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dc.contributor.author
Denofrio, Maria Paula
dc.contributor.author
Rasse Suriani, Federico Ariel Osvaldo
dc.contributor.author
Paredes, Jose M.
dc.contributor.author
Fassetta, Federico
dc.contributor.author
Crovetto, Luis
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Giron, Maria D.
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Salto, Rafael
dc.contributor.author
Epe, Bernd
dc.contributor.author
Cabrerizo, Franco Martín
dc.date.available
2022-05-18T02:47:23Z
dc.date.issued
2020-07
dc.identifier.citation
Denofrio, Maria Paula; Rasse Suriani, Federico Ariel Osvaldo; Paredes, Jose M.; Fassetta, Federico; Crovetto, Luis; et al.; N-methyl-β-carboline alkaloids: structure-dependent photosensitizing properties and localization in subcellular domains; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 33; 7-2020; 1-12
dc.identifier.issn
1477-0520
dc.identifier.uri
http://hdl.handle.net/11336/157812
dc.description.abstract
N-methyl-Beta-carboline (bC) alkaloids, including normelinonine F and melinonine F, have been found in a vast range of living species playing different biological, biomedical and/or pharmacological roles. Despite this, molecular bases of the mechanisms through which these alkaloids would exert their effect still remain unknown. Fundamental aspects including the photosensitizing properties and intracellular internalization of a selected group of N-methyl-bC alkaloids were investigated herein. Data reveal that methylation of the bC main ring enhances its photosensitizing properties either by increasing its binding affinity with DNA as biomolecular target and/or by increasing its oxidation potential, in a structure dependent manner. As a general rule, N(9)-substituted bCs showed the highest photosensitizing efficiency. With the exception of 2-methyl-harminium, all the N-methyl-bCs investigated herein induce a similar DNA photodamage profile, dominated largely by oxidized purines. This fact represents a distinctive behavior when comparing with N-unsubstituted-bCs. On the other hand, although all the investigated compounds might accumulate mainly into the mitochondria of HeLa cells, methylation provides a distinctive dynamic pattern for mitochondrial uptake. While rapid (passive) diffusion is most probably reponsible for the prompt uptake/release of neutral bCs, an active transport appears to mediate the (reatively slow) uptake of the quaternary cationic bCs. This might be a consequence of a distinctive subcellular localization (mitochondrial membrane and/or matrix) or interaction with intracellular components. Biomedical and biotechnological implications are also discussed herein.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.subject
N-METHYL-BETA-CARBOLINE
dc.subject
PHOTOSENSITIZING-PROPERTIES
dc.subject
INTRACELLULAR
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INTERNALIZATION
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Otras Ciencias Químicas
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
N-methyl-β-carboline alkaloids: structure-dependent photosensitizing properties and localization in subcellular domains
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-04-26T20:21:10Z
dc.journal.number
33
dc.journal.pagination
1-12
dc.journal.pais
Reino Unido
dc.journal.ciudad
Cambridge
dc.description.fil
Fil: Denofrio, Maria Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Biotecnológicas. Instituto de Investigaciones Biotecnológicas "Dr. Raúl Alfonsín" (sede Chascomús). Universidad Nacional de San Martín. Instituto de Investigaciones Biotecnológicas. Instituto de Investigaciones Biotecnológicas "Dr. Raúl Alfonsín" (sede Chascomús); Argentina
dc.description.fil
Fil: Rasse Suriani, Federico Ariel Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
dc.description.fil
Fil: Paredes, Jose M.. Universidad de Granada. Facultad de Farmacia. Departamento de Fisicoquimica.; España
dc.description.fil
Fil: Fassetta, Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Biotecnológicas. Instituto de Investigaciones Biotecnológicas "Dr. Raúl Alfonsín" (sede Chascomús). Universidad Nacional de San Martín. Instituto de Investigaciones Biotecnológicas. Instituto de Investigaciones Biotecnológicas "Dr. Raúl Alfonsín" (sede Chascomús); Argentina
dc.description.fil
Fil: Crovetto, Luis. Universidad de Granada. Facultad de Farmacia. Departamento de Fisicoquimica.; España
dc.description.fil
Fil: Giron, Maria D.. Universidad de Granada. Facultad de Farmacia.; España
dc.description.fil
Fil: Salto, Rafael. Universidad de Granada. Facultad de Farmacia.; España
dc.description.fil
Fil: Epe, Bernd. Johannes Gutenberg Universitat Mainz; Alemania
dc.description.fil
Fil: Cabrerizo, Franco Martín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Biotecnológicas. Instituto de Investigaciones Biotecnológicas "Dr. Raúl Alfonsín" (sede Chascomús). Universidad Nacional de San Martín. Instituto de Investigaciones Biotecnológicas. Instituto de Investigaciones Biotecnológicas "Dr. Raúl Alfonsín" (sede Chascomús); Argentina
dc.journal.title
Organic & Biomolecular Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/d0ob01122c
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/OB/D0OB01122C
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