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Petroselli, G.; Erra-Balsells, R.; Cabrerizo, F.M.; Lorente, C.; Capparelli, A.L.; Braun, A.M.; Oliveros, E.; Thomas, A.H. "Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin" (2007) Organic and Biomolecular Chemistry. 5(17):2792-2799
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Abstract:

UV-A radiation (320-400 nm) induces damages to the DNA molecule and its components through photosensitized reactions. Pterins, heterocyclic compounds widespread in biological systems, participate in relevant biological processes and are able to act as photosensitizers. We have investigated the photosensitization of 2′-deoxyadenosine-5′-monophosphate (dAMP) by pterin (PT) in aqueous solution under UV-A radiation. The effect of pH was evaluated, the participation of oxygen was investigated and the products analyzed. Kinetic studies revealed that the reactivity of dAMP towards singlet oxygen (1O2) is very low and that this reactive oxygen species does not participate in the mechanism of photosensitization, although it is produced by PT upon UV-A excitation. In contrast, analysis of irradiated solutions by means of electrospray ionization mass spectrometry strongly suggested that 8-oxo-7,8-dihydro-2′-deoxyadenosine-5′-monophosphate (8-oxo-dAMP) was produced, indicating that the photosensitized oxidation takes place via a type I mechanism (electron transfer). © The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin
Autor:Petroselli, G.; Erra-Balsells, R.; Cabrerizo, F.M.; Lorente, C.; Capparelli, A.L.; Braun, A.M.; Oliveros, E.; Thomas, A.H.
Filiación:Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Departamento de Química, CONICET, Casilla de Correo 16, Sucursal 4, (1900) La Plata, Argentina
CIHIDECAR - CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Argentina
Umweltmesstechnik, Engler-Bunte Institut, Universität Karlsruhe, D-76128 Karlsruhe, Germany
Laboratoire des IMRCP-UMR CNRS 5623, Université Paul Sabatier, 118 route de Narbonne, F-31062 Toulouse Cédex 9, France
Palabras clave:Biological systems; DNA; pH; Photosensitizers; Reaction kinetics; Ultraviolet radiation; Electrospray ionization mass spectrometry; Irradiated solutions; Photosensitized reactions; Pterin (PT); Nucleotides; 2' deoxy 5' adenosine monophosphate; 2'-deoxy-5'-adenosine monophosphate; deoxyadenosine phosphate; oxygen; photosensitizing agent; pterin derivative; singlet oxygen; unclassified drug; article; chemical structure; chemistry; electrospray mass spectrometry; tandem mass spectrometry; Deoxyadenine Nucleotides; Molecular Structure; Oxygen; Photosensitizing Agents; Pterins; Singlet Oxygen; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry
Año:2007
Volumen:5
Número:17
Página de inicio:2792
Página de fin:2799
DOI: http://dx.doi.org/10.1039/b707312g
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CAS:deoxyadenosine phosphate, 653-63-4; oxygen, 7782-44-7; pterin derivative, 948-60-7; 2'-deoxy-5'-adenosine monophosphate, 653-63-4; Deoxyadenine Nucleotides; Oxygen, 7782-44-7; Photosensitizing Agents; Pterins; Singlet Oxygen, 17778-80-2
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v5_n17_p2792_Petroselli

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Citas:

---------- APA ----------
Petroselli, G., Erra-Balsells, R., Cabrerizo, F.M., Lorente, C., Capparelli, A.L., Braun, A.M., Oliveros, E.,..., Thomas, A.H. (2007) . Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin. Organic and Biomolecular Chemistry, 5(17), 2792-2799.
http://dx.doi.org/10.1039/b707312g
---------- CHICAGO ----------
Petroselli, G., Erra-Balsells, R., Cabrerizo, F.M., Lorente, C., Capparelli, A.L., Braun, A.M., et al. "Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin" . Organic and Biomolecular Chemistry 5, no. 17 (2007) : 2792-2799.
http://dx.doi.org/10.1039/b707312g
---------- MLA ----------
Petroselli, G., Erra-Balsells, R., Cabrerizo, F.M., Lorente, C., Capparelli, A.L., Braun, A.M., et al. "Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin" . Organic and Biomolecular Chemistry, vol. 5, no. 17, 2007, pp. 2792-2799.
http://dx.doi.org/10.1039/b707312g
---------- VANCOUVER ----------
Petroselli, G., Erra-Balsells, R., Cabrerizo, F.M., Lorente, C., Capparelli, A.L., Braun, A.M., et al. Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin. Org. Biomol. Chem. 2007;5(17):2792-2799.
http://dx.doi.org/10.1039/b707312g