Ebselen has dehydroascorbate reductase and thioltransferase-like activities.
Identifieur interne : 000F95 ( Main/Exploration ); précédent : 000F94; suivant : 000F96Ebselen has dehydroascorbate reductase and thioltransferase-like activities.
Auteurs : Che-Hun Jung [Corée du Sud] ; Michael P. Washburn ; William W. WellsSource :
- Biochemical and biophysical research communications [ 0006-291X ] ; 2002.
Descripteurs français
- KwdFr :
- 1-Chloro-2,4-dinitro-benzène (métabolisme), Animaux (MeSH), Anti-inflammatoires non stéroïdiens (composition chimique), Anti-inflammatoires non stéroïdiens (métabolisme), Anti-inflammatoires non stéroïdiens (pharmacologie), Antioxydants (composition chimique), Antioxydants (métabolisme), Antioxydants (pharmacologie), Azoles (composition chimique), Azoles (métabolisme), Azoles (pharmacologie), Composés organiques du sélénium (composition chimique), Composés organiques du sélénium (métabolisme), Composés organiques du sélénium (pharmacologie), Glutarédoxines (MeSH), Glutathion (métabolisme), Modèles chimiques (MeSH), Oxidoreductases (métabolisme), Protein-disulfide reductase (glutathione) (MeSH), Relation dose-effet des médicaments (MeSH).
- MESH :
- composition chimique : Anti-inflammatoires non stéroïdiens, Antioxydants, Azoles, Composés organiques du sélénium.
- métabolisme : 1-Chloro-2,4-dinitro-benzène, Anti-inflammatoires non stéroïdiens, Antioxydants, Azoles, Composés organiques du sélénium, Glutathion, Oxidoreductases.
- pharmacologie : Anti-inflammatoires non stéroïdiens, Antioxydants, Azoles, Composés organiques du sélénium.
- Animaux, Glutarédoxines, Modèles chimiques, Protein-disulfide reductase (glutathione), Relation dose-effet des médicaments.
English descriptors
- KwdEn :
- Animals (MeSH), Anti-Inflammatory Agents, Non-Steroidal (chemistry), Anti-Inflammatory Agents, Non-Steroidal (metabolism), Anti-Inflammatory Agents, Non-Steroidal (pharmacology), Antioxidants (chemistry), Antioxidants (metabolism), Antioxidants (pharmacology), Azoles (chemistry), Azoles (metabolism), Azoles (pharmacology), Dinitrochlorobenzene (metabolism), Dose-Response Relationship, Drug (MeSH), Glutaredoxins (MeSH), Glutathione (metabolism), Models, Chemical (MeSH), Organoselenium Compounds (chemistry), Organoselenium Compounds (metabolism), Organoselenium Compounds (pharmacology), Oxidoreductases (metabolism), Protein Disulfide Reductase (Glutathione) (MeSH).
- MESH :
- chemical , chemistry : Anti-Inflammatory Agents, Non-Steroidal, Antioxidants, Azoles, Organoselenium Compounds.
- chemical , metabolism : Anti-Inflammatory Agents, Non-Steroidal, Antioxidants, Azoles, Dinitrochlorobenzene, Glutathione, Organoselenium Compounds, Oxidoreductases.
- chemical , pharmacology : Anti-Inflammatory Agents, Non-Steroidal, Antioxidants, Azoles, Organoselenium Compounds.
- Animals, Dose-Response Relationship, Drug, Glutaredoxins, Models, Chemical, Protein Disulfide Reductase (Glutathione).
Abstract
Ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one), a seleno-organic compound, has been reported to mimic glutathione peroxidase (GPX). Since bovine erythrocyte GPX showed dehydroascorbic acid (DHA) reductase and thioltransferase (TTase) activities, ebselen was also examined for DHA reductase and TTase-like activities. Evidence is reported that, in the presence of GSH, ebselen catalyzed the in vitro reduction of DHA to L-ascorbic acid in a dose-dependent manner. Using S-sulfocysteine and GSH as co-substrates, ebselen catalyzed the in vitro formation of glutathione disulfide in a dose-dependent manner, thereby acting as a TTase mimic. 1-Chloro-2,4-dinitrobezene (CDNB), a co-substrate with GSH for glutathione S-transferase, was used to measure rates of adduct formation with ebselen pretreated with GSH and compared with GSH alone. The reaction rate was proportional to ebselen, and ebselen was about 250 times more reactive than GSH on an equimolar basis. The DHA reductase and TTase-like activities, in addition to the powerful nucleophilic reactivity of ebselen selenol, may contribute to ebselen's significant anti-inflammatory and anti-oxidative properties in vivo.
DOI: 10.1006/bbrc.2002.6477
PubMed: 11855823
Affiliations:
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Le document en format XML
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Washburn</name></author><author><name sortKey="Wells, William W" sort="Wells, William W" uniqKey="Wells W" first="William W" last="Wells">William W. Wells</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2002">2002</date><idno type="RBID">pubmed:11855823</idno><idno type="pmid">11855823</idno><idno type="doi">10.1006/bbrc.2002.6477</idno><idno type="wicri:Area/Main/Corpus">001001</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">001001</idno><idno type="wicri:Area/Main/Curation">001001</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Curation">001001</idno><idno type="wicri:Area/Main/Exploration">001001</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Ebselen has dehydroascorbate reductase and thioltransferase-like activities.</title><author><name sortKey="Jung, Che Hun" sort="Jung, Che Hun" uniqKey="Jung C" first="Che-Hun" last="Jung">Che-Hun Jung</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Center for Separation and Analysis of Natural Products, Chonnam National University, Gwangju, 500-757, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Chemistry and Center for Separation and Analysis of Natural Products, Chonnam National University, Gwangju, 500-757</wicri:regionArea><wicri:noRegion>500-757</wicri:noRegion></affiliation></author><author><name sortKey="Washburn, Michael P" sort="Washburn, Michael P" uniqKey="Washburn M" first="Michael P" last="Washburn">Michael P. Washburn</name></author><author><name sortKey="Wells, William W" sort="Wells, William W" uniqKey="Wells W" first="William W" last="Wells">William W. Wells</name></author></analytic><series><title level="j">Biochemical and biophysical research communications</title><idno type="ISSN">0006-291X</idno><imprint><date when="2002" type="published">2002</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals (MeSH)</term><term>Anti-Inflammatory Agents, Non-Steroidal (chemistry)</term><term>Anti-Inflammatory Agents, Non-Steroidal (metabolism)</term><term>Anti-Inflammatory Agents, Non-Steroidal (pharmacology)</term><term>Antioxidants (chemistry)</term><term>Antioxidants (metabolism)</term><term>Antioxidants (pharmacology)</term><term>Azoles (chemistry)</term><term>Azoles (metabolism)</term><term>Azoles (pharmacology)</term><term>Dinitrochlorobenzene (metabolism)</term><term>Dose-Response Relationship, Drug (MeSH)</term><term>Glutaredoxins (MeSH)</term><term>Glutathione (metabolism)</term><term>Models, Chemical (MeSH)</term><term>Organoselenium Compounds (chemistry)</term><term>Organoselenium Compounds (metabolism)</term><term>Organoselenium Compounds (pharmacology)</term><term>Oxidoreductases (metabolism)</term><term>Protein Disulfide Reductase (Glutathione) (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>1-Chloro-2,4-dinitro-benzène (métabolisme)</term><term>Animaux (MeSH)</term><term>Anti-inflammatoires non stéroïdiens (composition chimique)</term><term>Anti-inflammatoires non stéroïdiens (métabolisme)</term><term>Anti-inflammatoires non stéroïdiens (pharmacologie)</term><term>Antioxydants (composition chimique)</term><term>Antioxydants (métabolisme)</term><term>Antioxydants (pharmacologie)</term><term>Azoles (composition chimique)</term><term>Azoles (métabolisme)</term><term>Azoles (pharmacologie)</term><term>Composés organiques du sélénium (composition chimique)</term><term>Composés organiques du sélénium (métabolisme)</term><term>Composés organiques du sélénium (pharmacologie)</term><term>Glutarédoxines (MeSH)</term><term>Glutathion (métabolisme)</term><term>Modèles chimiques (MeSH)</term><term>Oxidoreductases (métabolisme)</term><term>Protein-disulfide reductase (glutathione) (MeSH)</term><term>Relation dose-effet des médicaments (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anti-Inflammatory Agents, Non-Steroidal</term><term>Antioxidants</term><term>Azoles</term><term>Organoselenium Compounds</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Anti-Inflammatory Agents, Non-Steroidal</term><term>Antioxidants</term><term>Azoles</term><term>Dinitrochlorobenzene</term><term>Glutathione</term><term>Organoselenium Compounds</term><term>Oxidoreductases</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-Inflammatory Agents, Non-Steroidal</term><term>Antioxidants</term><term>Azoles</term><term>Organoselenium Compounds</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Anti-inflammatoires non stéroïdiens</term><term>Antioxydants</term><term>Azoles</term><term>Composés organiques du sélénium</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>1-Chloro-2,4-dinitro-benzène</term><term>Anti-inflammatoires non stéroïdiens</term><term>Antioxydants</term><term>Azoles</term><term>Composés organiques du sélénium</term><term>Glutathion</term><term>Oxidoreductases</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Anti-inflammatoires non stéroïdiens</term><term>Antioxydants</term><term>Azoles</term><term>Composés organiques du sélénium</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Dose-Response Relationship, Drug</term><term>Glutaredoxins</term><term>Models, Chemical</term><term>Protein Disulfide Reductase (Glutathione)</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Glutarédoxines</term><term>Modèles chimiques</term><term>Protein-disulfide reductase (glutathione)</term><term>Relation dose-effet des médicaments</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one), a seleno-organic compound, has been reported to mimic glutathione peroxidase (GPX). Since bovine erythrocyte GPX showed dehydroascorbic acid (DHA) reductase and thioltransferase (TTase) activities, ebselen was also examined for DHA reductase and TTase-like activities. Evidence is reported that, in the presence of GSH, ebselen catalyzed the in vitro reduction of DHA to L-ascorbic acid in a dose-dependent manner. Using S-sulfocysteine and GSH as co-substrates, ebselen catalyzed the in vitro formation of glutathione disulfide in a dose-dependent manner, thereby acting as a TTase mimic. 1-Chloro-2,4-dinitrobezene (CDNB), a co-substrate with GSH for glutathione S-transferase, was used to measure rates of adduct formation with ebselen pretreated with GSH and compared with GSH alone. The reaction rate was proportional to ebselen, and ebselen was about 250 times more reactive than GSH on an equimolar basis. The DHA reductase and TTase-like activities, in addition to the powerful nucleophilic reactivity of ebselen selenol, may contribute to ebselen's significant anti-inflammatory and anti-oxidative properties in vivo.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">11855823</PMID><DateCompleted><Year>2002</Year><Month>04</Month><Day>01</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0006-291X</ISSN><JournalIssue CitedMedium="Print"><Volume>291</Volume><Issue>3</Issue><PubDate><Year>2002</Year><Month>Mar</Month><Day>01</Day></PubDate></JournalIssue><Title>Biochemical and biophysical research communications</Title><ISOAbbreviation>Biochem Biophys Res Commun</ISOAbbreviation></Journal><ArticleTitle>Ebselen has dehydroascorbate reductase and thioltransferase-like activities.</ArticleTitle><Pagination><MedlinePgn>550-3</MedlinePgn></Pagination><Abstract><AbstractText>Ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one), a seleno-organic compound, has been reported to mimic glutathione peroxidase (GPX). Since bovine erythrocyte GPX showed dehydroascorbic acid (DHA) reductase and thioltransferase (TTase) activities, ebselen was also examined for DHA reductase and TTase-like activities. Evidence is reported that, in the presence of GSH, ebselen catalyzed the in vitro reduction of DHA to L-ascorbic acid in a dose-dependent manner. Using S-sulfocysteine and GSH as co-substrates, ebselen catalyzed the in vitro formation of glutathione disulfide in a dose-dependent manner, thereby acting as a TTase mimic. 1-Chloro-2,4-dinitrobezene (CDNB), a co-substrate with GSH for glutathione S-transferase, was used to measure rates of adduct formation with ebselen pretreated with GSH and compared with GSH alone. The reaction rate was proportional to ebselen, and ebselen was about 250 times more reactive than GSH on an equimolar basis. The DHA reductase and TTase-like activities, in addition to the powerful nucleophilic reactivity of ebselen selenol, may contribute to ebselen's significant anti-inflammatory and anti-oxidative properties in vivo.</AbstractText><CopyrightInformation>©2002 Elsevier Science (USA).</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Jung</LastName><ForeName>Che-Hun</ForeName><Initials>CH</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Center for Separation and Analysis of Natural Products, Chonnam National University, Gwangju, 500-757, Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Washburn</LastName><ForeName>Michael P</ForeName><Initials>MP</Initials></Author><Author ValidYN="Y"><LastName>Wells</LastName><ForeName>William W</ForeName><Initials>WW</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Biochem Biophys Res Commun</MedlineTA><NlmUniqueID>0372516</NlmUniqueID><ISSNLinking>0006-291X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000894">Anti-Inflammatory Agents, Non-Steroidal</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000975">Antioxidants</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001393">Azoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D054477">Glutaredoxins</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D016566">Organoselenium Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>40X2P7DPGH</RegistryNumber><NameOfSubstance UI="C042986">ebselen</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 1.-</RegistryNumber><NameOfSubstance UI="D010088">Oxidoreductases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 1.8.4.2</RegistryNumber><NameOfSubstance UI="D011490">Protein Disulfide Reductase (Glutathione)</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 1.8.5.1</RegistryNumber><NameOfSubstance UI="C020666">glutathione dehydrogenase (ascorbate)</NameOfSubstance></Chemical><Chemical><RegistryNumber>GAN16C9B8O</RegistryNumber><NameOfSubstance UI="D005978">Glutathione</NameOfSubstance></Chemical><Chemical><RegistryNumber>GE3IBT7BMN</RegistryNumber><NameOfSubstance UI="D004137">Dinitrochlorobenzene</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000894" MajorTopicYN="N">Anti-Inflammatory Agents, Non-Steroidal</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000975" MajorTopicYN="N">Antioxidants</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001393" MajorTopicYN="N">Azoles</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004137" MajorTopicYN="N">Dinitrochlorobenzene</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D054477" MajorTopicYN="N">Glutaredoxins</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005978" MajorTopicYN="N">Glutathione</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008956" MajorTopicYN="N">Models, Chemical</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D016566" MajorTopicYN="N">Organoselenium Compounds</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010088" MajorTopicYN="N">Oxidoreductases</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011490" MajorTopicYN="Y">Protein Disulfide Reductase (Glutathione)</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2002</Year><Month>2</Month><Day>22</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2002</Year><Month>4</Month><Day>2</Day><Hour>10</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2002</Year><Month>2</Month><Day>22</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">11855823</ArticleId><ArticleId IdType="doi">10.1006/bbrc.2002.6477</ArticleId><ArticleId IdType="pii">S0006291X02964776</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Corée du Sud</li></country></list><tree><noCountry><name sortKey="Washburn, Michael P" sort="Washburn, Michael P" uniqKey="Washburn M" first="Michael P" last="Washburn">Michael P. Washburn</name><name sortKey="Wells, William W" sort="Wells, William W" uniqKey="Wells W" first="William W" last="Wells">William W. Wells</name></noCountry><country name="Corée du Sud"><noRegion><name sortKey="Jung, Che Hun" sort="Jung, Che Hun" uniqKey="Jung C" first="Che-Hun" last="Jung">Che-Hun Jung</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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