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Gonzalez, M.M.; Vignoni, M.; Pellon-Maison, M.; Ales-Gandolfo, M.A.; Gonzalez-Baro, M.R.; Erra-Balsells, R.; Epe, B.; Cabrerizo, F.M. "Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization" (2012) Organic and Biomolecular Chemistry. 10(9):1807-1819
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Abstract:

β-Carbolines (βCs) are a group of alkaloids present in many plants and animals. It has been suggested that these alkaloids participate in a variety of significant photosensitized processes. Despite their well-established natural occurrence, the main biological role of these alkaloids and the mechanisms involved are, to date, poorly understood. In the present work, we examined the capability of three important βCs (norharmane, harmane and harmine) and two of its derivatives (N-methyl-norharmane and N-methyl-harmane) to induce DNA damage upon UV-A excitation, correlating the type and extent of the damage with the photophysical characteristics and DNA binding properties of the compounds. The results indicate that DNA damage is mostly mediated by a direct type-I photoreaction of the protonated βCs after non-intercalative electrostatic binding. Reactive oxygen species such as singlet oxygen and superoxide are not involved to a major extent, as indicated by the only small influence of D 2O and of superoxide dismutase on damage generation. An analysis with repair enzymes revealed that oxidative purine modifications such as 8-oxo-7,8-dihydroguanine, sites of base loss and single-strand breaks (SSB) are generated by all βCs, while only photoexcited harmine gives rise to the formation of cyclobutane pyrimidine dimers as well. © 2012 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization
Autor:Gonzalez, M.M.; Vignoni, M.; Pellon-Maison, M.; Ales-Gandolfo, M.A.; Gonzalez-Baro, M.R.; Erra-Balsells, R.; Epe, B.; Cabrerizo, F.M.
Filiación:CIHIDECAR-CONICET, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 3p, (1428) Buenos Aires, Argentina
INIFTA-CONICET, Universidad Nacional de la Plata, Casilla de Correo 16, Sucursal 4, (1900) La Plata, Argentina
INIBIOLP-CONICET, Universidad Nacional de la Plata, calle 60 y 120, (1900), La Plata, Argentina
IIB-INTECH-CONICET, Universidad Nacional de San Martín, Intendente Marino km 8, 2 CC 164, (B7130IWA), Chascomús Buenos Aires, Argentina
Institute of Pharmacy and Biochemistry, University of Mainz, Staudingerweg 5, D-55099 Mainz, Germany
Palabras clave:8-oxo-7 ,8-dihydroguanine; Carbolines; Cyclobutane pyrimidine dimers; DNA damages; DNA-binding properties; Electrostatic binding; Harmane; Kinetic analysis; Photophysical; Photoproducts; Photoreactions; Protonated; Reactive oxygen species; Repair enzymes; Single-strand breaks; Singlet oxygen; Super oxide dismutase; Superoxides; Animals; Binding energy; Butane; DNA; Metabolites; Nitrogen compounds; Oxygen; Pyridine; Cesium; carboline derivative; DNA; photosensitizing agent; reactive oxygen metabolite; thymidine; article; chemical structure; chemistry; kinetics; photochemistry; Carbolines; DNA; Kinetics; Molecular Structure; Photochemical Processes; Photosensitizing Agents; Reactive Oxygen Species; Thymidine
Año:2012
Volumen:10
Número:9
Página de inicio:1807
Página de fin:1819
DOI: http://dx.doi.org/10.1039/c2ob06505c
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
CAS:DNA, 9007-49-2; thymidine, 50-89-5; Carbolines; DNA, 9007-49-2; Photosensitizing Agents; Reactive Oxygen Species; Thymidine, 50-89-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v10_n9_p1807_Gonzalez

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Citas:

---------- APA ----------
Gonzalez, M.M., Vignoni, M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baro, M.R., Erra-Balsells, R., Epe, B.,..., Cabrerizo, F.M. (2012) . Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization. Organic and Biomolecular Chemistry, 10(9), 1807-1819.
http://dx.doi.org/10.1039/c2ob06505c
---------- CHICAGO ----------
Gonzalez, M.M., Vignoni, M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baro, M.R., Erra-Balsells, R., et al. "Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization" . Organic and Biomolecular Chemistry 10, no. 9 (2012) : 1807-1819.
http://dx.doi.org/10.1039/c2ob06505c
---------- MLA ----------
Gonzalez, M.M., Vignoni, M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baro, M.R., Erra-Balsells, R., et al. "Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization" . Organic and Biomolecular Chemistry, vol. 10, no. 9, 2012, pp. 1807-1819.
http://dx.doi.org/10.1039/c2ob06505c
---------- VANCOUVER ----------
Gonzalez, M.M., Vignoni, M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baro, M.R., Erra-Balsells, R., et al. Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization. Org. Biomol. Chem. 2012;10(9):1807-1819.
http://dx.doi.org/10.1039/c2ob06505c