Synthesis of a Hexavalent Betulinic Acid Derivative as a Hemagglutinin-Targeted Influenza Virus Entry Inhibitor
Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4...
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| Published in | Molecular pharmaceutics Vol. 17; no. 7; pp. 2546 - 2554 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
06.07.2020
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| Abstract | Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4-N-(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1H-1,2,3-triazol-1-yl]-2,3-di-O-acetyl-α-cyclodextrin (CYY1-11, 1), in a mini library of pentacyclic triterpene–cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate 1 possessed a high-level activity against the influenza virus A/WSN/33 with an IC50 value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate 1 inhibited viral replication by directly targeting the influenza hemagglutinin protein (K D = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors. |
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| AbstractList | Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4-N-(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1H-1,2,3-triazol-1-yl]-2,3-di-O-acetyl-α-cyclodextrin (CYY1-11, 1), in a mini library of pentacyclic triterpene-cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate 1 possessed a high-level activity against the influenza virus A/WSN/33 with an IC50 value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate 1 inhibited viral replication by directly targeting the influenza hemagglutinin protein (KD = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors.Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4-N-(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1H-1,2,3-triazol-1-yl]-2,3-di-O-acetyl-α-cyclodextrin (CYY1-11, 1), in a mini library of pentacyclic triterpene-cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate 1 possessed a high-level activity against the influenza virus A/WSN/33 with an IC50 value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate 1 inhibited viral replication by directly targeting the influenza hemagglutinin protein (KD = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors. Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4-N-(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1H-1,2,3-triazol-1-yl]-2,3-di-O-acetyl-α-cyclodextrin (CYY1-11, 1), in a mini library of pentacyclic triterpene–cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate 1 possessed a high-level activity against the influenza virus A/WSN/33 with an IC50 value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate 1 inhibited viral replication by directly targeting the influenza hemagglutinin protein (KD = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors. Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4- -(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1 -1,2,3-triazol-1-yl]-2,3-di- -acetyl-α-cyclodextrin (CYY1-11, ), in a mini library of pentacyclic triterpene-cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate possessed a high-level activity against the influenza virus A/WSN/33 with an IC value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate inhibited viral replication by directly targeting the influenza hemagglutinin protein ( = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors. Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4-N-(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1H-1,2,3-triazol-1-yl]-2,3-di-O-acetyl-α-cyclodextrin (CYY1-11, 1), in a mini library of pentacyclic triterpene–cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate 1 possessed a high-level activity against the influenza virus A/WSN/33 with an IC50 value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate 1 inhibited viral replication by directly targeting the influenza hemagglutinin protein (K D = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors. |
| Author | Zhang, Lihe Zhu, Yinbiao Si, Longlong Zhang, Yongmin Zhou, Demin Zhang, Bo Chen, Yingying Wang, Xinchen Xiao, Sulong |
| AuthorAffiliation | Chinese Academy of Sciences State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany CNRS UMR 8232, Sorbonne Université Institut Parisien de Chimie Moléculaire Wyss Institute for Biologically Inspired Engineering Chinese Academy of Medical Sciences and Peking Union Medical College Harvard University Department of Medical Research Center, Peking Union Medical College Hospital State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences |
| AuthorAffiliation_xml | – name: Department of Medical Research Center, Peking Union Medical College Hospital – name: Institut Parisien de Chimie Moléculaire – name: CNRS UMR 8232, Sorbonne Université – name: Chinese Academy of Sciences – name: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences – name: Chinese Academy of Medical Sciences and Peking Union Medical College – name: Harvard University – name: Wyss Institute for Biologically Inspired Engineering – name: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany |
| Author_xml | – sequence: 1 givenname: Yingying surname: Chen fullname: Chen, Yingying organization: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences – sequence: 2 givenname: Xinchen surname: Wang fullname: Wang, Xinchen organization: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences – sequence: 3 givenname: Yinbiao surname: Zhu fullname: Zhu, Yinbiao organization: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences – sequence: 4 givenname: Longlong surname: Si fullname: Si, Longlong organization: Harvard University – sequence: 5 givenname: Bo surname: Zhang fullname: Zhang, Bo organization: Chinese Academy of Medical Sciences and Peking Union Medical College – sequence: 6 givenname: Yongmin surname: Zhang fullname: Zhang, Yongmin organization: CNRS UMR 8232, Sorbonne Université – sequence: 7 givenname: Lihe surname: Zhang fullname: Zhang, Lihe organization: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences – sequence: 8 givenname: Demin surname: Zhou fullname: Zhou, Demin organization: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences – sequence: 9 givenname: Sulong orcidid: 0000-0002-6852-9504 surname: Xiao fullname: Xiao, Sulong email: slxiao@bjmu.edu.cn organization: Chinese Academy of Sciences |
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| SubjectTerms | A549 Cells Animals Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Antiviral Agents - therapeutic use Biochemistry, Molecular Biology Cyclodextrins - chemistry Dogs Hemagglutinins - chemistry Hemagglutinins - metabolism Humans Influenza A Virus, H1N1 Subtype - drug effects Influenza A Virus, H1N1 Subtype - metabolism Influenza A Virus, H1N1 Subtype - pathogenicity Influenza, Human - drug therapy Inhibitory Concentration 50 Life Sciences Madin Darby Canine Kidney Cells Mass Spectrometry Pentacyclic Triterpenes - chemistry Protein Binding Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology Triazoles - therapeutic use Virus Internalization - drug effects |
| Title | Synthesis of a Hexavalent Betulinic Acid Derivative as a Hemagglutinin-Targeted Influenza Virus Entry Inhibitor |
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