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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.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.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.publisherRoyal Society of Chemistryes_ES
dc.rightsAtribución-NoComercial 3.0 España*
dc.titleN-Methyl-β-carboline alkaloids: structuredependent photosensitizing properties and localization in subcellular domainses_ES

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