Artículo

Vignoni, M.; Lorente, C.; Cabrerizo, F.M.; Erra-Balsells, R.; Oliveros, E.; Thomas, A.H. "Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin" (2012) Photochemical and Photobiological Sciences. 11(6):979-987
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Abstract:

7,8-Dihydrobiopterin (H2Bip) and 7,8-dihydroneopterin (H2Nep) belong to a class of heterocyclic compounds present in a wide range of living systems. H2Bip accumulates in the skin of patients suffering from vitiligo, whereas H2Nep is secreted by human macrophages when the cellular immune system is activated. We have investigated the photochemical reactivity of both compounds upon UV-A irradiation (320-400 nm), the chemical structures of the products and their thermal stability. The study was performed in neutral aqueous solutions. The reactions were followed by UV/Visible spectrophotometry and HPLC and the products were analyzed by means of electrospray ionization mass spectrometry and 1H-NMR. Excitation of H2Bip and H2Nep leads to the formation, in each case, of two main isomeric dimers. The latter compounds undergo a thermal process that may consist in a retro [2 + 2]-cycloaddition and hydrolysis to yield the reactant (H2Bip or H2Nep) and a product that has incorporated a molecule of H2O. © The Royal Society of Chemistry and Owner Societies 2012.

Registro:

Documento: Artículo
Título:Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin
Autor:Vignoni, M.; Lorente, C.; Cabrerizo, F.M.; Erra-Balsells, R.; Oliveros, E.; Thomas, A.H.
Filiación:Instituto de Investigaciones Fisicoquímicas Teóricas Y Aplicadas (INIFTA), Departamento de Química, Universidad Nacional de La Plata, Casilla de Correo 16 Sucursal 4, La Plata, 1900, Argentina
Instituto de Investigaciones Biotecnológicas-Instituto Tecnológico de Chascomús (IIB-INTECH), Universidad Nacional de San Martín, CONICET, Intendente Marino Km 8.2 CC 164, Chascomús, 7130, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Buenos Aires, 1428, Argentina
Laboratoire des Interactions Moléculaires et Réactivité Chimique et Photochimique (IMRCP), UMR CNRS 5623, Université Paul Sabatier (Toulouse III), 118 route de Narbonne, Toulouse Cédex 9, F-31062, France
Palabras clave:7,8 dihydroneopterin; 7,8-dihydrobiopterin; 7,8-dihydroneopterin; biopterin; dihydrobiopterin; drug derivative; neopterin; article; chemistry; dimerization; electrospray mass spectrometry; high performance liquid chromatography; human; isomerism; macrophage; metabolism; nuclear magnetic resonance spectroscopy; photolysis; temperature; ultraviolet radiation; Biopterin; Chromatography, High Pressure Liquid; Dimerization; Humans; Isomerism; Macrophages; Magnetic Resonance Spectroscopy; Neopterin; Photolysis; Spectrometry, Mass, Electrospray Ionization; Temperature; Ultraviolet Rays
Año:2012
Volumen:11
Número:6
Página de inicio:979
Página de fin:987
DOI: http://dx.doi.org/10.1039/c2pp05363b
Título revista:Photochemical and Photobiological Sciences
Título revista abreviado:Photochem. Photobiol. Sci.
ISSN:1474905X
CODEN:PPSHC
CAS:7,8 dihydroneopterin, 1218-98-0; biopterin, 22150-76-1; dihydrobiopterin, 6779-87-9; neopterin, 670-65-5; 7,8-dihydrobiopterin, 6779-87-9; 7,8-dihydroneopterin, 1218-98-0; Biopterin, 22150-76-1; Neopterin, 670-65-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v11_n6_p979_Vignoni

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Citas:

---------- APA ----------
Vignoni, M., Lorente, C., Cabrerizo, F.M., Erra-Balsells, R., Oliveros, E. & Thomas, A.H. (2012) . Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin. Photochemical and Photobiological Sciences, 11(6), 979-987.
http://dx.doi.org/10.1039/c2pp05363b
---------- CHICAGO ----------
Vignoni, M., Lorente, C., Cabrerizo, F.M., Erra-Balsells, R., Oliveros, E., Thomas, A.H. "Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin" . Photochemical and Photobiological Sciences 11, no. 6 (2012) : 979-987.
http://dx.doi.org/10.1039/c2pp05363b
---------- MLA ----------
Vignoni, M., Lorente, C., Cabrerizo, F.M., Erra-Balsells, R., Oliveros, E., Thomas, A.H. "Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin" . Photochemical and Photobiological Sciences, vol. 11, no. 6, 2012, pp. 979-987.
http://dx.doi.org/10.1039/c2pp05363b
---------- VANCOUVER ----------
Vignoni, M., Lorente, C., Cabrerizo, F.M., Erra-Balsells, R., Oliveros, E., Thomas, A.H. Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin. Photochem. Photobiol. Sci. 2012;11(6):979-987.
http://dx.doi.org/10.1039/c2pp05363b