Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (1, -NH2; 2, -NHMe; 3, -NHEt) have been prepared and characterized. In both the X-ray structures of 1 and 3, two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in 1a and nitrate in 1b) or in the co-ligand (water in 3a and methanol in 3b). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes 1 and 3 confirmed the presence of such different species in the solution. The electrochemical behavior of the pro-ligands and of the complexes was investigated, as well as their biological activity. Complexes 2 and 3 exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes 2 and 3 also showed a high selectivity towards cancerous cell lines with respect to non-cancerous cell lines and were able to circumvent cisplatin resistance. Via the Transmission Electron Microscopy (TEM) imaging technique, preliminary insights into the biological activity of copper complexes were obtained.

Synthesis, characterization and biological activity of novel Cu(II) complexes of 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehy de-4N-substituted thiosemicarbazones / E. Ramachandran, V. Gandin, R. Bertani, P. Sgarbossa, K. Natarajan, N.S.P. Bhuvanesh, A. Venzo, A. Zoleo, M. Mozzon, A. Dolmella, A. Albinati, C. Castellano, N.R. Conceicao, M.F.C. Guedes Da Silva, C. Marzano. - In: MOLECULES. - ISSN 1420-3049. - 25:8(2020 Apr), pp. 1868.1-1868.31. [10.3390/molecules25081868]

Synthesis, characterization and biological activity of novel Cu(II) complexes of 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehy de-4N-substituted thiosemicarbazones

A. Albinati
Formal Analysis
;
C. Castellano
Formal Analysis
;
2020

Abstract

Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (1, -NH2; 2, -NHMe; 3, -NHEt) have been prepared and characterized. In both the X-ray structures of 1 and 3, two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in 1a and nitrate in 1b) or in the co-ligand (water in 3a and methanol in 3b). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes 1 and 3 confirmed the presence of such different species in the solution. The electrochemical behavior of the pro-ligands and of the complexes was investigated, as well as their biological activity. Complexes 2 and 3 exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes 2 and 3 also showed a high selectivity towards cancerous cell lines with respect to non-cancerous cell lines and were able to circumvent cisplatin resistance. Via the Transmission Electron Microscopy (TEM) imaging technique, preliminary insights into the biological activity of copper complexes were obtained.
Copper thiosemicarbazones complexes; Cytotoxicity in 3D spheroids; EPR and electrochemical measurements; TEM images; X ray crystal structure
Settore CHIM/03 - Chimica Generale e Inorganica
apr-2020
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/749162
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