Design, synthesis, and fungicidal evaluation of novel oxysterol binding protein inhibitors for combatting resistance associated with oxathiapiprolin.
Identifieur interne : 000251 ( Main/Exploration ); précédent : 000250; suivant : 000252Design, synthesis, and fungicidal evaluation of novel oxysterol binding protein inhibitors for combatting resistance associated with oxathiapiprolin.
Auteurs : Jian-Long Li [République populaire de Chine] ; Li-Ming Zhou [République populaire de Chine] ; Meng-Qi Gao [République populaire de Chine] ; Zhong-Qiao Huang [République populaire de Chine] ; Xi-Li Liu [République populaire de Chine] ; Xiao-Lei Zhu [République populaire de Chine] ; Guang-Fu Yang [République populaire de Chine]Source :
- Pesticide biochemistry and physiology [ 1095-9939 ] ; 2020.
Descripteurs français
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English descriptors
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- MESH :
Abstract
Oxathiapiprolin, the first successful oxysterol binding protein (OSBP) inhibitor for oomycete control, is regarded as an important milestone in the history of fungicide discovery. However, its interaction with OSBP remain unclear. Moreover, some plant pathogenic oomycetes have developed medium to high resistance to oxathiapiprolin. In this paper, the three-dimensional (3D) structure of OSBP from Phytophthora capsici (pcOSBP) was built, and its interaction with oxathiapiprolin was systematically investigated by integrating molecular docking, molecular dynamics simulations, and molecular mechanics Poisson-Boltzmann surface area (MM/PBSA) calculations. The computational results showed that oxathiapiprolin bound to pcOSBP forms H-bonds with Leu73, Lys74, Ser69, and water molecules. Then, based on its interaction with pcOSBP, oxathiapiprolin was structurally modified to discover new analogs with high fungicidal activity and a low risk of resistance. Fortunately, compound 1e was successfully designed and synthesized as the most potent candidate, and it showed a much lower resistance risk (RF < 1) against LP3-M and LP3-H in P. capsici. The present work indicated that the piperidinyl-thiazole-isoxazoline moiety is useful for further optimization. Furthermore, compound 1e could be used as a lead compound for the discovery of new OSBP inhibitors.
DOI: 10.1016/j.pestbp.2020.104673
PubMed: 32828378
Affiliations:
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Normal University, Wuhan 430079</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Huang, Zhong Qiao" sort="Huang, Zhong Qiao" uniqKey="Huang Z" first="Zhong-Qiao" last="Huang">Zhong-Qiao Huang</name><affiliation wicri:level="1"><nlm:affiliation>Department of Plant Pathology, China Agricultural University, Beijing 100193, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Plant Pathology, China Agricultural University, Beijing 100193</wicri:regionArea><placeName><settlement type="city">Pékin</settlement></placeName></affiliation></author><author><name sortKey="Liu, Xi Li" sort="Liu, Xi Li" uniqKey="Liu X" first="Xi-Li" last="Liu">Xi-Li Liu</name><affiliation wicri:level="1"><nlm:affiliation>Department of Plant Pathology, China Agricultural University, Beijing 100193, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Plant Pathology, China Agricultural University, Beijing 100193</wicri:regionArea><placeName><settlement type="city">Pékin</settlement></placeName></affiliation></author><author><name sortKey="Zhu, Xiao Lei" sort="Zhu, Xiao Lei" uniqKey="Zhu X" first="Xiao-Lei" last="Zhu">Xiao-Lei Zhu</name><affiliation wicri:level="1"><nlm:affiliation>Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensor Technology and Health of Ministry of Science and Technology, Central China Normal University, Wuhan 430079, People's Republic of China. 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Electronic address: gfyang@mail.ccnu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensor Technology and Health of Ministry of Science and Technology, Central China Normal University, Wuhan 430079, People's Republic of China; Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author></analytic><series><title level="j">Pesticide biochemistry and physiology</title><idno type="eISSN">1095-9939</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Fungicides, Industrial (MeSH)</term><term>Hydrocarbons, Fluorinated (MeSH)</term><term>Molecular Docking Simulation (MeSH)</term><term>Plant Diseases (MeSH)</term><term>Protein Binding (MeSH)</term><term>Pyrazoles (MeSH)</term><term>Receptors, Steroid (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Fongicides industriels (MeSH)</term><term>Hydrocarbures fluorés (MeSH)</term><term>Liaison aux protéines (MeSH)</term><term>Maladies des plantes (MeSH)</term><term>Pyrazoles (MeSH)</term><term>Récepteurs aux stéroïdes (MeSH)</term><term>Simulation de docking moléculaire (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Fungicides, Industrial</term><term>Hydrocarbons, Fluorinated</term><term>Pyrazoles</term><term>Receptors, Steroid</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Molecular Docking Simulation</term><term>Plant Diseases</term><term>Protein Binding</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Fongicides industriels</term><term>Hydrocarbures fluorés</term><term>Liaison aux protéines</term><term>Maladies des plantes</term><term>Pyrazoles</term><term>Récepteurs aux stéroïdes</term><term>Simulation de docking moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Oxathiapiprolin, the first successful oxysterol binding protein (OSBP) inhibitor for oomycete control, is regarded as an important milestone in the history of fungicide discovery. However, its interaction with OSBP remain unclear. Moreover, some plant pathogenic oomycetes have developed medium to high resistance to oxathiapiprolin. In this paper, the three-dimensional (3D) structure of OSBP from Phytophthora capsici (pcOSBP) was built, and its interaction with oxathiapiprolin was systematically investigated by integrating molecular docking, molecular dynamics simulations, and molecular mechanics Poisson-Boltzmann surface area (MM/PBSA) calculations. The computational results showed that oxathiapiprolin bound to pcOSBP forms H-bonds with Leu73, Lys74, Ser69, and water molecules. Then, based on its interaction with pcOSBP, oxathiapiprolin was structurally modified to discover new analogs with high fungicidal activity and a low risk of resistance. Fortunately, compound 1e was successfully designed and synthesized as the most potent candidate, and it showed a much lower resistance risk (RF < 1) against LP3-M and LP3-H in P. capsici. The present work indicated that the piperidinyl-thiazole-isoxazoline moiety is useful for further optimization. Furthermore, compound 1e could be used as a lead compound for the discovery of new OSBP inhibitors.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" IndexingMethod="Automated" Owner="NLM"><PMID Version="1">32828378</PMID><DateCompleted><Year>2020</Year><Month>08</Month><Day>25</Day></DateCompleted><DateRevised><Year>2020</Year><Month>08</Month><Day>25</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1095-9939</ISSN><JournalIssue CitedMedium="Internet"><Volume>169</Volume><PubDate><Year>2020</Year><Month>Oct</Month></PubDate></JournalIssue><Title>Pesticide biochemistry and physiology</Title><ISOAbbreviation>Pestic Biochem Physiol</ISOAbbreviation></Journal><ArticleTitle>Design, synthesis, and fungicidal evaluation of novel oxysterol binding protein inhibitors for combatting resistance associated with oxathiapiprolin.</ArticleTitle><Pagination><MedlinePgn>104673</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0048-3575(20)30168-1</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.pestbp.2020.104673</ELocationID><Abstract><AbstractText>Oxathiapiprolin, the first successful oxysterol binding protein (OSBP) inhibitor for oomycete control, is regarded as an important milestone in the history of fungicide discovery. However, its interaction with OSBP remain unclear. Moreover, some plant pathogenic oomycetes have developed medium to high resistance to oxathiapiprolin. In this paper, the three-dimensional (3D) structure of OSBP from Phytophthora capsici (pcOSBP) was built, and its interaction with oxathiapiprolin was systematically investigated by integrating molecular docking, molecular dynamics simulations, and molecular mechanics Poisson-Boltzmann surface area (MM/PBSA) calculations. The computational results showed that oxathiapiprolin bound to pcOSBP forms H-bonds with Leu73, Lys74, Ser69, and water molecules. Then, based on its interaction with pcOSBP, oxathiapiprolin was structurally modified to discover new analogs with high fungicidal activity and a low risk of resistance. Fortunately, compound 1e was successfully designed and synthesized as the most potent candidate, and it showed a much lower resistance risk (RF < 1) against LP3-M and LP3-H in P. capsici. The present work indicated that the piperidinyl-thiazole-isoxazoline moiety is useful for further optimization. Furthermore, compound 1e could be used as a lead compound for the discovery of new OSBP inhibitors.</AbstractText><CopyrightInformation>Copyright © 2020 Elsevier Inc. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Jian-Long</ForeName><Initials>JL</Initials><AffiliationInfo><Affiliation>Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensor Technology and Health of Ministry of Science and Technology, Central China Normal University, Wuhan 430079, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhou</LastName><ForeName>Li-Ming</ForeName><Initials>LM</Initials><AffiliationInfo><Affiliation>Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensor Technology and Health of Ministry of Science and Technology, Central China Normal University, Wuhan 430079, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gao</LastName><ForeName>Meng-Qi</ForeName><Initials>MQ</Initials><AffiliationInfo><Affiliation>Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensor Technology and Health of Ministry of Science and Technology, Central China Normal University, Wuhan 430079, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Huang</LastName><ForeName>Zhong-Qiao</ForeName><Initials>ZQ</Initials><AffiliationInfo><Affiliation>Department of Plant Pathology, China Agricultural University, Beijing 100193, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Xi-Li</ForeName><Initials>XL</Initials><AffiliationInfo><Affiliation>Department of Plant Pathology, China Agricultural University, Beijing 100193, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhu</LastName><ForeName>Xiao-Lei</ForeName><Initials>XL</Initials><AffiliationInfo><Affiliation>Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensor Technology and Health of Ministry of Science and Technology, Central China Normal University, Wuhan 430079, People's Republic of China. Electronic address: xlzhu@mail.ccnu.edu.cn.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Yang</LastName><ForeName>Guang-Fu</ForeName><Initials>GF</Initials><AffiliationInfo><Affiliation>Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensor Technology and Health of Ministry of Science and Technology, Central China Normal University, Wuhan 430079, People's Republic of China; Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071, People's Republic of China. Electronic address: gfyang@mail.ccnu.edu.cn.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>08</Month><Day>05</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Pestic Biochem Physiol</MedlineTA><NlmUniqueID>1301573</NlmUniqueID><ISSNLinking>0048-3575</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005659">Fungicides, Industrial</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006845">Hydrocarbons, Fluorinated</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011720">Pyrazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011987">Receptors, Steroid</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C054899">oxysterol binding protein</NameOfSubstance></Chemical><Chemical><RegistryNumber>56498AIV8R</RegistryNumber><NameOfSubstance UI="C000592431">oxathiapiprolin</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D005659" MajorTopicYN="Y">Fungicides, Industrial</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006845" MajorTopicYN="N">Hydrocarbons, Fluorinated</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D062105" MajorTopicYN="N">Molecular Docking Simulation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010935" MajorTopicYN="N">Plant Diseases</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011485" MajorTopicYN="N">Protein Binding</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011720" MajorTopicYN="N">Pyrazoles</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011987" MajorTopicYN="N">Receptors, Steroid</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Molecular design</Keyword><Keyword MajorTopicYN="N">Oxathiapiprolin</Keyword><Keyword MajorTopicYN="N">Oxysterol binding protein</Keyword><Keyword MajorTopicYN="N">Resistance</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>06</Month><Day>23</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>07</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>07</Month><Day>29</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>8</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>8</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>8</Month><Day>26</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32828378</ArticleId><ArticleId IdType="pii">S0048-3575(20)30168-1</ArticleId><ArticleId IdType="doi">10.1016/j.pestbp.2020.104673</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>République populaire de Chine</li></country><region><li>Hubei</li></region><settlement><li>Pékin</li><li>Tianjin</li><li>Wuhan</li></settlement></list><tree><country name="République populaire de Chine"><region name="Hubei"><name sortKey="Li, Jian Long" sort="Li, Jian Long" uniqKey="Li J" first="Jian-Long" last="Li">Jian-Long Li</name></region><name sortKey="Gao, Meng Qi" sort="Gao, Meng Qi" uniqKey="Gao M" first="Meng-Qi" last="Gao">Meng-Qi Gao</name><name sortKey="Huang, Zhong Qiao" sort="Huang, Zhong Qiao" uniqKey="Huang Z" first="Zhong-Qiao" last="Huang">Zhong-Qiao Huang</name><name sortKey="Liu, Xi Li" sort="Liu, Xi Li" uniqKey="Liu X" first="Xi-Li" last="Liu">Xi-Li Liu</name><name sortKey="Yang, Guang Fu" sort="Yang, Guang Fu" uniqKey="Yang G" first="Guang-Fu" last="Yang">Guang-Fu Yang</name><name sortKey="Zhou, Li Ming" sort="Zhou, Li Ming" uniqKey="Zhou L" first="Li-Ming" last="Zhou">Li-Ming Zhou</name><name sortKey="Zhu, Xiao Lei" sort="Zhu, Xiao Lei" uniqKey="Zhu X" first="Xiao-Lei" last="Zhu">Xiao-Lei Zhu</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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