Synthesis and Glycosidase Inhibition Activity of an Amphiphilic Fatty-Deoxynojirimycin Derivative

doi:10.6023/cjoc201908022

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3446-3453.DOI: 10.6023/cjoc201908022 Previous Articles Next Articles

脱氧野尻霉素类两亲化合物的合成及其超分子糖苷酶抑制活性研究

李敏^a,b, 刘茂华^a, 王琪^a, 王克让^a, 李小六^a

a 河北大学化学与环境科学学院药物化学与分子诊断教育部重点实验室河北省化学生物学重点实验室河北保定 071002;
b 邢台学院化学与化工学院河北邢台 054001

收稿日期:2019-08-14 修回日期:2019-09-24 发布日期:2019-10-25
通讯作者: 王克让, 李小六 E-mail:kerangwang@hbu.edu.cn;lixl@hbu.edu.cn
基金资助:
国家自然科学基金（Nos.21572044，21778013）、河北省自然科学基金（No.B2016201254）和河北省教育厅研究（No.QN2018310）资助项目.

Synthesis and Glycosidase Inhibition Activity of an Amphiphilic Fatty-Deoxynojirimycin Derivative

Li Min^a,b, Liu Maohua^a, Wang Qi^a, Wang Kerang^a, Li Xiaoliu^a

a Key Laboratory of Medicinal Chemistry and Molecular Diagnosis (Ministry of Education), Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002;
b College of Chemistry and Chemical Engineering, Xingtai University, Xingtai, Hebei 054001

Received:2019-08-14 Revised:2019-09-24 Published:2019-10-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572044, 21778013), the Natural Science Foundation of Hebei Province (No. B2016201254), and the Foundation of Hebei Education Department (No. QN2018310).

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Abstract

An amphiphilic derivative FA-DNJ-C6 with deoxynojirimycin modification was synthesized. The self-assembly behavior of FA-DNJ-C6 was studied by a surface tension test, dynamic light scattering test (DLS) and transmission electron microscopy (TEM). FA-DNJ-C6 formed stable supramolecular self-assembly in aqueous solution. Furthermore, the glycosidase inhibition activities of FA-DNJ-C6 were studied. FA-DNJ-C6 as multivalent glycosidase inhibitor showed potent glycosidase effect against α-mannosidase with K_i value of (0.107±0.021) μmol/L, an increase of approximately 339-fold compared with the control drug of miglitol, which was due to the multivalent binding sites in α-mannosidase.

Key words: glycosidase inhibitor, self-assembly, multivalent, 1-deoxynojirimycin

Cite this article

Li Min, Liu Maohua, Wang Qi, Wang Kerang, Li Xiaoliu. Synthesis and Glycosidase Inhibition Activity of an Amphiphilic Fatty-Deoxynojirimycin Derivative[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3446-3453.

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脱氧野尻霉素类两亲化合物的合成及其超分子糖苷酶抑制活性研究

Synthesis and Glycosidase Inhibition Activity of an Amphiphilic Fatty-Deoxynojirimycin Derivative

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