Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach.
Identifieur interne : 001077 ( Main/Exploration ); précédent : 001076; suivant : 001078Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach.
Auteurs : Xueyi Lu [République populaire de Chine] ; Xiao Li [République populaire de Chine] ; Jiapei Yang [République populaire de Chine] ; Boshi Huang [République populaire de Chine] ; Dongwei Kang [République populaire de Chine] ; Fabao Zhao [République populaire de Chine] ; Zhongxia Zhou [République populaire de Chine] ; Erik De Clercq [Belgique] ; Dirk Daelemans [Belgique] ; Christophe Pannecouque [Belgique] ; Peng Zhan [République populaire de Chine] ; Xinyong Liu [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2016.
Descripteurs français
- KwdFr :
- Acétanilides (), Acétanilides (pharmacologie), Agents antiVIH (), Agents antiVIH (pharmacologie), Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Modèles moléculaires, Relation structure-activité, Spectrométrie de masse ESI, Spectroscopie par résonance magnétique du carbone-13, Spectroscopie par résonance magnétique du proton, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ().
- MESH :
- pharmacologie : Acétanilides, Agents antiVIH, Inhibiteurs de la transcriptase inverse.
- Acétanilides, Agents antiVIH, Inhibiteurs de la transcriptase inverse, Modèles moléculaires, Relation structure-activité, Spectrométrie de masse ESI, Spectroscopie par résonance magnétique du carbone-13, Spectroscopie par résonance magnétique du proton, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Acetanilides (chemistry), Acetanilides (pharmacology), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Carbon-13 Magnetic Resonance Spectroscopy, HIV-1 (drug effects), Models, Molecular, Proton Magnetic Resonance Spectroscopy, Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Spectrometry, Mass, Electrospray Ionization, Structure-Activity Relationship.
- MESH :
- chemical , chemistry : Acetanilides, Anti-HIV Agents, Reverse Transcriptase Inhibitors.
- chemical , pharmacology : Acetanilides, Anti-HIV Agents, Reverse Transcriptase Inhibitors.
- drug effects : HIV-1.
- Carbon-13 Magnetic Resonance Spectroscopy, Models, Molecular, Proton Magnetic Resonance Spectroscopy, Spectrometry, Mass, Electrospray Ionization, Structure-Activity Relationship.
Abstract
By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1(IIIB) with EC50 in the range of 0.78-4.46μM. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50=0.78μM, SI=24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50=5.64μM) and double mutant strain RES056 (EC50=22.24μM). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization.
DOI: 10.1016/j.bmc.2016.07.041
PubMed: 27501911
Affiliations:
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wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Yang, Jiapei" sort="Yang, Jiapei" uniqKey="Yang J" first="Jiapei" last="Yang">Jiapei Yang</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR 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Zhao</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Zhou, Zhongxia" sort="Zhou, Zhongxia" uniqKey="Zhou Z" first="Zhongxia" last="Zhou">Zhongxia Zhou</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="1"><nlm:affiliation>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium.</nlm:affiliation><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><wicri:noRegion>B-3000 Leuven</wicri:noRegion></affiliation></author><author><name sortKey="Daelemans, Dirk" sort="Daelemans, Dirk" 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Electronic address: zhanpeng1982@sdu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China. Electronic address: xinyongl@sdu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:27501911</idno><idno type="pmid">27501911</idno><idno type="doi">10.1016/j.bmc.2016.07.041</idno><idno type="wicri:Area/PubMed/Corpus">000C22</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000C22</idno><idno type="wicri:Area/PubMed/Curation">000C22</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000C22</idno><idno type="wicri:Area/PubMed/Checkpoint">000D00</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000D00</idno><idno type="wicri:Area/Ncbi/Merge">002C94</idno><idno type="wicri:Area/Ncbi/Curation">002C94</idno><idno type="wicri:Area/Ncbi/Checkpoint">002C94</idno><idno type="wicri:Area/Main/Merge">001079</idno><idno type="wicri:Area/Main/Curation">001077</idno><idno type="wicri:Area/Main/Exploration">001077</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach.</title><author><name sortKey="Lu, Xueyi" sort="Lu, Xueyi" uniqKey="Lu X" first="Xueyi" last="Lu">Xueyi Lu</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Li, Xiao" sort="Li, Xiao" uniqKey="Li X" first="Xiao" last="Li">Xiao Li</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Yang, Jiapei" sort="Yang, Jiapei" uniqKey="Yang J" first="Jiapei" last="Yang">Jiapei Yang</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Huang, Boshi" sort="Huang, Boshi" uniqKey="Huang B" first="Boshi" last="Huang">Boshi Huang</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Kang, Dongwei" sort="Kang, Dongwei" uniqKey="Kang D" first="Dongwei" last="Kang">Dongwei Kang</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Zhao, Fabao" sort="Zhao, Fabao" uniqKey="Zhao F" first="Fabao" last="Zhao">Fabao Zhao</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Zhou, Zhongxia" sort="Zhou, Zhongxia" uniqKey="Zhou Z" first="Zhongxia" last="Zhou">Zhongxia Zhou</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="1"><nlm:affiliation>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium.</nlm:affiliation><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><wicri:noRegion>B-3000 Leuven</wicri:noRegion></affiliation></author><author><name sortKey="Daelemans, Dirk" sort="Daelemans, Dirk" uniqKey="Daelemans D" first="Dirk" last="Daelemans">Dirk Daelemans</name><affiliation wicri:level="1"><nlm:affiliation>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium.</nlm:affiliation><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><wicri:noRegion>B-3000 Leuven</wicri:noRegion></affiliation></author><author><name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name><affiliation wicri:level="1"><nlm:affiliation>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium. Electronic address: Christophe.Pannecouque@rega.kuleuven.be.</nlm:affiliation><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><wicri:noRegion>B-3000 Leuven</wicri:noRegion></affiliation></author><author><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China. Electronic address: zhanpeng1982@sdu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong, PR China. Electronic address: xinyongl@sdu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji'nan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="eISSN">1464-3391</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acetanilides (chemistry)</term><term>Acetanilides (pharmacology)</term><term>Anti-HIV Agents (chemistry)</term><term>Anti-HIV Agents (pharmacology)</term><term>Carbon-13 Magnetic Resonance Spectroscopy</term><term>HIV-1 (drug effects)</term><term>Models, Molecular</term><term>Proton Magnetic Resonance Spectroscopy</term><term>Reverse Transcriptase Inhibitors (chemistry)</term><term>Reverse Transcriptase Inhibitors (pharmacology)</term><term>Spectrometry, Mass, Electrospray Ionization</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acétanilides ()</term><term>Acétanilides (pharmacologie)</term><term>Agents antiVIH ()</term><term>Agents antiVIH (pharmacologie)</term><term>Inhibiteurs de la transcriptase inverse ()</term><term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term><term>Modèles moléculaires</term><term>Relation structure-activité</term><term>Spectrométrie de masse ESI</term><term>Spectroscopie par résonance magnétique du carbone-13</term><term>Spectroscopie par résonance magnétique du proton</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Acetanilides</term><term>Anti-HIV Agents</term><term>Reverse Transcriptase Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Acetanilides</term><term>Anti-HIV Agents</term><term>Reverse Transcriptase Inhibitors</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Acétanilides</term><term>Agents antiVIH</term><term>Inhibiteurs de la transcriptase inverse</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Carbon-13 Magnetic Resonance Spectroscopy</term><term>Models, Molecular</term><term>Proton Magnetic Resonance Spectroscopy</term><term>Spectrometry, Mass, Electrospray Ionization</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acétanilides</term><term>Agents antiVIH</term><term>Inhibiteurs de la transcriptase inverse</term><term>Modèles moléculaires</term><term>Relation structure-activité</term><term>Spectrométrie de masse ESI</term><term>Spectroscopie par résonance magnétique du carbone-13</term><term>Spectroscopie par résonance magnétique du proton</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1(IIIB) with EC50 in the range of 0.78-4.46μM. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50=0.78μM, SI=24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50=5.64μM) and double mutant strain RES056 (EC50=22.24μM). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Lu, Xueyi" sort="Lu, Xueyi" uniqKey="Lu X" first="Xueyi" last="Lu">Xueyi Lu</name></noRegion><name sortKey="Huang, Boshi" sort="Huang, Boshi" uniqKey="Huang B" first="Boshi" last="Huang">Boshi Huang</name><name sortKey="Kang, Dongwei" sort="Kang, Dongwei" uniqKey="Kang D" first="Dongwei" last="Kang">Dongwei Kang</name><name sortKey="Li, Xiao" sort="Li, Xiao" uniqKey="Li X" first="Xiao" last="Li">Xiao Li</name><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><name sortKey="Yang, Jiapei" sort="Yang, Jiapei" uniqKey="Yang J" first="Jiapei" last="Yang">Jiapei Yang</name><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name><name sortKey="Zhao, Fabao" sort="Zhao, Fabao" uniqKey="Zhao F" first="Fabao" last="Zhao">Fabao Zhao</name><name sortKey="Zhou, Zhongxia" sort="Zhou, Zhongxia" uniqKey="Zhou Z" first="Zhongxia" last="Zhou">Zhongxia Zhou</name></country><country name="Belgique"><noRegion><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></noRegion><name sortKey="Daelemans, Dirk" sort="Daelemans, Dirk" uniqKey="Daelemans D" first="Dirk" last="Daelemans">Dirk Daelemans</name><name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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