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    Effects of terminal substitution and iron coordination on antiproliferative activity of L-proline-salicylaldehyde-thiosemicarbazone hybrids

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    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‚Ä≤¬∑0.5Et2O¬∑H2O), where H2L1 = l‚Äźproline‚Äźsalicylaldehyde‚Äďthiosemicarbazone (l‚ÄźPro‚ÄźSTSC), H2L2 = pyrrolidine‚Äźsubstituted l‚ÄźPro‚ÄźSTSC, H2L3 = phenyl‚Äźsubstituted l‚ÄźPro‚ÄźSTSC, and H2L4 = naphthyl‚Äźsubstituted l‚ÄźPro‚ÄźSTSC, have been synthesized. The two ligand precursors (H2L3 and H2L4) and iron complexes were characterized by elemental analysis, spectroscopic methods (UV/Vis, IR, and NMR), ESI mass spectrometry, cyclic voltammetry, and single‚Äźcrystal X‚Äźray crystallography (1‚Äď3 and 4‚Ä≤). Magnetic properties of the five‚Äźcoordinate complex 2 and six‚Äźcoordinate complex 4 have also been investigated. The antiproliferative activity of the organic hybrids and their iron(III) complexes have been studied in vitro in five human cell lines and one murine cancer cell line, namely HeLa (cervical cancer), FemX (melanoma), A549 (alveolar basal adenocarcinoma), LS‚Äź174 (colon cancer), MDA‚ÄźMB‚Äź453 (breast cancer) and MS1 (transformed murine endothelial), as well as in human noncancerous fetal lung fibroblast cell line (MRC‚Äź5). According to the structure‚Äďactivity relationship, introduction of aromatic groups such as phenyl or naphthyl enhances the cytotoxic potency of the hybrids in the following order H2L1 < H2L2 < H2L3 < H2L4. Coordination of the hybrids to iron(III) improves their antiproliferative activity in the majority of investigated cell lines with exception of H2L3 in LS‚Äź174, H2L4 in MS1, and both H2L3 and H2L4 in FemX cell lines, where an opposite effect was observed.This study was financially supported by the Austrian Science Fund (project number P28223 N34), Research and Development Agency of the Slovak Republic under the contracts No. APVV 15-0079 and APVV-15-0053, Scientific Grant Agency of the Slovak Republic (VEGA Project 1/0871/16) and Slovak University of Technology in Bratislava (Young Researcher Grant, M. Milunovińá, PhD) This work was also supported by Ministry of Education, Science, Research and Sport of the Slovak Republic withinhe Research and Development Operational Program for the project "University Science Park of STU Bratislava", ITMS 26240220084, cofunded by the European Regional Development Fund