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

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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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Autor principal: Gonzalez, M.M
Otros Autores: Pellon-Maison, M., Ales-Gandolfo, M.A, Gonzalez-Baró, M.R, Erra-Balsells, R., Cabrerizo, F.M
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2010
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 scopus  |a 2-s2.0-77952631234 
024 7 |2 cas  |a 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 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
100 1 |a Gonzalez, M.M. 
245 1 0 |a Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring β-carboline 
260 |c 2010 
270 1 0 |m Erra-Balsells, R.; CIHIDECAR - CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, 3p, 1428, Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
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504 |a Kishikawa, H., Jiang, Y.-R., Goodisman, J., Dabrowiak, J.C., (1991) J. Am. Chem. Soc., 113, pp. 5434-5440. , The photophysical properties of N-methyl-norharmane (N-Me-nHo) have been described elsewhere. 54 Briefly, in both acidic and alkaline aqueous solution (i.e., pH = 4.8 and 10.2, respectively) the photophysical process occurs from the same excited state (i.e., the first excited state (S1) of the protonated form of N-Me-nHo). According to the fluorescence quantum yield (ΦF) reported (i.e., ΦF = 0.68 and 0.75 for the neutral and protonated form of N-Me-nHo, respectively), ∼ 90% of the neutral form of N-Me-nHo follows a quick protonation during the lifetime of its singlet excited states 
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504 |a Taira, Z., Kanzawa, S., Dohara, C., Ishida, S., Matsumoto, M., Sakiya, Y., (1997) Jap. J. Toxicol. Environ. Health, 43, pp. 83-91 
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504 |a García-Zubiri, I.X., Burrows, H.D., De Melo Seixas, J.S., Monteserín, M., Arroyo, A., Tapia, M.J., (2008) J. Fluoresc., 18, pp. 961-972. , Note that the KG value obtained for nHoH+ is higher than that reported for β-carboline-3-carboxylic acid N-methylamide or βCMAM (363 ± 58, 500 ± 90 and 239 ± 43 M-1, at pH 4, 6 and 9, respectively). The pKa value of βCMAM is 3.877. In the pH range 6-9, the neutral form of βCMAM is the predominant specie in the solution. Thus, the absence of the positive charge would decrease the interaction with the DNA molecule. On the other hand, at pH 4 ∼ 50% of each acid-base form of βCMAM are present. Although in the protonated βCMAM form, the norharmane skeleton plane is twisted by 19.58° with respect to the plane carbon 3 substituent,77 the availability of the protonated pyridinic nitrogen is not the same as in the case of norharmane 
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520 3 |a 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.  |l eng 
593 |a CIHIDECAR - CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, 3p, 1428, Buenos Aires, Argentina 
593 |a INIBIOLP-CONICET, Universidad Nacional de La Plata, Calle 60 y 120, 1900 La Plata, Argentina 
690 1 0 |a AQUEOUS SOLUTIONS 
690 1 0 |a BIOLOGICAL PROCESS 
690 1 0 |a CARBOLINES 
690 1 0 |a DNA MOLECULES 
690 1 0 |a DNA STRAND BREAK 
690 1 0 |a EFFECT OF PH 
690 1 0 |a ELECTRON TRANSFER 
690 1 0 |a ELECTRONIC EXCITED STATE 
690 1 0 |a HETEROCYCLIC COMPOUND 
690 1 0 |a HYDROXYL RADICALS 
690 1 0 |a KINETIC STUDY 
690 1 0 |a METHYL DERIVATIVES 
690 1 0 |a NATURALLY OCCURRING 
690 1 0 |a PHOTOCLEAVAGE REACTION 
690 1 0 |a PHYSIOLOGICAL PH 
690 1 0 |a PROTONATED 
690 1 0 |a REACTIVE OXYGEN SPECIES 
690 1 0 |a SINGLET OXYGEN 
690 1 0 |a SUPEROXIDE ANIONS 
690 1 0 |a UVA RADIATION 
690 1 0 |a CESIUM 
690 1 0 |a CESIUM COMPOUNDS 
690 1 0 |a DERIVATIVES 
690 1 0 |a DNA 
690 1 0 |a ELECTRIC EXCITATION 
690 1 0 |a EXCITED STATES 
690 1 0 |a FREE RADICAL REACTIONS 
690 1 0 |a OXYGEN 
690 1 0 |a PHOTOSENSITIZERS 
690 1 0 |a REACTION INTERMEDIATES 
690 1 0 |a PH EFFECTS 
690 1 0 |a BETA CARBOLINE 
690 1 0 |a CARBOLINE DERIVATIVE 
690 1 0 |a DNA 
690 1 0 |a DRUG DERIVATIVE 
690 1 0 |a HARMINE 
690 1 0 |a WATER 
690 1 0 |a ARTICLE 
690 1 0 |a CHEMISTRY 
690 1 0 |a DNA ADDUCT 
690 1 0 |a DNA DAMAGE 
690 1 0 |a DRUG EFFECT 
690 1 0 |a LIGHT 
690 1 0 |a PHOTOCHEMISTRY 
690 1 0 |a PLASMID 
690 1 0 |a SOLUTION AND SOLUBILITY 
690 1 0 |a SPECTROPHOTOMETRY 
690 1 0 |a CARBOLINES 
690 1 0 |a DNA 
690 1 0 |a DNA ADDUCTS 
690 1 0 |a DNA DAMAGE 
690 1 0 |a HARMINE 
690 1 0 |a HYDROGEN-ION CONCENTRATION 
690 1 0 |a LIGHT 
690 1 0 |a PHOTOCHEMISTRY 
690 1 0 |a PLASMIDS 
690 1 0 |a SOLUTIONS 
690 1 0 |a SPECTROPHOTOMETRY 
690 1 0 |a WATER 
650 1 7 |2 spines  |a GENES 
650 1 7 |2 spines  |a PH 
700 1 |a Pellon-Maison, M. 
700 1 |a Ales-Gandolfo, M.A. 
700 1 |a Gonzalez-Baró, M.R. 
700 1 |a Erra-Balsells, R. 
700 1 |a Cabrerizo, F.M. 
773 0 |d 2010  |g v. 8  |h pp. 2543-2552  |k n. 11  |p Org. Biomol. Chem.  |x 14770520  |w (AR-BaUEN)CENRE-2303  |t Organic and Biomolecular Chemistry 
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856 4 0 |u https://doi.org/10.1039/c002235g  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_14770520_v8_n11_p2543_Gonzalez  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v8_n11_p2543_Gonzalez  |y Registro en la Biblioteca Digital 
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962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 83849 

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