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Petroselli, G.; Dántola, M.L.; Cabrerizo, F.M.; Capparelli, A.L.; Lorente, C.; Oliveros, E.; Thomas, A.H. "Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism" (2008) Journal of the American Chemical Society. 130(10):3001-3011
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Abstract:

UV-A radiation (320-400 nm) induces damage to the DNA molecule and its components through different photosensitized reactions. Among these processes, photosensitized oxidations may occur through electron transfer or hydrogen abstraction (type I) and/or the production of singlet molecular oxygen ( 1O2) (type II). Pterins, heterocyclic compounds widespread in biological systems, participate in relevant biological processes and are able to act as photosensitizers. We have investigated the photosensitized oxidation of 2′-deoxyguanosine 5′-monophosphate (dGMP) by pterin (PT) in aqueous solution under UV-A irrradiation. Kinetic analysis was employed to evaluate the participation of both types of mechanism under different pH conditions. The rate constant of 1O2 total quenching (kt) by dGMP was determined by steady-state analysis of the 1O2 NIR luminescence, whereas the rate constant of the chemical reaction between 1O2 and dGMP (kr) was evaluated from kinetic analysis of concentration profiles obtained by HPLC. The results show that the oxidation of dGMP photosensitized by PT occurs through two competing mechanisms that contribute in different proportions depending on the pH. The dominant mechanism in alkaline media involves the reaction of dGMP with 1O2 produced by energy transfer from the PT triplet state to molecular oxygen (type II). In contrast, under acidic pH conditions, where PT and the guanine moiety of dGMP are not ionized, the main pathway for dGMP oxidation involves an initial electron transfer between dGMP and the PT triplet state (type I mechanism). The biological implications of the results obtained are also discussed. © 2008 American Chemical Society.

Registro:

Documento: Artículo
Título:Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism
Autor:Petroselli, G.; Dántola, M.L.; Cabrerizo, F.M.; Capparelli, A.L.; Lorente, C.; 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, Ciudad Universitaria, (1428) Buenos Aires, Argentina
Lehrstuhl für Umweltmesstechnik, Engler-Bunte Institut, Universität Karlsruhe, D-76128 Karlsruhe, Germany
Laboratoire IMRCP - UMR 5623, Université Paul Sabatier, 118 route de Narbonne, F-31062 Toulouse Cédex 9, France
Palabras clave:Hydrogen; Molecular oxygen; Oxidation; Photosensitizers; Ultraviolet radiation; Heterocyclic compounds; Hydrogen abstraction; Photosensitized oxidations; Phosphates; deoxyguanosine phosphate; heterocyclic compound; hydrogen; oxygen; photosensitizing agent; pterin; singlet oxygen; 2'-deoxyguanosine 5'-phosphate; pterin derivative; singlet oxygen; unclassified drug; acidity; alkalinity; animal tissue; aqueous solution; article; chemical reaction; concentration (parameters); electron transport; energy transfer; high performance liquid chromatography; kinetics; luminescence; nonhuman; oxidation; pH; photosensitization; steady state; ultraviolet A radiation; ultraviolet irradiation; chemistry; oxidation reduction reaction; photochemistry; radiation exposure; time; ultraviolet radiation; Deoxyguanine Nucleotides; Electron Transport; Kinetics; Oxidation-Reduction; Photochemistry; Pterins; Singlet Oxygen; Time Factors; Ultraviolet Rays
Año:2008
Volumen:130
Número:10
Página de inicio:3001
Página de fin:3011
DOI: http://dx.doi.org/10.1021/ja075367j
Título revista:Journal of the American Chemical Society
Título revista abreviado:J. Am. Chem. Soc.
ISSN:00027863
CODEN:JACSA
CAS:deoxyguanosine phosphate, 902-04-5; hydrogen, 12385-13-6, 1333-74-0; oxygen, 7782-44-7; pterin, 2236-60-4; pterin derivative, 948-60-7; 2'-deoxyguanosine 5'-phosphate, 902-04-5; Deoxyguanine Nucleotides; Pterins; Singlet Oxygen, 17778-80-2
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v130_n10_p3001_Petroselli

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Citas:

---------- APA ----------
Petroselli, G., Dántola, M.L., Cabrerizo, F.M., Capparelli, A.L., Lorente, C., Oliveros, E. & Thomas, A.H. (2008) . Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism. Journal of the American Chemical Society, 130(10), 3001-3011.
http://dx.doi.org/10.1021/ja075367j
---------- CHICAGO ----------
Petroselli, G., Dántola, M.L., Cabrerizo, F.M., Capparelli, A.L., Lorente, C., Oliveros, E., et al. "Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism" . Journal of the American Chemical Society 130, no. 10 (2008) : 3001-3011.
http://dx.doi.org/10.1021/ja075367j
---------- MLA ----------
Petroselli, G., Dántola, M.L., Cabrerizo, F.M., Capparelli, A.L., Lorente, C., Oliveros, E., et al. "Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism" . Journal of the American Chemical Society, vol. 130, no. 10, 2008, pp. 3001-3011.
http://dx.doi.org/10.1021/ja075367j
---------- VANCOUVER ----------
Petroselli, G., Dántola, M.L., Cabrerizo, F.M., Capparelli, A.L., Lorente, C., Oliveros, E., et al. Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism. J. Am. Chem. Soc. 2008;130(10):3001-3011.
http://dx.doi.org/10.1021/ja075367j