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Vignoni, M.; Cabrerizo, F.M.; Lorente, C.; Claparols, C.; Oliveros, E.; Thomas, A.H. "Photochemistry of dihydrobiopterin in aqueous solution" (2010) Organic and Biomolecular Chemistry. 8(4):800-810
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Abstract:

Dihydrobiopterin (H2Bip) and its oxidized analogue, biopterin (Bip), accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder in which the protection against UV radiation fails. The photochemistry of H2Bip was studied in neutral aqueous solutions upon UV-A irradiation (320-400 nm) at room temperature. The photochemical reactions were followed by UV/vis spectrophotometry, HPLC and enzymatic methods for hydrogen peroxide (H2O2) determination. Photoproducts were analyzed by means of electrospray ionization mass spectrometry. Under anaerobic conditions, excitation of H2Bip leads to the formation of at least two isomeric dimers with molecular masses equal to exactly twice the molecular mass of the reactant. This reaction takes place from the singlet excited state of the reactant. To the best of our knowledge, this is the first time that the photodimerization of a dihydropterin is reported. In the presence of air, the dimers are again the main photoproducts at the beginning of the reaction, but a small proportion of the reactant is converted into Bip. As the reaction proceeds and enough Bip accumulates in the solution, a photosensitized process starts, where Bip photoinduces the oxidation of H2Bip to Bip, and H 2O2 is formed. As a consequence, the rates of H 2Bip consumption and Bip formation increase as a function of irradiation time, resulting in an autocatalytic photochemical process. In this process, Bip in its triplet excited state reacts with the ground state of H 2Bip. The mechanisms involved are analyzed and the biological implications of the results are discussed. © The Royal Society of Chemistry 2010.

Registro:

Documento: Artículo
Título:Photochemistry of dihydrobiopterin in aqueous solution
Autor:Vignoni, M.; Cabrerizo, F.M.; Lorente, C.; Claparols, C.; Oliveros, E.; Thomas, A.H.
Filiación:Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de la Plata, Casilla de Correo 16 Sucursal 4, (1900) La Plata, Argentina
CIHIDECAR - CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2 3p, 1428 - Buenos Aires, Argentina
Service Commun de Spectrométrie de Masse (FR2599), Université de Toulouse (Paul Sabatier), 118 route de Narbonne, F-31062 Toulouse cédex 9, France
CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, Toulouse F-31077, France
Laboratoire des IMRCP, UMR CNRS 5623, Université de Toulouse (Paul Sabatier), 118 route de Narbonne, F-31062 Toulouse cédex 9, France
Palabras clave:Anaerobic conditions; Aqueous solutions; Autocatalytic; Biological implications; Biopterin; Electrospray ionization mass spectrometry; Enzymatic methods; Irradiation time; Neutral aqueous solution; Oxidation of H; Photochemical process; Photodimerization; Photoproducts; Room temperature; Singlet excited state; UV radiation; UV/vis spectrophotometry; Dimers; Electrospray ionization; Excited states; Hydrogels; Hydrogen peroxide; Irradiation; Mass spectrometry; Molecular mass; Oxidation; Radiation protection; Solutions; Ultraviolet radiation; Photochemical reactions; 7,8-dihydrobiopterin; biopterin; dihydrobiopterin; drug derivative; hydrogen peroxide; oxygen; water; article; chemistry; high performance liquid chromatography; human; methodology; oxidation reduction reaction; photochemistry; solution and solubility; ultraviolet spectrophotometry; Biopterin; Chromatography, High Pressure Liquid; Humans; Hydrogen Peroxide; Oxidation-Reduction; Oxygen; Pharmaceutical Solutions; Photochemistry; Solutions; Spectrophotometry, Ultraviolet; Water
Año:2010
Volumen:8
Número:4
Página de inicio:800
Página de fin:810
DOI: http://dx.doi.org/10.1039/b913095k
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CAS:biopterin, 22150-76-1; dihydrobiopterin, 6779-87-9; hydrogen peroxide, 7722-84-1; oxygen, 7782-44-7; water, 7732-18-5; 7,8-dihydrobiopterin, 6779-87-9; Biopterin, 22150-76-1; Hydrogen Peroxide, 7722-84-1; Oxygen, 7782-44-7; Pharmaceutical Solutions; Solutions; Water, 7732-18-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v8_n4_p800_Vignoni

Referencias:

  • Brown, D.J., (1988) The Chemistry of Heterocyclic Compounds, pp. 1-42. , John Wiley & Sons, New York
  • Pfleiderer, W., (1993) Chemistry and Biology of Pteridines and Folates, pp. 1-16. , Plenum Press, New York
  • Kappock, T.J., Caradonna, J.P., (1996) Chem. Rev., 96, pp. 2659-2756
  • Nichol, C.A., Smith, G.K., Duch, D.S., (1985) Annu. Rev. Biochem., 54, p. 729
  • Schallreuter, K.U., Moore, J., Wood, J.M., Beazley, W.D., Peters, E.M., Marles, L.K., Behrens-Williams, S.C., Thöny, B., (2001) J. Invest. Dermatol., 116, pp. 167-174
  • Schallreuter, K.U., Wood, J.M., Pittelkow, M.R., Gütlich, M., Lemke, K.R., Rödl, W., Swanson, N.N., Ziegler, I., (1994) Science, 263, pp. 1444-1446
  • Thomas, A.H., Lorente, C., Capparelli, A.L., Pokhrel, M.R., Braun, A.M., Oliveros, E., (2002) Photochem. Photobiol. Sci., 1, pp. 421-426
  • Lorente, C., Capparelli, A.L., Thomas, A.H., Braun, A.M., Oliveros, E., (2004) Photochem. Photobiol. Sci., 3, pp. 167-173
  • Rokos, H., Beazley, W.D., Schallreuter, K.U., (2002) Biochem. Biophys. Res. Commun., 292, pp. 805-811
  • Mengel, R., Pfleiderer, W., Knappe, W.R., (1977) Tetrahedron Lett., 18, pp. 2817-2820
  • Vignoni, M., Cabrerizo, F.M., Lorente, C., Thomas, A.H., (2009) Photochem. Photobiol., 85, pp. 365-373
  • Suárez, G., Cabrerizo, F.M., Lorente, C., Thomas, A.H., Capparelli, A.L., (2000) J. Photochem. Photobiol., A, 132, pp. 53-57
  • Lorente, C., Thomas, A.H., (2006) Acc. Chem. Res., 39, pp. 395-402
  • Petroselli, G., Bartsch, J.M., Thomas, A.H., (2006) Pteridines, 17, pp. 82-89
  • Thomas, A.H., Lorente, C., Capparelli, A.L., Martínez, C.G., Braun, A.M., Oliveros, E., (2003) Photochem. Photobiol. Sci., 2, pp. 245-250
  • Ito, K., Kawanishi, S., (1997) Biochemistry, 36, pp. 1774-1781
  • Petroselli, G., Erra-Balsells, R., Cabrerizo, F.M., Lorente, C., Capparelli, A.L., Braun, A.M., Oliveros, E., Thomas, A.H., (2007) Org. Biomol. Chem., 5, pp. 2792-2799
  • Petroselli, G., Dántola, M.L., Cabrerizo, F.M., Capparelli, A.L., Lorente, C., Oliveros, E., Thomas, A.H., (2008) J. Am. Chem. Soc., 130, pp. 3001-3011
  • Moore, J., Wood, J.M., Schallreuter, K.U., (2002) J. Raman Spectrosc., 33, pp. 610-617
  • Dántola, M.L., Schuler, T.M., Denofrio, M.P., Vignoni, M., Capparelli, A.L., Lorente, C., Thomas, A.H., (2008) Tetrahedron, 64, pp. 8692-8699
  • Dántola, M.L., Vignoni, M., Capparelli, A.L., Lorente, C., Thomas, A.H., (2008) Helv. Chim. Acta, 91, pp. 411-425
  • Pfleiderer, W., (1987) Biochemical and Clinical Aspects of Pteridines, pp. 3-21. , Walter de Gruyter & Co., Berlin, New York
  • Dántola, M.L., Thomas, A.H., Braun, A.M., Oliveros, E., Lorente, C., (2007) J. Phys. Chem. A, 111, pp. 4280-4288
  • Nixon, J.C., Lee, C.L., Milstien, S., Kaufman, S., Bartholomé, K., (1980) J. Neurochem., 35, pp. 898-904
  • Braun, A.M., Maurette, M.T., Oliveros, E., (1991) Photochemical Technology, pp. 85-88. , John Wiley & Sons, Chichester
  • Kuhn, H.J., Braslavsky, S.E., Schmidt, R., (2004) Pure Appl. Chem., 76, pp. 2105-2146
  • Allain, C.C., Poon, L.S., Chan, C.S.G., Richmond, W., Fu, P.C., (1974) Clin. Chem., 20, pp. 470-475
  • Flegg, H.M., (1973) Ann. Clin. Biochem., 10, pp. 79-84
  • Thomas, A.H., Suárez, G., Cabrerizo, F.M., Martino, R., Capparelli, A.L., (2000) J. Photochem. Photobiol., A, 135, pp. 147-154
  • Wood, J.M., Chavan, B., Hafeez, I., Schallreuter, K.U., (2004) Biochem. Biophys. Res. Commun., 325, pp. 1412-1417
  • Schallreuter, K.U., Elwary, S.M.A., Gibbons, N.C.J., Rokos, H., Wood, J.M., (2004) Biochem. Biophys. Res. Commun., 315, pp. 502-508
  • Cabrerizo, F.M., Dántola, M.L., Thomas, A.H., Lorente, C., Braun, A.M., Oliveros, E., Capparelli, A.L., (2004) Chem. Biodiversity, 1, pp. 1800-1811
  • Cabrerizo, F.M., Lorente, C., Vignoni, M., Cabrerizo, R., Thomas, A.H., Capparelli, A.L., (2005) Photochem. Photobiol., 81, pp. 793-801
  • Jennings, B.H., Pastra, S.C., Wellington, J.L., (1970) Photochem. Photobiol., 11, pp. 215-226
  • Jennings, B.H., Pastra-Landis, S., Lerman, J.W., (1972) Photochem. Photobiol., 15, pp. 479-491
  • Shen, R., (1994) Arch. Biochem. Biophys., 310, p. 60
  • Weiss, G., Fuchs, D., Hausen, A., Reibnegger, G., Werner, E.R., Werner-Felmayer, G., Semenitz, E., Wachter, H., (1993) FEBS Lett., 321, pp. 89-92
  • Ledbetter, J.W., Pfleiderer, W., Freisheim, J.H., (1995) Photochem. Photobiol., 62, pp. 71-81
  • Cabrerizo, F.M., Petroselli, G., Lorente, C., Capparelli, A.L., Thomas, A.H., Braun, A.M., Oliveros, E., (2005) Photochem. Photobiol., 81, pp. 1234-1240
  • Widengren, J., Mets, Ü., Rigler, R., (1995) J. Phys. Chem., 99, pp. 13368-13379
  • Vierstra, R.D., Poff, K.L., Walker, E.B., Song, P.-S., (1981) Plant Physiol., 67, pp. 996-998
  • Van Den Berg, P.A.W., Widengren, J., Hink, M.A., Rigler, R., Visser, A.J.W.G., (2001) Spectrochim. Acta, Part A, 57, pp. 2135-2144
  • Kritsky, M.S., Lyudnikova, T.A., Mironov, E.A., Moskaleva, I.V., (1997) J. Photochem. Photobiol., B, 39, pp. 43-48
  • Parker, R.T., (1979) Anal. Chem., 51, pp. 1921-1926
  • Schallreuter, K.U., Büttner, G., Pittelkow, M.R., Wood, J.M., Swanson, N.N., Korner, C., (1994) Biochem. Biophys. Res. Commun., 204, pp. 43-48

Citas:

---------- APA ----------
Vignoni, M., Cabrerizo, F.M., Lorente, C., Claparols, C., Oliveros, E. & Thomas, A.H. (2010) . Photochemistry of dihydrobiopterin in aqueous solution. Organic and Biomolecular Chemistry, 8(4), 800-810.
http://dx.doi.org/10.1039/b913095k
---------- CHICAGO ----------
Vignoni, M., Cabrerizo, F.M., Lorente, C., Claparols, C., Oliveros, E., Thomas, A.H. "Photochemistry of dihydrobiopterin in aqueous solution" . Organic and Biomolecular Chemistry 8, no. 4 (2010) : 800-810.
http://dx.doi.org/10.1039/b913095k
---------- MLA ----------
Vignoni, M., Cabrerizo, F.M., Lorente, C., Claparols, C., Oliveros, E., Thomas, A.H. "Photochemistry of dihydrobiopterin in aqueous solution" . Organic and Biomolecular Chemistry, vol. 8, no. 4, 2010, pp. 800-810.
http://dx.doi.org/10.1039/b913095k
---------- VANCOUVER ----------
Vignoni, M., Cabrerizo, F.M., Lorente, C., Claparols, C., Oliveros, E., Thomas, A.H. Photochemistry of dihydrobiopterin in aqueous solution. Org. Biomol. Chem. 2010;8(4):800-810.
http://dx.doi.org/10.1039/b913095k