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Multifunctional organometallic compounds for the treatment of Chagas disease: Re(I) tricarbonyl compounds with two different bioactive ligands. | LitMetric

AI Article Synopsis

Article Abstract

Chagas' disease (American Trypanosomiasis) is an ancient and endemic illness in Latin America caused by the protozoan parasite Although there is an urgent need for more efficient and less toxic chemotherapeutics, no new drugs to treat this disease have entered the clinic in the last decades. Searching for metal-based prospective antichagasic drugs, in this work, multifunctional Re(I) tricarbonyl compounds bearing two different bioactive ligands were designed: a polypyridyl NN derivative of 1,10-phenanthroline and a monodentate azole (Clotrimazole CTZ or Ketoconazol KTZ). Five -[Re(CO)(NN)(CTZ)](PF) compounds and a -[Re(CO)(NN)(KTZ)](PF) were synthesized and fully characterized. They showed activity against epimastigotes (IC 3.48-9.42 μM) and trypomastigotes of (IC 0.61-2.79 μM) and moderate to good selectivity towards the parasite compared to the VERO mammalian cell model. In order to unravel the mechanism of action of our compounds, two potential targets were experimentally and theoretically studied, namely DNA and one of the enzymes involved in the parasite ergosterol biosynthetic pathway, CYP51 (lanosterol 14-α-demethylase). As hypothesized, the multifunctional compounds shared a similar mode of action as that disclosed for the single bioactive moieties included in the new chemical entities. Additionally, two relevant physicochemical properties of biological interest in prospective drug development, namely lipophilicity and stability in solution in different media, were determined. The whole set of results demonstrates the potentiality of these Re(I) tricarbonyls as promising candidates for further antitrypanosomal drug development.

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http://dx.doi.org/10.1039/d2dt03869bDOI Listing

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