Synthesis, anti-cancer and anti-inflammatory activity of novel 2-substituted isoflavenes.
Identifieur interne : 001D71 ( Ncbi/Curation ); précédent : 001D70; suivant : 001D72Synthesis, 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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<term>Anti-Inflammatory Agents, Non-Steroidal (chemistry)</term>
<term>Anti-Inflammatory Agents, Non-Steroidal (pharmacology)</term>
<term>Antineoplastic Agents (chemical synthesis)</term>
<term>Antineoplastic Agents (chemistry)</term>
<term>Antineoplastic Agents (pharmacology)</term>
<term>Cell Line</term>
<term>Cell Proliferation (drug effects)</term>
<term>Dose-Response Relationship, Drug</term>
<term>Drug Screening Assays, Antitumor</term>
<term>Flavonoids (chemical synthesis)</term>
<term>Flavonoids (chemistry)</term>
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<term>Humans</term>
<term>Interleukin-6 (antagonists & inhibitors)</term>
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<term>Lipopolysaccharides (pharmacology)</term>
<term>Macrophages (drug effects)</term>
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<term>Anti-inflammatoires non stéroïdiens (synthèse chimique)</term>
<term>Antinéoplasiques ()</term>
<term>Antinéoplasiques (pharmacologie)</term>
<term>Antinéoplasiques (synthèse chimique)</term>
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<term>Flavonoïdes (pharmacologie)</term>
<term>Flavonoïdes (synthèse chimique)</term>
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<term>Lipopolysaccharides (pharmacologie)</term>
<term>Macrophages ()</term>
<term>Macrophages (métabolisme)</term>
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<term>Souris</term>
<term>Structure moléculaire</term>
<term>Tests de criblage d'agents antitumoraux</term>
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<term>Lipopolysaccharides</term>
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<term>Antineoplastic Agents</term>
<term>Flavonoids</term>
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<term>Antineoplastic Agents</term>
<term>Flavonoids</term>
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<term>Flavonoids</term>
<term>Lipopolysaccharides</term>
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<term>Lipopolysaccharides</term>
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<term>Macrophages</term>
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<term>Flavonoïdes</term>
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<term>Macrophages</term>
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<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
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<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>
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