Title :

Evaluation of ferrocenyl-containing γ-hydroxy-γ-lactam-derived tetramates as potential antiplasmodials

Author(s) :

Chopin, Nicolas [Auteur]
Bosson, Julien [Auteur]
Iikawa, Shinya [Auteur]
Picot, Stéphane [Auteur]
Bienvenu, Anne-Lise [Auteur]
Lavoignat, Adeline [Auteur]
Bonnot, Guillaume [Auteur]
Riou, Mickael [Auteur]
Beaugé, Corinne [Auteur]
Guillory, Vanaïque [Auteur]
Biot, Christophe [Auteur]
Unité de Glycobiologie Structurale et Fonctionnelle (UGSF) - UMR 8576
Pilet, Guillaume [Auteur]
Chessé, Matthieu [Auteur]
Davioud-Charvet, Elisabeth [Auteur]
Elhabiri, Mourad [Auteur]
Bouillon, Jean-Philippe [Auteur]
Médebielle, Maurice [Auteur]

Journal title :

European Journal of Medicinal Chemistry

Abbreviated title :

European Journal of Medicinal Chemistry

Volume number :

243

Pages :

114735

Publisher :

Elsevier BV

Publication date :

2022-12-05

ISSN :

0223-5234

English keyword(s) :

Antimalarial
Tetramate
Ferrocene
Lactam
Fenton
ROS

HAL domain(s) :

Sciences du Vivant [q-bio]
Chimie/Chimie théorique et/ou physique
Chimie/Chimie thérapeutique
Chimie/Chimie de coordination
Sciences du Vivant [q-bio]/Microbiologie et Parasitologie/Parasitologie

English abstract : [en]

A series of ferrocenyl-containing γ-hydroxy-γ-lactam tetramates were prepared in 2–3 steps through ring opening-ring closure (RORC) process of γ-ylidene-tetronate derivatives in the presence of ferrocenyl alkylamines. The ...
Show more >A series of ferrocenyl-containing γ-hydroxy-γ-lactam tetramates were prepared in 2–3 steps through ring opening-ring closure (RORC) process of γ-ylidene-tetronate derivatives in the presence of ferrocenyl alkylamines. The compounds were screened in vitro for their antiplasmodial activity against chloroquine-sensitive (3D7) and chloroquine-resistant (W2) clones of P. falciparum, displaying activity in the range of 0.12–100 μM, with generally good resistance index. The most active ferrocene in these series exhibited IC50 equal to 0.09 μM (3D7) and 0.12 μM (W2). The low cytotoxicity of the ferrocenyl-containing γ-hydroxy-γ-lactam tetramates against Human Umbilical Vein Endothelial (HUVEC) cell line demonstrated selective antiparasitic activity. The redox properties of these ferrocene-derived tetramates were studied and physico-biochemical studies evidenced that these derivatives can exert potent antimalarial activities via a mechanism distinct from ferroquine.Show less >

Language :

Anglais

Peer reviewed article :

Oui

Audience :

Internationale

Popular science :

Non

ANR Project :

Alliance française contre les maladies parasitaires
Optimisation et synthèse de nouvelles structures hétérocycliques 4-amino quinoléine-gamma-lactame comme agents antipaludiques. Du " hit " au " lead " potentiel.

Administrative institution(s) :

Université de Lille
CNRS

Collections :

• Unité de Glycobiologie Structurale et Fonctionnelle (UGSF) - UMR 8576

Research team(s) :

Chemical Glycobiology

Submission date :

2022-12-19T14:39:42Z
2023-01-04T15:16:03Z