Next Article in Journal
Manipulation of the Size and Phase Composition of Yttrium Iron Garnet Nanoparticles by Pulsed Laser Post-Processing in Liquid
Next Article in Special Issue
Antibacterial Activity of Amidodithiophosphonato Nickel(II) Complexes: An Experimental and Theoretical Approach
Previous Article in Journal
Rapid Raman Spectroscopic Analysis of Stress Induced Degradation of the Pharmaceutical Drug Tetracycline
Previous Article in Special Issue
Mono-, Di- and Tetra-iron Complexes with Selenium or Sulphur Functionalized Vinyliminium Ligands: Synthesis, Structural Characterization and Antiproliferative Activity
Open AccessFeature PaperArticle

Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones

1
Department of Industrial Engineering, University of Padova, 35131 Padova, Italy
2
Chemistry Research Center, National Engineering College, K. R. Nagar, Kovilpatti, Tamilnadu 628503, India
3
Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy
4
Department of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore, Tamil Nadu 641020, India
5
Department of Chemistry, Texas A&M University, College Station, TX 77842, USA
6
Department of Chemical Sciences, University of Padova, 35131 Padova, Italy
7
Department of Chemistry, University of Milan, 20133 Milan, Italy
8
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal
*
Authors to whom correspondence should be addressed.
Academic Editor: Maura Pellei
Molecules 2020, 25(8), 1868; https://doi.org/10.3390/molecules25081868
Received: 4 March 2020 / Revised: 11 April 2020 / Accepted: 13 April 2020 / Published: 17 April 2020
(This article belongs to the Special Issue Exclusive Feature Papers in Inorganic Chemistry)
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. View Full-Text
Keywords: copper thiosemicarbazones complexes; X ray crystal structure; cytotoxicity in 3D spheroids; EPR and electrochemical measurements; TEM images copper thiosemicarbazones complexes; X ray crystal structure; cytotoxicity in 3D spheroids; EPR and electrochemical measurements; TEM images
Show Figures

Chart 1

MDPI and ACS Style

Ramachandran, E.; Gandin, V.; Bertani, R.; Sgarbossa, P.; Natarajan, K.; Bhuvanesh, N.S.P.; Venzo, A.; Zoleo, A.; Mozzon, M.; Dolmella, A.; Albinati, A.; Castellano, C.; Reis Conceição, N.; C. Guedes da Silva, M.F.; Marzano, C. Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones. Molecules 2020, 25, 1868.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop