Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents
© 2021 Deutsche Pharmazeutische Gesellschaft..
A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen-Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2 O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16-5.45 µM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:354 |
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| Enthalten in: |
Archiv der Pharmazie - 354(2021), 9 vom: 10. Sept., Seite e2100094 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Insuasty, Daniel [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 12.01.2022 Date Revised 12.01.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1002/ardp.202100094 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a © 2021 Deutsche Pharmazeutische Gesellschaft. | ||
| 520 | |a A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen-Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2 O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16-5.45 µM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways | ||
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| 650 | 4 | |a anticancer activity | |
| 650 | 4 | |a molecular docking | |
| 650 | 4 | |a quinoline-based bis-chalcones | |
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| 700 | 1 | |a Quiroga, Jairo |e verfasserin |4 aut | |
| 700 | 1 | |a Nogueras, Manuel |e verfasserin |4 aut | |
| 700 | 1 | |a Cobo, Justo |e verfasserin |4 aut | |
| 700 | 1 | |a Borosky, Gabriela L |e verfasserin |4 aut | |
| 700 | 1 | |a Laali, Kenneth K |e verfasserin |4 aut | |
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