title: Synthesis, characterization and biological studies of new antimony(III) halide complexes with ω-thiocaprolactam.
abstract: Three new antimony(III) halide complexes (SbX(3), X=Cl, Br and I) with the heterocyclic thione ω-thiocaprolactam (1-azacycloheptane-2-thione, (Hthcl)) of formulae {[SbCl(2)(μ(2)-Cl)(Hthcl)(2)](n)} (1), {[(SbBr(2)(μ(2)-Br)(Hthcl)(2))(2)]} (2) and {[(SbI(2)(μ(2)-I)(Hthcl)(2))(2)]} (3) were synthesized from the reaction of antimony(III) halides with ω-thiocaprolactam in 1:2 stoichiometry. The complexes were characterized by elemental analysis, FT-IR spectroscopy, (1)H, (13)C NMR spectroscopy and Thermal Gravimetry-Differential Thermal Analysis (TG-DTA). Crystal structures of the ligand ω-thiocaprolactam and its complexes 1-3 were determined with single crystal X-ray diffraction analysis. Complexes 1-3 and ω-thiocaprolactam were evaluated for their in vitro cytotoxic activity against leiomyosarcoma (LMS) and human breast adenocarcinoma (MCF-7) tumor cell lines. Antimony complexes 1-3 exhibit strong antiproliferative activity against both cell lines tested. The higher such activity was found for 3 with IC(50) values of 0.12±0.04 μM (LMS) and 0.76±0.16 μM (MCF-7) which are 60 and 10 times respectively, stronger than that of cisplatin. The influence of these complexes 1-3 and ω-thiocaprolactam upon the catalytic peroxidation of linoleic acid to hyperoxolinoleic acid by the enzyme lipoxygenase (LOX) was kinetically and theoretically studied. The results were shown negligible inhibitory activity of 1-3 against LOX.
authors.affiliation: Department of Chemistry, Namık Kemal University, Tekirdag, Turkey. iiozturk@nku.edu.tr
authors.forename: Ibrahim I
authors.initials: II
authors.lastname: Ozturk
authors.forename: Christina N
authors.initials: CN
authors.lastname: Banti
authors.forename: Manos J
authors.initials: MJ
authors.lastname: Manos
authors.forename: Anastasios J
authors.initials: AJ
authors.lastname: Tasiopoulos
authors.forename: Nikolaos
authors.initials: N
authors.lastname: Kourkoumelis
authors.forename: Konstantinos
authors.initials: K
authors.lastname: Charalabopoulos
authors.forename: Sotiris K
authors.initials: SK
authors.lastname: Hadjikakou
mesh_terms: D000965:Antimony / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002209:Caprolactam / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D006801:Humans; D020128:Inhibitory Concentration 50; D008084:Lipoxygenase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D017550:Spectroscopy, Fourier Transform Infrared; D013871:Thiones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D056831:Coordination Complexes; D013871:Thiones; D002209:Caprolactam; D000965:Antimony; D008084:Lipoxygenase