Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones
Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (<b>1</b>, -NH<sub>2</sub>; <b>2</b>, -NHMe; <b>3</b>, -NHEt) have been prepared and characterized. In both the X-ray...
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MDPI AG
2020-04-01
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| Online Access: | https://www.mdpi.com/1420-3049/25/8/1868 |
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| author | Eswaran Ramachandran Valentina Gandin Roberta Bertani Paolo Sgarbossa Karuppannan Natarajan Nattamai S. P. Bhuvanesh Alfonso Venzo Alfonso Zoleo Mirto Mozzon Alessandro Dolmella Alberto Albinati Carlo Castellano Nuno Reis Conceição M. Fátima C. Guedes da Silva Cristina Marzano |
| author_facet | Eswaran Ramachandran Valentina Gandin Roberta Bertani Paolo Sgarbossa Karuppannan Natarajan Nattamai S. P. Bhuvanesh Alfonso Venzo Alfonso Zoleo Mirto Mozzon Alessandro Dolmella Alberto Albinati Carlo Castellano Nuno Reis Conceição M. Fátima C. Guedes da Silva Cristina Marzano |
| author_sort | Eswaran Ramachandran |
| collection | DOAJ |
| description | Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (<b>1</b>, -NH<sub>2</sub>; <b>2</b>, -NHMe; <b>3</b>, -NHEt) have been prepared and characterized. In both the X-ray structures of <b>1</b> and <b>3</b>, two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in <b>1a</b> and nitrate in <b>1b</b>) or in the co-ligand (water in <b>3a</b> and methanol in <b>3b</b>). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes <b>1</b> and <b>3</b> 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 <b>2</b> and <b>3</b> exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes <b>2</b> and <b>3</b> 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. |
| first_indexed | 2024-03-10T20:23:41Z |
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| id | doaj.art-e2febf980cf640a88a97abe80fbae655 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T20:23:41Z |
| publishDate | 2020-04-01 |
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| series | Molecules |
| spelling | doaj.art-e2febf980cf640a88a97abe80fbae6552023-11-19T22:00:16ZengMDPI AGMolecules1420-30492020-04-01258186810.3390/molecules25081868Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted ThiosemicarbazonesEswaran Ramachandran0Valentina Gandin1Roberta Bertani2Paolo Sgarbossa3Karuppannan Natarajan4Nattamai S. P. Bhuvanesh5Alfonso Venzo6Alfonso Zoleo7Mirto Mozzon8Alessandro Dolmella9Alberto Albinati10Carlo Castellano11Nuno Reis Conceição12M. Fátima C. Guedes da Silva13Cristina Marzano14Department of Industrial Engineering, University of Padova, 35131 Padova, ItalyDepartment of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, ItalyDepartment of Industrial Engineering, University of Padova, 35131 Padova, ItalyDepartment of Industrial Engineering, University of Padova, 35131 Padova, ItalyDepartment of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore, Tamil Nadu 641020, IndiaDepartment of Chemistry, Texas A&M University, College Station, TX 77842, USADepartment of Chemical Sciences, University of Padova, 35131 Padova, ItalyDepartment of Chemical Sciences, University of Padova, 35131 Padova, ItalyDepartment of Industrial Engineering, University of Padova, 35131 Padova, ItalyDepartment of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, ItalyDepartment of Chemistry, University of Milan, 20133 Milan, ItalyDepartment of Chemistry, University of Milan, 20133 Milan, ItalyCentro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, 1049-001 Lisboa, PortugalCentro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, 1049-001 Lisboa, PortugalDepartment of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, ItalyThree new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (<b>1</b>, -NH<sub>2</sub>; <b>2</b>, -NHMe; <b>3</b>, -NHEt) have been prepared and characterized. In both the X-ray structures of <b>1</b> and <b>3</b>, two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in <b>1a</b> and nitrate in <b>1b</b>) or in the co-ligand (water in <b>3a</b> and methanol in <b>3b</b>). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes <b>1</b> and <b>3</b> 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 <b>2</b> and <b>3</b> exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes <b>2</b> and <b>3</b> 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.https://www.mdpi.com/1420-3049/25/8/1868copper thiosemicarbazones complexesX ray crystal structurecytotoxicity in 3D spheroidsEPR and electrochemical measurementsTEM images |
| spellingShingle | Eswaran Ramachandran Valentina Gandin Roberta Bertani Paolo Sgarbossa Karuppannan Natarajan Nattamai S. P. Bhuvanesh Alfonso Venzo Alfonso Zoleo Mirto Mozzon Alessandro Dolmella Alberto Albinati Carlo Castellano Nuno Reis Conceição M. Fátima C. Guedes da Silva Cristina Marzano Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones Molecules copper thiosemicarbazones complexes X ray crystal structure cytotoxicity in 3D spheroids EPR and electrochemical measurements TEM images |
| title | Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones |
| title_full | Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones |
| title_fullStr | Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones |
| title_full_unstemmed | Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones |
| title_short | Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones |
| title_sort | synthesis characterization and biological activity of novel cu ii complexes of 6 methyl 2 oxo 1 2 dihydroquinoline 3 carbaldehyde 4n substituted thiosemicarbazones |
| topic | copper thiosemicarbazones complexes X ray crystal structure cytotoxicity in 3D spheroids EPR and electrochemical measurements TEM images |
| url | https://www.mdpi.com/1420-3049/25/8/1868 |
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