The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers.
Identifieur interne : 000091 ( PubMed/Curation ); précédent : 000090; suivant : 000092The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers.
Auteurs : Cécile Santos [France] ; Laurence Fleury [France] ; Frédéric Rodriguez [France] ; Jozef Markus [Slovaquie] ; Dušan Berkeš [Slovaquie] ; Adam Daïch [France] ; Frédéric Ausseil [France] ; Cécile Baudoin-Dehoux [France] ; Stéphanie Ballereau [France] ; Yves Génisson [France]Source :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2015.
English descriptors
- KwdEn :
- MESH :
- chemical , antagonists & inhibitors : Protein-Serine-Threonine Kinases.
- chemical , chemical synthesis : Amides.
- chemical , chemistry : Amides.
- chemical , pharmacology : Amides.
- drug effects : Binding Sites.
- Dose-Response Relationship, Drug, Humans, Models, Molecular, Molecular Conformation, Stereoisomerism, Structure-Activity Relationship.
Abstract
The first unified synthetic route to the four enantiopure HPA-12 stereoisomers in multi-gram scale is reported based on Crystallization-Induced Asymmetric Transformation (CIAT) technology. This preparative stereoselective synthesis allowed the unprecedented comparative evaluation of HPA-12 stereoisomers regarding their interaction with the CERT START domain. In vitro binding assay coupled to in silico docking approach indicate a possible interaction for the four derivatives. The first TR-FRET homogeneous-phase assay was developed to quantify their binding to the START domain, allowing complete determination of HPA-12 EC₅₀. Results indicate that not only the (1R,3S) lead to the strongest binding, but that both 1R and 3S stereocenters similarly contribute to extent of recognition This automated homogenous assay further opens up promising prospect for the identification of novel potential CERT antagonist by means of high throughput screening.
DOI: 10.1016/j.bmc.2015.03.019
PubMed: 25818765
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Electronic address: ballereau@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9</wicri:regionArea></affiliation></author><author><name sortKey="Genisson, Yves" sort="Genisson, Yves" uniqKey="Genisson Y" first="Yves" last="Génisson">Yves Génisson</name><affiliation wicri:level="1"><nlm:affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France. Electronic address: genisson@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2015">2015</date><idno type="RBID">pubmed:25818765</idno><idno type="pmid">25818765</idno><idno type="doi">10.1016/j.bmc.2015.03.019</idno><idno type="wicri:Area/PubMed/Corpus">000091</idno><idno type="wicri:Area/PubMed/Curation">000091</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers.</title><author><name sortKey="Santos, Cecile" sort="Santos, Cecile" uniqKey="Santos C" first="Cécile" last="Santos">Cécile Santos</name><affiliation wicri:level="1"><nlm:affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9</wicri:regionArea></affiliation></author><author><name sortKey="Fleury, Laurence" sort="Fleury, Laurence" uniqKey="Fleury L" first="Laurence" last="Fleury">Laurence Fleury</name><affiliation wicri:level="1"><nlm:affiliation>Unité de Service et de Recherche CNRS-Pierre Fabre n°3388 ETaC, CRDPF, 3 avenue H. Curien, 31035 Toulouse Cedex 01, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Unité de Service et de Recherche CNRS-Pierre Fabre n°3388 ETaC, CRDPF, 3 avenue H. Curien, 31035 Toulouse Cedex 01</wicri:regionArea></affiliation></author><author><name sortKey="Rodriguez, Frederic" sort="Rodriguez, Frederic" uniqKey="Rodriguez F" first="Frédéric" last="Rodriguez">Frédéric Rodriguez</name><affiliation wicri:level="1"><nlm:affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9</wicri:regionArea></affiliation></author><author><name sortKey="Markus, Jozef" sort="Markus, Jozef" uniqKey="Markus J" first="Jozef" last="Markus">Jozef Markus</name><affiliation wicri:level="1"><nlm:affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia.</nlm:affiliation><country xml:lang="fr">Slovaquie</country><wicri:regionArea>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava</wicri:regionArea></affiliation></author><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, Slovakia. Electronic address: dusan.berkes@stuba.sk.</nlm:affiliation><country xml:lang="fr">Slovaquie</country><wicri:regionArea>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava</wicri:regionArea></affiliation></author><author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><affiliation wicri:level="1"><nlm:affiliation>URCOM, EA 3221, INC3M CNRS FR-3038, UFR Sciences & Techniques, University of Le Havre, 25, rue Philippe Lebon, B.P. 540, F-76058 Le Havre Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>URCOM, EA 3221, INC3M CNRS FR-3038, UFR Sciences & Techniques, University of Le Havre, 25, rue Philippe Lebon, B.P. 540, F-76058 Le Havre Cedex</wicri:regionArea></affiliation></author><author><name sortKey="Ausseil, Frederic" sort="Ausseil, Frederic" uniqKey="Ausseil F" first="Frédéric" last="Ausseil">Frédéric Ausseil</name><affiliation wicri:level="1"><nlm:affiliation>Unité de Service et de Recherche CNRS-Pierre Fabre n°3388 ETaC, CRDPF, 3 avenue H. Curien, 31035 Toulouse Cedex 01, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Unité de Service et de Recherche CNRS-Pierre Fabre n°3388 ETaC, CRDPF, 3 avenue H. Curien, 31035 Toulouse Cedex 01</wicri:regionArea></affiliation></author><author><name sortKey="Baudoin Dehoux, Cecile" sort="Baudoin Dehoux, Cecile" uniqKey="Baudoin Dehoux C" first="Cécile" last="Baudoin-Dehoux">Cécile Baudoin-Dehoux</name><affiliation wicri:level="1"><nlm:affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9</wicri:regionArea></affiliation></author><author><name sortKey="Ballereau, Stephanie" sort="Ballereau, Stephanie" uniqKey="Ballereau S" first="Stéphanie" last="Ballereau">Stéphanie Ballereau</name><affiliation wicri:level="1"><nlm:affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France. Electronic address: ballereau@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9</wicri:regionArea></affiliation></author><author><name sortKey="Genisson, Yves" sort="Genisson, Yves" uniqKey="Genisson Y" first="Yves" last="Génisson">Yves Génisson</name><affiliation wicri:level="1"><nlm:affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France. Electronic address: genisson@chimie.ups-tlse.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9</wicri:regionArea></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="eISSN">1464-3391</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amides (chemical synthesis)</term><term>Amides (chemistry)</term><term>Amides (pharmacology)</term><term>Binding Sites (drug effects)</term><term>Dose-Response Relationship, Drug</term><term>Humans</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Protein-Serine-Threonine Kinases (antagonists & inhibitors)</term><term>Stereoisomerism</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Protein-Serine-Threonine Kinases</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Amides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Amides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Amides</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Binding Sites</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term><term>Humans</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Stereoisomerism</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The first unified synthetic route to the four enantiopure HPA-12 stereoisomers in multi-gram scale is reported based on Crystallization-Induced Asymmetric Transformation (CIAT) technology. This preparative stereoselective synthesis allowed the unprecedented comparative evaluation of HPA-12 stereoisomers regarding their interaction with the CERT START domain. In vitro binding assay coupled to in silico docking approach indicate a possible interaction for the four derivatives. The first TR-FRET homogeneous-phase assay was developed to quantify their binding to the START domain, allowing complete determination of HPA-12 EC₅₀. Results indicate that not only the (1R,3S) lead to the strongest binding, but that both 1R and 3S stereocenters similarly contribute to extent of recognition This automated homogenous assay further opens up promising prospect for the identification of novel potential CERT antagonist by means of high throughput screening.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25818765</PMID><DateCreated><Year>2015</Year><Month>4</Month><Day>14</Day></DateCreated><DateCompleted><Year>2016</Year><Month>02</Month><Day>12</Day></DateCompleted><DateRevised><Year>2015</Year><Month>4</Month><Day>14</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3391</ISSN><JournalIssue CitedMedium="Internet"><Volume>23</Volume><Issue>9</Issue><PubDate><Year>2015</Year><Month>May</Month><Day>1</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry</Title><ISOAbbreviation>Bioorg. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers.</ArticleTitle><Pagination><MedlinePgn>2004-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmc.2015.03.019</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0968-0896(15)00186-8</ELocationID><Abstract><AbstractText>The first unified synthetic route to the four enantiopure HPA-12 stereoisomers in multi-gram scale is reported based on Crystallization-Induced Asymmetric Transformation (CIAT) technology. This preparative stereoselective synthesis allowed the unprecedented comparative evaluation of HPA-12 stereoisomers regarding their interaction with the CERT START domain. In vitro binding assay coupled to in silico docking approach indicate a possible interaction for the four derivatives. The first TR-FRET homogeneous-phase assay was developed to quantify their binding to the START domain, allowing complete determination of HPA-12 EC₅₀. Results indicate that not only the (1R,3S) lead to the strongest binding, but that both 1R and 3S stereocenters similarly contribute to extent of recognition This automated homogenous assay further opens up promising prospect for the identification of novel potential CERT antagonist by means of high throughput screening.</AbstractText><CopyrightInformation>Copyright © 2015 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Santos</LastName><ForeName>Cécile</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Fleury</LastName><ForeName>Laurence</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>Unité de Service et de Recherche CNRS-Pierre Fabre n°3388 ETaC, CRDPF, 3 avenue H. Curien, 31035 Toulouse Cedex 01, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rodriguez</LastName><ForeName>Frédéric</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Markus</LastName><ForeName>Jozef</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia.</Affiliation></AffiliationInfo></Author><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, Slovakia. Electronic address: dusan.berkes@stuba.sk.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Daïch</LastName><ForeName>Adam</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>URCOM, EA 3221, INC3M CNRS FR-3038, UFR Sciences & Techniques, University of Le Havre, 25, rue Philippe Lebon, B.P. 540, F-76058 Le Havre Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ausseil</LastName><ForeName>Frédéric</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Unité de Service et de Recherche CNRS-Pierre Fabre n°3388 ETaC, CRDPF, 3 avenue H. Curien, 31035 Toulouse Cedex 01, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Baudoin-Dehoux</LastName><ForeName>Cécile</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ballereau</LastName><ForeName>Stéphanie</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France. Electronic address: ballereau@chimie.ups-tlse.fr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Génisson</LastName><ForeName>Yves</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France. Electronic address: genisson@chimie.ups-tlse.fr.</Affiliation></AffiliationInfo></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>Mar</Month><Day>12</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem</MedlineTA><NlmUniqueID>9413298</NlmUniqueID><ISSNLinking>0968-0896</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000577">Amides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C441643">N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.1.-</RegistryNumber><NameOfSubstance UI="C119090">COL4A3BP protein, human</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.11.1</RegistryNumber><NameOfSubstance UI="D017346">Protein-Serine-Threonine Kinases</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000577" MajorTopicYN="N">Amides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001665" MajorTopicYN="N">Binding Sites</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008968" MajorTopicYN="N">Molecular Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D017346" MajorTopicYN="N">Protein-Serine-Threonine Kinases</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">CERT</Keyword><Keyword MajorTopicYN="N">CIAT</Keyword><Keyword MajorTopicYN="N">HPA-12</Keyword><Keyword MajorTopicYN="N">Sphingolipid</Keyword><Keyword MajorTopicYN="N">TR-FRET</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>1</Month><Day>27</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2015</Year><Month>3</Month><Day>2</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2015</Year><Month>3</Month><Day>5</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>3</Month><Day>31</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>3</Month><Day>31</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>2</Month><Day>13</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25818765</ArticleId><ArticleId IdType="pii">S0968-0896(15)00186-8</ArticleId><ArticleId IdType="doi">10.1016/j.bmc.2015.03.019</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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