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Editor, Senior Moderator
Chem Pharm Bull (Tokyo). 2019 Aug 22. doi: 10.1248/cpb.c19-00485. [Epub ahead of print]
[h=1]Synthesis, structure activity relationship and anti-influenza A virus evaluation of oleanolic acid-linear amino derivatives.[/h] Li W[SUP]1[/SUP], Yang F[SUP]1[/SUP], Meng L[SUP]1[/SUP], Sun J[SUP]2[/SUP], Su Y[SUP]1[/SUP], Shao L[SUP]1[/SUP], Zhou D[SUP]2[/SUP], Yu F[SUP]1[/SUP].
[h=3]Author information[/h] 1 Medical School of Kunming University of Science and Technology. 2 State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University.
[h=3]Abstract[/h] Oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor in our earlier studies. In the present work, 20 compounds were prepared by structural modifications of OA, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in MDCK cells were evaluated. Based on the biological result, structure-activity relationship (SAR) was discussed. Compound 10 with six-carbon chain and a terminal hydroxyl group showed the strongest anti-influenza activity with an IC[SUB]50[/SUB] of 2.98 μM, which is an order of magnitude more potent than OA. Hemagglutination inhibition and Surface plasmon resonance (SPR) assay indicated that compound 10 might interfere with influenza invasion by interacting with HA protein.
[h=4]KEYWORDS:[/h] Cytotoxicity; Entry inhibitor; Influenza virus; Oleanolic acid; Synthesis design
PMID: 31434835 DOI: 10.1248/cpb.c19-00485
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[h=1]Synthesis, structure activity relationship and anti-influenza A virus evaluation of oleanolic acid-linear amino derivatives.[/h] Li W[SUP]1[/SUP], Yang F[SUP]1[/SUP], Meng L[SUP]1[/SUP], Sun J[SUP]2[/SUP], Su Y[SUP]1[/SUP], Shao L[SUP]1[/SUP], Zhou D[SUP]2[/SUP], Yu F[SUP]1[/SUP].
[h=3]Author information[/h] 1 Medical School of Kunming University of Science and Technology. 2 State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University.
[h=3]Abstract[/h] Oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor in our earlier studies. In the present work, 20 compounds were prepared by structural modifications of OA, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in MDCK cells were evaluated. Based on the biological result, structure-activity relationship (SAR) was discussed. Compound 10 with six-carbon chain and a terminal hydroxyl group showed the strongest anti-influenza activity with an IC[SUB]50[/SUB] of 2.98 μM, which is an order of magnitude more potent than OA. Hemagglutination inhibition and Surface plasmon resonance (SPR) assay indicated that compound 10 might interfere with influenza invasion by interacting with HA protein.
[h=4]KEYWORDS:[/h] Cytotoxicity; Entry inhibitor; Influenza virus; Oleanolic acid; Synthesis design
PMID: 31434835 DOI: 10.1248/cpb.c19-00485
Free full text