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...
Guardado en:
| Autores principales: | , , , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14770520_v8_n11_p2543_Gonzalez |
| Aporte de: |
| id |
todo:paper_14770520_v8_n11_p2543_Gonzalez |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_14770520_v8_n11_p2543_Gonzalez2023-10-03T16:19:07Z Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline Gonzalez, M.M. Pellon-Maison, M. Ales-Gandolfo, M.A. Gonzalez-Baró, M.R. Erra-Balsells, R. Cabrerizo, F.M. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 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 |
| 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. |
| format |
JOUR |
| author |
Gonzalez, M.M. Pellon-Maison, M. Ales-Gandolfo, M.A. Gonzalez-Baró, M.R. Erra-Balsells, R. Cabrerizo, F.M. |
| author_facet |
Gonzalez, M.M. Pellon-Maison, M. Ales-Gandolfo, M.A. Gonzalez-Baró, M.R. Erra-Balsells, R. Cabrerizo, F.M. |
| author_sort |
Gonzalez, M.M. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_14770520_v8_n11_p2543_Gonzalez |
| work_keys_str_mv |
AT gonzalezmm photosensitizedcleavageofplasmidicdnabynorharmaneanaturallyoccurringbcarboline AT pellonmaisonm photosensitizedcleavageofplasmidicdnabynorharmaneanaturallyoccurringbcarboline AT alesgandolfoma photosensitizedcleavageofplasmidicdnabynorharmaneanaturallyoccurringbcarboline AT gonzalezbaromr photosensitizedcleavageofplasmidicdnabynorharmaneanaturallyoccurringbcarboline AT errabalsellsr photosensitizedcleavageofplasmidicdnabynorharmaneanaturallyoccurringbcarboline AT cabrerizofm photosensitizedcleavageofplasmidicdnabynorharmaneanaturallyoccurringbcarboline |
| _version_ |
1782027919102574592 |