4-Phenyl-1,3-thiazole-2-amines as scaffolds for new antileishmanial agents View Full Text


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Article Info

DATE

2018-09-10

AUTHORS

Carina Agostinho Rodrigues, Paloma Freire dos Santos, Marcela Oliveira Legramanti da Costa, Thais Fernanda Amorim Pavani, Patrícia Xander, Mariana Marques Geraldo, Ana Mengarda, Josué de Moraes, Daniela Gonçales Galasse Rando

ABSTRACT

BackgroundThere is still a need for new alternatives in pharmacological therapy for neglected diseases, as the drugs available show high toxicity and parenteral administration. That is the case for the treatment of leishmaniasis, particularly to the cutaneous clinical form of the disease. In this study, we present the synthesis and biological screening of eight 4-phenyl-1,3-thiazol-2-amines assayed against Leishmania amazonensis. Herein we propose that these compounds are good starting points for the search of new antileishmanial drugs by demonstrating some of the structural aspects which could interfere with the observed activity, as well as suggesting potential macromolecular targets.MethodsThe compounds were easily synthesized by the methodology of Hantzsch and Weber, had their purities determined by Gas Chromatography-Mass spectrometry and assayed against the promastigote forms of Leishmania amazonensis as well as against two white cell lines (L929 and THP-1) and the monkey’s kidney Vero cells. PrestoBlue® and MTT viability assays were the methodologies applied to measure the antileishmanial and cytotoxic activities, respectively. A molecular modeling target fishing study was performed aiming to propose potential macromolecular targets which could explain the observed biological behavior.ResultsFour out of the eight compounds tested exhibited important anti-promastigote activity associated with good selectivity indexes when considering Vero cells. For the most promising compound, compound 6, IC50 against promastigotes was 20.78 while SI was 5.69. Compounds 3 (IC50: 46.63 μM; SI: 26.11) and 4 (IC50: 53.12 μM; SI: 4.80) also presented important biological behavior. A target fishing study suggested that S-methyl-5-thioadenosine phosphorylase is a potential target to these compounds, which could be explored to enhance activity and decrease the potential toxic side effects.ConclusionsThis study shows that 4-phenyl-1,3-thiazol-2-amines could be good scaffolds to the development of new antileishmanial agents. The S-methyl-5-thioadenosine phosphorylase could be one of the macromolecular targets involved in the action. More... »

PAGES

26

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1186/s40409-018-0163-x

DOI

http://dx.doi.org/10.1186/s40409-018-0163-x

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1106911006

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30214457


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