, Flavin reduction potential tuning by substitution and bending, J. Mol. Struct. (Theochem), 2003, 623, 185, 195 |
| Библиографическая ссылка | M.F. Teitell, J.L. Fox, MO study of flavin reduction, Int. J. Quant. Chem., 1982, 22, 583, 594 |
| Библиографическая ссылка | L.H. Hall, B.J. Orchard, S.K. Tripathy, The structure and properties of flavins: molecular orbital study based on totally optimized geometries. 1. Molecular geometry investigations, Int. J. Quant. Chem., 1987, 31, 195, 216 |
| Библиографическая ссылка | J.D. Walsh, A.-F. Miller, 5, J. Phys. Chem. B, 2003, 107, 854, 863 |
| Библиографическая ссылка | C.B. Martin, X. Shi, M.-L. Tsao, D. Karweik, J. Brooke, C.M. Hadad, M.S. Platz, The photochemistry of riboflavin tetraacetate and nucleosides. A study using density functional theory, laser flash photolysis, fluorescence, UV-VIS, and time-resolved infrared spectroscopy, J. Phys. Chem. B, 2002, 106, 10263, 10271 |
| Библиографическая ссылка | R.M. Kowalczyk, E. Schleicher, R. Bittl, S. Weber, The photoinduced triplet of flavins and its protonation states, J. Am. Chem. Soc., 2004, 126, 11393, 11399 |
| Библиографическая ссылка | C.B. Martin, M.-L. Tsao, C.M. Hadad, M.S. Platz, The reaction of triplet flavin with indole. A study of the cascade of reactive intermediates using density functional theory and time-resolved infrared spectroscopy, J. Am. Chem. Soc., 2002, 124, 7226, 7234 |
| Библиографическая ссылка | N. Mataga, H. Chorsowjan, Y. Shibata, Dynamics and mechanisms of ultrafast fluorescence quenching reactions of flavin chromophores in protein nanospace, J. Phys. Chem. B, 2000, 104, 10667, 10677 |
| Библиографическая ссылка | I.H.M. van Stokkum, D.S. Larsen, R. van Grondelle, Global and target analysis of time-resolved spectra, Biochim. Biophys. Acta, 2004, 1657, 82, 104 |
| Библиографическая ссылка | P.F. Heelis, A. Koziolowa, The effect of hydrogen bonding on the electron transfer reactions of excited singlet and triplet states of flavins, J. Photochem. Photobiol. B: Biol., 1991, 11, 365, 370 |
| Библиографическая ссылка | P.F. Heelis, R.F. Hartman, S.D. Rose, Detection of the excited singlet of a deprotonated reduced, flavin, Photochem. Photobiol., 1993, 57, 1053, 1055 |
| Библиографическая ссылка | P.F. Heelis, B.J. Parsons, Y. Yano, Spectral and redox properties of benzodipteridine. A pulse radiolysis, laser flash photolysis and semi-emperical orbital study, J. Chem. Soc., Perkin Trans., 1997, 2, 795, 798 |
| Библиографическая ссылка | F. Bosca, L. Fernandez, P.F. Heelis, Y. Yano, Substituent effects on electrophilicity of flavins: an experimental and semi-empirical molecular orbital study, J. Photochem. Photobiol. B: Biol., 2000, 55, 183, 187 |
| Библиографическая ссылка | S. Ishizaka, N. Kitamura, Photoinduced redox cycle of riboflavin at a water/oil interface, Anal. Sci., 2004, 20, 1587, 1592 |
| Библиографическая ссылка | M.B. Murataliev, R. Feyereisen, F.A. Walker, Electron transfer by diflavin reductases, Biochim. Biophys. Acta, 2004, 1698, 1, 26 |
| Библиографическая ссылка | I. Ahmad, G. Tollin, Solvent effect on flavin electron transfer reactions, Biochemistry, 1981, 20, 5925, 5928 |
| Библиографическая ссылка | G. Viteri, A.M. Edwards, J. De la Fuente, E. Silva, H, L, Photochem. Photobiol., 2003, 77, 535, 540 |
| Библиографическая ссылка | J.A. Navarro, M.A. De la Rosa, G. Tollin, Transient kinetics of flavin-photosensitized oxidation of reduced redox proteins, Eur. J. Biochem., 1991, 199, 239, 243 |
| Библиографическая ссылка | M. Roncel, M. Hervas, J.A. Navarro, M.A. De la Rosa, G. Tollin, c, Eur. J. Biochem., 1990, 191, 531, 536 |
| Библиографическая ссылка | J. Garcia, E. Silva, Flavin-sensitized photooxidation of amino acids present in a parenteral nutrition infusate protection: by ascorbic acid, Nutr. Biochem., 1997, 8, 341, 345 |
| Библиографическая ссылка | E. Silva, V. Ruckert, E. Lissi, E. Abuin, Effects of pH and ionic micelles on the riboflavin-sensitized photoprocesses of tryptophan in aqueous solution, J. Photochem. Photobiol. B: Biol., 1991, 11, 57, 68 |
| Библиографическая ссылка | E. Silva, C. Almarza, D. Berndt, L. Larrondo, Photoreactions of riboflavin with spermine and their role in tryptophan photoconsumption induced by riboflavin, J. Photochem. Photobiol. B: Biol., 1993, 21, 197, 201 |
| Библиографическая ссылка | E. Silva, P. Ugarte, A. Andrade, A.M. Edwards, Riboflavin-sensitized photoprocesses of tryptophan, J. Photochem. Photobiol. B: Biol., 1994, 23, 43, 48 |
| Библиографическая ссылка | E. Silva, A.M. Edwards, Generation of radical species by irradiation of tryptophan and tyrosine solutions sensitized by riboflavin. Biological implications, Cienc. Cult. (Sao Paulo), 1996, 48, 47, 50 |
| Библиографическая ссылка | A.M. Edwards, C. Bueno, A. Saldano, E. Silva, K. Kassab, L. Polo, G. Jori, Photochemical and pharmacokinetic properties of selected flavins, J. Photochem. Photobiol. B: Biol., 1999, 48, 36, 41 |
| Библиографическая ссылка | A. de La Rochette, E. Silva, I. Biriouez-Aragon, M. Mancini, A.M. Edwards, P. Morliere, Riboflavin photodegradation and photosensitizing effects are highly dependent on oxygen and ascorbate concentration, Photochem. Photobiol., 2000, 72, 815, 820 |
| Библиографическая ссылка | A. de La Rochette, I. Birlouez-Aragon, E. Silva, P. Morliere, Advanced glycation endproducts as UVA photosensitizers of tryptophan and ascorbic acid: consequences for the lens, Biochim. Biophys. Acta, 2003, 1621, 235, 241 |
| Библиографическая ссылка | D.R. Cardoso, D.W. Franco, K. Olsen, M.L. Andersen, L.F. Skibsted, Reactivity of bovine whey proteins, peptides, and amino acids toward triplet riboflavin as studied by laser flash photolysis, J. Agric. Food Chem., 2004, 52, 6602, 6606 |
| Библиографическая ссылка | E. Silva, J. Godoy, Riboflavin-sensitized photooxidation of tyrosine, Int. J. Vit. Nutr. Res., 1994, 64, 253, 256 |
| Библиографическая ссылка | C.-Y. Lu, Y.-Y. Liu, Electron transfer oxidation of tryptophan and tyrosine by triplet states and oxidized radicals of flavin sensitizers: a laser flash photolysis study, Biochim. Biophys. Acta, 2002, 1571, 71, 76 |
| Библиографическая ссылка | J.J. Lopez, M.A.G. Garter, Yu.P. Tsentalovich, O.B. Morozova, A.V. Yurkovskaya, P.J. Hore, Effects of surfactants on the photosensitized production of tyrosine radicals studied by photo-CIDNP, Photochem. Photobiol., 2002, 75, 6, 10 |
| Библиографическая ссылка | P.F. Heelis, B.J. Parsons, G.O. Phillips, J.F. McKeller, The flavin sensitized photooxidation of ascorbic acid. A continuous and flash photolysis study, Photochem. Photobiol., 1981, 33, 7, 13 |
| Библиографическая ссылка | M.Y. Jung, S.M. Kim, S.Y. Kim, Riboflavin-sensitized photooxidation of ascorbic acid: kinetics and amino acid effects, Food Chem., 1995, 53, 397, 403 |
| Библиографическая ссылка | H. Kim, L.J. Kirschenbaum, I. Rosenthal, P. Riesz, Photosensitized formation of ascorbate radicals by riboflavin: an ESR study, Photochem. Photobiol., 1993, 57, 777, 784 |
| Библиографическая ссылка | F.H.M. Vaid, R.H. Shaikh, I.A. Ansari, I. Ahmad, Spectral study of the photolysis of aqueous thiamine hydrochloride and ascorbic acid solutions in the presence and absence of riboflavin, J. Chem. Soc. Pak., 2005, 27, 227, 232 |
| Библиографическая ссылка | E. Silva, A.M. Edwards, D. Pacheco, Visible light-induced photooxidation of glucose sensitized by riboflavin, J. Nutr. Biochem., 1999, 10, 181, 185 |
| Библиографическая ссылка | E. Silva, L. Herrera, A.M. Edwards, J.R. De la Fuente, E. Lissi, Enhancement of riboflavin-mediated photooxidation of glucose 6-phosphate dehydrogenase by urocanic acid, Photochem. Photobiol., 2005, 81, 206, 211 |
| Библиографическая ссылка | S. Criado, C. Guardianelli, J. Tuninetti, P. Molina, N.A. Garcia, Scavenging of photogenerated oxidative species by antimuscarinic drugs: atropine and derivatives, Redox Rep., 2002, 7, 385, 394 |
| Библиографическая ссылка | W.A. Massad, S. Bertolotti, N. Garcia, 2, Photochem. Photobiol., 2004, 79, 428, 433 |
| Библиографическая ссылка | A. Ramu, M.M. Mehta, The riboflavin-mediated photooxidation of doxorubicin, Cancer Chemoth. Pharm., 2000, 46, 449, 458 |
| Библиографическая ссылка | K. Uekama, T. Irie, F. Hirayama, F. Yoneda, Riboflavin-sensitized photooxidation of phenothiazines in aqueous solution by laser-irradiation, Chem. Pharm. Bull., 1979, 27, 1039, 1042 |
| Библиографическая ссылка | M.J. Akhtar, M. Ataullah, I. Ahmad, Effect of riboflavin on the photolysis of folic acid in aqueous solution, J. Pharm. Biomed. Anal., 2000, 23, 1039, 1044 |
| Библиографическая ссылка | K. Tatsumi, H. Ichikawa, S. Wada, Flavin-sensitized photooxidation of substituted phenols in natural water, J. Contam. Hydrol., 1992, 9, 207, 219 |
| Библиографическая ссылка | S. Caffieri, Furocoumarin photolysis: chemical and biological aspects, Photochem. Photobiol. Sci., 2002, 1, 149, 157 |
| Библиографическая ссылка | K. Huvaere, K. Olsen, M.L. Andernon, L.H. Skibsted, Riboflavin-sensitized photooxidation of isohumulones, Photochem. Photobiol. Sci., 2004, 3, 337, 340 |
| Библиографическая ссылка | K. Huvaere, B. Sinnaeve, J.V. Boexlaer, D. De Keukeleire, Photooxidative degradation of beer bittering principles: product analysis with respect to lightstruck flavour formation, Photochem. Photobiol. Sci., 2004, 3, 854, 858 |
| Библиографическая ссылка | A. Heyerick, K. Huvaere, D. De Keukeleire, M.D.E. Forbes, Fate of flavins in sensitized photodegradation of isohumulones reduced derivatives: studies on formation of radicals via EPR combined with detailed product analyses, Photochem. Photobiol. Sci., 2005, 4, 412, 419 |
| Библиографическая ссылка | E. Silva, M. Jopai, A.M. Edwards, E. Lemp, J.R. De la Fuente, F. Lissi, 2,, Photochem. Photobiol., 2002, 75, 585, 590 |
| Библиографическая ссылка | E. Knobloch, F. Mandys, R. Hodr, R. Hujer, R. Mader, Study of the mechanism of the photoisomerization and photooxidation of bilirubin using a model for the phototherapy of hyperbilirubinemia, J. Chromatogr., 1991, 566, 89, 99 |
| Библиографическая ссылка | E. Silva, T. Gonzalez, A.M. Edwards, F. Zuloaga, Visible light induced lipoperoxidation of a parenteral nutrition fat emulsion sensitized by flavins, J. Nutr. Biochem., 1998, 9, 149, 154 |
| Библиографическая ссылка | I. Ahmad, G. Tollin, Flavin triplet quenching and semiquinone formation by aliphatic α-substituted acetic acids: intermediates in flavin sensitized photodecarboxylation, Photochem. Photobiol., 1981, 34, 441, 445 |
| Библиографическая ссылка | M. Novak, A. Miller, T.C. Bruce, G. Tollin, The mechanism of flavin 4a substitution which accompanies photolytic decarboxylation of α-substituted acetic acids. Carbanion vs. radical intermediates, J. Am. Chem. Soc., 1980, 102, 1465, 1467 |
| Библиографическая ссылка | K. Miyake, Y. Masaki, I. Miyamoto, S. Yanagida, T. Ohno, A. Yoshimura, C. Pac, Flavin-photosensitized monomerization of dimethylthymine cyclobutane dimer in the presence of magnesium perchlorate, Photochem. Photobiol., 1993, 58, 631, 636 |
| Библиографическая ссылка | R.F. Hartman, S.D. Rose, P.J. Pouwels, R. Kaptein, Flavin-sensitized photochemically induced dynamic nuclear polarization detection of pyrimidine dimer radicals, Photochem. Photobiol., 1992, 56, 305, 310 |
| Библиографическая ссылка | O.W. Parks, Photodegradation of sulpha drugs by fluorescent light, J. Assoc. Off. Anal. Chem., 1985, 68, 1232, 1234 |
| Библиографическая ссылка | M.V. Encinas, S.G. Bertolotti, C.M. Previtali, The interaction of ground and excited states of lumichrome with aliphatic and aromatic amines in methanol, Helv. Chim. Acta, 2002, 85, 1427, 1438 |
| Библиографическая ссылка | R.P. Patel, F.K. Soni, Photolysis of cyanocobalamin in the presence of riboflavin, Indian J. Pharm., 1964, 26, 35, 37 |
| Библиографическая ссылка | I. Ahmad, W. Hussain, Multicomponent spectrophotometric assay of cyanocobalamin, hydroxocobalamin and riboflavin, Pak. J. Pharm. Sci., 1992, 5, 2, 121, 127 |
| Библиографическая ссылка | I.A. Ansari, F.H.M. Vaid, I. Ahmad, Spectral study of photolysis of aqueous cyanocobalamin solutions in presence of vitamins B and C, Pak. J. Pharm. Sci., 2004, 17, 2, 83, 93 |
| Библиографическая ссылка | H. Cui, H.M. Hwang, K. Zeng, H. Glover, H. Yu, Y. Liu, Riboflavin-photosensitized degradation of atrazine in a freshwater environment, Chemosphere, 2002, 47, 991, 999 |
| Библиографическая ссылка | H. Glover, H.M. Hwang, K. Zeng, Effect of riboflavin photoproducts on microbial activity during photosensitization of atrazine transformation, Environ. Toxicol., 2003, 18, 361, 367 |
| Библиографическая ссылка | E. Haggi, S. Bertolotti, S. Miskoski, F. Amat-Guerri, N.A. Garcia, Environmental photodegradation of pyrimidine fungicides â Kinetics of the visible-light-promoted interactions between riboflavin and 2-amino-4-hydroxy-6-methylpyrimidine, Can. J. Chem., 2002, 80, 62, 67 |
| Библиографическая ссылка | W. Massad, S. Criado, S. Bertolotti, A. Pajares, J. Gianotti, J.P. Escalada, F. Amat-Guerri, N.A. Garcia, Photodegradation of the herbicide norflurazon sensitized by riboflavin. A kinetic and mechanistic study, Chemosphere, 2004, 57, 455, 461 |
| Библиографическая ссылка | P.P. Fu, S.-H. Cheng, L. Coop, Q. Xia, S.J. Culp, W.H. Tollesen, W.G. Wamer, P.C. Howard, Photoreaction, phototoxicity, and photocarcinogenicity of retinoids, J. Environ. Sci. Health Part C: Environ., 2003, 21, 165, 197 |
| Библиографическая ссылка | M. Korycka-Dahl, T. Richardson, Photodegradation of DNA with fluorescent light in the presence of riboflavin and photoprotection by flavin-triplet state quenchers, Biochim. Biophys. Acta, 1980, 610, 229, 234 |
| Библиографическая ссылка | P. Burgstaller, T. Hermann, C. Huber, E. Westhof, M. Famulok, Isoalloxazine derivatives promote photocleavage of natural RNAs at G U base pairs embedded within helicles, Nucleic Acids Res., 1997, 25, 4018, 4027 |
| Библиографическая ссылка | M.Y. Jung, K.H. Lee, S.Y. Kim, Riboflavin-sensitized photochemical changes in beta-lactoglobulin in an aqueous buffer solution as affected by ascorbic acid, J. Agric. Food Chem., 2000, 48, 3847, 3850 |
| Библиографическая ссылка | F. Corbin III, Pathogenic inactivation of blood components. Current status and introduction of an approach using riboflavin as a photosensitizer, Int. J. Hematol., 2002, 76, 253, 257 |
| Библиографическая ссылка | A.M. Edwards, E. Silva, Effect of visible light on selected enzymes: vitamins and amino acids, J. Photochem. Photobiol. B: Biol., 2001, 63, 126, 131 |
| Библиографическая ссылка | A. Saha, Photo-induced inactivation of dihydroorotate dehydrogenase in dilute aqueous solution, Int. J. Radiat. Biol., 1997, 72, 55, 61 |
| Библиографическая ссылка | A. Mahns, I. Melchheier, C.V. Suschek, H. Sies, L.O. Klotz, Irradiation of cells with ultraviolet-A (320â 400) in the presence of cell culture medium elicits biological effects due to extracellular generation of hydrogen peroxide, Free Radical Res., 2003, 37, 391, 397 |
| Библиографическая ссылка | A.M. Edwards, F. Barredo, E. Silva, A.E. De Ioannes, M.I. Becker, Apoptosis induction in nonirradiated human HL-60 and murine NSO/2 tumor cells by photoproducts of indole-3-acetic acid and riboflavin, Photochem. Photobiol., 1999, 70, 645, 649 |
| Библиографическая ссылка | M. Diaz, M.I. Becker, A.E. De Ioannes, E. Silva, Development of photoinduced adduct: reactivity to eye lens proteins, Photochem. Photobiol., 1996, 63, 762, 767 |
| Библиографическая ссылка | R. Ugarte, A.M. Edwards, M.S. Diez, A. Valenzuela, E. Silva, Riboflavin-photosensitized anaerobic modification of rat lens proteins. A correlation with age-related changes, J. Photochem. Photobiol. B Biol., 1992, 13, 161, 168 |
| Библиографическая ссылка | S.P. Baba, D.K. Patel, B. Bano, Modification of sheep plasma kininogen by free radicals, Free Radical Res., 2004, 38, 393, 403 |
| Библиографическая ссылка | G. Porcal, S.G. Bertolotti, C.M. Previtali, M.V. Encinas, Electron transfer quenching of singlet and triplet excited states of flavins and lumichrome by aromatic and aliphatic electron donors, Phys. Chem. Chem. Phys., 2003, 5, 4123, 4128 |
| Библиографическая ссылка | A. Yoshimura, T. Ohno, Lumiflavin-sensitized photooxygenation of indole, Photochem. Photobiol., 1988, 48, 561, 565 |
| Библиографическая ссылка | P.F. Heelis, C.A. Rowley-Williams, R.F. Hartman, S.D. Rose, Detection of a reduced-flavin triplet state in free flavins and DNA photolyase, J. Photochem. Photobiol. B Biol., 1994, 23, 155, 159 |
| Библиографическая ссылка | E. DeRitter, Vitamins in pharmaceutical formulations, J. Pharm. Sci., 1982, 71, 1073, 1096 |
| Библиографическая ссылка | M.C. Allwood, Compatibility and stability of TPN mixtures in big bags, J. Clin. Pharm. Ther., 1984, 9, 181, 198 |
| Библиографическая ссылка | M.C. Allwood, M.C.J. Kearney, Compatibility and stability of additives in parenteral nutrition admixtures, Nutrition, 1998, 14, 697, 706 |
| Библиографическая ссылка | P.C. Buxton, S.M. Conduit, J. Hathaway, Stability of parentrovit in infusion fluids, Br. J. Intravenous Ther., 1983, 4, 5, 12 |
| Библиографическая ссылка | M.F. Chen, H.W. Boyce, L. Triplett, Stability of the B vitamins in mixed parenteral nutrition solution, JPEN, 1983, 7, 462, 464 |
| Библиографическая ссылка | J.L. Smith, J.E. Canham, P.A. Wells, Effect of phototherapy light, sodium bisulfite and pH on vitamin stability in total parenteral nutrition admixtures, JPEN, 1988, 12, 394, 402 |
| Библиографическая ссылка | H.J. Martens, Stability of water soluble vitamins in various infusion bags, Krankenhauspharmazie, 1989, 10, 359, 361 |
| Библиографическая ссылка | X.C. Zhan, G.K. Yin, Obtaining natural light photostability of drugs from lamp light exposure experiments, Acta Pharm. Sin., 1992, 27, 544, 548 |
| Библиографическая ссылка | K. Yamaoka, Y. Nakajima, T. Terashima, Stability of vitamins in TPN mixture in a double-chambered bag, Jpn. J. Hosp. Pharm., 1995, 21, 357, 364 |
| Библиографическая ссылка | D.B. Min, J.M. Boff, Chemistry and reactions of singlet oxygen in foods, CRFSFS, 2002, 1, 58, 72 |
| Библиографическая ссылка | G. Casini, N. De Laurentis, N. Maggi, S. Ottolino, Protective effect of hydroxybenzoic acid esters on the photodegradation of riboflavin, Farm. Ed. Prat., 1981, 36, 553, 558 |
| Библиографическая ссылка | A.F. Asker, M.J. Habib, Effect of certain Stabilizers on photobleaching of riboflavin solutions, Drug. Dev. Ind. Pharm., 1990, 16, 149, 156 |
| Библиографическая ссылка | M.J. Habib, A.F. Asker, Photostabilization of riboflavin by incorporation into liposomes, J. Parent. Sci. Technol., 1991, 45, 124, 127 |
| Библиографическая ссылка | Y.L. Loukas, P. Jayasekera, G. Gregoriadis, Novel liposome-based multicomponent systems for the protection of photolabile agents, Int. J. Pharm., 1995, 117, 85, 94 |
| Библиографическая ссылка | Y.L. Loukas, V. Vraka, G. Gregoriadis, Use of nonlinear least-square model for the kinetic determination of the stability constant of cyclodextrin inclusion complexes, Int. J. Pharm., 1996, 144, 225, 231 |
| Библиографическая ссылка | H.H. Tonnesen, J. Karlsen, A comment on photostability testing according to ICH guidelines: calibration of light sources, PharmEuropa, 1997, 9, 735, 736 |
