Show simple item record

dc.contributor.authorDenofrio, M. Paula
dc.contributor.authorRasse-Suriani, Federico A. O.
dc.contributor.authorParedes Martínez, José Manuel 
dc.contributor.authorFassetta, Federico
dc.contributor.authorCrovetto González, Luis 
dc.contributor.authorGirón González, María Dolores 
dc.contributor.authorSalto González, Rafael 
dc.contributor.authorEpe, Bernd
dc.contributor.authorCabrerizo, Franco M.
dc.date.accessioned2020-09-25T06:56:20Z
dc.date.available2020-09-25T06:56:20Z
dc.date.issued2020-07-01
dc.identifier.citationLuis Crovetto, Franco M. Cabrerizo et al.. N-Methyl-β-carboline alkaloids: structuredependent photosensitizing properties and localization in subcellular domains. Org. Biomol. Chem., 2020, 18, 6519 [DOI: 10.1039/d0ob01122c]es_ES
dc.identifier.urihttp://hdl.handle.net/10481/63549
dc.description.abstractN-Methyl-β-carboline (βC) alkaloids, including normelinonine F (1b) and melinonine F (2b), 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-βC alkaloids were investigated herein. Data reveal that methylation of the βC main ring enhances its photosensitizing properties either by increasing its binding affinity with DNA as a biomolecular target and/or by increasing its oxidation potential, in a structure- dependent manner. As a general rule, N(9)-substituted βCs showed the highest photosensitizing efficiency. With the exception of 2-methyl-harminium, all the N-methyl-βCs investigated herein induce a similar DNA photodamage profile, dominated largely by oxidized purines. This fact represents a distinctive behavior when comparing with N-unsubstituted-βCs. 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 βCs, an active transport appears to mediate the (reatively slow) uptake of the quaternary cationic βCs. 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.es_ES
dc.description.sponsorshipANPCyT PICT-2015-0374 2016-0370 2018-3193es_ES
dc.description.sponsorshipSpanish Ministry of Economy and Competitiveness CTQ201785658-R CTQ2014-55474-C2-2-Res_ES
dc.language.isoenges_ES
dc.publisherRoyal Society of Chemistryes_ES
dc.rightsAtribución-NoComercial 3.0 España*
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/es/*
dc.titleN-Methyl-β-carboline alkaloids: structuredependent photosensitizing properties and localization in subcellular domainses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses_ES
dc.identifier.doi10.1039/d0ob01122c
dc.type.hasVersioninfo:eu-repo/semantics/publishedVersiones_ES


Files in this item

[PDF]

This item appears in the following Collection(s)

Show simple item record

Atribución-NoComercial 3.0 España
Except where otherwise noted, this item's license is described as Atribución-NoComercial 3.0 España