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dc.contributor.author
Vignoni, Mariana
dc.contributor.author
Rasse Suriani, Federico Ariel Osvaldo
dc.contributor.author
Butzbach, Kathrin
dc.contributor.author
Erra Balsells, Rosa
dc.contributor.author
Epe, Bernd
dc.contributor.author
Cabrerizo, Franco Martín
dc.date.available
2015-09-28T20:23:05Z
dc.date.issued
2013-06-18
dc.identifier.citation
Vignoni, Mariana; Rasse Suriani, Federico Ariel Osvaldo; Butzbach, Kathrin; Erra Balsells, Rosa; Epe, Bernd; et al.; Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 32; 18-6-2013; 5300-5309
dc.identifier.issn
1477-0520
dc.identifier.uri
http://hdl.handle.net/11336/2178
dc.description.abstract
It has been well documented that β-carboline alkaloids, particularly the 9-methyl derivatives, are efficient photosensitizers. However, structure–activity relationships are missing and the photochemical mechanisms involved in the DNA photodamage still remain unknown. In the present work, we examined the capability of three 9-methyl-β-carbolines (9-methyl-norharmane, 9-methyl-harmane and 9-methylharmine) to induce DNA damage upon UVA excitation at physiological pH. The type and extent of the damage was analyzed together with the photophysical and binding properties of the β-carboline derivatives investigated. The results indicate that even at neutral pH most of the DNA damage is generated from the protonated form of the excited β-carbolines in a type-I reaction. Oxidized purine residues are produced in high excess over oxidized pyrimidines, single-strand breaks and sites of base loss. In addition, the excited neutral form of the β-carbolines is responsible for significant generation of cyclobutane pyrimidine dimers (CPDs) by triplet–triplet-energy transfer. In the case of 9-methyl-norharmane, the yield of CPDs is increased in D2O, probably due to less rapid protonation in the deuterated solvent.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
9-Methyl-B-Carbolines
dc.subject
Dna
dc.subject
Photosensitization
dc.subject.classification
Química Orgánica
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.subject.classification
Genética y Herencia
dc.subject.classification
Ciencias Biológicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2016-03-30 10:35:44.97925-03
dc.journal.volume
11
dc.journal.number
32
dc.journal.pagination
5300-5309
dc.journal.pais
Gbr
dc.journal.ciudad
Londres
dc.description.fil
Fil: Vignoni, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Instituto de Investigaciones Biotecnológicas - Instituto Tecnológico Chascomús. Instituto de Investigaciones Biotecnológicas (sede Chascomús); Argentina;
dc.description.fil
Fil: Rasse Suriani, Federico Ariel Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Instituto de Investigaciones Biotecnológicas - Instituto Tecnológico Chascomús. Instituto de Investigaciones Biotecnológicas (sede Chascomús); Argentina;
dc.description.fil
Fil: Butzbach, Kathrin. University of Mainz. Institute of Pharmacy and Biochemistry; Alemania;
dc.description.fil
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina;
dc.description.fil
Fil: Epe, Bernd. University of Mainz. Institute of Pharmacy and Biochemistry; Alemania;
dc.description.fil
Fil: Cabrerizo, Franco Martín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Instituto de Investigaciones Biotecnológicas - Instituto Tecnológico Chascomús. Instituto de Investigaciones Biotecnológicas (sede Chascomús); Argentina;
dc.journal.title
Organic & Biomolecular Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/c3ob40344k#!divAbstract
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/DOI:10.1039/C3OB40344K


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