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Metal−azole fungistatic drug complexes as anti-Sporothrix spp.

Abstract

The new complexes [Cu(PPh3)2(KTZ)2]NO3 (1), [Cu(PPh3)2(CTZ)2]NO3 (2), [Au(KTZ)2]Cl (3), [Au(CTZ)2]Cl (4) and Pt(KTZ)2Cl2 (5) were prepared by reaction of KTZ, CTZ (where CTZ: 1-[(2-chlorophenyl)-diphenylmethyl-1H-imidazole and KTZ: cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine and their respective metal salts or metal complexes in mild conditions. They were characterized by NMR, UV-Vis and IR spectroscopies, microanalytical analyses and mass spectrometry. Complex (5) was also investigated by computational methods (DFT) to evaluate the geometry configuration around Pt(II) coordination sphere; results point out to the trans complex as the most stable one. Antifungal activities of these new compounds 1-5 and some of our reported metal-based azole drug derivatives such as Pt(CTZ)2Cl2 (6), [Au(PPh3)(KTZ)]PF6 (7) and [Au(PPh3)(CTZ)]PF6 (8) were evaluated against sporotrichosis agents (Sporothrix schenckii, Sporothrix brasiliensis and Sporothrix globosa). Their selectivities towards fungal cells were also estimated. Complexes [Cu(PPh3)2(KTZ)2]NO3 (1), [Cu(PPh3)2(CTZ)2]NO3 (2), [Au(PPh3)(KTZ)]PF6 (7) and [Au(PPh3)(CTZ)]PF6 (8) inhibited fungal growth and killed fungus at concentrations in the nanomolar range and were more active than CTZ or KTZ alone. Microscopy analysis by scanning electron microscopy showed that the complexes 1, 2, 7 and 8 interfered with the cell shape. All metal-azole complexes tested were more selective for fungus than for mammalian cells and human red blood cells, revealing that they are promising molecules for the development of new antifungal compounds.

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Supplementary files

Publication details

The article was received on 29 Mar 2018, accepted on 21 Jun 2018 and first published on 29 Jun 2018


Article type: Paper
DOI: 10.1039/C8NJ01544A
Citation: New J. Chem., 2018, Accepted Manuscript
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    Metal−azole fungistatic drug complexes as anti-Sporothrix spp.

    T. Gagini, L. Colina-Vegas, W. Villarreal, L. P. Borba-Santos, C. de Souza Pereira, A. A. Batista, M. Kneip Fleury, W. de Souza, S. Rozental, L. A. Sodre Costa and M. Navarro, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ01544A

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