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<PubmedArticle><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31319298</PMID><DateCompleted><Year>2020</Year><Month>10</Month><Day>21</Day></DateCompleted><DateRevised><Year>2020</Year><Month>10</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1090-2120</ISSN><JournalIssue CitedMedium="Internet"><Volume>91</Volume><PubDate><Year>2019</Year><Month>Oct</Month></PubDate></JournalIssue><Title>Bioorganic chemistry</Title><ISOAbbreviation>Bioorg Chem</ISOAbbreviation></Journal><ArticleTitle>Chemo-sensitizing activity of natural cadinanes from Heterotheca inuloides in human uterine sarcoma cells and their in silico interaction with ABC transporters.</ArticleTitle><Pagination><StartPage>103091</StartPage><MedlinePgn>103091</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bioorg.2019.103091</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0045-2068(19)30261-5</ELocationID><Abstract><AbstractText>Sensitizing activities exerted by 3,4-dihydro-7-hydroxycadalene (1), rac-3,7-dihydroxy-3(4H)-isocadalen-4-one (4) and (1R,4R)-4H-1,2,3,4-tetrahydro-1-hydroxycadalen-15-oic acid (9), the major cadinanes isolated from Heterotheca inuloides, towards multidrug-resistant MES-SA/MX2 and parental MES-SA epithelial human uterine sarcoma cell lines were evaluated. We also evaluated the in silico interactions (expressed as &#x394;G<sub>binding</sub> in kcal/mol) of cadinanes 1, 4 and 9 in an in vitro assay, and also tested several structurally related natural compounds with the multidrug resistance protein (MDR1, P-glycoprotein), human multidrug resistance protein 1 (MRP1), and breast cancer resistance protein (BCRP) structures as pharmacological targets using AutoDock and AutoDock Vina. Compound 1 potentiated the cytotoxicity of doxorubicin and mitoxantrone drugs in resistant MES-SA/MX2 cells, compared to cells treated with each drug alone. Compound 1 could reverse the resistance to doxorubicin 12.44 fold at a concentration of 5&#x202f;&#x3bc;M. It also re-sensitized cells to mitoxantrone 3.94 fold. Hence, compound 1 may be considered as a potential chemosensitizing agent to overcome multidrug resistance in cancer. The docking analysis suggested that there are interactions between cadinanes from H. inuloides and MDR1, MRP1, and BCRP proteins mainly through &#x3c0;-&#x3c0; interactions and hydrogen bonds.</AbstractText><CopyrightInformation>Copyright &#xa9; 2019 Elsevier Inc. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Rodr&#xed;guez-Ch&#xe1;vez</LastName><ForeName>Jos&#xe9; Luis</ForeName><Initials>JL</Initials><AffiliationInfo><Affiliation>Instituto de Qu&#xed;mica, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Ciudad Universitaria, 04510 Ciudad de M&#xe9;xico, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>M&#xe9;ndez-Cuesta</LastName><ForeName>Carlos A</ForeName><Initials>CA</Initials><AffiliationInfo><Affiliation>Departamento de Sistemas Biol&#xf3;gicos, Universidad Aut&#xf3;noma Metropolitana-Xochimilco, Calzada del Hueso 1100, Ciudad de M&#xe9;xico 04960, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ram&#xed;rez-Apan</LastName><ForeName>Teresa</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Instituto de Qu&#xed;mica, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Ciudad Universitaria, 04510 Ciudad de M&#xe9;xico, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Egas</LastName><ForeName>Ver&#xf3;nica</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>Instituto de Qu&#xed;mica, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Ciudad Universitaria, 04510 Ciudad de M&#xe9;xico, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>&#xc1;vila</LastName><ForeName>Jos&#xe9; Luis</ForeName><Initials>JL</Initials><AffiliationInfo><Affiliation>Instituto de Qu&#xed;mica, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Ciudad Universitaria, 04510 Ciudad de M&#xe9;xico, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Neira-Gonz&#xe1;lez</LastName><ForeName>Adriana</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Instituto de Qu&#xed;mica, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Ciudad Universitaria, 04510 Ciudad de M&#xe9;xico, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hern&#xe1;ndez</LastName><ForeName>Tzasna</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>FES-Iztacala, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Av. de los Barrios No. 1, Tlalnepantla 54090, Estado de M&#xe9;xico, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Espinosa-Garc&#xed;a</LastName><ForeName>Francisco J</ForeName><Initials>FJ</Initials><AffiliationInfo><Affiliation>Instituto de Investigaciones en Ecosistemas y Sustentabilidad, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Ex Hacienda de San Jos&#xe9; de la Huerta 58190, Morelia, Michoac&#xe1;n, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Delgado</LastName><ForeName>Guillermo</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Instituto de Qu&#xed;mica, Universidad Nacional Aut&#xf3;noma de M&#xe9;xico, Ciudad Universitaria, 04510 Ciudad de M&#xe9;xico, Mexico. Electronic address: delgado@unam.mx.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2019</Year><Month>07</Month><Day>02</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Bioorg Chem</MedlineTA><NlmUniqueID>1303703</NlmUniqueID><ISSNLinking>0045-2068</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018528">ATP-Binding Cassette Transporters</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000972">Antineoplastic Agents, Phytogenic</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001688">Biological Products</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000081223">Polycyclic Sesquiterpenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C508039">cadinane</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D018528" MajorTopicYN="N">ATP-Binding Cassette Transporters</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000972" MajorTopicYN="N">Antineoplastic Agents, Phytogenic</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation &amp; purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D019659" MajorTopicYN="N">Asteraceae</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001688" MajorTopicYN="N">Biological Products</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation &amp; purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045744" MajorTopicYN="N">Cell Line, Tumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D049109" MajorTopicYN="N">Cell Proliferation</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018432" MajorTopicYN="N">Drug Resistance, Multiple</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D019008" MajorTopicYN="N">Drug Resistance, Neoplasm</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004354" MajorTopicYN="N">Drug Screening Assays, Antitumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D062105" MajorTopicYN="N">Molecular Docking Simulation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000081223" MajorTopicYN="N">Polycyclic Sesquiterpenes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation &amp; purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Cadinanes</Keyword><Keyword MajorTopicYN="N">Cancer resistance</Keyword><Keyword MajorTopicYN="N">Docking</Keyword><Keyword MajorTopicYN="N">P-glycoprotein</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year><Month>2</Month><Day>16</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2019</Year><Month>6</Month><Day>20</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2019</Year><Month>6</Month><Day>25</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2019</Year><Month>7</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>10</Month><Day>22</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2019</Year><Month>7</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">31319298</ArticleId><ArticleId IdType="doi">10.1016/j.bioorg.2019.103091</ArticleId><ArticleId IdType="pii">S0045-2068(19)30261-5</ArticleId></ArticleIdList></PubmedData></PubmedArticle></PubmedArticleSet>