Comparisons of the influenza virus A M2 channel binding affinities, anti-influenza virus potencies and NMDA antagonistic activities of 2-alkyl-2-aminoadamantanes and analogues
Identifieur interne : 001348 ( Main/Exploration ); précédent : 001347; suivant : 001349Comparisons of the influenza virus A M2 channel binding affinities, anti-influenza virus potencies and NMDA antagonistic activities of 2-alkyl-2-aminoadamantanes and analogues
Auteurs : Antonios Kolocouris [Grèce] ; Philip Spearpoint [Royaume-Uni] ; Stephen R. Martin [Royaume-Uni] ; Alan J. Hay [Royaume-Uni] ; Marta Lopez-Querol [Espagne] ; Francesc X. Sureda [Espagne] ; Elizaveta Padalko [Belgique] ; Johan Neyts [Belgique] ; Erik De Clercq [Belgique]Source :
- Bioorganic & medicinal chemistry letters : (Print) [ 0960-894X ] ; 2008.
Descripteurs français
- Pascal (Inist)
- Etude comparative, Virus grippal A, Fixation biologique, Antiviral, Proton, Antagoniste, Protéine transmembranaire, Récepteur NMDA, Affinité, Canal ionique, Alcool tertiaire, Amine primaire, Composé tricyclique, Composé saturé, Relation structure activité, Synthèse chimique, In vitro, Récepteur glutamate, Adamantane(2-alkyl-2-amino), Protéine M2, Adamantan-2-ol(2-alkyl).
English descriptors
- KwdEn :
- Affinity, Antagonist, Antiviral, Biological fixation, Chemical synthesis, Comparative study, Glutamate receptor, In vitro, Influenza A virus, Ionic channel, NMDA receptor, Primary amine, Proton, Saturated compound, Structure activity relation, Tertiary alcohol, Transmembrane protein, Tricyclic compound.
Abstract
The new 2-alkyl-2-aminoadamantanes and analogues 4-10 were designed and synthesized by simplification of the structure of the potent anti-influenza virus A spiranic aminoadamantane heterocycles 2 and 3. The aim of the present work was to examine the effects of bulky and extended lipophilic moieties attached to amantadine 1 on binding to the M2 channel and the resulting antiviral potency. The binding affinities of the compounds to the M2 protein of influenza virus A/chicken/Germany/27 (Weybridge strain; H7N7) were measured for the first time using an assay based on quenching ofTrp-41 fluorescence by His-37 protonation, and their antiviral potencies were evaluated against the replication of influenza virus A H2N2 and H3N2 subtypes and influenza virus B in MDCK cells. Of the various 2-alkyl-2-amino-adamantanes, and analogues, spiro[piperidine-2,2'-adamantane] 3 had the strongest M2 binding and antiviral potency, which were similar those of amantadine 1. The relative binding affinities suggested that the rigid carbon framework provided by the pyrrolidine or piperidine rings results in a more favorable orientation inside the M2 channel pore as compared to large, freely rotating alkyl groups. The aminoadamantane derivatives exhibited similar NMDA antagonistic activity to amantadine 1. A striking finding was the antiviral activity of the adamantanols 4, and 6, which lack any NMDA antagonist activity.
Affiliations:
- Belgique, Espagne, Grèce, Royaume-Uni
- Attique (région), Catalogne, Province du Brabant flamand
- Athènes, Louvain
- Katholieke Universiteit Leuven
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Sureda</name><affiliation wicri:level="2"><inist:fA14 i1="03"><s1>Unitat de Farmacologia, Facultat de Medicina i Ciències de la Salut, Universitat Rovira i Virgili, c./St. Llorenç 21</s1><s2>43201 Reus</s2><s3>ESP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Espagne</country><placeName><region nuts="2" type="communauté">Catalogne</region></placeName></affiliation><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>CIBERNED Centras de Biomedicina en Red de Enfermedades Neurodegenerativas</s1><s3>ESP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Espagne</country><wicri:noRegion>CIBERNED Centras de Biomedicina en Red de Enfermedades Neurodegenerativas</wicri:noRegion></affiliation></author><author><name sortKey="Padalko, Elizaveta" sort="Padalko, Elizaveta" uniqKey="Padalko E" first="Elizaveta" last="Padalko">Elizaveta Padalko</name><affiliation wicri:level="4"><inist:fA14 i1="05"><s1>Rega Institute for Medical Research, Katholieke Universiteit Leuven</s1><s2>3000 Leuven</s2><s3>BEL</s3><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Belgique</country><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author><author><name sortKey="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name><affiliation wicri:level="4"><inist:fA14 i1="05"><s1>Rega Institute for Medical Research, Katholieke Universiteit Leuven</s1><s2>3000 Leuven</s2><s3>BEL</s3><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Belgique</country><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="4"><inist:fA14 i1="05"><s1>Rega Institute for Medical Research, Katholieke Universiteit Leuven</s1><s2>3000 Leuven</s2><s3>BEL</s3><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Belgique</country><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">INIST</idno><idno type="inist">09-0066894</idno><date when="2008">2008</date><idno type="stanalyst">PASCAL 09-0066894 INIST</idno><idno type="RBID">Pascal:09-0066894</idno><idno type="wicri:Area/PascalFrancis/Corpus">000029</idno><idno type="wicri:Area/PascalFrancis/Curation">000045</idno><idno type="wicri:Area/PascalFrancis/Checkpoint">000032</idno><idno type="wicri:explorRef" wicri:stream="PascalFrancis" wicri:step="Checkpoint">000032</idno><idno type="wicri:doubleKey">0960-894X:2008:Kolocouris A:comparisons:of:the</idno><idno type="wicri:Area/Main/Merge">001361</idno><idno type="wicri:Area/Main/Curation">001348</idno><idno type="wicri:Area/Main/Exploration">001348</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Comparisons of the influenza virus A M2 channel binding affinities, anti-influenza virus potencies and NMDA antagonistic activities of 2-alkyl-2-aminoadamantanes and analogues</title><author><name sortKey="Kolocouris, Antonios" sort="Kolocouris, Antonios" uniqKey="Kolocouris A" first="Antonios" last="Kolocouris">Antonios Kolocouris</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Faculty of Pharmacy, Department of Pharmaceutical Chemistry, National and Kapodistrian University ofAthens, Panepistimioupolis-Zografou</s1><s2>15771 Athens</s2><s3>GRC</s3><sZ>1 aut.</sZ></inist:fA14><country>Grèce</country><placeName><settlement type="city">Athènes</settlement><region nuts="2" type="region">Attique (région)</region></placeName></affiliation></author><author><name sortKey="Spearpoint, Philip" sort="Spearpoint, Philip" uniqKey="Spearpoint P" first="Philip" last="Spearpoint">Philip Spearpoint</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>MRC National Institute for Medical Research, The Ridgeway</s1><s2>Mill Hill, London NW7 1AA</s2><s3>GBR</s3><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ></inist:fA14><country>Royaume-Uni</country><wicri:noRegion>Mill Hill, London NW7 1AA</wicri:noRegion></affiliation></author><author><name sortKey="Martin, Stephen R" sort="Martin, Stephen R" uniqKey="Martin S" first="Stephen R." last="Martin">Stephen R. Martin</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>MRC National Institute for Medical Research, The Ridgeway</s1><s2>Mill Hill, London NW7 1AA</s2><s3>GBR</s3><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ></inist:fA14><country>Royaume-Uni</country><wicri:noRegion>Mill Hill, London NW7 1AA</wicri:noRegion></affiliation></author><author><name sortKey="Hay, Alan J" sort="Hay, Alan J" uniqKey="Hay A" first="Alan J." last="Hay">Alan J. Hay</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>MRC National Institute for Medical Research, The Ridgeway</s1><s2>Mill Hill, London NW7 1AA</s2><s3>GBR</s3><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ></inist:fA14><country>Royaume-Uni</country><wicri:noRegion>Mill Hill, London NW7 1AA</wicri:noRegion></affiliation></author><author><name sortKey="Lopez Querol, Marta" sort="Lopez Querol, Marta" uniqKey="Lopez Querol M" first="Marta" last="Lopez-Querol">Marta Lopez-Querol</name><affiliation wicri:level="2"><inist:fA14 i1="03"><s1>Unitat de Farmacologia, Facultat de Medicina i Ciències de la Salut, Universitat Rovira i Virgili, c./St. Llorenç 21</s1><s2>43201 Reus</s2><s3>ESP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Espagne</country><placeName><region nuts="2" type="communauté">Catalogne</region></placeName></affiliation><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>CIBERNED Centras de Biomedicina en Red de Enfermedades Neurodegenerativas</s1><s3>ESP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Espagne</country><wicri:noRegion>CIBERNED Centras de Biomedicina en Red de Enfermedades Neurodegenerativas</wicri:noRegion></affiliation></author><author><name sortKey="Sureda, Francesc X" sort="Sureda, Francesc X" uniqKey="Sureda F" first="Francesc X." last="Sureda">Francesc X. Sureda</name><affiliation wicri:level="2"><inist:fA14 i1="03"><s1>Unitat de Farmacologia, Facultat de Medicina i Ciències de la Salut, Universitat Rovira i Virgili, c./St. Llorenç 21</s1><s2>43201 Reus</s2><s3>ESP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Espagne</country><placeName><region nuts="2" type="communauté">Catalogne</region></placeName></affiliation><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>CIBERNED Centras de Biomedicina en Red de Enfermedades Neurodegenerativas</s1><s3>ESP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Espagne</country><wicri:noRegion>CIBERNED Centras de Biomedicina en Red de Enfermedades Neurodegenerativas</wicri:noRegion></affiliation></author><author><name sortKey="Padalko, Elizaveta" sort="Padalko, Elizaveta" uniqKey="Padalko E" first="Elizaveta" last="Padalko">Elizaveta Padalko</name><affiliation wicri:level="4"><inist:fA14 i1="05"><s1>Rega Institute for Medical Research, Katholieke Universiteit Leuven</s1><s2>3000 Leuven</s2><s3>BEL</s3><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Belgique</country><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author><author><name sortKey="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name><affiliation wicri:level="4"><inist:fA14 i1="05"><s1>Rega Institute for Medical Research, Katholieke Universiteit Leuven</s1><s2>3000 Leuven</s2><s3>BEL</s3><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Belgique</country><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="4"><inist:fA14 i1="05"><s1>Rega Institute for Medical Research, Katholieke Universiteit Leuven</s1><s2>3000 Leuven</s2><s3>BEL</s3><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Belgique</country><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author></analytic><series><title level="j" type="main">Bioorganic & medicinal chemistry letters : (Print)</title><title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title><idno type="ISSN">0960-894X</idno><imprint><date when="2008">2008</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Bioorganic & medicinal chemistry letters : (Print)</title><title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title><idno type="ISSN">0960-894X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Affinity</term><term>Antagonist</term><term>Antiviral</term><term>Biological fixation</term><term>Chemical synthesis</term><term>Comparative study</term><term>Glutamate receptor</term><term>In vitro</term><term>Influenza A virus</term><term>Ionic channel</term><term>NMDA receptor</term><term>Primary amine</term><term>Proton</term><term>Saturated compound</term><term>Structure activity relation</term><term>Tertiary alcohol</term><term>Transmembrane protein</term><term>Tricyclic compound</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Etude comparative</term><term>Virus grippal A</term><term>Fixation biologique</term><term>Antiviral</term><term>Proton</term><term>Antagoniste</term><term>Protéine transmembranaire</term><term>Récepteur NMDA</term><term>Affinité</term><term>Canal ionique</term><term>Alcool tertiaire</term><term>Amine primaire</term><term>Composé tricyclique</term><term>Composé saturé</term><term>Relation structure activité</term><term>Synthèse chimique</term><term>In vitro</term><term>Récepteur glutamate</term><term>Adamantane(2-alkyl-2-amino)</term><term>Protéine M2</term><term>Adamantan-2-ol(2-alkyl)</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The new 2-alkyl-2-aminoadamantanes and analogues 4-10 were designed and synthesized by simplification of the structure of the potent anti-influenza virus A spiranic aminoadamantane heterocycles 2 and 3. The aim of the present work was to examine the effects of bulky and extended lipophilic moieties attached to amantadine 1 on binding to the M2 channel and the resulting antiviral potency. The binding affinities of the compounds to the M2 protein of influenza virus A/chicken/Germany/27 (Weybridge strain; H7N7) were measured for the first time using an assay based on quenching ofTrp-41 fluorescence by His-37 protonation, and their antiviral potencies were evaluated against the replication of influenza virus A H2N2 and H3N2 subtypes and influenza virus B in MDCK cells. Of the various 2-alkyl-2-amino-adamantanes, and analogues, spiro[piperidine-2,2'-adamantane] 3 had the strongest M2 binding and antiviral potency, which were similar those of amantadine 1. The relative binding affinities suggested that the rigid carbon framework provided by the pyrrolidine or piperidine rings results in a more favorable orientation inside the M2 channel pore as compared to large, freely rotating alkyl groups. The aminoadamantane derivatives exhibited similar NMDA antagonistic activity to amantadine 1. A striking finding was the antiviral activity of the adamantanols 4, and 6, which lack any NMDA antagonist activity.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>Espagne</li><li>Grèce</li><li>Royaume-Uni</li></country><region><li>Attique (région)</li><li>Catalogne</li><li>Province du Brabant flamand</li></region><settlement><li>Athènes</li><li>Louvain</li></settlement><orgName><li>Katholieke Universiteit Leuven</li></orgName></list><tree><country name="Grèce"><region name="Attique (région)"><name sortKey="Kolocouris, Antonios" sort="Kolocouris, Antonios" uniqKey="Kolocouris A" first="Antonios" last="Kolocouris">Antonios Kolocouris</name></region></country><country name="Royaume-Uni"><noRegion><name sortKey="Spearpoint, Philip" sort="Spearpoint, Philip" uniqKey="Spearpoint P" first="Philip" last="Spearpoint">Philip Spearpoint</name></noRegion><name sortKey="Hay, Alan J" sort="Hay, Alan J" uniqKey="Hay A" first="Alan J." last="Hay">Alan J. Hay</name><name sortKey="Martin, Stephen R" sort="Martin, Stephen R" uniqKey="Martin S" first="Stephen R." last="Martin">Stephen R. Martin</name></country><country name="Espagne"><region name="Catalogne"><name sortKey="Lopez Querol, Marta" sort="Lopez Querol, Marta" uniqKey="Lopez Querol M" first="Marta" last="Lopez-Querol">Marta Lopez-Querol</name></region><name sortKey="Lopez Querol, Marta" sort="Lopez Querol, Marta" uniqKey="Lopez Querol M" first="Marta" last="Lopez-Querol">Marta Lopez-Querol</name><name sortKey="Sureda, Francesc X" sort="Sureda, Francesc X" uniqKey="Sureda F" first="Francesc X." last="Sureda">Francesc X. Sureda</name><name sortKey="Sureda, Francesc X" sort="Sureda, Francesc X" uniqKey="Sureda F" first="Francesc X." last="Sureda">Francesc X. Sureda</name></country><country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="Padalko, Elizaveta" sort="Padalko, Elizaveta" uniqKey="Padalko E" first="Elizaveta" last="Padalko">Elizaveta Padalko</name></region><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><name sortKey="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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