LeHavreV1, Main, Exploration, bibRecord, 000079

Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.

Identifieur interne : 000079 ( Main/Exploration ); précédent : 000078; suivant : 000080

Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.

Auteurs : Dušan Berkeš [Slovaquie] ; Adam Daïch [France] ; Cécile Santos [France] ; Stéphanie Ballereau [France] ; Yves Génisson [France]

Source :

Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2016.

RBID : pubmed:27628428

Abstract

In 2001, two years before the disclosure of the CERT-associated Cer transfer machinery, N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)alkanamides (HPAs) were described as the first, and to date unique, family of intracellular Cer trafficking inhibitors. The dodecanamide derivative, HPA-12, turned out to be a benchmark as a cellular inhibitor of CERT-mediated de novo sphingomyelin biosynthesis. In only 15 years after its first disclosure, this compound has prompted a growing number of biological and chemical studies. Its initial chemical development closely paralleled the study of the CERT protein. It was only after its structural revision in 2011 that HPA-12 received broad attention from the synthetic chemistry community, leading to novel analogues with enhanced protein binding. This Minireview aims at presenting an exhaustive report of the syntheses of HPA-12 and analogues. Biological activities of this CERT inhibitor and structure-activity relationships are also presented to afford a comprehensive overview of the chemistry and biology of the HPA series.

DOI: 10.1002/chem.201602947
PubMed: 27628428

Affiliations:

Le document en format XML

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<front><div type="abstract" xml:lang="en">In 2001, two years before the disclosure of the CERT-associated Cer transfer machinery, N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)alkanamides (HPAs) were described as the first, and to date unique, family of intracellular Cer trafficking inhibitors. The dodecanamide derivative, HPA-12, turned out to be a benchmark as a cellular inhibitor of CERT-mediated de novo sphingomyelin biosynthesis. In only 15 years after its first disclosure, this compound has prompted a growing number of biological and chemical studies. Its initial chemical development closely paralleled the study of the CERT protein. It was only after its structural revision in 2011 that HPA-12 received broad attention from the synthetic chemistry community, leading to novel analogues with enhanced protein binding. This Minireview aims at presenting an exhaustive report of the syntheses of HPA-12 and analogues. Biological activities of this CERT inhibitor and structure-activity relationships are also presented to afford a comprehensive overview of the chemistry and biology of the HPA series.</div>
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Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.

Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.

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Abstract

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