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2-Amino-thiophene derivatives present antileishmanial activity mediated by apoptosis and immunomodulation in vitro.

Abstract：

:This study evaluated the effects of 2-amino-thiophene derivatives on the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis and their possible mechanisms of action. Initially, we evaluated the antileishmanial activity of ten 2-amino-thiophene derivatives on promastigote and axenic amastigote forms of Leishmania amazonensis and their cytotoxicity against murine macrophages and human red blood cells. Three promising compounds were selected for studies of the cell death process using flow cytometry analysis and a DNA fragmentation assay. The effects of the compounds were assessed on intramacrophagic amastigotes, and the modulation of cytokine and NO production was investigated. All thiophene derivatives showed antileishmanial activity against promastigotes and axenic amastigotes with less toxicity for murine macrophages and human red blood cells. The best values were obtained for compounds containing a lateral indole ring. Docking studies suggested that these compounds played an important role in inhibiting trypanothione reductase (TryR) activity. The selected compounds SB-200, SB-44, and SB-83 induced apoptosis in promastigotes involving phosphatidylserine externalization and DNA fragmentation in a pattern similar to that observed for the positive control. Additionally, SB-200, SB-44, and SB-83 significantly reduced the infection index of macrophages by the parasites; for compounds SB-200 and SB-83 this reduction was associated with increased TNF-α, IL-12, and NO levels. This study demonstrated the effective and selective action of 2-amino-thiophene derivatives against L. amazonensis, resulting in apoptosis-like cell death and immunomodulation in vitro. The results suggest that they are promising compounds for the development of new leishmanicidal drugs.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Rodrigues KA,Dias CN,Néris PL,Rocha Jda C,Scotti MT,Scotti L,Mascarenhas SR,Veras RC,de Medeiros IA,Keesen Tde S,de Oliveira TB,de Lima Mdo C,Balliano TL,de Aquino TM,de Moura RO,Mendonça Junior FJ,de Oliveira MR

doi

10.1016/j.ejmech.2015.10.011

subject

Has Abstract

pub_date

2015-12-01 00:00:00

pages

1-14

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)30296-8

journal_volume

106

pub_type

杂志文章

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