Synthesis, crystal structures, in vitro biological evaluation of zinc(II) and bismuth(III) complexes of 2-acetylpyrazine N(4)-phenylthiosemicarbazone

doi:10.1016/j.bmcl.2012.02.024

Bioorganic & Medicinal Chemistry Letters

Volume 22, Issue 7, 1 April 2012, Pages 2418-2423

https://doi.org/10.1016/j.bmcl.2012.02.024 Get rights and content

Abstract

Two metal complexes formulated as [Zn(L)₂]₂·H₂O (1) and [Bi(L)(NO₃)₂(CH₃OH)] (2), where HL = 2-acetylpyrazine N(4)-phenylthiosemicarbazone, have been synthesized and characterized by elemental analysis, IR, MS, NMR and single-crystal X-ray diffraction studies. Biological studies, carried out in vitro against selected bacteria and the K562 leukemia cell lines, respectively, have shown that the free ligand and its two complexes may be endowed with important biological properties, especially HL with MIC = 3.90 μg/mL against Pseudomonas aeruginosa, the zinc(II) complex 1 with IC₅₀ = 1.0 μM against K562 leukemia cell lines, respectively. The compounds HL and 1 may exert their cytotoxicity activity via induced loss of mitochondria membrane potential (MMP).

Graphical abstract

2-Acetylpyrazine N(4)-phenylthiosemicarbazone (HL) and its metal complexes formulated as [Zn(L)₂]₂·H₂O (1) and [Bi(L)(NO₃)₂(CH₃OH)] (2) have been synthesized and structurally characterized. Biological studies, carried out in vitro against selected bacteria and the K562 leukemia cell lines, respectively, have shown that the free ligand and its complexes may be endowed with important biological properties. Compounds HL and 1 may exert their cytotoxicity via induced loss of MMP.

Section snippets

Supplementary data

CCDC 806018 and 827307 contain the supplementary crystallographic data for complexes 1 and 2, respectively. These data can be obtained free of charge from the Cambridge Crystallographic Centre via www.ccdc.cam.ac.uk/data_request/cif.

Acknowledgment

This work was financially supported by the National Natural Science Foundation of China (21071043).

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Synthesis, crystal structures, in vitro biological evaluation of zinc(II) and bismuth(III) complexes of 2-acetylpyrazine N(4)-phenylthiosemicarbazone

Abstract

Graphical abstract

Section snippets

Supplementary data

Acknowledgment

Inorg. Chem. Commun.

Inorg. Chem.

Inorg. Chem.

J. Med. Chem.

Cancer Control

Chem. Commun.

Metal Based Drugs

J. Inorg. Biochem.

J. Chem. Soc., Dalton Trans.

Chem. Commun.

Dalton Trans.

J. Inorg. Biochem.

J. Inorg. Biochem.

Coord. Chem. Rev.

J. Physiol.

Pediatr. Res.

Inorg. Chem.