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Gonzalez, M.M.; Pellon-Maison, M.; Ales-Gandolfo, M.A.; Gonzalez-Baró, M.R.; Erra-Balsells, R.; Cabrerizo, F.M. "Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline" (2010) Organic and Biomolecular Chemistry. 8(11):2543-2552
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Abstract:

UV-A radiation (320-400 nm) induces damages to the DNA molecule and its components through photosensitized reactions. β-Carbolines (βCs), heterocyclic compounds widespread in biological systems, participate in several biological processes and are able to act as photosensitizers. The photosensitization of plasmidic DNA by norharmane in aqueous solution under UV-A radiation was studied. The effect of pH was evaluated and the participation of reactive oxygen species (ROS), such as hydroxyl radical (HO), superoxide anion (O2 -) and singlet oxygen (1O2) was investigated. A strong dependence of the photosensitized DNA relaxation on the pH was observed. The extent of the reaction was shown to be higher in the experiments performed at pH 4.7 than those performed at pH 10.2. As was expected, an intermediate extent of the reaction was observed at physiological pH (pH 7.4). Kinetic studies using ROS scavengers revealed that the chemical reactions between ROS and DNA are not the main pathways responsible for the damage of DNA. Consequently, the predominant mechanism yielding the DNA strand break takes place most probably via a type I mechanism (electron transfer) from the single excited state (S1) of the protonated form of norharmane (1[nHoH+]*). Additional information about the nature of the norharmane electronic excited states involved in the photocleavage reaction was obtained by using the N-methyl derivative of norharmane (N-methyl-norharmane). © The Royal Society of Chemistry 2010.

Registro:

Documento: Artículo
Título:Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline
Autor:Gonzalez, M.M.; Pellon-Maison, M.; Ales-Gandolfo, M.A.; Gonzalez-Baró, M.R.; Erra-Balsells, R.; Cabrerizo, F.M.
Filiación:CIHIDECAR - CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, 3p, 1428, Buenos Aires, Argentina
INIBIOLP-CONICET, Universidad Nacional de La Plata, Calle 60 y 120, 1900 La Plata, Argentina
Palabras clave:Aqueous solutions; Biological process; Carbolines; DNA molecules; DNA strand break; Effect of pH; Electron transfer; Electronic excited state; Heterocyclic compound; Hydroxyl radicals; Kinetic study; Methyl derivatives; Naturally occurring; Photocleavage reaction; Physiological pH; Protonated; Reactive oxygen species; Singlet oxygen; Superoxide anions; UVA radiation; Cesium; Cesium compounds; Derivatives; DNA; Electric excitation; Excited states; Free radical reactions; Genes; Oxygen; Photosensitizers; Reaction intermediates; pH effects; beta carboline; carboline derivative; DNA; drug derivative; harmine; water; article; chemistry; DNA adduct; DNA damage; drug effect; light; pH; photochemistry; plasmid; solution and solubility; spectrophotometry; Carbolines; DNA; DNA Adducts; DNA Damage; Harmine; Hydrogen-Ion Concentration; Light; Photochemistry; Plasmids; Solutions; Spectrophotometry; Water
Año:2010
Volumen:8
Número:11
Página de inicio:2543
Página de fin:2552
DOI: http://dx.doi.org/10.1039/c002235g
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CAS:DNA, 9007-49-2; beta carboline, 244-63-3; harmine, 343-27-1, 442-51-3; water, 7732-18-5; Carbolines; DNA, 9007-49-2; DNA Adducts; Harmine, 442-51-3; Solutions; Water, 7732-18-5; norharman, 244-63-3
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v8_n11_p2543_Gonzalez

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Citas:

---------- APA ----------
Gonzalez, M.M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baró, M.R., Erra-Balsells, R. & Cabrerizo, F.M. (2010) . Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline. Organic and Biomolecular Chemistry, 8(11), 2543-2552.
http://dx.doi.org/10.1039/c002235g
---------- CHICAGO ----------
Gonzalez, M.M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baró, M.R., Erra-Balsells, R., Cabrerizo, F.M. "Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline" . Organic and Biomolecular Chemistry 8, no. 11 (2010) : 2543-2552.
http://dx.doi.org/10.1039/c002235g
---------- MLA ----------
Gonzalez, M.M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baró, M.R., Erra-Balsells, R., Cabrerizo, F.M. "Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline" . Organic and Biomolecular Chemistry, vol. 8, no. 11, 2010, pp. 2543-2552.
http://dx.doi.org/10.1039/c002235g
---------- VANCOUVER ----------
Gonzalez, M.M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baró, M.R., Erra-Balsells, R., Cabrerizo, F.M. Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline. Org. Biomol. Chem. 2010;8(11):2543-2552.
http://dx.doi.org/10.1039/c002235g