{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T04:29:56Z","timestamp":1767846596997,"version":"3.49.0"},"reference-count":131,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2020,4,17]],"date-time":"2020-04-17T00:00:00Z","timestamp":1587081600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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.<\/jats:p>","DOI":"10.3390\/molecules25081868","type":"journal-article","created":{"date-parts":[[2020,4,21]],"date-time":"2020-04-21T05:48:52Z","timestamp":1587448132000},"page":"1868","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7611-9663","authenticated-orcid":false,"given":"Eswaran","family":"Ramachandran","sequence":"first","affiliation":[{"name":"Department of Industrial Engineering, University of Padova, 35131 Padova, Italy"},{"name":"Chemistry Research Center, National Engineering College, K. R. Nagar, Kovilpatti, Tamilnadu 628503, India"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0442-0670","authenticated-orcid":false,"given":"Valentina","family":"Gandin","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy"}]},{"given":"Roberta","family":"Bertani","sequence":"additional","affiliation":[{"name":"Department of Industrial Engineering, University of Padova, 35131 Padova, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0938-953X","authenticated-orcid":false,"given":"Paolo","family":"Sgarbossa","sequence":"additional","affiliation":[{"name":"Department of Industrial Engineering, University of Padova, 35131 Padova, Italy"}]},{"given":"Karuppannan","family":"Natarajan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore, Tamil Nadu 641020, India"}]},{"given":"Nattamai S. P.","family":"Bhuvanesh","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Texas A&amp;M University, College Station, TX 77842, USA"}]},{"given":"Alfonso","family":"Venzo","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences, University of Padova, 35131 Padova, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9432-0723","authenticated-orcid":false,"given":"Alfonso","family":"Zoleo","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences, University of Padova, 35131 Padova, Italy"}]},{"given":"Mirto","family":"Mozzon","sequence":"additional","affiliation":[{"name":"Department of Industrial Engineering, University of Padova, 35131 Padova, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1287-6635","authenticated-orcid":false,"given":"Alessandro","family":"Dolmella","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8779-3327","authenticated-orcid":false,"given":"Alberto","family":"Albinati","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Milan, 20133 Milan, Italy"}]},{"given":"Carlo","family":"Castellano","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Milan, 20133 Milan, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5102-8482","authenticated-orcid":false,"given":"Nuno","family":"Reis Concei\u00e7\u00e3o","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4836-2409","authenticated-orcid":false,"given":"M. F\u00e1tima","family":"C. Guedes da Silva","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0565-2596","authenticated-orcid":false,"given":"Cristina","family":"Marzano","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy"}]}],"member":"1968","published-online":{"date-parts":[[2020,4,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1016\/j.ejmech.2016.03.078","article-title":"Design, synthesis and biological evaluation of thiosemicarbazones, hydrazinobenzothiazoles and arylhydrazones as anticancer agents with a potential overcome multidrug resistance","volume":"117","author":"Pape","year":"2016","journal-title":"Eur. J. Med. 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