The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers.
Identifieur interne : 000156 ( Main/Exploration ); précédent : 000155; suivant : 000157The 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
Affiliations:
- France, Slovaquie
- Haute-Normandie, Midi-Pyrénées, Occitanie (région administrative), Région Normandie
- Le Havre, Toulouse
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Le document en format XML
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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. 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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><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="Baudoin Dehoux, Cecile" sort="Baudoin Dehoux, Cecile" uniqKey="Baudoin Dehoux C" first="Cécile" last="Baudoin-Dehoux">Cécile Baudoin-Dehoux</name><affiliation wicri:level="3"><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><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, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, F-31062 Toulouse Cedex 9, France. 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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><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">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><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="France"><region name="Occitanie (région administrative)"><name sortKey="Santos, Cecile" sort="Santos, Cecile" uniqKey="Santos C" first="Cécile" last="Santos">Cécile Santos</name></region><name sortKey="Ausseil, Frederic" sort="Ausseil, Frederic" uniqKey="Ausseil F" first="Frédéric" last="Ausseil">Frédéric Ausseil</name><name sortKey="Ballereau, Stephanie" sort="Ballereau, Stephanie" uniqKey="Ballereau S" first="Stéphanie" last="Ballereau">Stéphanie Ballereau</name><name sortKey="Baudoin Dehoux, Cecile" sort="Baudoin Dehoux, Cecile" uniqKey="Baudoin Dehoux C" first="Cécile" last="Baudoin-Dehoux">Cécile Baudoin-Dehoux</name><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><name sortKey="Fleury, Laurence" sort="Fleury, Laurence" uniqKey="Fleury L" first="Laurence" last="Fleury">Laurence Fleury</name><name sortKey="Genisson, Yves" sort="Genisson, Yves" uniqKey="Genisson Y" first="Yves" last="Génisson">Yves Génisson</name><name sortKey="Rodriguez, Frederic" sort="Rodriguez, Frederic" uniqKey="Rodriguez F" first="Frédéric" last="Rodriguez">Frédéric Rodriguez</name></country><country name="Slovaquie"><noRegion><name sortKey="Markus, Jozef" sort="Markus, Jozef" uniqKey="Markus J" first="Jozef" last="Markus">Jozef Markus</name></noRegion><name sortKey="Berkes, Dusan" sort="Berkes, Dusan" uniqKey="Berkes D" first="Dušan" last="Berkeš">Dušan Berkeš</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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