New Tetromycin Derivatives with Anti-Trypanosomal and Protease Inhibitory Activities †
Identifieur interne : 002411 ( Ncbi/Curation ); précédent : 002410; suivant : 002412New Tetromycin Derivatives with Anti-Trypanosomal and Protease Inhibitory Activities †
Auteurs : Sheila M. Pimentel-Elardo ; Verena Buback ; Tobias A. M. Gulder ; Tim S. Bugni ; Jason Reppart ; Gerhard Bringmann ; Chris M. Ireland ; Tanja Schirmeister ; Ute HentschelSource :
- Marine Drugs [ 1660-3397 ] ; 2011.
Descripteurs français
- KwdFr :
- Animaux, Antiprotozoaires (isolement et purification), Antiprotozoaires (pharmacologie), Axinella (microbiologie), Cathepsine B (antagonistes et inhibiteurs), Cathepsine L (antagonistes et inhibiteurs), Composés hétérocycliques avec 4 noyaux ou plus (isolement et purification), Composés hétérocycliques avec 4 noyaux ou plus (pharmacologie), Cysteine endopeptidases (), Inhibiteurs de protéases (isolement et purification), Inhibiteurs de protéases (pharmacologie), Leishmania major (), Protéines virales (antagonistes et inhibiteurs), Spectroscopie par résonance magnétique, Streptomyces (), Trypanocides (isolement et purification), Trypanocides (pharmacologie), Trypanosoma brucei brucei (), Virus du SRAS ().
- MESH :
- antagonistes et inhibiteurs : Cathepsine B, Cathepsine L, Protéines virales.
- isolement et purification : Antiprotozoaires, Composés hétérocycliques avec 4 noyaux ou plus, Inhibiteurs de protéases, Trypanocides.
- microbiologie : Axinella.
- pharmacologie : Antiprotozoaires, Composés hétérocycliques avec 4 noyaux ou plus, Inhibiteurs de protéases, Trypanocides.
- Animaux, Cysteine endopeptidases, Leishmania major, Spectroscopie par résonance magnétique, Streptomyces, Trypanosoma brucei brucei, Virus du SRAS.
English descriptors
- KwdEn :
- Animals, Antiprotozoal Agents (isolation & purification), Antiprotozoal Agents (pharmacology), Axinella (microbiology), Cathepsin B (antagonists & inhibitors), Cathepsin L (antagonists & inhibitors), Cysteine Endopeptidases (drug effects), Heterocyclic Compounds, 4 or More Rings (isolation & purification), Heterocyclic Compounds, 4 or More Rings (pharmacology), Leishmania major (drug effects), Magnetic Resonance Spectroscopy, Protease Inhibitors (isolation & purification), Protease Inhibitors (pharmacology), SARS Virus (drug effects), Streptomyces (chemistry), Trypanocidal Agents (isolation & purification), Trypanocidal Agents (pharmacology), Trypanosoma brucei brucei (drug effects), Viral Proteins (antagonists & inhibitors).
- MESH :
- chemical , antagonists & inhibitors : Cathepsin B, Cathepsin L, Viral Proteins.
- chemical , drug effects : Cysteine Endopeptidases.
- chemical , isolation & purification : Antiprotozoal Agents, Heterocyclic Compounds, 4 or More Rings, Protease Inhibitors, Trypanocidal Agents.
- chemical , pharmacology : Antiprotozoal Agents, Heterocyclic Compounds, 4 or More Rings, Protease Inhibitors, Trypanocidal Agents.
- chemistry : Streptomyces.
- drug effects : Leishmania major, SARS Virus, Trypanosoma brucei brucei.
- microbiology : Axinella.
- Animals, Magnetic Resonance Spectroscopy.
Abstract
Four new tetromycin derivatives, tetromycins
Url:
DOI: 10.3390/md9101682
PubMed: 22072992
PubMed Central: 3210601
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PMC:3210601Le document en format XML
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<author><name sortKey="Pimentel Elardo, Sheila M" sort="Pimentel Elardo, Sheila M" uniqKey="Pimentel Elardo S" first="Sheila M." last="Pimentel-Elardo">Sheila M. Pimentel-Elardo</name>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">New Tetromycin Derivatives with Anti-Trypanosomal and Protease Inhibitory Activities <xref ref-type="fn" rid="fn5-marinedrugs-09-01682">†</xref>
</title>
<author><name sortKey="Pimentel Elardo, Sheila M" sort="Pimentel Elardo, Sheila M" uniqKey="Pimentel Elardo S" first="Sheila M." last="Pimentel-Elardo">Sheila M. Pimentel-Elardo</name>
<affiliation><nlm:aff id="af1-marinedrugs-09-01682">Julius-von-Sachs Institute for Biological Sciences, University of Würzburg, Julius-von-Sachs-Platz 3, Würzburg 97082, Germany; E-Mail:<email>ute.hentschel@uni-wuerzburg.de</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Buback, Verena" sort="Buback, Verena" uniqKey="Buback V" first="Verena" last="Buback">Verena Buback</name>
<affiliation><nlm:aff id="af2-marinedrugs-09-01682">Institute for Pharmacy and Food Chemistry, Am Hubland, Würzburg 97074, Germany; E-Mails:<email>verena.buback@uni-wuerzburg.de</email>
(V.B.);<email>schirmei@pharmazie.uni-wuerzburg.de</email>
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<author><name sortKey="Gulder, Tobias A M" sort="Gulder, Tobias A M" uniqKey="Gulder T" first="Tobias A. M." last="Gulder">Tobias A. M. Gulder</name>
<affiliation><nlm:aff id="af3-marinedrugs-09-01682">Institute of Organic Chemistry, University of Würzburg, Am Hubland, Würzburg 97074, Germany; E-Mails:<email>tgulder@uni-bonn.de</email>
(T.A.M.G.);<email>bringman@chemie.uni-wuerzburg.de</email>
(G.B.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Bugni, Tim S" sort="Bugni, Tim S" uniqKey="Bugni T" first="Tim S." last="Bugni">Tim S. Bugni</name>
<affiliation><nlm:aff id="af4-marinedrugs-09-01682">Department of Medicinal Chemistry, University of Utah, Salt Lake City, UT 84112, USA; E-Mails:<email>tbugni@pharmacy.wisc.edu</email>
(T.S.B.);<email>jreppart@gmail.com</email>
(J.R.);<email>cireland@pharm.utah.edu</email>
(C.M.I.)</nlm:aff>
</affiliation>
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<author><name sortKey="Reppart, Jason" sort="Reppart, Jason" uniqKey="Reppart J" first="Jason" last="Reppart">Jason Reppart</name>
<affiliation><nlm:aff id="af4-marinedrugs-09-01682">Department of Medicinal Chemistry, University of Utah, Salt Lake City, UT 84112, USA; E-Mails:<email>tbugni@pharmacy.wisc.edu</email>
(T.S.B.);<email>jreppart@gmail.com</email>
(J.R.);<email>cireland@pharm.utah.edu</email>
(C.M.I.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Bringmann, Gerhard" sort="Bringmann, Gerhard" uniqKey="Bringmann G" first="Gerhard" last="Bringmann">Gerhard Bringmann</name>
<affiliation><nlm:aff id="af3-marinedrugs-09-01682">Institute of Organic Chemistry, University of Würzburg, Am Hubland, Würzburg 97074, Germany; E-Mails:<email>tgulder@uni-bonn.de</email>
(T.A.M.G.);<email>bringman@chemie.uni-wuerzburg.de</email>
(G.B.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Ireland, Chris M" sort="Ireland, Chris M" uniqKey="Ireland C" first="Chris M." last="Ireland">Chris M. Ireland</name>
<affiliation><nlm:aff id="af4-marinedrugs-09-01682">Department of Medicinal Chemistry, University of Utah, Salt Lake City, UT 84112, USA; E-Mails:<email>tbugni@pharmacy.wisc.edu</email>
(T.S.B.);<email>jreppart@gmail.com</email>
(J.R.);<email>cireland@pharm.utah.edu</email>
(C.M.I.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Schirmeister, Tanja" sort="Schirmeister, Tanja" uniqKey="Schirmeister T" first="Tanja" last="Schirmeister">Tanja Schirmeister</name>
<affiliation><nlm:aff id="af2-marinedrugs-09-01682">Institute for Pharmacy and Food Chemistry, Am Hubland, Würzburg 97074, Germany; E-Mails:<email>verena.buback@uni-wuerzburg.de</email>
(V.B.);<email>schirmei@pharmazie.uni-wuerzburg.de</email>
(T.S.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Hentschel, Ute" sort="Hentschel, Ute" uniqKey="Hentschel U" first="Ute" last="Hentschel">Ute Hentschel</name>
<affiliation><nlm:aff id="af1-marinedrugs-09-01682">Julius-von-Sachs Institute for Biological Sciences, University of Würzburg, Julius-von-Sachs-Platz 3, Würzburg 97082, Germany; E-Mail:<email>ute.hentschel@uni-wuerzburg.de</email>
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<series><title level="j">Marine Drugs</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term>
<term>Antiprotozoal Agents (isolation & purification)</term>
<term>Antiprotozoal Agents (pharmacology)</term>
<term>Axinella (microbiology)</term>
<term>Cathepsin B (antagonists & inhibitors)</term>
<term>Cathepsin L (antagonists & inhibitors)</term>
<term>Cysteine Endopeptidases (drug effects)</term>
<term>Heterocyclic Compounds, 4 or More Rings (isolation & purification)</term>
<term>Heterocyclic Compounds, 4 or More Rings (pharmacology)</term>
<term>Leishmania major (drug effects)</term>
<term>Magnetic Resonance Spectroscopy</term>
<term>Protease Inhibitors (isolation & purification)</term>
<term>Protease Inhibitors (pharmacology)</term>
<term>SARS Virus (drug effects)</term>
<term>Streptomyces (chemistry)</term>
<term>Trypanocidal Agents (isolation & purification)</term>
<term>Trypanocidal Agents (pharmacology)</term>
<term>Trypanosoma brucei brucei (drug effects)</term>
<term>Viral Proteins (antagonists & inhibitors)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term>
<term>Antiprotozoaires (isolement et purification)</term>
<term>Antiprotozoaires (pharmacologie)</term>
<term>Axinella (microbiologie)</term>
<term>Cathepsine B (antagonistes et inhibiteurs)</term>
<term>Cathepsine L (antagonistes et inhibiteurs)</term>
<term>Composés hétérocycliques avec 4 noyaux ou plus (isolement et purification)</term>
<term>Composés hétérocycliques avec 4 noyaux ou plus (pharmacologie)</term>
<term>Cysteine endopeptidases ()</term>
<term>Inhibiteurs de protéases (isolement et purification)</term>
<term>Inhibiteurs de protéases (pharmacologie)</term>
<term>Leishmania major ()</term>
<term>Protéines virales (antagonistes et inhibiteurs)</term>
<term>Spectroscopie par résonance magnétique</term>
<term>Streptomyces ()</term>
<term>Trypanocides (isolement et purification)</term>
<term>Trypanocides (pharmacologie)</term>
<term>Trypanosoma brucei brucei ()</term>
<term>Virus du SRAS ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Cathepsin B</term>
<term>Cathepsin L</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="drug effects" xml:lang="en"><term>Cysteine Endopeptidases</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Antiprotozoal Agents</term>
<term>Heterocyclic Compounds, 4 or More Rings</term>
<term>Protease Inhibitors</term>
<term>Trypanocidal Agents</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiprotozoal Agents</term>
<term>Heterocyclic Compounds, 4 or More Rings</term>
<term>Protease Inhibitors</term>
<term>Trypanocidal Agents</term>
</keywords>
<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Cathepsine B</term>
<term>Cathepsine L</term>
<term>Protéines virales</term>
</keywords>
<keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Streptomyces</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Leishmania major</term>
<term>SARS Virus</term>
<term>Trypanosoma brucei brucei</term>
</keywords>
<keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Antiprotozoaires</term>
<term>Composés hétérocycliques avec 4 noyaux ou plus</term>
<term>Inhibiteurs de protéases</term>
<term>Trypanocides</term>
</keywords>
<keywords scheme="MESH" qualifier="microbiologie" xml:lang="fr"><term>Axinella</term>
</keywords>
<keywords scheme="MESH" qualifier="microbiology" xml:lang="en"><term>Axinella</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiprotozoaires</term>
<term>Composés hétérocycliques avec 4 noyaux ou plus</term>
<term>Inhibiteurs de protéases</term>
<term>Trypanocides</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Animals</term>
<term>Magnetic Resonance Spectroscopy</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Cysteine endopeptidases</term>
<term>Leishmania major</term>
<term>Spectroscopie par résonance magnétique</term>
<term>Streptomyces</term>
<term>Trypanosoma brucei brucei</term>
<term>Virus du SRAS</term>
</keywords>
</textClass>
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<front><div type="abstract" xml:lang="en"><p>Four new tetromycin derivatives, tetromycins <bold>1</bold>
–<bold>4</bold>
and a previously known one, tetromycin B (<bold>5</bold>
) were isolated from <italic>Streptomyces axinellae</italic>
Pol001<sup>T</sup>
cultivated from the Mediterranean sponge <italic>Axinella polypoides</italic>
. Structures were assigned using extensive 1D and 2D NMR spectroscopy as well as HRESIMS analysis. The compounds were tested for antiparasitic activities against <italic>Leishmania major</italic>
and <italic>Trypanosoma brucei</italic>
, and for protease inhibition against several cysteine proteases such as falcipain, rhodesain, cathepsin L, cathepsin B, and viral proteases SARS-CoV M<sup>pro</sup>
, and PL<sup>pro</sup>
. The compounds showed antiparasitic activities against <italic>T. brucei</italic>
and time-dependent inhibition of cathepsin L-like proteases with <italic>K</italic>
<sub>i</sub>
values in the low micromolar range.</p>
</div>
</front>
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<author><name sortKey="Fieseler, L" uniqKey="Fieseler L">L Fieseler</name>
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<author><name sortKey="Grozdanov, L" uniqKey="Grozdanov L">L Grozdanov</name>
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