The toxicity of soluble derivatives (potassium salt) of lapachol and isolapachol in different stages of the life cycle of Schistosoma mansoni is evaluated. The potassium salts of isolapachol and lapachol showed significant molluscicidal activity against the adult snail (LC90<7 ppm) and snail egg masses (LC90<3 ppm). Cercaricidal assays revealed strong activities for both compounds. Lethality assays against brine shrimp eggs (Artemia salina Leach) indicated very high toxicity for the potassium salt of isolapachol (LC90=1.54 ppm), differently from the potassium salt of lapachol that can be considered non toxic (LC90=176.3 ppm). The same tendency is observed with piscicidal activity, for which the isolapachol salt has showed higher toxicity. The obtained selectivity ratios concerning LC50 and LC90 for lapachol, in relation to Tilapia nilotica lethality assay are 2.33 and 1.26, respectively. Despite the piscicidal toxicity, the use of the salt of lapachol can be recommended for field tests in Schistosomiasis, with caution.
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http://dx.doi.org/10.1016/s0001-706x(02)00055-4 | DOI Listing |
Prep Biochem Biotechnol
June 2019
a School of Pharmaceutical Sciences of Ribeirao Preto , University of São Paulo, Ribeirão Preto , Brazil.
Lapachol is a natural naphthoquinone with a range of biological effects, including anticancer activity. Microbial transformations of lapachol can lead to the formation of new biologically active compounds. In addition, fungi can produce secondary metabolites that are also important for drug discovery.
View Article and Find Full Text PDFJ Enzyme Inhib Med Chem
April 2016
Fundação Oswaldo Cruz, Centro de Pesquisas Gonçalo Moniz , Salvador, BA , Brazil .
This study reports on the design, synthesis and antiparasitic activity of three new semi-synthetic naphthoquinones structurally related to the naturally-occurring lapachol and lapachone. Of the compounds tested, 3-(3-methylbut-1-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate (1) was the most active against Plasmodium falciparum among both natural and semi-synthetic naphthoquinones, showing potent and selective activity. Compound 1 was able to reduce the in vitro parasite burden, in vitro parasite cell cycle, as well as the blood parasitemia in Plasmodium berghei-infected mice.
View Article and Find Full Text PDFMem Inst Oswaldo Cruz
August 2014
Laboratório de Malária, Centro de Pesquisas René-Rachou-Fiocruz, Belo Horizonte, MG, Brasil.
Due to the recent advances of atovaquone, a naphthoquinone, through clinical trials as treatment for malarial infection, 19 quinone derivatives with previously reported structures were also evaluated for blood schizonticide activity against the malaria parasite Plasmodium falciparum. These compounds include 2-hydroxy-3-methylamino naphthoquinones (2-9), lapachol (10), nor-lapachol (11), iso-lapachol (12), phthiocol (13) and phenazines (12-20). Their cytotoxicities were also evaluated against human hepatoma and normal monkey kidney cell lines.
View Article and Find Full Text PDFMem Inst Oswaldo Cruz
November 2004
Departamento de Química, CCEN, Universidade Federal de Alagoas, Tabuleiro do Martins, 57072-970 Maceió, AL, Brazil.
The antileishmanial activity of lapachol, isolapachol, and dihydrolapachol, along with soluble derivatives (potassium salt) and acetate was obtained. All the compounds were assayed against metacyclic promastigotes of two different species of Leishmania associated to tegumentar leishmaniasis: L. amazonensis and L.
View Article and Find Full Text PDFActa Trop
July 2002
Departamento de Química/CCEN Campus A.C. Simoes, Universidade Federal de Alagoas, Tabuleiro dos Martins Maceió, Alagoas, Brazil.
The toxicity of soluble derivatives (potassium salt) of lapachol and isolapachol in different stages of the life cycle of Schistosoma mansoni is evaluated. The potassium salts of isolapachol and lapachol showed significant molluscicidal activity against the adult snail (LC90<7 ppm) and snail egg masses (LC90<3 ppm). Cercaricidal assays revealed strong activities for both compounds.
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