Novel amphiphilic pyridinium ionic liquids-supported Schiff bases: ultrasound assisted synthesis, molecular docking and anticancer evaluation
Identifieur interne : 000502 ( Main/Exploration ); précédent : 000501; suivant : 000503Novel amphiphilic pyridinium ionic liquids-supported Schiff bases: ultrasound assisted synthesis, molecular docking and anticancer evaluation
Auteurs : Fawzia Faleh Al-Blewi [Arabie saoudite] ; Nadjet Rezki [Arabie saoudite, Algérie] ; Salsabeel Abdullah Al-Sodies [Arabie saoudite] ; Sanaa K. Bardaweel [Jordanie] ; Dima A. Sabbah [Jordanie] ; Mouslim Messali [Arabie saoudite] ; Mohamed Reda Aouad [Arabie saoudite]Source :
- Chemistry Central Journal [ 1752-153X ] ; 2018.
Abstract
Pyridinium Schiff bases and ionic liquids have attracted increasing interest in medicinal chemistry.
A library of 32 cationic fluorinated pyridinium hydrazone-based amphiphiles tethering fluorinated counteranions was synthesized by alkylation of 4-fluoropyridine hydrazone with various long alkyl iodide exploiting lead quaternization and metathesis strategies. All compounds were assessed for their anticancer inhibition activity towards different cancer cell lines and the results revealed that increasing the length of the hydrophobic chain of the synthesized analogues appears to significantly enhance their anticancer activities. Substantial increase in caspase-3 activity was demonstrated upon treatment with the most potent compounds, namely
Quantum-polarized ligand docking studies against phosphoinositide 3-kinase α displayed that compounds
The online version of this article (10.1186/s13065-018-0489-z) contains supplementary material, which is available to authorized users.
Url:
DOI: 10.1186/s13065-018-0489-z
PubMed: 30467608
PubMed Central: 6768046
Affiliations:
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Box 1505, El M‘nouar, 31000 Oran</wicri:regionArea></affiliation></author><author><name sortKey="Al Sodies, Salsabeel Abdullah" sort="Al Sodies, Salsabeel Abdullah" uniqKey="Al Sodies S" first="Salsabeel Abdullah" last="Al-Sodies">Salsabeel Abdullah Al-Sodies</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0004 1754 9358</institution-id><institution-id institution-id-type="GRID">grid.412892.4</institution-id><institution>Department of Chemistry, Faculty of Science,</institution><institution>Taibah University,</institution></institution-wrap>Al-Madinah Al-Munawarah, Medina, 30002 Saudi Arabia</nlm:aff><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Al-Madinah Al-Munawarah, Medina</wicri:regionArea></affiliation></author><author><name sortKey="Bardaweel, Sanaa K" sort="Bardaweel, Sanaa K" uniqKey="Bardaweel S" first="Sanaa K." last="Bardaweel">Sanaa K. 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All compounds were assessed for their anticancer inhibition activity towards different cancer cell lines and the results revealed that increasing the length of the hydrophobic chain of the synthesized analogues appears to significantly enhance their anticancer activities. Substantial increase in caspase-3 activity was demonstrated upon treatment with the most potent compounds, namely <bold>8</bold>, <bold>28</bold>, <bold>29</bold> and <bold>32</bold> suggesting an apoptotic cellular death pathway.</p></sec><sec><title>Conclusions</title><p id="Par3">Quantum-polarized ligand docking studies against phosphoinositide 3-kinase α displayed that compounds <bold>2</bold>–<bold>6</bold> bind to the kinase site and form H-bond with S774, K802, H917 and D933. <graphic position="anchor" xlink:href="13065_2018_489_Figa_HTML" id="MO1"></graphic></p></sec><sec><title>Electronic supplementary material</title><p>The online version of this article (10.1186/s13065-018-0489-z) contains supplementary material, which is available to authorized users.</p></sec></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Rollas, S" uniqKey="Rollas S">S Rollas</name></author><author><name sortKey="Kucukguzel, Sg" uniqKey="Kucukguzel 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sortKey="Sidransky, D" uniqKey="Sidransky D">D Sidransky</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Beaver, Ja" uniqKey="Beaver J">JA Beaver</name></author><author><name sortKey="Gustin, Jp" uniqKey="Gustin J">JP Gustin</name></author><author><name sortKey="Yi, Kh" uniqKey="Yi K">KH Yi</name></author><author><name sortKey="Rajpurohit, A" uniqKey="Rajpurohit A">A Rajpurohit</name></author><author><name sortKey="Thomas, M" uniqKey="Thomas M">M Thomas</name></author><author><name sortKey="Gilbert, Sf" uniqKey="Gilbert S">SF Gilbert</name></author><author><name sortKey="Rose, Dm" uniqKey="Rose D">DM Rose</name></author><author><name sortKey="Park, Bh" uniqKey="Park B">BH Park</name></author><author><name sortKey="Lauring, J" uniqKey="Lauring J">J Lauring</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="She, Q B" uniqKey="She Q">Q-B She</name></author><author><name sortKey="Chandarlapaty, S" uniqKey="Chandarlapaty S">S Chandarlapaty</name></author><author><name sortKey="Ye, Q" uniqKey="Ye Q">Q Ye</name></author><author><name sortKey="Lobo, J" uniqKey="Lobo J">J Lobo</name></author><author><name sortKey="Haskell, Km" uniqKey="Haskell K">KM Haskell</name></author><author><name sortKey="Leander, Kr" uniqKey="Leander K">KR Leander</name></author><author><name sortKey="Defeo Jones, D" uniqKey="Defeo Jones D">D DeFeo-Jones</name></author><author><name sortKey="Huber, He" uniqKey="Huber H">HE Huber</name></author><author><name sortKey="Rosen, N" uniqKey="Rosen N">N Rosen</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Weigelt, B" uniqKey="Weigelt B">B Weigelt</name></author><author><name sortKey="Warne, Ph" uniqKey="Warne P">PH Warne</name></author><author><name sortKey="Downward, J" uniqKey="Downward J">J Downward</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Zardavas, D" uniqKey="Zardavas D">D Zardavas</name></author><author><name sortKey="Phillips, Wa" uniqKey="Phillips W">WA Phillips</name></author><author><name sortKey="Loi, S" uniqKey="Loi S">S Loi</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Algérie</li><li>Arabie saoudite</li><li>Jordanie</li></country></list><tree><country name="Arabie saoudite"><noRegion><name sortKey="Al Blewi, Fawzia Faleh" sort="Al Blewi, Fawzia Faleh" uniqKey="Al Blewi F" first="Fawzia Faleh" last="Al-Blewi">Fawzia Faleh Al-Blewi</name></noRegion><name sortKey="Al Sodies, Salsabeel Abdullah" sort="Al Sodies, Salsabeel Abdullah" uniqKey="Al Sodies S" first="Salsabeel Abdullah" last="Al-Sodies">Salsabeel Abdullah Al-Sodies</name><name sortKey="Aouad, Mohamed Reda" sort="Aouad, Mohamed Reda" uniqKey="Aouad M" first="Mohamed Reda" last="Aouad">Mohamed Reda Aouad</name><name sortKey="Messali, Mouslim" sort="Messali, Mouslim" uniqKey="Messali M" first="Mouslim" last="Messali">Mouslim Messali</name><name sortKey="Rezki, Nadjet" sort="Rezki, Nadjet" uniqKey="Rezki N" first="Nadjet" last="Rezki">Nadjet Rezki</name></country><country name="Algérie"><noRegion><name sortKey="Rezki, Nadjet" sort="Rezki, Nadjet" uniqKey="Rezki N" first="Nadjet" last="Rezki">Nadjet Rezki</name></noRegion></country><country name="Jordanie"><noRegion><name sortKey="Bardaweel, Sanaa K" sort="Bardaweel, Sanaa K" uniqKey="Bardaweel S" first="Sanaa K." last="Bardaweel">Sanaa K. Bardaweel</name></noRegion><name sortKey="Sabbah, Dima A" sort="Sabbah, Dima A" uniqKey="Sabbah D" first="Dima A." last="Sabbah">Dima A. Sabbah</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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