Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.
Identifieur interne : 000049 ( PubMed/Checkpoint ); précédent : 000048; suivant : 000050Chemistry 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.
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:
- France, Slovaquie
- Haute-Normandie, Midi-Pyrénées, Occitanie (région administrative), Région Normandie
- Le Havre, Toulouse
Links toward previous steps (curation, corpus...)
Links to Exploration step
pubmed:27628428Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.</title><author><name sortKey="Berkes, Dusan" sort="Berkes, Dusan" uniqKey="Berkes D" first="Dušan" last="Berkeš">Dušan Berkeš</name><affiliation wicri:level="1"><nlm:affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237, Bratislava, Slovak Republic. dusan.berkes@stuba.sk.</nlm:affiliation><country wicri:rule="url">Slovaquie</country></affiliation></author><author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><affiliation wicri:level="3"><nlm:affiliation>Normandie Univ, UNIHAVRE, CNRS, URCOM, Université du Havre, URCOM EA-3221, INC3 M CNRS FR-3038, UFR des Sciences et Techniques, 25 rue Philippe Lebon, B.P. 1123, 76063, Le Havre Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Univ, UNIHAVRE, CNRS, URCOM, Université du Havre, URCOM EA-3221, INC3 M CNRS FR-3038, UFR des Sciences et Techniques, 25 rue Philippe Lebon, B.P. 1123, 76063, Le Havre Cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author><author><name sortKey="Santos, Cecile" sort="Santos, Cecile" uniqKey="Santos C" first="Cécile" last="Santos">Cécile Santos</name><affiliation wicri:level="3"><nlm:affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author><author><name sortKey="Ballereau, Stephanie" sort="Ballereau, Stephanie" uniqKey="Ballereau S" first="Stéphanie" last="Ballereau">Stéphanie Ballereau</name><affiliation wicri:level="3"><nlm:affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France. ballereau@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author><author><name sortKey="Genisson, Yves" sort="Genisson, Yves" uniqKey="Genisson Y" first="Yves" last="Génisson">Yves Génisson</name><affiliation wicri:level="3"><nlm:affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France. genisson@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:27628428</idno><idno type="pmid">27628428</idno><idno type="doi">10.1002/chem.201602947</idno><idno type="wicri:Area/PubMed/Corpus">000014</idno><idno type="wicri:Area/PubMed/Curation">000014</idno><idno type="wicri:Area/PubMed/Checkpoint">000014</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.</title><author><name sortKey="Berkes, Dusan" sort="Berkes, Dusan" uniqKey="Berkes D" first="Dušan" last="Berkeš">Dušan Berkeš</name><affiliation wicri:level="1"><nlm:affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237, Bratislava, Slovak Republic. dusan.berkes@stuba.sk.</nlm:affiliation><country wicri:rule="url">Slovaquie</country></affiliation></author><author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><affiliation wicri:level="3"><nlm:affiliation>Normandie Univ, UNIHAVRE, CNRS, URCOM, Université du Havre, URCOM EA-3221, INC3 M CNRS FR-3038, UFR des Sciences et Techniques, 25 rue Philippe Lebon, B.P. 1123, 76063, Le Havre Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Univ, UNIHAVRE, CNRS, URCOM, Université du Havre, URCOM EA-3221, INC3 M CNRS FR-3038, UFR des Sciences et Techniques, 25 rue Philippe Lebon, B.P. 1123, 76063, Le Havre Cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author><author><name sortKey="Santos, Cecile" sort="Santos, Cecile" uniqKey="Santos C" first="Cécile" last="Santos">Cécile Santos</name><affiliation wicri:level="3"><nlm:affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author><author><name sortKey="Ballereau, Stephanie" sort="Ballereau, Stephanie" uniqKey="Ballereau S" first="Stéphanie" last="Ballereau">Stéphanie Ballereau</name><affiliation wicri:level="3"><nlm:affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France. ballereau@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author><author><name sortKey="Genisson, Yves" sort="Genisson, Yves" uniqKey="Genisson Y" first="Yves" last="Génisson">Yves Génisson</name><affiliation wicri:level="3"><nlm:affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France. genisson@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="eISSN">1521-3765</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><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></front></TEI><pubmed><MedlineCitation Status="Publisher" Owner="NLM"><PMID Version="1">27628428</PMID><DateCreated><Year>2016</Year><Month>9</Month><Day>15</Day></DateCreated><DateRevised><Year>2016</Year><Month>9</Month><Day>15</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><PubDate><Year>2016</Year><Month>Sep</Month><Day>15</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.</ArticleTitle><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201602947</ELocationID><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></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Berkeš</LastName><ForeName>Dušan</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237, Bratislava, Slovak Republic. dusan.berkes@stuba.sk.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Daïch</LastName><ForeName>Adam</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Normandie Univ, UNIHAVRE, CNRS, URCOM, Université du Havre, URCOM EA-3221, INC3 M CNRS FR-3038, UFR des Sciences et Techniques, 25 rue Philippe Lebon, B.P. 1123, 76063, Le Havre Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Santos</LastName><ForeName>Cécile</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ballereau</LastName><ForeName>Stéphanie</ForeName><Initials>S</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-7250-6188</Identifier><AffiliationInfo><Affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France. ballereau@chimie.ups-tlse.fr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Génisson</LastName><ForeName>Yves</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>SPCMIB, UMR5068 CNRS-, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062, Toulouse, France. genisson@chimie.ups-tlse.fr.</Affiliation></AffiliationInfo></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="">REVIEW</PublicationType><PublicationType UI="">JOURNAL ARTICLE</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>Sep</Month><Day>15</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><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></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>6</Month><Day>20</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>9</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>9</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>9</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>aheadofprint</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27628428</ArticleId><ArticleId IdType="doi">10.1002/chem.201602947</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>France</li><li>Slovaquie</li></country><region><li>Haute-Normandie</li><li>Midi-Pyrénées</li><li>Occitanie (région administrative)</li><li>Région Normandie</li></region><settlement><li>Le Havre</li><li>Toulouse</li></settlement></list><tree><country name="Slovaquie"><noRegion><name sortKey="Berkes, Dusan" sort="Berkes, Dusan" uniqKey="Berkes D" first="Dušan" last="Berkeš">Dušan Berkeš</name></noRegion></country><country name="France"><region name="Région Normandie"><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name></region><name sortKey="Ballereau, Stephanie" sort="Ballereau, Stephanie" uniqKey="Ballereau S" first="Stéphanie" last="Ballereau">Stéphanie Ballereau</name><name sortKey="Genisson, Yves" sort="Genisson, Yves" uniqKey="Genisson Y" first="Yves" last="Génisson">Yves Génisson</name><name sortKey="Santos, Cecile" sort="Santos, Cecile" uniqKey="Santos C" first="Cécile" last="Santos">Cécile Santos</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/France/explor/LeHavreV1/Data/PubMed/Checkpoint
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000049 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/PubMed/Checkpoint/biblio.hfd -nk 000049 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/France
|area= LeHavreV1
|flux= PubMed
|étape= Checkpoint
|type= RBID
|clé= pubmed:27628428
|texte= Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Checkpoint/RBID.i -Sk "pubmed:27628428" \
| HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Checkpoint/biblio.hfd \
| NlmPubMed2Wicri -a LeHavreV1
| This area was generated with Dilib version V0.6.25. |  |