Photosensitized Oxidation of Oxopurines by Rose Bengal

Photosensitized oxidations of oxopurines (OP) as caffeine, theophylline, theobromine and 1,3,7-trimethyluric acid (TMU) by Rose Bengal were investigated. In all cases photooxidations occur by a type II mechanism. Reactive and nonreactive 1O2 quenching rate constants by OP were determined in differen...

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Autor principal: Murgida, D.H
Otros Autores: Aramendía, P.F, Erra Balsells, R.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: American Society for Photobiology 1998
Acceso en línea:Registro en Scopus
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040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a PHCBA 
100 1 |a Murgida, D.H. 
245 1 0 |a Photosensitized Oxidation of Oxopurines by Rose Bengal 
260 |b American Society for Photobiology  |c 1998 
270 1 0 |m Murgida, D.H.; Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: murgida@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Ravanat, J.L., Berger, M., Benard, F., Langlois, R., Quellet, R., Van Lier, J.E., Cadet, J., Phthalocyanine and naphthalocyanine photosensitized oxidation of 2′-deoxyguanosine: Distinct type I and type II products (1992) Photochem. Photobiol., 55, pp. 809-814 
504 |a Morin, B., Cadet, J., Benzophenone photosensitization of 2′-N-deoxyguanosine: Characterization of the 2R and 2S diastereoisomers of 1-(2-deoxy-b-erythro-pentafuranosyl)-2-methoxy-4,5-imidazolidinedione. A model system for the investigation of photosensitized formation of DNA-protein crosslinks (1994) Photochem. Photobiol., 60, pp. 102-109 
504 |a Cadet, J., Berger, M., Buchko, G.W., Joshi, P.C., Raoul, S., Ravanat, J.L., 2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-β-D-erythro-peritafuranosyl) amino]-5-(2H)-oxazolone: A novel and predominant radical oxidation product of 3′,5′-di-O-acetyl-2′-deoxyguanosine (1994) J. Am. Chem. Soc., 116, pp. 7403-7404 
504 |a Morin, B., Cadet, J., Chemical aspects of the benzophenone-photosensitized formation of two lysine-2′-deoxyguanosine cross links (1995) J. Am. Chem. Soc., 117, pp. 12408-12415 
504 |a Raoul, S., Cadet, J., Photosensitized reaction of 8-oxo-7,8-dihydro-2′-deoxyguanosine: Identification of 1-(2-deoxy-β-D-erythro-pentofuranosil)cyanuric acid as the major singlet oxygen oxidation product (1996) J. Am. Chem. Soc., 118, pp. 1892-1898 
504 |a Adam, W., Saha-Möller, C.R., Schönberger, A., Berger, M., Cadet, J., Formation of 7,8-dihydro-8-oxoguanine in the 1,2-dioxetane-induced oxidation of calf thymus DNA: Evidence for photosensitized DNA damage by thermally generated triplet ketones in the dark (1995) Photochem. Photobiol., 62, pp. 231-238 
504 |a Adam, W., Saha-Möller, C.R., Schönberger, A., Photooxidation of 8-oxo-7,8-dihydro-2′-deoxyguanosine by thermally generated triplet-excited ketones from 3-(hydroxymetlhyl)-3,4.4-trimethyl-1,2-dioxetane and comparison with type I and type II photosensitizers (1996) J. Am. Chem. Soc., 118, pp. 9233-9238 
504 |a Adam, W., Saha-Möller, C.R., Schönberger, A., Type I and type II photosensitized oxidative modification of 2′-deoxyguanosine (dGuo) by triplet-excited ketones generated thermally from the 1,2-dioxetane HTMD (1997) J. Am. Chem. Soc., 119, pp. 719-723 
504 |a Sheu, C., Foote, C.S., Endoperoxide formation in a guanosine derivative (1993) J. Am. Chem. Soc., 115, pp. 10446-10447 
504 |a Sheu, C., Foote, C.S., Photosensitized oxygenation of a 7,8-dihydro-8-oxoguanosine derivative. Formation of dioxetane and hydroperoxide intermediates (1995) J. Am. Chem. Soc., 117, pp. 474-477 
504 |a Sheu, C., Foote, C.S., Reactivity towards singlet oxygen of a 7,8-dihydro-8-oxoguanosine ("8-hydroxyguanosine") formed by photooxidation of a guanosine derivative (1995) J. Am. Chem. Soc., 117, pp. 6439-6442 
504 |a Devasagayam, T.P.A., Steenken, S., Obendorf, M.W., Schulz, W.A., Sies, H., Formation of 8-hydroxy(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen (1991) Biochemistry, 25, pp. 3283-6289 
504 |a Boiteux, S., Gajewski, E., Laval, J., Dizdaroglu, M., Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): Excision of purine lesions in DNA produced by ionizing radiation or photosensitization (1992) Biochemistry, 31, pp. 106-110 
504 |a Simon, M.I., Van Vunakis, H., The dye-sensitized photooxidation of purine and pyrimidine derivatives (1964) Arch. Biochem. Biophys., 105, pp. 197-206 
504 |a Clennan, E.L., Synthetic and mechanistic aspects of 1,3-diene photooxidation (1991) Tetrahedron, 47, pp. 1343-1382 
504 |a Murgida, D.H., Aramendía, P.F., Erra-Balsells, R., Benzophenone photosensitized reactions of xanthinic compounds. A mechanistic study (1998) Photochem. Photobiol., 67, pp. 487-494 
504 |a Murgida, D.H., Bilmes, G.M., Erra-Balsells, R., Photoacoustic determination of energy content and quantum yield of formation of transient states (1994) J. Phys., 4, pp. C7-417-420 
504 |a Murgida, D.H., Bilmes, G.M., Erra-Balsells, R., New photocalorimetric references for UV excitation (1996) Chem. Phys. Lett., 250, pp. 198-202 
504 |a Murgida, D.H., Bilmes, G.M., Erra-Balsells, R., A photophysical study of purines and theophylline by using laser induced photoacoustic spectroscopy (1996) Photochem. Photobiol., 64, pp. 777-784 
504 |a Acs, A., Schmidt, R., Brauer, H.D., Mesodiphenylhelianthrene. The most reactive singlet oxygen acceptor (1983) Photochem. Photobiol., 38, pp. 527-531 
504 |a Brauer, H.D., Schmidt, R., Gauglitz, G., Hubig, S., Chemical actinometry in the visible (475-610 nm) by mesodiphenylhelianthrene (1983) Photochem. Photobiol., 37, pp. 595-598 
504 |a (1996) Hyperchem Release 5.0 for Windows, , Autodesk, Ontario, Canada 
504 |a Wilkinson, F., Helman, W.P., Ross, A.B., Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation (1995) J. Phys. Chem. Ref. Data, 24, pp. 663-1021 
504 |a Lambert, C.R., Kochevar, I.E., Does rose bengal triplet generate superoxide anion? (1996) J. Am. Chem. Soc., 118, pp. 3297-3298 
504 |a Wintgens, V., Scaiano, J.C., Linden, S.M., Neckers, D.C., Transient phenomena in the laser flash photolysis of the rose bengal C-2′ ethyl ester C-6 sodium salt (1989) J. Org. Chem., 54, pp. 5242-5246 
504 |a Lambert, C., Sarna, T., Truscott, T.G., Rose bengal radicals and their reactivity (1990) J. Chem. Soc. Faraday Trans., 86, pp. 3879-3882 
504 |a Stiel, H., Teuchner, K., Paul, A., Leupold, D., Kochevar, I.E., Quantitative comparision of excited state properties and intensity-dependent photosensitization by rose bengal (1996) J. Photochem. Photobiol. B Biol., 33, pp. 245-254 
504 |a Murov, S.L., Carmichael, I., Hug, G.L., (1993) Handbook of Photochemistry, , Marcel Dekker, New York 
504 |a Gorman, A.A., Rodgers, M.A.J., Singlet oxygen (1989) Handbook of Organic Photochemistry, 2. , (Edited by J. C. Scaiano), Chapter 10. CRC Press, Boca Raton, FL 
504 |a Reichardt, C., (1979) Solvent Effects in Organic Chemistry, , Verlag Chemie, Weinheim 
504 |a Marcus, Y., The properties of organic liquids that are relevant to their use as solvating solvents (1993) Chem. Soc. Rev., pp. 409-416 
504 |a Wilkinson, F., Phillip Helman, W., Ross, A.B., Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution (1993) J. Phys. Chem. Ref. Data, 22, pp. 113-262 
504 |a Manring, L.E., Kanner, R.C., Foote, C.S., Chemistry of singlet oxygen. 43. Quenching by conjugated olefins (1983) J. Am. Chem. Soc., 105, pp. 4707-4710 
504 |a Manring, L.E., Foote, C.S., Chemistry of singlet oxygen. 44. Mechanism of photooxidation of 2,5-dimethylhexa-2,4-diene (1983) J. Am. Chem. Soc., 105, pp. 4710-4717 
504 |a Liang, J.L., Gu, C.L., Kacher, M.L., Foote, C.S., Chemistry of singlet oxygen. 45. Mechanism of the photooxidation of sulfides (1983) J. Am. Chem. Soc., 105, pp. 4717-4721 
520 3 |a Photosensitized oxidations of oxopurines (OP) as caffeine, theophylline, theobromine and 1,3,7-trimethyluric acid (TMU) by Rose Bengal were investigated. In all cases photooxidations occur by a type II mechanism. Reactive and nonreactive 1O2 quenching rate constants by OP were determined in different solvents. Based on the correlations of the rate constants with different solvent parameters (α, β, ET[30], AN, DN, π*, ∈), the initial formation of an exciplex between 1O2 and OP is proposed that evolves to a zwitterionic transition state. Some reaction products were characterized, among them 3-methyl-5-(methylamine)-1,5-dehydrohydantoin was obtained as the main photooxidation product of TMU. A reaction mechanism is proposed for the formation of this and other reaction products.  |l eng 
593 |a Depto. de Quim. Orgánica, Universidad de Buenos Aires, Buenos Aires, Argentina 
593 |a INQUIMAE, Depto. Quim. Inorg., Analitica Q., Universidad de Buenos Aires, Buenos Aires, Argentina 
593 |a Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina 
700 1 |a Aramendía, P.F. 
700 1 |a Erra Balsells, R. 
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