Abstract:
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.
Registro:
Documento: |
Artículo
|
Título: | Photosensitized Oxidation of Oxopurines by Rose Bengal |
Autor: | Murgida, D.H.; Aramendía, P.F.; Erra Balsells, R. |
Filiación: | Depto. de Quim. Orgánica, Universidad de Buenos Aires, Buenos Aires, Argentina INQUIMAE, Depto. Quim. Inorg., Analitica Q., Universidad de Buenos Aires, Buenos Aires, Argentina Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
|
Año: | 1998
|
Volumen: | 68
|
Número: | 4
|
Página de inicio: | 467
|
Página de fin: | 473
|
DOI: |
http://dx.doi.org/10.1111/j.1751-1097.1998.tb02501.x |
Título revista: | Photochemistry and Photobiology
|
Título revista abreviado: | Photochem. Photobiol.
|
ISSN: | 00318655
|
CODEN: | PHCBA
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00318655_v68_n4_p467_Murgida |
Referencias:
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Sheu, C., Foote, C.S., Endoperoxide formation in a guanosine derivative (1993) J. Am. Chem. Soc., 115, pp. 10446-10447
- 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
- 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
- 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
- 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
- Simon, M.I., Van Vunakis, H., The dye-sensitized photooxidation of purine and pyrimidine derivatives (1964) Arch. Biochem. Biophys., 105, pp. 197-206
- Clennan, E.L., Synthetic and mechanistic aspects of 1,3-diene photooxidation (1991) Tetrahedron, 47, pp. 1343-1382
- 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
- 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
- Murgida, D.H., Bilmes, G.M., Erra-Balsells, R., New photocalorimetric references for UV excitation (1996) Chem. Phys. Lett., 250, pp. 198-202
- 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
- Acs, A., Schmidt, R., Brauer, H.D., Mesodiphenylhelianthrene. The most reactive singlet oxygen acceptor (1983) Photochem. Photobiol., 38, pp. 527-531
- 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
- (1996) Hyperchem Release 5.0 for Windows, , Autodesk, Ontario, Canada
- 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
- Lambert, C.R., Kochevar, I.E., Does rose bengal triplet generate superoxide anion? (1996) J. Am. Chem. Soc., 118, pp. 3297-3298
- 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
- Lambert, C., Sarna, T., Truscott, T.G., Rose bengal radicals and their reactivity (1990) J. Chem. Soc. Faraday Trans., 86, pp. 3879-3882
- 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
- Murov, S.L., Carmichael, I., Hug, G.L., (1993) Handbook of Photochemistry, , Marcel Dekker, New York
- 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
- Reichardt, C., (1979) Solvent Effects in Organic Chemistry, , Verlag Chemie, Weinheim
- Marcus, Y., The properties of organic liquids that are relevant to their use as solvating solvents (1993) Chem. Soc. Rev., pp. 409-416
- 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
- 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
- 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
- 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
Citas:
---------- APA ----------
Murgida, D.H., Aramendía, P.F. & Erra Balsells, R.
(1998)
. Photosensitized Oxidation of Oxopurines by Rose Bengal. Photochemistry and Photobiology, 68(4), 467-473.
http://dx.doi.org/10.1111/j.1751-1097.1998.tb02501.x---------- CHICAGO ----------
Murgida, D.H., Aramendía, P.F., Erra Balsells, R.
"Photosensitized Oxidation of Oxopurines by Rose Bengal"
. Photochemistry and Photobiology 68, no. 4
(1998) : 467-473.
http://dx.doi.org/10.1111/j.1751-1097.1998.tb02501.x---------- MLA ----------
Murgida, D.H., Aramendía, P.F., Erra Balsells, R.
"Photosensitized Oxidation of Oxopurines by Rose Bengal"
. Photochemistry and Photobiology, vol. 68, no. 4, 1998, pp. 467-473.
http://dx.doi.org/10.1111/j.1751-1097.1998.tb02501.x---------- VANCOUVER ----------
Murgida, D.H., Aramendía, P.F., Erra Balsells, R. Photosensitized Oxidation of Oxopurines by Rose Bengal. Photochem. Photobiol. 1998;68(4):467-473.
http://dx.doi.org/10.1111/j.1751-1097.1998.tb02501.x