Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline

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 photosensitizati...

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Publicado:	2010
Materias:	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 drug derivative harmine water article chemistry DNA adduct DNA damage drug effect light pH photochemistry plasmid solution and solubility spectrophotometry DNA Adducts DNA Damage Harmine Hydrogen-Ion Concentration Light Photochemistry Plasmids Solutions Spectrophotometry Water
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v8_n11_p2543_Gonzalez http://hdl.handle.net/20.500.12110/paper_14770520_v8_n11_p2543_Gonzalez
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_14770520_v8_n11_p2543_Gonzalez
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spelling	paper:paper_14770520_v8_n11_p2543_Gonzalez2023-06-08T16:18:07Z Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline 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 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. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v8_n11_p2543_Gonzalez http://hdl.handle.net/20.500.12110/paper_14770520_v8_n11_p2543_Gonzalez
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline
topic_facet	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
description	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.
title	Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline
title_short	Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline
title_full	Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline
title_fullStr	Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline
title_full_unstemmed	Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline
title_sort	photosensitized cleavage of plasmidic dna by norharmane, a naturally occurring β-carboline
publishDate	2010
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v8_n11_p2543_Gonzalez http://hdl.handle.net/20.500.12110/paper_14770520_v8_n11_p2543_Gonzalez
_version_	1768542142066589696

Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline

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