Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.
Identifieur interne : 000014 ( PubMed/Corpus ); précédent : 000013; suivant : 000015Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.
Auteurs : Dušan Berkeš ; Adam Daïch ; Cécile Santos ; Stéphanie Ballereau ; Yves GénissonSource :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2016.
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
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<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
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<author><name sortKey="Santos, Cecile" sort="Santos, Cecile" uniqKey="Santos C" first="Cécile" last="Santos">Cécile Santos</name>
<affiliation><nlm:affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France.</nlm:affiliation>
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<author><name sortKey="Genisson, Yves" sort="Genisson, Yves" uniqKey="Genisson Y" first="Yves" last="Génisson">Yves Génisson</name>
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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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<Abstract><AbstractText NlmCategory="UNASSIGNED">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.</AbstractText>
<CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation>
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<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">1,3-amino alcohol</Keyword>
<Keyword MajorTopicYN="N">CERT protein</Keyword>
<Keyword MajorTopicYN="N">HPA-12</Keyword>
<Keyword MajorTopicYN="N">ceramide</Keyword>
<Keyword MajorTopicYN="N">sphingolipids</Keyword>
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