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A structural investigation of heteroleptic pentavalent antimonials and their leishmanicidal activity
Author(s) -
Mushtaq Rabia,
Rauf Muhammad Khawar,
Bond Marcus,
Badshah Amin,
Ali Muhammad Irshad,
Nadhman Akhtar,
Yasinzai Masoom,
Tahir Muhammad Nawaz
Publication year - 2016
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3456
Subject(s) - chemistry , cytotoxicity , trigonal bipyramidal molecular geometry , monomer , stereochemistry , carboxylate , nuclear chemistry , biocompatible material , crystal structure , in vitro , organic chemistry , biochemistry , polymer , medicine , biomedical engineering
In the quest for new drug candidates for the safe treatment of parasitic diseases like leishmaniasis, a series of heteroleptic pentavalent antimonials of the type [SbR 3 (OOCR′) 2 ] were synthesized and characterized using elemental analysis, Fourier transform infrared spectroscopy and multinuclear ( 1 H and 13 C) NMR spectroscopy. The carboxylate moieties are predominantly substituted benzoates with some complexes that fit in acetato or nicotinato ligands. The crystal structures of [Sb( p ‐Tol) 3 ( p ‐CH 3 C 6 H 4 COO) 2 ], [Sb( p ‐Tol) 3 (3,5‐Cl 2 C 6 H 3 COO) 2 ] and [Sb( p ‐Tol) 3 (3‐nicotinato) 2 ] were determined crystallographically and shown to adopt geometries intermediate between trigonal bipyramidal and square pyramidal, and essentially monomeric with a five‐coordinated Sb center. The leishmanicidal activity was assessed against the Leishmania tropica KWH23 parasite, and the cytotoxicity level was also measured on human macrophage blood cells. It was observed that IC 50 of the antimonials was 100‐fold superior as compared with the standard antimonial drug used. Cytotoxicity results showed that these antimonials are highly active even at low concentrations and are biocompatible with human macrophages, making them highly promising drug candidates for further investigation. Copyright © 2016 John Wiley & Sons, Ltd.