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• W3040074155 endingPage "6530" @default.
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• W3040074155 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." @default.
• W3040074155 created "2020-07-10" @default.
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• W3040074155 date "2020-01-01" @default.
• W3040074155 modified "2023-10-18" @default.
• W3040074155 title "<i>N</i>-Methyl-β-carboline alkaloids: structure-dependent photosensitizing properties and localization in subcellular domains" @default.
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• W3040074155 doi "https://doi.org/10.1039/d0ob01122c" @default.
• W3040074155 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/32628228" @default.
• W3040074155 hasPublicationYear "2020" @default.
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