Hydrophobic benzoic acids as inhibitors of influenza neuraminidase
Identifieur interne : 001997 ( Main/Exploration ); précédent : 001996; suivant : 001998Hydrophobic benzoic acids as inhibitors of influenza neuraminidase
Auteurs : Venkatram R. Atigadda [États-Unis] ; Wayne J. Brouillette [États-Unis] ; Franco Duarte [États-Unis] ; Yarlagadda S. Babu [États-Unis] ; Shanta Bantia [États-Unis] ; Pooran Chand [États-Unis] ; Naiming Chu [États-Unis] ; John A. Montgomery [États-Unis] ; David A. Walsh [États-Unis] ; Elise Sudbeck [États-Unis] ; James Finley [États-Unis] ; Gillian M. Air [États-Unis] ; Ming Luo [États-Unis] ; Graeme W. Laver [Australie]Source :
- Bioorganic & Medicinal Chemistry [ 0968-0896 ] ; 1999.
Descripteurs français
- KwdFr :
- Antienzymes (pharmacologie), Antienzymes (synthèse chimique), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Benzoates (), Benzoates (pharmacologie), Benzoates (synthèse chimique), Conformation des protéines, Cristallographie aux rayons X, Modèles moléculaires, Orthomyxoviridae (), Orthomyxoviridae (enzymologie), Sialidase (), Sialidase (antagonistes et inhibiteurs).
- MESH :
- antagonistes et inhibiteurs : Sialidase.
- enzymologie : Orthomyxoviridae.
- pharmacologie : Antienzymes, Antiviraux, Benzoates.
- synthèse chimique : Antienzymes, Antiviraux, Benzoates.
- Pascal (Inist)
- Acide carboxylique, Antiviral, Benzoates, Benzoïque acide(4-acétamido-3-[1-éthylpropoxy]-5-guanidino), Carboxamide, Complexe enzyme inhibiteur, Composé benzénique, Conformation des protéines, Cristallographie aux rayons X, Exo-α-sialidase, Guanidines, Influenzavirus A, Inhibiteur enzyme, Interaction hydrophobe, Modèle moléculaire, Modèles moléculaires, Modélisation, Orthomyxoviridae, Relation structure activité, Sialidase, Site fixation, Synthèse chimique, Sélectivité.
English descriptors
- KwdEn :
- Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Benzenic compound, Benzoates (chemical synthesis), Benzoates (chemistry), Benzoates (pharmacology), Binding site, Carboxamide, Carboxylic acid, Chemical synthesis, Crystallography, X-Ray, Enzyme Inhibitors (chemical synthesis), Enzyme Inhibitors (pharmacology), Enzyme inhibitor, Exo-α-sialidase, Guanidines, Hydrophobic interaction, Influenzavirus A, Inhibitor enzyme complex, Modeling, Models, Molecular, Molecular model, Neuraminidase (antagonists & inhibitors), Neuraminidase (chemistry), Orthomyxoviridae (drug effects), Orthomyxoviridae (enzymology), Protein Conformation, Selectivity, Structure activity relation.
- MESH :
- chemical , antagonists & inhibitors : Neuraminidase.
- chemical , chemical synthesis : Antiviral Agents, Benzoates, Enzyme Inhibitors.
- chemical , chemistry : Benzoates, Neuraminidase.
- chemical , pharmacology : Antiviral Agents, Benzoates, Enzyme Inhibitors.
- drug effects : Orthomyxoviridae.
- enzymology : Orthomyxoviridae.
- Crystallography, X-Ray, Models, Molecular, Protein Conformation.
- Teeft :
- Acetic, Acetic anhydride, Active site, Anal, Anhydride, Aqueous layer, Aqueous layers, Atigadda, Bana, Benzoic, Benzoic acids, Binding site region, Bioorg, Calcd, Cdcl3, Chem, Cold water, Crystal structure, Dark reaction mixture, Dmso, Ether, Ethyl acetate, Glacial acetic acid, Glycerol binding subsite, Guanidine, Guanidino, Guanidino group, Hydrophobic, Hydrophobic pocket, Inhibitor, Inhibitor complexes, Laver, Lipophilic side chain, Ltered, Methanol, Methyl, Mmol, Naoh, Neuraminidase, Organic layer, Organic layers, Reaction mixture, Room temperature, Sodium bicarbonate, Sodium sulfate, Subsite, Varghese.
Abstract
Abstract: Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A new benzoic acid inhibitor (11 1 ) containing a lipophilic side chain at C-3 and a guanidine at C-5 was synthesized. The X-ray structure of 4-(N-acetylamino)-5-guanidino-3-(3-pentyloxy)benzoic acid in complex with NA revealed that the lipophilic side chain binds in a newly created hydrophobic pocket formed by the movement of Glu 278 to interact with Arg 226, whereas the guanidine of 11 interacts in a negatively charged pocket created by Asp 152, Glu 120 and Glu 229. Compound 11 was highly selective for type A (H2N2) influenza NA (IC50 1 μM) over type B (B/Lee/40) influenza NA (IC50 500 μM).
Url:
DOI: 10.1016/S0968-0896(99)00197-2
Affiliations:
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Le document en format XML
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<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Benzenic compound</term>
<term>Benzoates (chemical synthesis)</term>
<term>Benzoates (chemistry)</term>
<term>Benzoates (pharmacology)</term>
<term>Binding site</term>
<term>Carboxamide</term>
<term>Carboxylic acid</term>
<term>Chemical synthesis</term>
<term>Crystallography, X-Ray</term>
<term>Enzyme Inhibitors (chemical synthesis)</term>
<term>Enzyme Inhibitors (pharmacology)</term>
<term>Enzyme inhibitor</term>
<term>Exo-α-sialidase</term>
<term>Guanidines</term>
<term>Hydrophobic interaction</term>
<term>Influenzavirus A</term>
<term>Inhibitor enzyme complex</term>
<term>Modeling</term>
<term>Models, Molecular</term>
<term>Molecular model</term>
<term>Neuraminidase (antagonists & inhibitors)</term>
<term>Neuraminidase (chemistry)</term>
<term>Orthomyxoviridae (drug effects)</term>
<term>Orthomyxoviridae (enzymology)</term>
<term>Protein Conformation</term>
<term>Selectivity</term>
<term>Structure activity relation</term>
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<term>Antienzymes (synthèse chimique)</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Benzoates ()</term>
<term>Benzoates (pharmacologie)</term>
<term>Benzoates (synthèse chimique)</term>
<term>Conformation des protéines</term>
<term>Cristallographie aux rayons X</term>
<term>Modèles moléculaires</term>
<term>Orthomyxoviridae ()</term>
<term>Orthomyxoviridae (enzymologie)</term>
<term>Sialidase ()</term>
<term>Sialidase (antagonistes et inhibiteurs)</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term>
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<term>Enzyme Inhibitors</term>
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<term>Enzyme Inhibitors</term>
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<term>Benzoates</term>
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<term>Carboxamide</term>
<term>Complexe enzyme inhibiteur</term>
<term>Composé benzénique</term>
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<term>Cristallographie aux rayons X</term>
<term>Exo-α-sialidase</term>
<term>Guanidines</term>
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<term>Modèle moléculaire</term>
<term>Modèles moléculaires</term>
<term>Modélisation</term>
<term>Orthomyxoviridae</term>
<term>Relation structure activité</term>
<term>Sialidase</term>
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<term>Anhydride</term>
<term>Aqueous layer</term>
<term>Aqueous layers</term>
<term>Atigadda</term>
<term>Bana</term>
<term>Benzoic</term>
<term>Benzoic acids</term>
<term>Binding site region</term>
<term>Bioorg</term>
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<term>Crystal structure</term>
<term>Dark reaction mixture</term>
<term>Dmso</term>
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<term>Ethyl acetate</term>
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<term>Inhibitor</term>
<term>Inhibitor complexes</term>
<term>Laver</term>
<term>Lipophilic side chain</term>
<term>Ltered</term>
<term>Methanol</term>
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<term>Neuraminidase</term>
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<term>Organic layers</term>
<term>Reaction mixture</term>
<term>Room temperature</term>
<term>Sodium bicarbonate</term>
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<front><div type="abstract" xml:lang="en">Abstract: Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A new benzoic acid inhibitor (11 1 ) containing a lipophilic side chain at C-3 and a guanidine at C-5 was synthesized. The X-ray structure of 4-(N-acetylamino)-5-guanidino-3-(3-pentyloxy)benzoic acid in complex with NA revealed that the lipophilic side chain binds in a newly created hydrophobic pocket formed by the movement of Glu 278 to interact with Arg 226, whereas the guanidine of 11 interacts in a negatively charged pocket created by Asp 152, Glu 120 and Glu 229. Compound 11 was highly selective for type A (H2N2) influenza NA (IC50 1 μM) over type B (B/Lee/40) influenza NA (IC50 500 μM).</div>
</front>
</TEI>
<affiliations><list><country><li>Australie</li>
<li>États-Unis</li>
</country>
<region><li>Alabama</li>
<li>Oklahoma</li>
</region>
</list>
<tree><country name="États-Unis"><region name="Alabama"><name sortKey="Atigadda, Venkatram R" sort="Atigadda, Venkatram R" uniqKey="Atigadda V" first="Venkatram R." last="Atigadda">Venkatram R. Atigadda</name>
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<name sortKey="Air, Gillian M" sort="Air, Gillian M" uniqKey="Air G" first="Gillian M." last="Air">Gillian M. Air</name>
<name sortKey="Babu, Yarlagadda S" sort="Babu, Yarlagadda S" uniqKey="Babu Y" first="Yarlagadda S." last="Babu">Yarlagadda S. Babu</name>
<name sortKey="Bantia, Shanta" sort="Bantia, Shanta" uniqKey="Bantia S" first="Shanta" last="Bantia">Shanta Bantia</name>
<name sortKey="Brouillette, Wayne J" sort="Brouillette, Wayne J" uniqKey="Brouillette W" first="Wayne J." last="Brouillette">Wayne J. Brouillette</name>
<name sortKey="Brouillette, Wayne J" sort="Brouillette, Wayne J" uniqKey="Brouillette W" first="Wayne J." last="Brouillette">Wayne J. Brouillette</name>
<name sortKey="Chand, Pooran" sort="Chand, Pooran" uniqKey="Chand P" first="Pooran" last="Chand">Pooran Chand</name>
<name sortKey="Chu, Naiming" sort="Chu, Naiming" uniqKey="Chu N" first="Naiming" last="Chu">Naiming Chu</name>
<name sortKey="Duarte, Franco" sort="Duarte, Franco" uniqKey="Duarte F" first="Franco" last="Duarte">Franco Duarte</name>
<name sortKey="Finley, James" sort="Finley, James" uniqKey="Finley J" first="James" last="Finley">James Finley</name>
<name sortKey="Luo, Ming" sort="Luo, Ming" uniqKey="Luo M" first="Ming" last="Luo">Ming Luo</name>
<name sortKey="Montgomery, John A" sort="Montgomery, John A" uniqKey="Montgomery J" first="John A." last="Montgomery">John A. Montgomery</name>
<name sortKey="Sudbeck, Elise" sort="Sudbeck, Elise" uniqKey="Sudbeck E" first="Elise" last="Sudbeck">Elise Sudbeck</name>
<name sortKey="Walsh, David A" sort="Walsh, David A" uniqKey="Walsh D" first="David A." last="Walsh">David A. Walsh</name>
</country>
<country name="Australie"><noRegion><name sortKey="Laver, Graeme W" sort="Laver, Graeme W" uniqKey="Laver G" first="Graeme W." last="Laver">Graeme W. Laver</name>
</noRegion>
</country>
</tree>
</affiliations>
</record>
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