3 years ago

Effects of Terminal Substitution and Iron Coordination on Antiproliferative Activity of L-Proline-salicylaldehyde Thiosemicarbazone Hybrids

Nevenka Gligorijevic, Peter Rapta, Aliona Dobrova, Eva Enyedy, Jozef Kozisek, Sinisa Radulovic, Ghenadie Novitchi, Arion Vladimir, Miljan Milunović
A series of five iron(III) complexes, namely [Fe(HL1)Cl2] (1), [Fe(HL2)Cl2]*1.6H2O (2*1.6H2O), [Fe(HL3)(MeOH)Cl2]*0.5H2O (3*0.5H2O), [Fe(HL4)(MeOH)Cl2]*0.5H2O (4*0.5H2O) and [Fe(HL4)(dmf)Cl2]*0.5Et2O*H2O (4´*0.5Et2O*H2O, where H2L1=L-proline salicylaldehyde thiosemicarbazone (L-Pro-STSC), H2L2=pyrrolidine substituted L-Pro-STSC, H2L3=phenyl substituted L-Pro-STSC and H2L4=naphthyl substituted L-Pro-STSC, has been synthesised. The two ligand precursors (H2L3 and H2L4) and iron complexes were characterised by elemental analysis, spectroscopic methods (UV-vis, IR and NMR), ESI mass spectrometry and single crystal X-ray crystallography (1‒3 and 4'). Magnetic properties of the five-coordinate complex 2 and six-coordinate complex 4 have been also investigated. The antiproliferative activity of the organic hybrids and their iron(III) complexes have been studied in vitro in five human and one murine cancer cell lines, namely HeLa (cervical cancer), FemX (melanoma), A549 (alveolar basal adenocarcinoma), LS-174 (colon cancer), MDA-MB-453 (breast cancer) and MS1 (transformed murine endothelial), as well as in human noncancerous fetal lung fibroblast cell line (MRC-5). According to structure-activity relationship, introduction of aromatic groups such as phenyl or naphthyl enhances the cytotoxic potency of the hybrids in the following order H2L1

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejic.201700962

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