New tin (IV) and organotin (IV) complexes with a hybrid thiosemicarbazone/hydrazone ligand: synthesis, crystal structure and antiproliferative activity
Nowadays, the search for new chemotherapeutic agents with low toxicity and high selectivity is a major concern. In this paper, we report the synthesis and characterization of a hybrid thiosemicarbazone/hydrazone ligand in its neutral form (L1 H2) and as the chloride salt ([L1 H3]Cl)-, three diorgano...
| Autores: | , , , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2024 |
| País: | España |
| Institución: | Universidad Autónoma de Madrid |
| Repositorio: | Biblos-e Archivo. Repositorio Institucional de la UAM |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.uam.es:10486/711702 |
| Acceso en línea: | http://hdl.handle.net/10486/711702 https://dx.doi.org/10.1155/2024/1018375 |
| Access Level: | acceso abierto |
| Palabra clave: | Tin Thiosemicarbazone Crystal Structure Metallocene Organotin Química |
| Sumario: | Nowadays, the search for new chemotherapeutic agents with low toxicity and high selectivity is a major concern. In this paper, we report the synthesis and characterization of a hybrid thiosemicarbazone/hydrazone ligand in its neutral form (L1 H2) and as the chloride salt ([L1 H3]Cl)-, three diorganotin (IV) complexes, and one complex with Sn (IV). Te compounds have been fully characterized by IR, mass spectra, 1 H, 13C, and 119Sn NMR, 119Sn CP/MAS NMR, and by single crystal X-ray difraction. Te organotin compounds have the empirical formula [SnR2L1 ] (R = Me, Bu, and Ph), but in the solid state, they are polymeric species with seven coordination number due to weak coordination of the pyridine nitrogen, whereas in solution, the polymeric structure is lost to aford hexacoordinate monomeric species. Reaction with SnI4 yields complex [Sn (L1 )2]·EtOH, with the metal in a distorted dodecahedral arrangement. We have evaluated the antiproliferative activity of the two forms of the ligands and the four coordination compounds against MDA-MB-231, HeLa, PC3, and HepG2 cancer cell lines, and WI-38 normal cell line, and all the compounds present higher activity than cisplatin, used as the standard control. To investigate the mode of action, we have selected the most active complex, containing phenyl substituents, and used the triple negative breast cancer cell line MDA-MB-231. Te results show that the complex induces apoptotic cell death promoted by generation of reactive oxygen species and by disruption of mitochondrial membrane potential |
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