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Evaluation of ferrocenyl-containing γ-hydroxy-γ-lactam-derived tetramates as potential antiplasmodials.
Chopin, Nicolas; Bosson, Julien; Iikawa, Shinya; Picot, Stéphane; Bienvenu, Anne-Lise; Lavoignat, Adeline; Bonnot, Guillaume; Riou, Mickael; Beaugé, Corinne; Guillory, Vanaïque; Biot, Christophe; Pilet, Guillaume; Chessé, Matthieu; Davioud-Charvet, Elisabeth; Elhabiri, Mourad; Bouillon, Jean-Philippe; Médebielle, Maurice.
Afiliación
  • Chopin N; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France.
  • Bosson J; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France.
  • Iikawa S; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France.
  • Picot S; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France; Institut de Parasitologie et Mycologie Médicale, Groupement Hospitalier Nord, Hospices Civils de Lyon, Lyon, France.
  • Bienvenu AL; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France; Service Pharmacie, Groupement Hospitalier Nord, Hospices Civils de Lyon, Lyon, France.
  • Lavoignat A; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France.
  • Bonnot G; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France.
  • Riou M; INRAE, UE-1277 Plateforme d'Infectiologie Expérimentale (PFIE), Centre Val de Loire, Nouzilly, France.
  • Beaugé C; INRAE, UE-1277 Plateforme d'Infectiologie Expérimentale (PFIE), Centre Val de Loire, Nouzilly, France.
  • Guillory V; INRAE, UE-1277 Plateforme d'Infectiologie Expérimentale (PFIE), Centre Val de Loire, Nouzilly, France; INRAE, UMR-1282 Infectiologie et Santé Publique (ISP), Centre Val de Loire - Université de Tours, Nouzilly, France.
  • Biot C; Université de Lille, CNRS, UMR 8576, UGSF, Unité de Glycobiologie Structurale et Fonctionnelle, Lille, France.
  • Pilet G; Univ. Lyon, Université Lyon 1, CNRS, LMI, UMR 5615, Villeurbanne, France.
  • Chessé M; UMR 7042 Université de Strasbourg‒CNRS‒UHA, Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), 25 Rue Becquerel, F-67087 Strasbourg, France.
  • Davioud-Charvet E; UMR 7042 Université de Strasbourg‒CNRS‒UHA, Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), 25 Rue Becquerel, F-67087 Strasbourg, France.
  • Elhabiri M; UMR 7042 Université de Strasbourg‒CNRS‒UHA, Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), 25 Rue Becquerel, F-67087 Strasbourg, France. Electronic address: elhabiri@unistra.fr
  • Bouillon JP; Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen, INSA Rouen, CNRS, Mont Saint-Aignan, France. Electronic address: jean-philippe.bouillon@univ-rouen.fr.
  • Médebielle M; Univ. Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, Villeurbanne, France. Electronic address: maurice.medebielle@univ-lyon1.fr.
Eur J Med Chem ; 243: 114735, 2022 Dec 05.
Article en En | MEDLINE | ID: mdl-36122550
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Malaria Falciparum / Antimaláricos Límite: Humans Idioma: En Revista: Eur J Med Chem Año: 2022 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Francia

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Malaria Falciparum / Antimaláricos Límite: Humans Idioma: En Revista: Eur J Med Chem Año: 2022 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Francia