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Gonzalez, M.M.; Salum, M.L.; Gholipour, Y.; Cabrerizo, F.M.; Erra-Balsells, R. "Photochemistry of norharmane in aqueous solution" (2009) Photochemical and Photobiological Sciences. 8(8):1139-1149
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Abstract:

The photochemistry of norharmane (9H-pyrido[3,4-b]indole) in acidic (pH 5.0 ± 0.1) and alkaline (pH 10.0 ± 0.1) aqueous solutions was studied. The photochemical reactions were monitored by TLC, UV/VIS absorption spectroscopy, high-performance liquid chromatography (HPLC), electronic ionization-mass spectrometry (EI-MS), UV-laser desorption/ionization-time of flight-mass spectrometry (UV-LDI-TOF-MS) and an enzymatic method for H 2O2 determination. The neutral (nHoN) and the protonated (nHoH+) forms of norharmane irradiated under Ar atmosphere were photostable, but they suffered a photochemical transformation in the presence of O2, yielding as photoproducts norharmane dimers, trimers and tetramers. nHoN shown to be more photostable than nHoH+. The nHoH+ and nHoN consumption quantum yields were 1.82 × 10 -3 and 0.51 × 10-3, respectively, and the mechanisms involved in its photochemistry are discussed. H2O2 and singlet oxygen (1O2) were also detected and quantified in irradiated solutions of norharmane, and their role in the photochemistry of norharmane is discussed. © 2009 The Royal Society of Chemistry and Owner Societies.

Registro:

Documento: Artículo
Título:Photochemistry of norharmane in aqueous solution
Autor:Gonzalez, M.M.; Salum, M.L.; Gholipour, Y.; Cabrerizo, F.M.; Erra-Balsells, R.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, 3p, 1428 Buenos Aires, Argentina
Plant Biophysics/Biochemistry Research Laboratory, College of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama 790-8566, Japan
Palabras clave:beta carboline; hydrogen peroxide; aqueous solution; article; atmosphere; high performance liquid chromatography; mass spectrometry; matrix assisted laser desorption ionization time of flight mass spectrometry; molecular stability; photochemistry; priority journal; quantum yield; thin layer chromatography; ultraviolet spectroscopy; Harmine; Hydrogen Peroxide; Hydrogen-Ion Concentration; Mass Spectrometry; Mutagens; Oxygen; Photochemistry; Reactive Oxygen Species; Singlet Oxygen; Solutions; Spectrometry, Fluorescence; Water
Año:2009
Volumen:8
Número:8
Página de inicio:1139
Página de fin:1149
DOI: http://dx.doi.org/10.1039/b822173a
Título revista:Photochemical and Photobiological Sciences
Título revista abreviado:Photochem. Photobiol. Sci.
ISSN:1474905X
CODEN:PPSHC
CAS:beta carboline, 244-63-3; hydrogen peroxide, 7722-84-1; Harmine, 442-51-3; Hydrogen Peroxide, 7722-84-1; Mutagens; Oxygen, 7782-44-7; Reactive Oxygen Species; Singlet Oxygen, 17778-80-2; Solutions; Water, 7732-18-5; norharman, 244-63-3
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v8_n8_p1139_Gonzalez

Referencias:

  • De Meester, C., (1995) Mutat. Res., 339, p. 139. , -153
  • Fekkes, D., Schouten, M.J., Pepplinkhuizen, L., Bruinvels, J., Lauwers, W., Brinkman, U.A., (1992) Lancet, 339, p. 506
  • Breyer-Pfaff, U., Wiatr, G., Stevens, I., Gaertner, H., Mundle, G., Mann, K., (1996) Life Sci., 58, p. 1425. , -1432
  • Spijkerman, R., Van Den Eijnden, R., Van De Mheen, D., Bongers, I., Fekkes, D., (2002) Eur. Neuropsychopharmacol., 12, p. 61. , -71
  • Kuhn, W., Muller, T., Große, H., Rommelspacher, H., (1996) J. Neural. Transm., 103, p. 1435. , -1440
  • Hiroaki, N., (2003) Mutat. Res., 541, p. 123. , -136
  • Mori, T., Nakagawa, A., Kobayashi, N., Hashimoto, M.W., Wakabayashi, K., Shimoi, K., Kinae, N., (1998) J. Radiat. Res., 39, p. 21. , -33
  • Towers, G.H., Hudson, J.B., (1987) Photochem. Photobiol., 46, p. 61. , -66
  • Varela, A.P., Burrows, H.D., Douglas, P., Da Graa Miguel, M., (2001) J. Photochem. Photobiol., A, 146, p. 29. , -36
  • Reyman, D., Tapia, M., Caicedo, C., Viñas, M., (2003) Biophys. Chem., 104, p. 683. , -696
  • Reyman, D., Viñas, M., Poyato, J., Pardo, A., (1997) J. Phys. Chem. A, 101, p. 768. , -775
  • Becker, R.S., Ferreirar, L.F.V., Elisei, F., MacHado, I., Latterini, L., (2005) Photochem. Photobiol., 81, p. 1195. , -1204
  • Biondic, M.C., Erra-Balsells, R., (1994) J. Photochem. Photobiol., A, 77, p. 149. , -159
  • Biondic, M.C., Erra-Balsells, R., (1992) J. Chem. Soc., Perkin Trans. 2, p. 1049. , -1058
  • Biondic, M.C., Erra-Balsells, R., (1997) J. Chem. Soc., Perkin Trans. 2, p. 1323. , -1327
  • Olba Torrent, A., Tomas Vert, F., Zabala Sanchez, I., Medina Casamayor, P., (1987) J. Photochem., 37, p. 109. , -116
  • Tapia, M., Reyman, D., Vinas, M., Arroyo, A., Poyato, J., (2003) J. Photochem. Photobiol., A, 156, p. 1. , -7
  • Balón, M., Angulo, G., Carmona, C., Muñoz, M., Guardado, P., Galán, M., (2002) Chem. Phys., 276, p. 155. , -165
  • Carmona, C., Galán, M., Angulo, G., Muñoz, M., Guardado, P., Balón, M., (2000) Phys. Chem. Chem. Phys., 2, p. 5076. , -5083
  • Carmona, C., Balón, M., Galán, M., Angulo, G., Guardado, P., Muñoz, M., (2001) J. Phys. Chem. A, 105, p. 10334. , -10338
  • Wolfbeis, O.S., Fürlinger, E., (1982) Z. Phys. Chem., Neue Folge, 129, p. 171. , -183
  • Muñoz, M., Balón, M., Hidalgo, J., Carmona, C., Pappalardo, R.R., Sanchez Marcos, E., (1991) J. Chem. Soc., Perkin Trans. 2, p. 1729. , -1734
  • Krishnamurthy, M., Kumar Dogra, S., (1986) J. Chem. Soc., Perkin Trans. 2, p. 1247. , -1251
  • Pardo, A., Reyman, D., Poyato, J.M.L., Medina, F., (1992) J. Lumin., 51, p. 269. , -274
  • Draxler, S., Lippitsch, M.E., (1993) J. Phys. Chem., 97, p. 11493. , -11496
  • Tomas Vert, F., Zabala Sanchez, I., Olba Torrent, A., (1983) J. Photochem., 23, p. 355. , -368
  • Balon, M., Munoz, M.A., Guardado, P., Carmona, C., (1996) Photochem. Photobiol., 64, p. 531. , The presence of an additional proton, interacting with the pyridinic nitrogen, increases the p character of the n electron pair located at the pyridinic nitrogen. As a consequence, the probability of the interaction of this electron pair with the π aromatic system is higher and a clear bathocromic shift effect (resonance effect) is observed in the absorption spectrum of nHoH+ (i.e. spectrum recorded at pH 5.0, λMAX = 370 nm) with respect to that of nHoN (i.e. spectrum recorded at pH 10.0, λMAX = 348 nm) -536
  • Wilkinson, F., Helman, W.P., Ross, A.B., (1993) J. Phys. Chem. Ref. Data, 22, p. 113
  • Turro, N.J., (1978) Modern Molecular Photochemistry, , The Benjaming/Cummings Publishing Co., Inc., California
  • Clennan, E.L., (2000) Tetrahedron, 56, p. 9151. , -9179
  • Chae, K.H., Ham, H.S., (1986) Bull. Korean Chem. Soc., 7, p. 478. , -479
  • Ogilby, P.R., Foote, C.S., (1983) J. Am. Chem. Soc., 105, p. 3423. , -3430
  • Erra-Balsells, R., Frasca, A.R., (1983) Tetrahedron, 39, p. 33. , -39
  • Perkin, Jr.W.H., Tucker, S.H., (1921) J. Chem. Soc., Trans., 119, p. 216. , -225
  • Erra-Balsells, R., Frasca, A.R., (1984) Tetrahedron Lett., 25, p. 5363. , -5366
  • Erra-Balsells, R., Frasca, A.R., (1985) An. Asoc. Quim. Argentina, 73, p. 207. , -214
  • Erra-Balsells, R., (1988) Magn. Reson. Chem., 26, p. 1109. , -1113
  • Sakurovs, R., Ghiggino, K.P.J., (1982) J. Photochem., 18, p. 1. , -8
  • Braun, A.M., Maurette, M.T., Oliveros, E., (1991) Photochemical Technology, , John Wiley & Sons, Chichester
  • Suárez, G., Cabrerizo, F.M., Lorente, C., Thomas, A.H., Capparelli, A.L., (2000) J. Photochem. Photobiol., A, 132, p. 53. , -57
  • Allain, C.C., Poon, L.S., Chan, C.S.G., Richmond, W., Fu, P.C., (1974) Clin. Chem., 20, p. 470. , -475
  • Flegg, H.M., (1973) Ann. Clin. Biochem., 10, p. 79. , -84
  • Buxton, G.V., Greenstock, C.L., Helman, W.P., Ross, A.B., (1988) J. Phys. Chem. Ref. Data, 17, p. 513. , -886
  • Arnbjerg, J., Johnsen, M., Frederiksen, P.K., Braslavsky, S.E., Ogilby, P.R., (2006) J. Phys. Chem. A, 110, p. 7375. , -7385
  • Marti, C., Jürgens, O., Cuenca, O., Casals, M., Nonell, S.J., (1996) J. Photochem. Photobiol., A, 97, p. 11. , -18
  • Mardelli, M., Olmsted, J., (1977) J. Photochem., 7, p. 277. , -285
  • Eastman, J.W., (1967) Photochem. Photobiol., 6, p. 55. , -72
  • Nonami, H., Tanaka, K., Fukuyama, Y., Erra-Balsells, R., (1998) Rapid Commun. Mass Spectrom., 12, p. 285. , -296

Citas:

---------- APA ----------
Gonzalez, M.M., Salum, M.L., Gholipour, Y., Cabrerizo, F.M. & Erra-Balsells, R. (2009) . Photochemistry of norharmane in aqueous solution. Photochemical and Photobiological Sciences, 8(8), 1139-1149.
http://dx.doi.org/10.1039/b822173a
---------- CHICAGO ----------
Gonzalez, M.M., Salum, M.L., Gholipour, Y., Cabrerizo, F.M., Erra-Balsells, R. "Photochemistry of norharmane in aqueous solution" . Photochemical and Photobiological Sciences 8, no. 8 (2009) : 1139-1149.
http://dx.doi.org/10.1039/b822173a
---------- MLA ----------
Gonzalez, M.M., Salum, M.L., Gholipour, Y., Cabrerizo, F.M., Erra-Balsells, R. "Photochemistry of norharmane in aqueous solution" . Photochemical and Photobiological Sciences, vol. 8, no. 8, 2009, pp. 1139-1149.
http://dx.doi.org/10.1039/b822173a
---------- VANCOUVER ----------
Gonzalez, M.M., Salum, M.L., Gholipour, Y., Cabrerizo, F.M., Erra-Balsells, R. Photochemistry of norharmane in aqueous solution. Photochem. Photobiol. Sci. 2009;8(8):1139-1149.
http://dx.doi.org/10.1039/b822173a