3‐Arylidene‐N‐hydroxyoxindoles: A New Class of Compounds Endowed with Antitumor Activity
Identifieur interne : 000F23 ( Istex/Corpus ); précédent : 000F22; suivant : 000F243‐Arylidene‐N‐hydroxyoxindoles: A New Class of Compounds Endowed with Antitumor Activity
Auteurs : Loana Musso ; Raffaella Cincinelli ; Valentina Zuco ; Michelandrea De Esare ; Franco Zunino ; Anna Lucia Fallacara ; Maurizio Botta ; Sabrina DallavalleSource :
- ChemMedChem [ 1860-7179 ] ; 2016-08-19.
Abstract
A series of compounds containing the N‐hydroxyoxindole scaffold were synthesized and evaluated for antitumor activity. The compounds showed potent antiproliferative activity against the wild‐type p53 IGROV‐1 ovarian carcinoma cell line and considerably lower efficacy against the mutant IGROV‐1/Pt1 subline that lacks p53 function. The differential response of ovarian carcinoma cells depending on p53 status was also reflected in the varied susceptibility to apoptosis of the treated cell lines. These results support a role for the p53 transcription factor as a determinant of cytotoxicity. The therapeutic potential of the most promising compound of the series was evaluated in the treatment of an IGROV‐1 xenograft growing as ascitic tumor in mice. Using intraperitoneal administration, daily treatment with the compound for four weeks produced a significant delay in the onset of ascites.
Exploring new scaffolds: A series of 3‐arylidene‐N‐hydroxyoxindoles show potent antiproliferative and pro‐apoptotic activity against wild‐type p53 IGROV‐1 ovarian carcinoma cells and a considerably lower efficacy against the mutant IGROV‐1/Pt1 subline lacking p53 function. These results support a role for this transcription factor as a determinant of cytotoxicity. Treatment of an IGROV‐1 xenograft growing as an ascitic tumor produced a significant delay in the onset of ascites.
Url:
DOI: 10.1002/cmdc.201600225
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ISTEX:2B842C376A7A410ACAF70F18C1C7E2F1AEBDF50BLe document en format XML
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sort="Zuco, Valentina" uniqKey="Zuco V" first="Valentina" last="Zuco">Valentina Zuco</name><affiliation><mods:affiliation>Department of Experimental Oncology and Molecular Medicine, Fondazione IRCCS – Istituto Nazionale dei Tumori, Via Amadeo 42, 20133, Milano, Italy</mods:affiliation></affiliation></author><author><name sortKey="De Esare, Michelandrea" sort="De Esare, Michelandrea" uniqKey="De Esare M" first="Michelandrea" last="De Esare">Michelandrea De Esare</name><affiliation><mods:affiliation>Department of Experimental Oncology and Molecular Medicine, Fondazione IRCCS – Istituto Nazionale dei Tumori, Via Amadeo 42, 20133, Milano, Italy</mods:affiliation></affiliation></author><author><name sortKey="Zunino, Franco" sort="Zunino, Franco" uniqKey="Zunino F" first="Franco" last="Zunino">Franco Zunino</name><affiliation><mods:affiliation>Department of Experimental Oncology and Molecular Medicine, Fondazione IRCCS – Istituto Nazionale dei Tumori, Via Amadeo 42, 20133, Milano, 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Using intraperitoneal administration, daily treatment with the compound for four weeks produced a significant delay in the onset of ascites.</div><div type="abstract" xml:lang="en">Exploring new scaffolds: A series of 3‐arylidene‐N‐hydroxyoxindoles show potent antiproliferative and pro‐apoptotic activity against wild‐type p53 IGROV‐1 ovarian carcinoma cells and a considerably lower efficacy against the mutant IGROV‐1/Pt1 subline lacking p53 function. These results support a role for this transcription factor as a determinant of cytotoxicity. 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Using intraperitoneal administration, daily treatment with the compound for four weeks produced a significant delay in the onset of ascites.</p></abstract><abstract xml:lang="en" style="graphical"><p><hi rend="bold">Exploring new scaffolds</hi>: A series of 3‐arylidene‐<hi rend="italic">N</hi>‐hydroxyoxindoles show potent antiproliferative and pro‐apoptotic activity against wild‐type p53 IGROV‐1 ovarian carcinoma cells and a considerably lower efficacy against the mutant IGROV‐1/Pt1 subline lacking p53 function. These results support a role for this transcription factor as a determinant of cytotoxicity. Treatment of an IGROV‐1 xenograft growing as an ascitic tumor produced a significant delay in the onset of ascites.<figure type="box"><media mimeType="image" url="urn:x-wiley:18607179:media:cmdc201600225:cmdc201600225-toc-0001"></media></figure></p></abstract><textClass><keywords xml:lang="en"><term xml:id="cmdc201600225-kwd-0001">antiproliferative activity</term><term xml:id="cmdc201600225-kwd-0002">antitumor agents</term><term xml:id="cmdc201600225-kwd-0003">apoptosis</term><term xml:id="cmdc201600225-kwd-0004"><hi rend="italic">N</hi>-hydroxyoxindole</term><term xml:id="cmdc201600225-kwd-0005">p53</term></keywords><keywords rend="articleCategory"><term>Communication</term></keywords><keywords rend="tocHeading1"><term>Communications</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc><revisionDesc><change when="2019-12-20" who="#istex" xml:id="pub2tei">formatting</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-7S7FNDF2-7/fulltext.txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en" xml:id="cmdc201600225"><header><publicationMeta level="product"><doi origin="wiley" registered="yes">10.1002/(ISSN)1860-7187</doi><issn type="print">1860-7179</issn><issn type="electronic">1860-7187</issn><idGroup><id type="product" value="CMDC"></id></idGroup><titleGroup><title type="main" sort="CHEMMEDCHEM">ChemMedChem</title><title type="short">ChemMedChem</title></titleGroup></publicationMeta><publicationMeta level="part" position="160"><doi>10.1002/cmdc.v11.16</doi><titleGroup><title type="specialIssueTitle">23rd National Meeting on Medicinal Chemistry (NMMC)</title></titleGroup><copyright ownership="publisher">© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><numberingGroup><numbering type="journalVolume" number="11">11</numbering><numbering type="journalIssue">16</numbering></numberingGroup><coverDate startDate="2016-08-19">August 19, 2016</coverDate></publicationMeta><publicationMeta level="unit" type="shortCommunication" position="17000" status="forIssue"><doi origin="wiley">10.1002/cmdc.201600225</doi><idGroup><id type="unit" value="CMDC201600225"></id></idGroup><countGroup><count type="pageTotal" number="5"></count></countGroup><titleGroup><title type="articleCategory">Communication</title><title type="tocHeading1">Communications</title></titleGroup><copyright ownership="publisher">© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2016-04-27"></event><event type="manuscriptRevised" date="2016-05-20"></event><event type="xmlConverted" agent="Triltsch" date="2016-08-22"></event><event type="firstOnline" date="2016-06-17"></event><event type="publishedOnlineEarlyUnpaginated" date="2016-06-17"></event><event type="publishedOnlineFinalForm" date="2016-08-22"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:5.0.6 mode:FullText" date="2017-02-10"></event></eventGroup><numberingGroup><numbering type="pageFirst">1700</numbering><numbering type="pageLast">1704</numbering></numberingGroup><selfCitationGroup><citation type="self" xml:id="cmdc201600225-self">L. Musso, R. Cincinelli, V. Zuco, M. De Cesare, F. Zunino, A. L. Fallacara, M. Botta, S. Dallavalle, <i>ChemMedChem</i> <b>2016</b>, <i>11</i>, 1700.</citation></selfCitationGroup><objectNameGroup><objectName elementName="figure">Figure</objectName><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:CMDC.CMDC201600225.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="10"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="32"></count></countGroup><titleGroup><title type="main" xml:lang="en">3‐Arylidene‐<i>N</i>‐hydroxyoxindoles: A New Class of Compounds Endowed with Antitumor Activity</title></titleGroup><creators><creator xml:id="cmdc201600225-cr-0001" creatorRole="author" affiliationRef="#cmdc201600225-aff-0001"><personName><honorifics>Dr.</honorifics><givenNames>Loana</givenNames><familyName>Musso</familyName></personName></creator><creator xml:id="cmdc201600225-cr-0002" creatorRole="author" 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affiliationRef="#cmdc201600225-aff-0003"><personName><honorifics>Dr.</honorifics><givenNames>Anna Lucia</givenNames><familyName>Fallacara</familyName></personName></creator><creator xml:id="cmdc201600225-cr-0007" creatorRole="author" affiliationRef="#cmdc201600225-aff-0003 #cmdc201600225-aff-0004"><personName><honorifics>Prof.</honorifics><givenNames>Maurizio</givenNames><familyName>Botta</familyName></personName></creator><creator xml:id="cmdc201600225-cr-0008" creatorRole="author" affiliationRef="#cmdc201600225-aff-0001" corresponding="yes"><idGroup><id type="orcid" value="http://orcid.org/0000-0002-8813-8922"></id></idGroup><personName><honorifics>Prof.</honorifics><givenNames>Sabrina</givenNames><familyName>Dallavalle</familyName></personName><contactDetails><email>sabrina.dallavalle@unimi.it</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="cmdc201600225-aff-0001" countryCode="IT" type="organization"><orgDiv>Department of 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2</orgName><address><postCode>53100</postCode><city>Siena</city><country>Italy</country></address></affiliation><affiliation xml:id="cmdc201600225-aff-0004" countryCode="US" type="organization"><orgDiv>Sbarro Institute for Cancer Research and Molecular Medicine</orgDiv><orgDiv>Center for Biotechnology</orgDiv><orgDiv>College of Science and Technology</orgDiv><orgName>Temple University, BioLife Science Building, Suite 333</orgName><address><street>1900 North 12th Street</street><city>Philadelphia</city><countryPart>PA</countryPart><postCode>19122</postCode><country>USA</country></address></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="cmdc201600225-kwd-0001">antiproliferative activity</keyword><keyword xml:id="cmdc201600225-kwd-0002">antitumor agents</keyword><keyword xml:id="cmdc201600225-kwd-0003">apoptosis</keyword><keyword xml:id="cmdc201600225-kwd-0004"><i>N</i>-hydroxyoxindole</keyword><keyword xml:id="cmdc201600225-kwd-0005">p53</keyword></keywordGroup><fundingInfo><fundingAgency>COST Actions</fundingAgency><fundingNumber>CM1106</fundingNumber></fundingInfo><fundingInfo><fundingAgency>Chemical Approaches to Targeting Drug Resistance in Cancer Stem Cells</fundingAgency></fundingInfo><supportingInformation><p>As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.</p><supportingInfoItem><mediaResource alt="supplementary_material" rendition="webOriginal" href="urn-x:wiley:18607179:media:cmdc201600225:cmdc201600225-sup-0001-misc_information"></mediaResource><caption>Supplementary</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>A series of compounds containing the <i>N</i>‐hydroxyoxindole scaffold were synthesized and evaluated for antitumor activity. The compounds showed potent antiproliferative activity against the wild‐type p53 IGROV‐1 ovarian carcinoma cell line and considerably lower efficacy against the mutant IGROV‐1/Pt1 subline that lacks p53 function. The differential response of ovarian carcinoma cells depending on p53 status was also reflected in the varied susceptibility to apoptosis of the treated cell lines. These results support a role for the p53 transcription factor as a determinant of cytotoxicity. The therapeutic potential of the most promising compound of the series was evaluated in the treatment of an IGROV‐1 xenograft growing as ascitic tumor in mice. Using intraperitoneal administration, daily treatment with the compound for four weeks produced a significant delay in the onset of ascites.</p></abstract><abstract type="graphical" xml:lang="en"><p><b>Exploring new scaffolds</b>: A series of 3‐arylidene‐<i>N</i>‐hydroxyoxindoles show potent antiproliferative and pro‐apoptotic activity against wild‐type p53 IGROV‐1 ovarian carcinoma cells and a considerably lower efficacy against the mutant IGROV‐1/Pt1 subline lacking p53 function. These results support a role for this transcription factor as a determinant of cytotoxicity. Treatment of an IGROV‐1 xenograft growing as an ascitic tumor produced a significant delay in the onset of ascites.<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" href="urn:x-wiley:18607179:media:cmdc201600225:cmdc201600225-toc-0001"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>3‐Arylidene‐N‐hydroxyoxindoles: A New Class of Compounds Endowed with Antitumor Activity</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>3‐Arylidene‐N‐hydroxyoxindoles: A New Class of Compounds Endowed with Antitumor Activity</title></titleInfo><name type="personal"><namePart type="termsOfAddress">Dr.</namePart><namePart type="given">Loana</namePart><namePart type="family">Musso</namePart><affiliation>Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, University of Milan, via Celoria 2, 20133, Milano, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Dr.</namePart><namePart type="given">Raffaella</namePart><namePart type="family">Cincinelli</namePart><affiliation>Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, University of Milan, via Celoria 2, 20133, Milano, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Dr.</namePart><namePart type="given">Valentina</namePart><namePart type="family">Zuco</namePart><affiliation>Department of Experimental Oncology and Molecular Medicine, Fondazione IRCCS – Istituto Nazionale dei Tumori, Via Amadeo 42, 20133, Milano, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Dr.</namePart><namePart type="given">Michelandrea</namePart><namePart type="family">De Cesare</namePart><affiliation>Department of Experimental Oncology and Molecular Medicine, Fondazione IRCCS – Istituto Nazionale dei Tumori, Via Amadeo 42, 20133, Milano, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Dr.</namePart><namePart type="given">Franco</namePart><namePart type="family">Zunino</namePart><affiliation>Department of Experimental Oncology and Molecular Medicine, Fondazione IRCCS – Istituto Nazionale dei Tumori, Via Amadeo 42, 20133, Milano, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Dr.</namePart><namePart type="given">Anna Lucia</namePart><namePart type="family">Fallacara</namePart><affiliation>Department of Biotechnology Chemistry and Pharmaceutical Science, University of Siena, Via Aldo Moro 2, 53100, Siena, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Prof.</namePart><namePart type="given">Maurizio</namePart><namePart type="family">Botta</namePart><affiliation>Department of Biotechnology Chemistry and Pharmaceutical Science, University of Siena, Via Aldo Moro 2, 53100, Siena, Italy</affiliation><affiliation>Sbarro Institute for Cancer Research and Molecular Medicine, Center for Biotechnology, College of Science and Technology, Temple University, BioLife Science Building, Suite 333, 1900 North 12th Street, PA, 19122, Philadelphia, USA</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Prof.</namePart><namePart type="given">Sabrina</namePart><namePart type="family">Dallavalle</namePart><affiliation>Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, University of Milan, via Celoria 2, 20133, Milano, Italy</affiliation><affiliation>E-mail: sabrina.dallavalle@unimi.it</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="brief-communication" displayLabel="shortCommunication" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-S9SX2MFS-0">brief-communication</genre><originInfo><publisher>Blackwell Publishing Ltd</publisher><dateIssued encoding="w3cdtf">2016-08-19</dateIssued><dateCaptured encoding="w3cdtf">2016-04-27</dateCaptured><edition>L. Musso, R. Cincinelli, V. Zuco, M. De Cesare, F. Zunino, A. L. Fallacara, M. Botta, S. Dallavalle, ChemMedChem 2016, 11, 1700.</edition><copyrightDate encoding="w3cdtf">2016</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">10</extent><extent unit="tables">1</extent><extent unit="references">32</extent></physicalDescription><abstract lang="en">A series of compounds containing the N‐hydroxyoxindole scaffold were synthesized and evaluated for antitumor activity. The compounds showed potent antiproliferative activity against the wild‐type p53 IGROV‐1 ovarian carcinoma cell line and considerably lower efficacy against the mutant IGROV‐1/Pt1 subline that lacks p53 function. The differential response of ovarian carcinoma cells depending on p53 status was also reflected in the varied susceptibility to apoptosis of the treated cell lines. These results support a role for the p53 transcription factor as a determinant of cytotoxicity. The therapeutic potential of the most promising compound of the series was evaluated in the treatment of an IGROV‐1 xenograft growing as ascitic tumor in mice. Using intraperitoneal administration, daily treatment with the compound for four weeks produced a significant delay in the onset of ascites.</abstract><abstract type="graphical" lang="en">Exploring new scaffolds: A series of 3‐arylidene‐N‐hydroxyoxindoles show potent antiproliferative and pro‐apoptotic activity against wild‐type p53 IGROV‐1 ovarian carcinoma cells and a considerably lower efficacy against the mutant IGROV‐1/Pt1 subline lacking p53 function. These results support a role for this transcription factor as a determinant of cytotoxicity. Treatment of an IGROV‐1 xenograft growing as an ascitic tumor produced a significant delay in the onset of ascites.</abstract><note type="funding">COST Actions - No. CM1106; </note><note type="funding">Chemical Approaches to Targeting Drug Resistance in Cancer Stem Cells</note><subject lang="en"><genre>keywords</genre><topic>antiproliferative activity</topic><topic>antitumor agents</topic><topic>apoptosis</topic><topic>N-hydroxyoxindole</topic><topic>p53</topic></subject><relatedItem type="host"><titleInfo><title>ChemMedChem</title></titleInfo><titleInfo type="abbreviated"><title>ChemMedChem</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><note type="content"> As a service to our authors and readers, this journal provides supporting information supplied by the authors. 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