Phosphatidyl myo-inositol mannosides mimics built on an acyclic or heterocyclic core: synthesis and anti-inflammatory properties. - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue ChemMedChem Année : 2011

Phosphatidyl myo-inositol mannosides mimics built on an acyclic or heterocyclic core: synthesis and anti-inflammatory properties.

Résumé

Phosphatidyl myo-inositol mannosides (PIMs) are constituents of the mycobacterial cell wall and possess immunomodulatory activities. Certain PIM derivatives have immunoprotective activity and are of interest as anti-inflammatory agents. In order to identify simplified analogues of PIMs that retain this interesting activity, we have prepared a series of new analogues based either on an acyclic or on a heterocyclic scaffold that replaces the inositol moiety, and evaluated these compounds for their inhibition of LPS-induced release of NO and pro-inflammatory cytokines by macrophages. It was found that the inositol moiety can be favourably replaced by an aza-cyclitol (trihydroxy-piperidine) or an oxa-cyclitol (trihydroxy-tetrahydropyran) unit, and that the configuration of the OH-carrying carbons does not play a significant role. The biological activity is reduced if the nitrogen atom is free in the aza-cyclitol unit.

Domaines

Immunologie

Dates et versions

hal-00935774 , version 1 (24-01-2014)

Identifiants

Citer

Sophie Front, Nathalie Court, Marie-Laure Bourigault, Stéphanie Rose, Bernhard Ryffel, et al.. Phosphatidyl myo-inositol mannosides mimics built on an acyclic or heterocyclic core: synthesis and anti-inflammatory properties.. ChemMedChem, 2011, 6 (11), pp.2081-93. ⟨10.1002/cmdc.201100291⟩. ⟨hal-00935774⟩
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