Evaluation of ferrocenyl-containing ...
Document type :
Article dans une revue scientifique
Permalink :
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]
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
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
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 >
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 :
Administrative institution(s) :
Université de Lille
CNRS
CNRS
Research team(s) :
Chemical Glycobiology
Submission date :
2022-12-19T14:39:42Z
2023-01-04T15:16:03Z
2023-01-04T15:16:03Z
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