Synthesis, anti-cancer and anti-inflammatory activity of novel 2-substituted isoflavenes.
Identifieur interne : 003277 ( PubMed/Curation ); précédent : 003276; suivant : 003278Synthesis, anti-cancer and anti-inflammatory activity of novel 2-substituted isoflavenes.
Auteurs : Eleanor Eiffe [Australie] ; Eddy Pasquier [France] ; Maria Kavallaris [Australie] ; Cristan Herbert [Australie] ; David Stc Black [Australie] ; Naresh Kumar [Australie]Source :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2014.
Descripteurs français
- KwdFr :
- Animaux, Anti-inflammatoires non stéroïdiens (), Anti-inflammatoires non stéroïdiens (pharmacologie), Anti-inflammatoires non stéroïdiens (synthèse chimique), Antinéoplasiques (), Antinéoplasiques (pharmacologie), Antinéoplasiques (synthèse chimique), Flavonoïdes (), Flavonoïdes (pharmacologie), Flavonoïdes (synthèse chimique), Humains, Interleukine-6 (antagonistes et inhibiteurs), Interleukine-6 (biosynthèse), Lignée cellulaire, Lipopolysaccharides (antagonistes et inhibiteurs), Lipopolysaccharides (pharmacologie), Macrophages (), Macrophages (métabolisme), Prolifération cellulaire (), Relation dose-effet des médicaments, Relation structure-activité, Souris, Structure moléculaire, Tests de criblage d'agents antitumoraux.
- MESH :
- antagonistes et inhibiteurs : Interleukine-6, Lipopolysaccharides.
- biosynthèse : Interleukine-6.
- métabolisme : Macrophages.
- pharmacologie : Anti-inflammatoires non stéroïdiens, Antinéoplasiques, Flavonoïdes, Lipopolysaccharides.
- synthèse chimique : Anti-inflammatoires non stéroïdiens, Antinéoplasiques, Flavonoïdes.
- Animaux, Anti-inflammatoires non stéroïdiens, Antinéoplasiques, Flavonoïdes, Humains, Lignée cellulaire, Macrophages, Prolifération cellulaire, Relation dose-effet des médicaments, Relation structure-activité, Souris, Structure moléculaire, Tests de criblage d'agents antitumoraux.
English descriptors
- KwdEn :
- Animals, Anti-Inflammatory Agents, Non-Steroidal (chemical synthesis), Anti-Inflammatory Agents, Non-Steroidal (chemistry), Anti-Inflammatory Agents, Non-Steroidal (pharmacology), Antineoplastic Agents (chemical synthesis), Antineoplastic Agents (chemistry), Antineoplastic Agents (pharmacology), Cell Line, Cell Proliferation (drug effects), Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Flavonoids (chemical synthesis), Flavonoids (chemistry), Flavonoids (pharmacology), Humans, Interleukin-6 (antagonists & inhibitors), Interleukin-6 (biosynthesis), Lipopolysaccharides (antagonists & inhibitors), Lipopolysaccharides (pharmacology), Macrophages (drug effects), Macrophages (metabolism), Mice, Molecular Structure, Structure-Activity Relationship.
- MESH :
- chemical , antagonists & inhibitors : Interleukin-6, Lipopolysaccharides.
- chemical , biosynthesis : Interleukin-6.
- chemical , chemical synthesis : Anti-Inflammatory Agents, Non-Steroidal, Antineoplastic Agents, Flavonoids.
- chemical , chemistry : Anti-Inflammatory Agents, Non-Steroidal, Antineoplastic Agents, Flavonoids.
- chemical , pharmacology : Anti-Inflammatory Agents, Non-Steroidal, Antineoplastic Agents, Flavonoids, Lipopolysaccharides.
- drug effects : Cell Proliferation, Macrophages.
- metabolism : Macrophages.
- Animals, Cell Line, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Humans, Mice, Molecular Structure, Structure-Activity Relationship.
Abstract
Fifteen novel 2-substituted isoflavenes were synthesised via nucleophilic addition to isoflavylium salts. Twelve of the newly synthesised isoflavenes, along with the unsubstituted parent isoflavene, were tested in cell viability assays against the SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. While the 2-substituted isoflavenes displayed a range of anti-proliferative activities, in most cases they were less active that the unsubstituted isoflavene (IC50=9.9 μM vs SHEP; IC50=33 μM vs MDA-MB-231). However, compound 7f, derived from the reaction between isoflavylium salt 5 and para-methoxyacetophenone, showed improved anti-proliferative activity against breast cancer cells (IC50=7.6 μM). Furthermore, compound 7f, as well as analogues 7a, 7c, 11d and 14, inhibited the production of interleukin-6 in LPS-activated RAW 264.7 cells.
DOI: 10.1016/j.bmc.2014.08.010
PubMed: 25189689
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pubmed:25189689Le document en format XML
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Drug</term><term>Drug Screening Assays, Antitumor</term><term>Flavonoids (chemical synthesis)</term><term>Flavonoids (chemistry)</term><term>Flavonoids (pharmacology)</term><term>Humans</term><term>Interleukin-6 (antagonists & inhibitors)</term><term>Interleukin-6 (biosynthesis)</term><term>Lipopolysaccharides (antagonists & inhibitors)</term><term>Lipopolysaccharides (pharmacology)</term><term>Macrophages (drug effects)</term><term>Macrophages (metabolism)</term><term>Mice</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Anti-inflammatoires non stéroïdiens ()</term><term>Anti-inflammatoires non stéroïdiens (pharmacologie)</term><term>Anti-inflammatoires non stéroïdiens (synthèse chimique)</term><term>Antinéoplasiques ()</term><term>Antinéoplasiques (pharmacologie)</term><term>Antinéoplasiques (synthèse chimique)</term><term>Flavonoïdes ()</term><term>Flavonoïdes (pharmacologie)</term><term>Flavonoïdes (synthèse chimique)</term><term>Humains</term><term>Interleukine-6 (antagonistes et inhibiteurs)</term><term>Interleukine-6 (biosynthèse)</term><term>Lignée cellulaire</term><term>Lipopolysaccharides (antagonistes et inhibiteurs)</term><term>Lipopolysaccharides (pharmacologie)</term><term>Macrophages ()</term><term>Macrophages (métabolisme)</term><term>Prolifération cellulaire ()</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Souris</term><term>Structure moléculaire</term><term>Tests de criblage d'agents antitumoraux</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Interleukin-6</term><term>Lipopolysaccharides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>Interleukin-6</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Anti-Inflammatory Agents, Non-Steroidal</term><term>Antineoplastic Agents</term><term>Flavonoids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anti-Inflammatory Agents, Non-Steroidal</term><term>Antineoplastic Agents</term><term>Flavonoids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-Inflammatory Agents, Non-Steroidal</term><term>Antineoplastic Agents</term><term>Flavonoids</term><term>Lipopolysaccharides</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Interleukine-6</term><term>Lipopolysaccharides</term></keywords><keywords scheme="MESH" qualifier="biosynthèse" xml:lang="fr"><term>Interleukine-6</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Cell Proliferation</term><term>Macrophages</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Macrophages</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Macrophages</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Anti-inflammatoires non stéroïdiens</term><term>Antinéoplasiques</term><term>Flavonoïdes</term><term>Lipopolysaccharides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Anti-inflammatoires non stéroïdiens</term><term>Antinéoplasiques</term><term>Flavonoïdes</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Cell Line</term><term>Dose-Response Relationship, Drug</term><term>Drug Screening Assays, Antitumor</term><term>Humans</term><term>Mice</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Anti-inflammatoires non stéroïdiens</term><term>Antinéoplasiques</term><term>Flavonoïdes</term><term>Humains</term><term>Lignée cellulaire</term><term>Macrophages</term><term>Prolifération cellulaire</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Souris</term><term>Structure moléculaire</term><term>Tests de criblage d'agents antitumoraux</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Fifteen novel 2-substituted isoflavenes were synthesised via nucleophilic addition to isoflavylium salts. Twelve of the newly synthesised isoflavenes, along with the unsubstituted parent isoflavene, were tested in cell viability assays against the SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. While the 2-substituted isoflavenes displayed a range of anti-proliferative activities, in most cases they were less active that the unsubstituted isoflavene (IC50=9.9 μM vs SHEP; IC50=33 μM vs MDA-MB-231). However, compound 7f, derived from the reaction between isoflavylium salt 5 and para-methoxyacetophenone, showed improved anti-proliferative activity against breast cancer cells (IC50=7.6 μM). Furthermore, compound 7f, as well as analogues 7a, 7c, 11d and 14, inhibited the production of interleukin-6 in LPS-activated RAW 264.7 cells.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25189689</PMID><DateCreated><Year>2014</Year><Month>09</Month><Day>22</Day></DateCreated><DateCompleted><Year>2015</Year><Month>04</Month><Day>06</Day></DateCompleted><DateRevised><Year>2014</Year><Month>09</Month><Day>22</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3391</ISSN><JournalIssue CitedMedium="Internet"><Volume>22</Volume><Issue>19</Issue><PubDate><Year>2014</Year><Month>Oct</Month><Day>01</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry</Title><ISOAbbreviation>Bioorg. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>Synthesis, anti-cancer and anti-inflammatory activity of novel 2-substituted isoflavenes.</ArticleTitle><Pagination><MedlinePgn>5182-93</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmc.2014.08.010</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0968-0896(14)00587-2</ELocationID><Abstract><AbstractText>Fifteen novel 2-substituted isoflavenes were synthesised via nucleophilic addition to isoflavylium salts. Twelve of the newly synthesised isoflavenes, along with the unsubstituted parent isoflavene, were tested in cell viability assays against the SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. While the 2-substituted isoflavenes displayed a range of anti-proliferative activities, in most cases they were less active that the unsubstituted isoflavene (IC50=9.9 μM vs SHEP; IC50=33 μM vs MDA-MB-231). However, compound 7f, derived from the reaction between isoflavylium salt 5 and para-methoxyacetophenone, showed improved anti-proliferative activity against breast cancer cells (IC50=7.6 μM). Furthermore, compound 7f, as well as analogues 7a, 7c, 11d and 14, inhibited the production of interleukin-6 in LPS-activated RAW 264.7 cells.</AbstractText><CopyrightInformation>Copyright © 2014 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Eiffe</LastName><ForeName>Eleanor</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pasquier</LastName><ForeName>Eddy</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>Children's Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, University of New South Wales, Randwick, NSW 2052, Australia; Metronomics Global Health Initiative, Marseille, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kavallaris</LastName><ForeName>Maria</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Children's Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, University of New South Wales, Randwick, NSW 2052, Australia; Australian Centre for Nanomedicine, School of Chemical Engineering, UNSW, Sydney, New South Wales 2052, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Herbert</LastName><ForeName>Cristan</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>School of Medical Sciences, The University of New South Wales, Sydney, NSW 2052, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>StC Black</LastName><ForeName>David</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kumar</LastName><ForeName>Naresh</ForeName><Initials>N</Initials><AffiliationInfo><Affiliation>School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia. Electronic address: n.kumar@unsw.edu.au.</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>2014</Year><Month>08</Month><Day>17</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem</MedlineTA><NlmUniqueID>9413298</NlmUniqueID><ISSNLinking>0968-0896</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000894">Anti-Inflammatory Agents, Non-Steroidal</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000970">Antineoplastic Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005419">Flavonoids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D015850">Interleukin-6</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D008070">Lipopolysaccharides</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000894" MajorTopicYN="N">Anti-Inflammatory Agents, Non-Steroidal</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000970" MajorTopicYN="N">Antineoplastic Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002460" MajorTopicYN="N">Cell Line</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="D004354" MajorTopicYN="N">Drug Screening Assays, Antitumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005419" MajorTopicYN="N">Flavonoids</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015850" MajorTopicYN="N">Interleukin-6</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName><QualifierName UI="Q000096" MajorTopicYN="N">biosynthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008070" MajorTopicYN="N">Lipopolysaccharides</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="N">antagonists & inhibitors</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008264" MajorTopicYN="N">Macrophages</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D051379" MajorTopicYN="N">Mice</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Anti-cancer</Keyword><Keyword MajorTopicYN="N">Anti-inflammatory</Keyword><Keyword MajorTopicYN="N">Isoflavene</Keyword><Keyword MajorTopicYN="N">Isoflavonoid</Keyword><Keyword MajorTopicYN="N">Isoflavylium</Keyword><Keyword MajorTopicYN="N">Nucleophilic addition</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year><Month>06</Month><Day>03</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2014</Year><Month>07</Month><Day>31</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2014</Year><Month>08</Month><Day>09</Day></PubMedPubDate><PubMedPubDate 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|texte= Synthesis, anti-cancer and anti-inflammatory activity of novel 2-substituted isoflavenes.
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Pour générer des pages wiki
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