Boronate affinity glycosyl molecularly imprinted polymer microspheres for the determination of teicoplanin using ultra-high performance liquid chromatography coupled with tandem mass spectrometry.
Identifieur interne : 000122 ( Main/Exploration ); précédent : 000121; suivant : 000123Boronate affinity glycosyl molecularly imprinted polymer microspheres for the determination of teicoplanin using ultra-high performance liquid chromatography coupled with tandem mass spectrometry.
Auteurs : Lei Tan [Espagne] ; Yongxian Li [République populaire de Chine] ; Xinhong Pan [République populaire de Chine] ; María Luisa Marina [Espagne] ; Zhengjin Jiang [République populaire de Chine]Source :
- Journal of chromatography. A [ 1873-3778 ] ; 2020.
Descripteurs français
- KwdFr :
- Analyse d'aliment (méthodes), Animaux (MeSH), Antibactériens (analyse), Antibactériens (isolement et purification), Chromatographie en phase liquide à haute performance (MeSH), Composés vinyliques (composition chimique), Eau (composition chimique), Empreinte moléculaire (MeSH), Extraction en phase solide (instrumentation), Lait (composition chimique), Limite de détection (MeSH), Microsphères (MeSH), Polymères (composition chimique), Polymérisation (MeSH), Reproductibilité des résultats (MeSH), Spectrométrie de masse en tandem (MeSH), Téicoplanine (analyse).
- MESH :
- analyse : Antibactériens, Téicoplanine.
- composition chimique : Composés vinyliques, Eau, Lait, Polymères.
- isolement et purification : Antibactériens, Extraction en phase solide.
- méthodes : Analyse d'aliment.
- Animaux, Chromatographie en phase liquide à haute performance, Empreinte moléculaire, Limite de détection, Microsphères, Polymérisation, Reproductibilité des résultats, Spectrométrie de masse en tandem.
English descriptors
- KwdEn :
- Animals (MeSH), Anti-Bacterial Agents (analysis), Anti-Bacterial Agents (isolation & purification), Chromatography, High Pressure Liquid (MeSH), Food Analysis (methods), Limit of Detection (MeSH), Microspheres (MeSH), Milk (chemistry), Molecular Imprinting (MeSH), Polymerization (MeSH), Polymers (chemistry), Reproducibility of Results (MeSH), Solid Phase Extraction (instrumentation), Tandem Mass Spectrometry (MeSH), Teicoplanin (analysis), Vinyl Compounds (chemistry), Water (chemistry).
- MESH :
- chemical , analysis : Anti-Bacterial Agents, Teicoplanin.
- chemical , chemistry : Polymers, Vinyl Compounds, Water.
- chemical , isolation & purification : Anti-Bacterial Agents.
- chemistry : Milk.
- instrumentation : Solid Phase Extraction.
- methods : Food Analysis.
- Animals, Chromatography, High Pressure Liquid, Limit of Detection, Microspheres, Molecular Imprinting, Polymerization, Reproducibility of Results, Tandem Mass Spectrometry.
Abstract
Inspired by the fact that antibody recognizes antigen's epitope rather than its whole structure, we selected the glycosyl moiety of teicoplanin as the template, 4-vinylphenylboronic acid and methyl methacrylate as the functional monomers, and divinylbenzene as the cross-linker to synthesis molecularly imprinted polymer microspheres via precipitation co-polymerization. The glycosyl-imprinted microspheres can selectively capture the target glycopeptide antibiotic in aqueous solutions when the pH of surrounding environment is 9.0, and the captured antibiotic can be reversibly released when the pH falls below 4.0 again. This pH-controlled catch-and-release mechanism permits entrapping of glycopeptide antibiotics in slightly basic environments and keeping them entrapped under neutral conditions, and eluting in acidic media. Five teicoplanin components were selectively captured by using the prepared glycosyl-imprinted microspheres as solid-phase extraction adsorbents, and then detected using ultra-high performance liquid chromatography coupled with tandem mass spectrometry (UPLC-MS/MS). Finally, the method was thoroughly validated for accuracy and reproducibility by determining teicoplanin in food and biological samples, and achieving quantification limits of 0.1 μg/kg, 0.5 μg/L and 1.0 μg/L for milk, urine and plasma samples, respectively.
DOI: 10.1016/j.chroma.2019.460776
PubMed: 31839354
Affiliations:
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Madrid-Barcelona Km. 33.600, 28871 Alcalá de Henares, Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute of Pharmaceutical Analysis, College of Pharmacy, Jinan University, Guangzhou 510632, China; Guangzhou Center for Disease Control and Prevention, Guangzhou 510440, China; Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871 Alcalá de Henares, Madrid</wicri:regionArea><placeName><settlement type="city">Madrid</settlement><region nuts="2" type="region">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Li, Yongxian" sort="Li, Yongxian" uniqKey="Li Y" first="Yongxian" last="Li">Yongxian Li</name><affiliation wicri:level="1"><nlm:affiliation>Guangzhou Center for Disease Control and Prevention, Guangzhou 510440, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Guangzhou Center for Disease Control and Prevention, Guangzhou 510440</wicri:regionArea><placeName><settlement type="city">Jiangmen</settlement><region type="province">Guangdong</region></placeName></affiliation></author><author><name sortKey="Pan, Xinhong" sort="Pan, Xinhong" uniqKey="Pan X" first="Xinhong" last="Pan">Xinhong Pan</name><affiliation wicri:level="1"><nlm:affiliation>Guangzhou Center for Disease Control and Prevention, Guangzhou 510440, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Guangzhou Center for Disease Control and Prevention, Guangzhou 510440</wicri:regionArea><placeName><settlement type="city">Jiangmen</settlement><region type="province">Guangdong</region></placeName></affiliation></author><author><name sortKey="Marina, Maria Luisa" sort="Marina, Maria Luisa" uniqKey="Marina M" first="María Luisa" last="Marina">María Luisa Marina</name><affiliation wicri:level="3"><nlm:affiliation>Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871 Alcalá de Henares, Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871 Alcalá de Henares, Madrid</wicri:regionArea><placeName><settlement type="city">Madrid</settlement><region nuts="2" type="region">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Jiang, Zhengjin" sort="Jiang, Zhengjin" uniqKey="Jiang Z" first="Zhengjin" last="Jiang">Zhengjin Jiang</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Pharmaceutical Analysis, College of Pharmacy, Jinan University, Guangzhou 510632, China. Electronic address: jzjjackson@hotmail.com.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Pharmaceutical Analysis, College of Pharmacy, Jinan University, Guangzhou 510632</wicri:regionArea><placeName><settlement type="city">Jiangmen</settlement><region type="province">Guangdong</region></placeName></affiliation></author></analytic><series><title level="j">Journal of chromatography. A</title><idno type="eISSN">1873-3778</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals (MeSH)</term><term>Anti-Bacterial Agents (analysis)</term><term>Anti-Bacterial Agents (isolation & purification)</term><term>Chromatography, High Pressure Liquid (MeSH)</term><term>Food Analysis (methods)</term><term>Limit of Detection (MeSH)</term><term>Microspheres (MeSH)</term><term>Milk (chemistry)</term><term>Molecular Imprinting (MeSH)</term><term>Polymerization (MeSH)</term><term>Polymers (chemistry)</term><term>Reproducibility of Results (MeSH)</term><term>Solid Phase Extraction (instrumentation)</term><term>Tandem Mass Spectrometry (MeSH)</term><term>Teicoplanin (analysis)</term><term>Vinyl Compounds (chemistry)</term><term>Water (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Analyse d'aliment (méthodes)</term><term>Animaux (MeSH)</term><term>Antibactériens (analyse)</term><term>Antibactériens (isolement et purification)</term><term>Chromatographie en phase liquide à haute performance (MeSH)</term><term>Composés vinyliques (composition chimique)</term><term>Eau (composition chimique)</term><term>Empreinte moléculaire (MeSH)</term><term>Extraction en phase solide (instrumentation)</term><term>Lait (composition chimique)</term><term>Limite de détection (MeSH)</term><term>Microsphères (MeSH)</term><term>Polymères (composition chimique)</term><term>Polymérisation (MeSH)</term><term>Reproductibilité des résultats (MeSH)</term><term>Spectrométrie de masse en tandem (MeSH)</term><term>Téicoplanine (analyse)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Teicoplanin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Polymers</term><term>Vinyl Compounds</term><term>Water</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Anti-Bacterial Agents</term></keywords><keywords scheme="MESH" qualifier="analyse" xml:lang="fr"><term>Antibactériens</term><term>Téicoplanine</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Milk</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Composés vinyliques</term><term>Eau</term><term>Lait</term><term>Polymères</term></keywords><keywords scheme="MESH" qualifier="instrumentation" xml:lang="en"><term>Solid Phase Extraction</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Antibactériens</term><term>Extraction en phase solide</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Food Analysis</term></keywords><keywords scheme="MESH" qualifier="méthodes" xml:lang="fr"><term>Analyse d'aliment</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Chromatography, High Pressure Liquid</term><term>Limit of Detection</term><term>Microspheres</term><term>Molecular Imprinting</term><term>Polymerization</term><term>Reproducibility of Results</term><term>Tandem Mass Spectrometry</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Chromatographie en phase liquide à haute performance</term><term>Empreinte moléculaire</term><term>Limite de détection</term><term>Microsphères</term><term>Polymérisation</term><term>Reproductibilité des résultats</term><term>Spectrométrie de masse en tandem</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Inspired by the fact that antibody recognizes antigen's epitope rather than its whole structure, we selected the glycosyl moiety of teicoplanin as the template, 4-vinylphenylboronic acid and methyl methacrylate as the functional monomers, and divinylbenzene as the cross-linker to synthesis molecularly imprinted polymer microspheres via precipitation co-polymerization. The glycosyl-imprinted microspheres can selectively capture the target glycopeptide antibiotic in aqueous solutions when the pH of surrounding environment is 9.0, and the captured antibiotic can be reversibly released when the pH falls below 4.0 again. This pH-controlled catch-and-release mechanism permits entrapping of glycopeptide antibiotics in slightly basic environments and keeping them entrapped under neutral conditions, and eluting in acidic media. Five teicoplanin components were selectively captured by using the prepared glycosyl-imprinted microspheres as solid-phase extraction adsorbents, and then detected using ultra-high performance liquid chromatography coupled with tandem mass spectrometry (UPLC-MS/MS). Finally, the method was thoroughly validated for accuracy and reproducibility by determining teicoplanin in food and biological samples, and achieving quantification limits of 0.1 μg/kg, 0.5 μg/L and 1.0 μg/L for milk, urine and plasma samples, respectively.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" IndexingMethod="Curated" Owner="NLM"><PMID Version="1">31839354</PMID><DateCompleted><Year>2020</Year><Month>05</Month><Day>26</Day></DateCompleted><DateRevised><Year>2020</Year><Month>05</Month><Day>26</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1873-3778</ISSN><JournalIssue CitedMedium="Internet"><Volume>1615</Volume><PubDate><Year>2020</Year><Month>Mar</Month><Day>29</Day></PubDate></JournalIssue><Title>Journal of chromatography. A</Title><ISOAbbreviation>J Chromatogr A</ISOAbbreviation></Journal><ArticleTitle>Boronate affinity glycosyl molecularly imprinted polymer microspheres for the determination of teicoplanin using ultra-high performance liquid chromatography coupled with tandem mass spectrometry.</ArticleTitle><Pagination><MedlinePgn>460776</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0021-9673(19)31224-5</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.chroma.2019.460776</ELocationID><Abstract><AbstractText>Inspired by the fact that antibody recognizes antigen's epitope rather than its whole structure, we selected the glycosyl moiety of teicoplanin as the template, 4-vinylphenylboronic acid and methyl methacrylate as the functional monomers, and divinylbenzene as the cross-linker to synthesis molecularly imprinted polymer microspheres via precipitation co-polymerization. The glycosyl-imprinted microspheres can selectively capture the target glycopeptide antibiotic in aqueous solutions when the pH of surrounding environment is 9.0, and the captured antibiotic can be reversibly released when the pH falls below 4.0 again. This pH-controlled catch-and-release mechanism permits entrapping of glycopeptide antibiotics in slightly basic environments and keeping them entrapped under neutral conditions, and eluting in acidic media. Five teicoplanin components were selectively captured by using the prepared glycosyl-imprinted microspheres as solid-phase extraction adsorbents, and then detected using ultra-high performance liquid chromatography coupled with tandem mass spectrometry (UPLC-MS/MS). Finally, the method was thoroughly validated for accuracy and reproducibility by determining teicoplanin in food and biological samples, and achieving quantification limits of 0.1 μg/kg, 0.5 μg/L and 1.0 μg/L for milk, urine and plasma samples, respectively.</AbstractText><CopyrightInformation>Copyright © 2019 Elsevier B.V. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Tan</LastName><ForeName>Lei</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>Institute of Pharmaceutical Analysis, College of Pharmacy, Jinan University, Guangzhou 510632, China; Guangzhou Center for Disease Control and Prevention, Guangzhou 510440, China; Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871 Alcalá de Henares, Madrid, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Yongxian</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>Guangzhou Center for Disease Control and Prevention, Guangzhou 510440, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pan</LastName><ForeName>Xinhong</ForeName><Initials>X</Initials><AffiliationInfo><Affiliation>Guangzhou Center for Disease Control and Prevention, Guangzhou 510440, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Marina</LastName><ForeName>María Luisa</ForeName><Initials>ML</Initials><AffiliationInfo><Affiliation>Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871 Alcalá de Henares, Madrid, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Jiang</LastName><ForeName>Zhengjin</ForeName><Initials>Z</Initials><AffiliationInfo><Affiliation>Institute of Pharmaceutical Analysis, College of Pharmacy, Jinan University, Guangzhou 510632, China. Electronic address: jzjjackson@hotmail.com.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2019</Year><Month>12</Month><Day>09</Day></ArticleDate></Article><MedlineJournalInfo><Country>Netherlands</Country><MedlineTA>J Chromatogr A</MedlineTA><NlmUniqueID>9318488</NlmUniqueID><ISSNLinking>0021-9673</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000900">Anti-Bacterial Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011108">Polymers</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014753">Vinyl Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>059QF0KO0R</RegistryNumber><NameOfSubstance UI="D014867">Water</NameOfSubstance></Chemical><Chemical><RegistryNumber>61036-62-2</RegistryNumber><NameOfSubstance UI="D017334">Teicoplanin</NameOfSubstance></Chemical><Chemical><RegistryNumber>IZ715T4SBU</RegistryNumber><NameOfSubstance UI="C004985">divinyl benzene</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000900" MajorTopicYN="N">Anti-Bacterial Agents</DescriptorName><QualifierName UI="Q000032" MajorTopicYN="N">analysis</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002851" MajorTopicYN="Y">Chromatography, High Pressure Liquid</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005504" MajorTopicYN="N">Food Analysis</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="Y">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D057230" MajorTopicYN="N">Limit of Detection</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008863" MajorTopicYN="Y">Microspheres</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008892" MajorTopicYN="N">Milk</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D054802" MajorTopicYN="N">Molecular Imprinting</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D058105" MajorTopicYN="N">Polymerization</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011108" MajorTopicYN="N">Polymers</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015203" MajorTopicYN="N">Reproducibility of Results</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D052616" MajorTopicYN="N">Solid Phase Extraction</DescriptorName><QualifierName UI="Q000295" MajorTopicYN="Y">instrumentation</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053719" MajorTopicYN="Y">Tandem Mass Spectrometry</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D017334" MajorTopicYN="N">Teicoplanin</DescriptorName><QualifierName UI="Q000032" MajorTopicYN="Y">analysis</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014753" MajorTopicYN="N">Vinyl Compounds</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014867" MajorTopicYN="N">Water</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Glycopeptide antibiotics</Keyword><Keyword MajorTopicYN="N">Molecular imprinting</Keyword><Keyword MajorTopicYN="N">Monodisperse microspheres</Keyword><Keyword MajorTopicYN="N">Solid-phase extraction</Keyword><Keyword MajorTopicYN="N">Teicoplanin</Keyword></KeywordList><CoiStatement>Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.</CoiStatement></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year><Month>10</Month><Day>21</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2019</Year><Month>12</Month><Day>03</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2019</Year><Month>12</Month><Day>07</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2019</Year><Month>12</Month><Day>17</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>5</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2019</Year><Month>12</Month><Day>17</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">31839354</ArticleId><ArticleId IdType="pii">S0021-9673(19)31224-5</ArticleId><ArticleId IdType="doi">10.1016/j.chroma.2019.460776</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Espagne</li><li>République populaire de Chine</li></country><region><li>Communauté de Madrid</li><li>Guangdong</li></region><settlement><li>Jiangmen</li><li>Madrid</li></settlement></list><tree><country name="Espagne"><region name="Communauté de Madrid"><name sortKey="Tan, Lei" sort="Tan, Lei" uniqKey="Tan L" first="Lei" last="Tan">Lei Tan</name></region><name sortKey="Marina, Maria Luisa" sort="Marina, Maria Luisa" uniqKey="Marina M" first="María Luisa" last="Marina">María Luisa Marina</name></country><country name="République populaire de Chine"><region name="Guangdong"><name sortKey="Li, Yongxian" sort="Li, Yongxian" uniqKey="Li Y" first="Yongxian" last="Li">Yongxian Li</name></region><name sortKey="Jiang, Zhengjin" sort="Jiang, Zhengjin" uniqKey="Jiang Z" first="Zhengjin" last="Jiang">Zhengjin Jiang</name><name sortKey="Pan, Xinhong" sort="Pan, Xinhong" uniqKey="Pan X" first="Xinhong" last="Pan">Xinhong Pan</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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