Copper(I) and copper(II) complexes of 5-nitroimidazole conjugated heteroscorpionate ligands have been synthesized. In particular, the new 2,2-bis(pyrazol-1-yl)-N-(2-(2-methy1-5-nitro-1H-imidazol-1-y)ethypacetamide ligand (LHMN) was synthesized by direct coupling of preformed side chain acid with 5-nitroimidazole and its coordination chemistry was investigated towards Cu(I) and Cu(II) acceptors and compared with that of the related 2,2-bis(3,5-dimethyl-1-H-pyrazol-1-yl)-N-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethypacetamide ligand ((LMN)-M-Me). The copper(II) complexes {[((LMN)-M-me)(2)Cu]Cl-2} and {[((LMN)-M-H)(2)Cu]Cl-2} were prepared by the reaction of CuCl2 center dot 2H(2)O with (LMN)-M-H or (LMN)-M-Me ligands in methanol solution. The water soluble copper(I) complexes {[((LMN)-M-me)Cu(PTA)(2)]}(PF6) and {[((LMN)-M-H)Cu(PTA)(2)]}(PF6) were prepared by the reaction of Cu(CH3CN)(4)PF6 and 1,3,5-triaza-7-phosphaadamantane (PTA) with LHMN or LMeMN ligands in acetonitrile solution. The new Cu (I) and Cu(II) complexes as well as the corresponding uncoordinated ligands were evaluated for their cytotoxic activity against 2D monolayer cultures of multiple human cancer cell lines and 3D-cultured HCT-15 colon cancer spheroids. Morphological analysis by Transmission Electron Microscopy (TEM) revealed the induction of a massive cytoplasmic vacuolization consistent with a paraptotic-like cancer cell death.

Syntheses and biological studies of nitroimidazole conjugated heteroscorpionate ligands and related Cu(I) and Cu(II) complexes

Gandin, Valentina;Marzano, Cristina;
2018

Abstract

Copper(I) and copper(II) complexes of 5-nitroimidazole conjugated heteroscorpionate ligands have been synthesized. In particular, the new 2,2-bis(pyrazol-1-yl)-N-(2-(2-methy1-5-nitro-1H-imidazol-1-y)ethypacetamide ligand (LHMN) was synthesized by direct coupling of preformed side chain acid with 5-nitroimidazole and its coordination chemistry was investigated towards Cu(I) and Cu(II) acceptors and compared with that of the related 2,2-bis(3,5-dimethyl-1-H-pyrazol-1-yl)-N-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethypacetamide ligand ((LMN)-M-Me). The copper(II) complexes {[((LMN)-M-me)(2)Cu]Cl-2} and {[((LMN)-M-H)(2)Cu]Cl-2} were prepared by the reaction of CuCl2 center dot 2H(2)O with (LMN)-M-H or (LMN)-M-Me ligands in methanol solution. The water soluble copper(I) complexes {[((LMN)-M-me)Cu(PTA)(2)]}(PF6) and {[((LMN)-M-H)Cu(PTA)(2)]}(PF6) were prepared by the reaction of Cu(CH3CN)(4)PF6 and 1,3,5-triaza-7-phosphaadamantane (PTA) with LHMN or LMeMN ligands in acetonitrile solution. The new Cu (I) and Cu(II) complexes as well as the corresponding uncoordinated ligands were evaluated for their cytotoxic activity against 2D monolayer cultures of multiple human cancer cell lines and 3D-cultured HCT-15 colon cancer spheroids. Morphological analysis by Transmission Electron Microscopy (TEM) revealed the induction of a massive cytoplasmic vacuolization consistent with a paraptotic-like cancer cell death.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11577/3279423
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