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四种五环三萜-唾液酸糖肽缀合物的合成及其与血凝素的亲和力测定。

Synthesis of Four Pentacyclic Triterpene-Sialylglycopeptide Conjugates and Their Affinity Assays with Hemagglutinin.

机构信息

School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.

出版信息

Molecules. 2021 Feb 8;26(4):895. doi: 10.3390/molecules26040895.

DOI:10.3390/molecules26040895
PMID:33567740
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7915185/
Abstract

Influenza outbreaks pose a serious threat to human health. Hemagglutinin (HA) is an important target for influenza virus entry inhibitors. In this study, we synthesized four pentacyclic triterpene conjugates with a sialylglycopeptide scaffold through the Cu(I)-catalyzed alkyne-azide cycloaddition reaction (CuAAC) and prepared affinity assays of these conjugates with two HAs, namely H1N1 (A/WSN/1933) and H5N1 (A/Hong Kong/483/97), respectively. With a dissociation constant () of 6.89 μM, SCT-Asn-betulinic acid exhibited the strongest affinity with the H1N1 protein. Furthermore, with a value of 9.10 μM, SCT-Asn-oleanolic acid exhibited the strongest affinity with the H5N1 protein. The conjugates considerably enhanced antiviral activity, which indicates that pentacyclic triterpenes can be used as a ligand to improve the anti-influenza ability of the sialylglycopeptide molecule by acting on the HA protein.

摘要

流感爆发对人类健康构成严重威胁。血凝素 (HA) 是流感病毒进入抑制剂的重要靶标。在这项研究中，我们通过铜 (I) 催化的炔烃-叠氮化物环加成反应 (CuAAC) 合成了四个具有唾液酸糖肽支架的五环三萜缀合物，并分别用两种 HA（即 H1N1（A/WSN/1933）和 H5N1（A/Hong Kong/483/97））制备了这些缀合物的亲和测定。具有解离常数 (Kd) 为 6.89 μM，SCT-Asn-齐墩果酸表现出与 H1N1 蛋白最强的亲和力。此外，SCT-Asn-熊果酸与 H5N1 蛋白的亲和力最强， 值为 9.10 μM。缀合物大大增强了抗病毒活性，表明五环三萜可以作为配体通过作用于 HA 蛋白来提高唾液酸糖肽分子的抗流感能力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/fc790bca1d00/molecules-26-00895-g002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/12283227d9b0/molecules-26-00895-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/2875073bd8bf/molecules-26-00895-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/d7e9d2bc9e8c/molecules-26-00895-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/2f50b6f00559/molecules-26-00895-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/fc790bca1d00/molecules-26-00895-g002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/12283227d9b0/molecules-26-00895-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/2875073bd8bf/molecules-26-00895-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/d7e9d2bc9e8c/molecules-26-00895-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/2f50b6f00559/molecules-26-00895-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10c2/7915185/fc790bca1d00/molecules-26-00895-g002a.jpg

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