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Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis.

Identifieur interne : 003F77 ( Main/Merge ); précédent : 003F76; suivant : 003F78

Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis.

Auteurs : Pi-Hui Liang [Taïwan] ; Wei-Chieh Cheng ; Yi-Ling Lee ; Han-Pang Yu ; Ying-Ta Wu ; Yi-Ling Lin ; Chi-Huey Wong

Source :

RBID : pubmed:16397876

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English descriptors

Abstract

A novel 5-membered iminocyclitol derivative was found to be a potent and selective inhibitor of the glycoprotein-processing alpha-glucosidase with a Ki value of 53 nM. This compound was further derivatized to antiviral agents against Japanese encephalitis virus, dengue virus serotype 2 (DEN-2), human SARS coronavirus, and human beta-hexosaminidase (Ki = 2.6 nM), a new target for the development of osteoarthritis therapeutics.

DOI: 10.1002/cbic.200500321
PubMed: 16397876

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pubmed:16397876

Le document en format XML

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<name sortKey="Cheng, Wei Chieh" sort="Cheng, Wei Chieh" uniqKey="Cheng W" first="Wei-Chieh" last="Cheng">Wei-Chieh Cheng</name>
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<name sortKey="Yu, Han Pang" sort="Yu, Han Pang" uniqKey="Yu H" first="Han-Pang" last="Yu">Han-Pang Yu</name>
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<name sortKey="Wu, Ying Ta" sort="Wu, Ying Ta" uniqKey="Wu Y" first="Ying-Ta" last="Wu">Ying-Ta Wu</name>
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<name sortKey="Lin, Yi Ling" sort="Lin, Yi Ling" uniqKey="Lin Y" first="Yi-Ling" last="Lin">Yi-Ling Lin</name>
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<name sortKey="Yu, Han Pang" sort="Yu, Han Pang" uniqKey="Yu H" first="Han-Pang" last="Yu">Han-Pang Yu</name>
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<name sortKey="Wu, Ying Ta" sort="Wu, Ying Ta" uniqKey="Wu Y" first="Ying-Ta" last="Wu">Ying-Ta Wu</name>
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<name sortKey="Lin, Yi Ling" sort="Lin, Yi Ling" uniqKey="Lin Y" first="Yi-Ling" last="Lin">Yi-Ling Lin</name>
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<name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name>
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<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Cell Line</term>
<term>Cell Proliferation (drug effects)</term>
<term>Combinatorial Chemistry Techniques</term>
<term>Dengue Virus (drug effects)</term>
<term>Encephalitis Virus, Japanese (drug effects)</term>
<term>Enzyme Inhibitors (chemical synthesis)</term>
<term>Enzyme Inhibitors (chemistry)</term>
<term>Enzyme Inhibitors (pharmacology)</term>
<term>Glycoside Hydrolases (antagonists & inhibitors)</term>
<term>Heterocyclic Compounds, 1-Ring (chemical synthesis)</term>
<term>Heterocyclic Compounds, 1-Ring (chemistry)</term>
<term>Heterocyclic Compounds, 1-Ring (pharmacology)</term>
<term>Humans</term>
<term>Imino Pyranoses (chemical synthesis)</term>
<term>Imino Pyranoses (chemistry)</term>
<term>Imino Pyranoses (pharmacology)</term>
<term>Microbial Sensitivity Tests</term>
<term>Models, Biological</term>
<term>Models, Molecular</term>
<term>Osteoarthritis (enzymology)</term>
<term>SARS Virus (drug effects)</term>
<term>Structure-Activity Relationship</term>
<term>Substrate Specificity</term>
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<term>Antienzymes (synthèse chimique)</term>
<term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Arthrose (enzymologie)</term>
<term>Composés hétéromonocycliques ()</term>
<term>Composés hétéromonocycliques (pharmacologie)</term>
<term>Composés hétéromonocycliques (synthèse chimique)</term>
<term>Glycosidases (antagonistes et inhibiteurs)</term>
<term>Humains</term>
<term>Iminopyranoses ()</term>
<term>Iminopyranoses (pharmacologie)</term>
<term>Iminopyranoses (synthèse chimique)</term>
<term>Lignée cellulaire</term>
<term>Modèles biologiques</term>
<term>Modèles moléculaires</term>
<term>Prolifération cellulaire ()</term>
<term>Relation structure-activité</term>
<term>Spécificité du substrat</term>
<term>Techniques de chimie combinatoire</term>
<term>Tests de sensibilité microbienne</term>
<term>Virus de l'encéphalite japonaise (espèce) ()</term>
<term>Virus de la dengue ()</term>
<term>Virus du SRAS ()</term>
<term>beta-N-Acetylhexosaminidases (antagonistes et inhibiteurs)</term>
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<term>Antiviral Agents</term>
<term>Enzyme Inhibitors</term>
<term>Heterocyclic Compounds, 1-Ring</term>
<term>Imino Pyranoses</term>
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<term>Antiviral Agents</term>
<term>Enzyme Inhibitors</term>
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<term>beta-N-Acetylhexosaminidases</term>
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<term>Dengue Virus</term>
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<term>Antienzymes</term>
<term>Antiviraux</term>
<term>Composés hétéromonocycliques</term>
<term>Iminopyranoses</term>
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<term>Composés hétéromonocycliques</term>
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<term>Cell Line</term>
<term>Combinatorial Chemistry Techniques</term>
<term>Humans</term>
<term>Microbial Sensitivity Tests</term>
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<term>Models, Molecular</term>
<term>Structure-Activity Relationship</term>
<term>Substrate Specificity</term>
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<term>Antienzymes</term>
<term>Antiviraux</term>
<term>Composés hétéromonocycliques</term>
<term>Humains</term>
<term>Iminopyranoses</term>
<term>Lignée cellulaire</term>
<term>Modèles biologiques</term>
<term>Modèles moléculaires</term>
<term>Prolifération cellulaire</term>
<term>Relation structure-activité</term>
<term>Spécificité du substrat</term>
<term>Techniques de chimie combinatoire</term>
<term>Tests de sensibilité microbienne</term>
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<front>
<div type="abstract" xml:lang="en">A novel 5-membered iminocyclitol derivative was found to be a potent and selective inhibitor of the glycoprotein-processing alpha-glucosidase with a Ki value of 53 nM. This compound was further derivatized to antiviral agents against Japanese encephalitis virus, dengue virus serotype 2 (DEN-2), human SARS coronavirus, and human beta-hexosaminidase (Ki = 2.6 nM), a new target for the development of osteoarthritis therapeutics.</div>
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