title: Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes.
abstract: Two novel vicinal dioxime ligands containing thiosemicarbazone units, (2E)-2-[4-(diethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazine carbothioamide (L(1)H2) and (2E)-2-[4-(dimethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazinecarbothioamide (L(2)H2), were synthesized. Using the HL-60 human leukemia cell line, the in vitro anti-neoplastic activity of these thiosemicarbazone-oxime derivatives was evaluated. Mononuclear nickel(II), copper(II), and cobalt(II) complexes with a metal:ligand ratio of 1:2 for both the L(1)H2 and L(2)H2 ligands were also synthesized. To characterize these compounds, Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), magnetic susceptibility measurements, (1)H and (13)C nuclear magnetic resonance (NMR), ultraviolet-visible (UV-Vis) absorption spectroscopy, heteronuclear multiple-bond correlation (HMQC), and elemental analysis were performed. For L(1)H2, L(2)H2, and each of their derivatives, antiproliferative effects against HL-60 cells were exhibited and the associated IpC50 values ranged from 5μM to 20μM. Furthermore, L(1)H2 and its derivatives inhibited the proliferation of HL-60 cells more effectively than L(2)H2, and 5μM [Cu(L(1)H)2] exhibited the strongest antiproliferative activity.
authors.affiliation: Adnan Menderes University, Faculty of Science and Art, Department of Chemistry, 09010 Aydin, Turkey. Electronic address: ilknurbabahan@yahoo.com.
authors.forename: İlknur
authors.initials: İ
authors.lastname: Babahan
authors.affiliation: Adnan Menderes University, Faculty of Science and Art, Department of Biology, 09010 Aydin, Turkey.
authors.forename: Ali
authors.initials: A
authors.lastname: Özmen
authors.affiliation: Adnan Menderes University, Faculty of Science and Art, Department of Chemistry, 09010 Aydin, Turkey.
authors.forename: Nil
authors.initials: N
authors.lastname: Orhan
authors.affiliation: Adnan Menderes University, Faculty of Science and Art, Department of Chemistry, 09010 Aydin, Turkey.
authors.forename: Didem
authors.initials: D
authors.lastname: Kazar
authors.affiliation: Adnan Menderes University, Faculty of Science and Art, Department of Biology, 09010 Aydin, Turkey.
authors.forename: Esin Hafize
authors.initials: EH
authors.lastname: Değirmenci
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D003035:Cobalt / Q000737:chemistry; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003300:Copper / Q000737:chemistry; D018922:HL-60 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D009532:Nickel / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D056831:Coordination Complexes; D010091:Oximes; D013882:Thiosemicarbazones; D003035:Cobalt; D003300:Copper; D009532:Nickel
keywords: Antiproliferative; Hydrogen-bridge complex; Leukemia; Thiosemicarbazone; Transition metal complex; Vic-dioxime