Mostrar el registro sencillo del ítem
N-Methyl-β-carboline alkaloids: structuredependent photosensitizing properties and localization in subcellular domains
dc.contributor.author | Denofrio, M. Paula | |
dc.contributor.author | Rasse-Suriani, Federico A. O. | |
dc.contributor.author | Paredes Martínez, José Manuel | |
dc.contributor.author | Fassetta, Federico | |
dc.contributor.author | Crovetto González, Luis | |
dc.contributor.author | Girón González, María Dolores | |
dc.contributor.author | Salto González, Rafael | |
dc.contributor.author | Epe, Bernd | |
dc.contributor.author | Cabrerizo, Franco M. | |
dc.date.accessioned | 2020-09-25T06:56:20Z | |
dc.date.available | 2020-09-25T06:56:20Z | |
dc.date.issued | 2020-07-01 | |
dc.identifier.citation | Luis 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.uri | http://hdl.handle.net/10481/63549 | |
dc.description.abstract | N-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.sponsorship | ANPCyT PICT-2015-0374 2016-0370 2018-3193 | es_ES |
dc.description.sponsorship | Spanish Ministry of Economy and Competitiveness CTQ201785658-R CTQ2014-55474-C2-2-R | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Royal Society of Chemistry | es_ES |
dc.rights | Atribución-NoComercial 3.0 España | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc/3.0/es/ | * |
dc.title | N-Methyl-β-carboline alkaloids: structuredependent photosensitizing properties and localization in subcellular domains | es_ES |
dc.type | journal article | es_ES |
dc.rights.accessRights | open access | es_ES |
dc.identifier.doi | 10.1039/d0ob01122c | |
dc.type.hasVersion | VoR | es_ES |