Artículo
Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
Autor/es | Carrasco Carrasco, Carlos Jesús
Montilla Ramos, Francisco Javier Álvarez González, Eleuterio Calderón Montaño, José Manuel López Lázaro, Miguel Galindo del Pozo, Agustín |
Departamento | Universidad de Sevilla. Departamento de Química Inorgánica Universidad de Sevilla. Departamento de Farmacología |
Fecha de publicación | 2022 |
Fecha de depósito | 2022-08-31 |
Publicado en |
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Premios | Premio Mensual Publicación Científica Destacada de la US. Facultad de Química |
Resumen | Complexes Na3[Ag(NHCR)2], 2a-e and 2b’-c’, where NHCR is a N-heterocyclic carbene of the 2,2′-(1H-2λ3,3λ4-imidazole-1,3-diyl)dicarboxylate type, were prepared by treatment of compounds HLR, 1a-e and 1b’-c’ (2-(1-(carboxy ... Complexes Na3[Ag(NHCR)2], 2a-e and 2b’-c’, where NHCR is a N-heterocyclic carbene of the 2,2′-(1H-2λ3,3λ4-imidazole-1,3-diyl)dicarboxylate type, were prepared by treatment of compounds HLR, 1a-e and 1b’-c’ (2-(1-(carboxyalkyl)-1H-imidazol-3-ium-3-yl)carboxylate), with silver oxide in the presence of aqueous sodium hydroxide. They were characterized by analytical, spectroscopic (infrared, IR, 1H and 13C nuclear magnetic resonance, NMR, and circular dichroism) and X-ray methods (2a). In the solid state, the anionic part of complex 2a, [Ag(NHCH)2]3−, shows a linear disposition of Ccarbene-Ag-Ccarbene atoms and an eclipsed conformation of the two NHC ligands. The proposed bis(NHC) nature of the silver complexes was maintained in solution according to NMR and density functional theory (DFT) calculations. The cytotoxic activity of compounds 2 was evaluated against four cancer cell lines and one non-cancerous cell line and several structure-activity correlations were found for these complexes. For instance, the activity decreased when the bulkiness of the R alkyl group in Na3[Ag(NHCR)2] increased. More interesting is the detected chirality-anticancer relationship, where complexes Na3[Ag{(S,S)-NHCR}2] (R = Me, 2b; iPr, 2c) showed better anticancer activity than those of their enantiomeric derivatives Na3[Ag{(R,R)-NHCR}2] (R = Me, 2b’; iPr, 2c’). |
Agencias financiadoras | Ministerio de Ciencia e Innovación (MICIN). España Universidad de Sevilla |
Identificador del proyecto | PGC2018-093443-B-I00
VIPPIT-2021-I.5 |
Cita | Carrasco Carrasco, C.J., Montilla Ramos, F.J., Álvarez González, E., Calderón Montaño, J.M., López Lázaro, M. y Galindo del Pozo, A. (2022). Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes. Journal of Inorganic Biochemistry, 235, 111924. |
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