ArticlePure and applied chemistry. Chimie pure et appliquee2012
First total synthesis of the (±)-2-methoxy-6-heptadecynoic acid and related 2-methoxylated analogs as effective inhibitors of the leishmania topoisomerase IB enzyme.
Article in Pure and applied chemistry. Chimie pure et appliquee, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Potential therapeutic targets shared between leishmaniasis and cancer.Parasitology · 2021Review
- Synthesis of a novel brominated vinylic fatty acid with antileishmanial activity that effectively inhibits thePure and applied chemistry. Chimie pure et appliquee · 2019Article
- First Total Synthesis of ω-Phenyl Δ6 Fatty Acids and their Leishmanicidal and Anticancer Properties.Current topics in medicinal chemistry · 2018Article
- Article
- Arrabidaea chica hexanic extract induces mitochondrion damage and peptidase inhibition on Leishmania spp.BioMed research international · 2014Article
- Article
- Synthesis of the novel (±)-2-methoxy-6-icosynoic acid--a fatty acid that induces death of neuroblastoma cells.Chemistry and physics of lipidsArticle
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Authors and funding
8 authors.
Funding
Abstract
The fatty acids (±)-2-methoxy-6Z-heptadecenoic acid (1), (±)-2-methoxy-6-heptadecynoic acid (2) and (±)-2-methoxyheptadecanoic acid (3) were synthesized and their inhibitory activity against the Leishmania DNA topoisomerase IB enzyme (LdTopIB) determined. Acids 1 and 2 were synthesized from 4-bromo-1-pentanol, the former in ten steps and in 7% overall yield, while the latter in seven steps and in 14% overall yield. Acid 3 was prepared in six steps and in 42% yield from 1-hexadecanol. Acids 1-3 inhibited the LdTopIB enzyme following the order 2 > 1 ⪢ 3, with 2 displaying an EC(50) = 16.6 ± 1.1 μM and 3 not inhibiting the enzyme. Acid 1 preferentially inhibited the LdTopIB enzyme over the human TopIB enzyme. Unsaturation seems to be a prerequisite for effective inhibition, rationalized in terms of weak intermolecular interactions between the active site of LdTopIB and either the double or triple bonds of the fatty acids. Toxicity towards Leishmania donovani promastigotes was also investigated resulting in the same order 2 > 1 > 3, with 2 displaying an EC(50) = 74.0 ± 17.1 μM. Our results indicate that α-methoxylation decreases the toxicity of C(17:1) fatty acids towards L. donovani promastigotes, but improves their selectivity index.
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Registered trials
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