Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview

Synthesis, structural characterization and antimicrobial activities of 12 zinc(II) complexes with four thiosemicarbazone and two semicarbazone ligands.

The structural features of copper(II), nickel(II), cobalt(II) and zinc(II) complexes with the antimicrobial drugs quinolones and non-steroidal anti-inflammatory drugs (NSAIDs) as ligands are discussed. The binding properties of these complexes to biomolecules (calf-thymus DNA, bovine or human serum albumin) are presented and evaluated. The biological activity (antimicrobial, antioxidant and antiproliferative) of selected complexes is investigated. Further perspectives concerning the synthesis and the biological activity of novel complexes with quinolones or NSAIDs attractive to synthetic chemists, biochemists and/or biologists are presented.

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Quinolones and non-steroidal anti-inflammatory drugs interacting with copper(II), nickel(II), cobalt(II) and zinc(II): structural features, biological evaluation and perspectives

Synthesis, structural characterization and antimicrobial activities of 4- and 6-coordinate nickel(II) complexes with three thiosemicarbazones and semicarbazone ligands.

Through systematic structure−activity studies of the 2-benzoylpyridine thiosemicarbazone (HBpT), 2-(3-nitrobenzoyl)pyridine thiosemicarbazone (HNBpT) and dipyridylketone thiosemicarbazone (HDpT) series of iron (Fe) chelators, we identified structural features necessary to form Fe complexes with potent anticancer activity (J. Med. Chem. 2007, 50, 3716−3729). In this investigation, we generated the related 2-acetylpyridine thiosemicarbazone (HApT) analogues to examine the influence of the methyl group at the imine carbon. Four of the six HApT chelators had potent antitumor activity (IC50: 0.001−0.002 μM) and Fe chelation efficacy that was similar to the most effective HBpT and HDpT ligands. The HApT Fe complexes had the lowest FeIII/II redox potentials of any thiosemicarbazone series we have generated. This property, in combination with their ability to effectively chelate cellular Fe, make the HApT series one of the most potent antiproliferative agents developed by our group.

2-Acetylpyridine Thiosemicarbazones are Potent Iron Chelators and Antiproliferative Agents: Redox Activity, Iron Complexation and Characterization of their Antitumor Activity

The reaction of Ni(OAc)2 with N′-[1-(2-pyridyl)ethylidene]morpholine-4-carbothiohydrazide (HL) afforded two nickel(II) complexes, [Ni(L)2] (1) and [Ni(L)(OAc)] (2), depending on reaction temperature and starting molar ratio; the former was a 6-coordinate, paramagnetic complex and the latter a 4-coordinate, diamagnetic complex. X-ray analysis of the complex 2 revealed that the ligands, L and OAc, were coordinated to the central metal ion to form a square-planar geometry. The complex 2 showed enhanced antimicrobial activities against selected Gram-positive bacteria, compared with those of the ligand alone, whereas the other complex 1 showed no activity.

Synthesis, Structural Characterization, and Biological Activity of Two Different Nickel(II)Complexes Derived from N'-[1-(2-pyridyl)ethylidene]morpholine-4-carbothiohydrazide

Chisa Koumo

Papers

Synthesis, structural characterization and antimicrobial activities of 12 zinc(II) complexes with four thiosemicarbazone and two semicarbazone ligands.

Synthesis, structural characterization and antimicrobial activities of 4- and 6-coordinate nickel(II) complexes with three thiosemicarbazones and semicarbazone ligands.

Synthesis, Structural Characterization, and Biological Activity of Two Different Nickel(II)Complexes Derived from N'-[1-(2-pyridyl)ethylidene]morpholine-4-carbothiohydrazide