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Issue 1, 2019
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Cytoprotective effects of imidazole-based [S1] and [S2]-donor ligands against mercury toxicity: a bioinorganic approach

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Abstract

Here we report the coordination behaviour of an imidazole-based [S1]-donor ligand, 1,3-dimethyl-imidazole-2(3H)-thione (L1), and [S2]-donor ligand, 3,3′-methylenebis(1-methyl-imidazole-2(3H)-thione) (L2) or 4,4′-(3,3′-methylenebis-(2-thioxo-2,3-dihydro-imidazole-3,1-diyl))dibutanoic acid (L3), with HgX2 (X = Cl, Br or I) in solution and the solid state. NMR, UV-Vis spectroscopic, and single crystal X-ray studies demonstrated that L1 or L2 coordinated rapidly and reversibly to the mercury center of HgX2 through the thione moiety. Treatment of L2 with HgCl2 or HgBr2 afforded 16-membered metallacycle k1-(L2)2Hg2Cl4 or k1-(L2)2Hg2Br4 where two Cl or Br atoms are located inside the ring. In contrast, treatment of L2 with HgI2 afforded a chain-like structure of k1-[L2Hgl2]n, possibly due to the large size of the iodine atom. Interestingly, [S1] and [S2]-donor ligands (L1, L2, and L3) showed an excellent efficacy to protect liver cells against HgCl2 induced toxicity and the strength of their efficacy is in the order of L3 > L2 > L1. 30% decrease of ROS production was observed when liver cells were co-treated with HgCl2 and L1 in comparison to those cells treated with HgCl2 only. In contrast, 45% and 60% decrease of ROS production was observed in the case of cells co-treated with HgCl2 and thiones L2 and L3, respectively, indicating that [S2]-donor ligands L2 and L3 have better cytoprotective effects against oxidative stress induced by HgCl2 than [S1]-donor ligand L1. Water-soluble ligand L3 with N-(CH2)3CO2H substituents showed a better cytoprotective effect against HgCl2 toxicity than L2 in liver cells.

Graphical abstract: Cytoprotective effects of imidazole-based [S1] and [S2]-donor ligands against mercury toxicity: a bioinorganic approach

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Publication details

The article was received on 11 Aug 2018, accepted on 12 Nov 2018 and first published on 15 Nov 2018


Article type: Paper
DOI: 10.1039/C8MT00237A
Citation: Metallomics, 2019,11, 213-225

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    Cytoprotective effects of imidazole-based [S1] and [S2]-donor ligands against mercury toxicity: a bioinorganic approach

    R. Karri, A. Chalana, R. Das, R. K. Rai and G. Roy, Metallomics, 2019, 11, 213
    DOI: 10.1039/C8MT00237A

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