Antiviral activity of glycyrrhizic acid derivatives against SARS-coronavirus
Identifieur interne : 000703 ( PascalFrancis/Checkpoint ); précédent : 000702; suivant : 000704Antiviral activity of glycyrrhizic acid derivatives against SARS-coronavirus
Auteurs : Gerold Hoever [Allemagne] ; Lidia Baltina [Russie] ; Martin Michaelis [Allemagne] ; Rimma Kondratenko [Russie] ; Lia Baltina [Russie] ; Genrich A. Tolstikov [Russie] ; Hans W. Doerr [Allemagne] ; Jindrich Jr Cinatl [Allemagne]Source :
- Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2005.
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Abstract
Glycyrrhizin (GL) was shown to inhibit SARS-coronavirus (SARS-CoV) replication in vitro. Here the anti-SARS-CoV activity of 15 GL derivatives was tested. The introduction of 2-acetamido-β-D-glucopyranosylamine into the glycoside chain of GL resulted in 10-fold increased anti-SARS-CoV activity compared to GL. Amides of GL and conjugates of GL with two amino acid residues and a free 30-COOH function presented up to 70-fold increased activity against SARS-CoV but also increased cytotoxicity resulting in decreased selectivity index.
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Tolstikov</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Institute of Organic Chemistry, Ufa Research Centre of Russian Academy of Sciences, Prospect Oktyabrya, 71</s1><s2>450054, Ufa</s2><s3>RUS</s3><sZ>2 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Russie</country><wicri:noRegion>450054, Ufa</wicri:noRegion></affiliation></author><author><name sortKey="Doerr, Hans W" sort="Doerr, Hans W" uniqKey="Doerr H" first="Hans W." last="Doerr">Hans W. Doerr</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Institute of Medical Virology, Johann Wolfgang Goethe University Frankfurt, Paul-Ehrlich-Strasse 40</s1><s2>60596 Frankfurt</s2><s3>DEU</s3><sZ>1 aut.</sZ><sZ>3 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Allemagne</country><placeName><region type="land" nuts="1">Hesse (Land)</region><region type="district" nuts="2">District de Darmstadt</region><settlement type="city">Francfort-sur-le-Main</settlement></placeName></affiliation></author><author><name sortKey="Cinatl, Jindrich Jr" sort="Cinatl, Jindrich Jr" uniqKey="Cinatl J" first="Jindrich Jr" last="Cinatl">Jindrich Jr Cinatl</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Institute of Medical Virology, Johann Wolfgang Goethe University Frankfurt, Paul-Ehrlich-Strasse 40</s1><s2>60596 Frankfurt</s2><s3>DEU</s3><sZ>1 aut.</sZ><sZ>3 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Allemagne</country><placeName><region type="land" nuts="1">Hesse (Land)</region><region type="district" nuts="2">District de Darmstadt</region><settlement type="city">Francfort-sur-le-Main</settlement></placeName></affiliation></author></analytic><series><title level="j" type="main">Journal of medicinal chemistry : (Print)</title><title level="j" type="abbreviated">J. med. chem. : (Print)</title><idno type="ISSN">0022-2623</idno><imprint><date when="2005">2005</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Journal of medicinal chemistry : (Print)</title><title level="j" type="abbreviated">J. med. chem. : (Print)</title><idno type="ISSN">0022-2623</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term><term>Chemical synthesis</term><term>Coronavirus</term><term>Enone</term><term>Glycopeptide</term><term>Glycoside</term><term>Glycosylamine</term><term>Glycyrrhizic acid</term><term>In vitro</term><term>Oleanane derivatives</term><term>Pentacyclic compound</term><term>Saponin</term><term>Severe acute respiratory syndrome</term><term>Structure activity relation</term><term>Terpenoid</term><term>Triterpene</term><term>Uronic acid</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Relation structure activité</term><term>Synthèse chimique</term><term>Glycyrrhizique acide</term><term>Saponine</term><term>Oléanane dérivé</term><term>Acide uronique</term><term>Glycoside</term><term>Triterpène</term><term>Terpénoïde</term><term>Composé pentacyclique</term><term>Enone</term><term>Glycosylamine</term><term>Glycopeptide</term><term>Antiviral</term><term>Coronavirus</term><term>Syndrome respiratoire aigu sévère</term><term>In vitro</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Glycyrrhizin (GL) was shown to inhibit SARS-coronavirus (SARS-CoV) replication in vitro. Here the anti-SARS-CoV activity of 15 GL derivatives was tested. The introduction of 2-acetamido-β-D-glucopyranosylamine into the glycoside chain of GL resulted in 10-fold increased anti-SARS-CoV activity compared to GL. Amides of GL and conjugates of GL with two amino acid residues and a free 30-COOH function presented up to 70-fold increased activity against SARS-CoV but also increased cytotoxicity resulting in decreased selectivity index.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0022-2623</s0></fA01><fA02 i1="01"><s0>JMCMAR</s0></fA02><fA03 i2="1"><s0>J. med. chem. : (Print)</s0></fA03><fA05><s2>48</s2></fA05><fA06><s2>4</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Antiviral activity of glycyrrhizic acid derivatives against SARS-coronavirus</s1></fA08><fA11 i1="01" i2="1"><s1>HOEVER (Gerold)</s1></fA11><fA11 i1="02" i2="1"><s1>BALTINA (Lidia)</s1></fA11><fA11 i1="03" i2="1"><s1>MICHAELIS (Martin)</s1></fA11><fA11 i1="04" i2="1"><s1>KONDRATENKO (Rimma)</s1></fA11><fA11 i1="05" i2="1"><s1>BALTINA (Lia)</s1></fA11><fA11 i1="06" i2="1"><s1>TOLSTIKOV (Genrich A.)</s1></fA11><fA11 i1="07" i2="1"><s1>DOERR (Hans W.)</s1></fA11><fA11 i1="08" i2="1"><s1>CINATL (Jindrich JR)</s1></fA11><fA14 i1="01"><s1>Institute of Medical Virology, Johann Wolfgang Goethe University Frankfurt, Paul-Ehrlich-Strasse 40</s1><s2>60596 Frankfurt</s2><s3>DEU</s3><sZ>1 aut.</sZ><sZ>3 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></fA14><fA14 i1="02"><s1>Institute of Organic Chemistry, Ufa Research Centre of Russian Academy of Sciences, Prospect Oktyabrya, 71</s1><s2>450054, Ufa</s2><s3>RUS</s3><sZ>2 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ></fA14><fA20><s1>1256-1259</s1></fA20><fA21><s1>2005</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>9165</s2><s5>354000127045660370</s5></fA43><fA44><s0>0000</s0><s1>© 2005 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>29 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>05-0238636</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Journal of medicinal chemistry : (Print)</s0></fA64><fA66 i1="01"><s0>USA</s0></fA66><fC01 i1="01" l="ENG"><s0>Glycyrrhizin (GL) was shown to inhibit SARS-coronavirus (SARS-CoV) replication in vitro. Here the anti-SARS-CoV activity of 15 GL derivatives was tested. The introduction of 2-acetamido-β-D-glucopyranosylamine into the glycoside chain of GL resulted in 10-fold increased anti-SARS-CoV activity compared to GL. Amides of GL and conjugates of GL with two amino acid residues and a free 30-COOH function presented up to 70-fold increased activity against SARS-CoV but also increased cytotoxicity resulting in decreased selectivity index.</s0></fC01><fC02 i1="01" i2="X"><s0>002B02S05</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Relation structure activité</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Structure activity relation</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Relación estructura actividad</s0><s5>01</s5></fC03><fC03 i1="02" i2="X" l="FRE"><s0>Synthèse chimique</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="ENG"><s0>Chemical synthesis</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="SPA"><s0>Síntesis química</s0><s5>02</s5></fC03><fC03 i1="03" i2="X" l="FRE"><s0>Glycyrrhizique acide</s0><s2>NK</s2><s5>03</s5></fC03><fC03 i1="03" i2="X" l="ENG"><s0>Glycyrrhizic acid</s0><s2>NK</s2><s5>03</s5></fC03><fC03 i1="03" i2="X" l="SPA"><s0>Glicirrícico 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l="ENG"><s0>Triterpene</s0><s5>09</s5></fC03><fC03 i1="08" i2="X" l="SPA"><s0>Triterpeno</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="FRE"><s0>Terpénoïde</s0><s2>FX</s2><s5>10</s5></fC03><fC03 i1="09" i2="X" l="ENG"><s0>Terpenoid</s0><s2>FX</s2><s5>10</s5></fC03><fC03 i1="09" i2="X" l="SPA"><s0>Terpenoide</s0><s2>FX</s2><s5>10</s5></fC03><fC03 i1="10" i2="X" l="FRE"><s0>Composé pentacyclique</s0><s5>12</s5></fC03><fC03 i1="10" i2="X" l="ENG"><s0>Pentacyclic compound</s0><s5>12</s5></fC03><fC03 i1="10" i2="X" l="SPA"><s0>Compuesto pentacíclico</s0><s5>12</s5></fC03><fC03 i1="11" i2="X" l="FRE"><s0>Enone</s0><s5>13</s5></fC03><fC03 i1="11" i2="X" l="ENG"><s0>Enone</s0><s5>13</s5></fC03><fC03 i1="11" i2="X" l="SPA"><s0>Enona</s0><s5>13</s5></fC03><fC03 i1="12" i2="X" l="FRE"><s0>Glycosylamine</s0><s5>14</s5></fC03><fC03 i1="12" i2="X" l="ENG"><s0>Glycosylamine</s0><s5>14</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Glicosilamina</s0><s5>14</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Glycopeptide</s0><s5>15</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>Glycopeptide</s0><s5>15</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>Glicopéptido</s0><s5>15</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>Antiviral</s0><s5>17</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>Antiviral</s0><s5>17</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>Antiviral</s0><s5>17</s5></fC03><fC03 i1="15" i2="X" l="FRE"><s0>Coronavirus</s0><s2>NW</s2><s5>18</s5></fC03><fC03 i1="15" i2="X" l="ENG"><s0>Coronavirus</s0><s2>NW</s2><s5>18</s5></fC03><fC03 i1="15" i2="X" l="SPA"><s0>Coronavirus</s0><s2>NW</s2><s5>18</s5></fC03><fC03 i1="16" i2="X" l="FRE"><s0>Syndrome respiratoire aigu sévère</s0><s2>NM</s2><s5>19</s5></fC03><fC03 i1="16" i2="X" l="ENG"><s0>Severe acute respiratory syndrome</s0><s2>NM</s2><s5>19</s5></fC03><fC03 i1="16" i2="X" l="SPA"><s0>Síndrome respiratorio agudo severo</s0><s2>NM</s2><s5>19</s5></fC03><fC03 i1="17" i2="X" l="FRE"><s0>In vitro</s0><s5>20</s5></fC03><fC03 i1="17" i2="X" l="ENG"><s0>In vitro</s0><s5>20</s5></fC03><fC03 i1="17" i2="X" l="SPA"><s0>In vitro</s0><s5>20</s5></fC03><fC07 i1="01" i2="X" l="FRE"><s0>Coronaviridae</s0><s2>NW</s2></fC07><fC07 i1="01" i2="X" l="ENG"><s0>Coronaviridae</s0><s2>NW</s2></fC07><fC07 i1="01" i2="X" l="SPA"><s0>Coronaviridae</s0><s2>NW</s2></fC07><fC07 i1="02" i2="X" l="FRE"><s0>Nidovirales</s0><s2>NW</s2></fC07><fC07 i1="02" i2="X" l="ENG"><s0>Nidovirales</s0><s2>NW</s2></fC07><fC07 i1="02" i2="X" l="SPA"><s0>Nidovirales</s0><s2>NW</s2></fC07><fC07 i1="03" i2="X" l="FRE"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="03" i2="X" l="ENG"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="03" i2="X" l="SPA"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="04" i2="X" l="FRE"><s0>Virose</s0></fC07><fC07 i1="04" i2="X" l="ENG"><s0>Viral disease</s0></fC07><fC07 i1="04" i2="X" l="SPA"><s0>Virosis</s0></fC07><fC07 i1="05" i2="X" l="FRE"><s0>Infection</s0></fC07><fC07 i1="05" i2="X" l="ENG"><s0>Infection</s0></fC07><fC07 i1="05" i2="X" l="SPA"><s0>Infección</s0></fC07><fN21><s1>164</s1></fN21><fN44 i1="01"><s1>PSI</s1></fN44><fN82><s1>PSI</s1></fN82></pA></standard></inist><affiliations><list><country><li>Allemagne</li><li>Russie</li></country><region><li>District de Darmstadt</li><li>Hesse (Land)</li></region><settlement><li>Francfort-sur-le-Main</li></settlement></list><tree><country name="Allemagne"><region name="Hesse (Land)"><name sortKey="Hoever, Gerold" sort="Hoever, Gerold" uniqKey="Hoever G" first="Gerold" last="Hoever">Gerold Hoever</name></region><name sortKey="Cinatl, Jindrich Jr" sort="Cinatl, Jindrich Jr" uniqKey="Cinatl J" first="Jindrich Jr" last="Cinatl">Jindrich Jr Cinatl</name><name sortKey="Doerr, Hans W" sort="Doerr, Hans W" uniqKey="Doerr H" first="Hans W." last="Doerr">Hans W. Doerr</name><name sortKey="Michaelis, Martin" sort="Michaelis, Martin" uniqKey="Michaelis M" first="Martin" last="Michaelis">Martin Michaelis</name></country><country name="Russie"><noRegion><name sortKey="Baltina, Lidia" sort="Baltina, Lidia" uniqKey="Baltina L" first="Lidia" last="Baltina">Lidia Baltina</name></noRegion><name sortKey="Baltina, Lia" sort="Baltina, Lia" uniqKey="Baltina L" first="Lia" last="Baltina">Lia Baltina</name><name sortKey="Kondratenko, Rimma" sort="Kondratenko, Rimma" uniqKey="Kondratenko R" first="Rimma" last="Kondratenko">Rimma Kondratenko</name><name sortKey="Tolstikov, Genrich A" sort="Tolstikov, Genrich A" uniqKey="Tolstikov G" first="Genrich A." last="Tolstikov">Genrich A. Tolstikov</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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|wiki= Sante
|area= SrasV1
|flux= PascalFrancis
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|texte= Antiviral activity of glycyrrhizic acid derivatives against SARS-coronavirus
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