Citation: 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. doi: 10.6023/cjoc201908022 shu

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

Corresponding author: Wang Kerang, kerangwang@hbu.edu.cn Li Xiaoliu, lixl@hbu.edu.cn
Received Date: 14 August 2019
Revised Date: 24 September 2019
Available Online: 25 December 2019
Fund Project: the Foundation of Hebei Education Department QN2018310the Natural Science Foundation of Hebei Province B2016201254the National Natural Science Foundation of China 21572044the National Natural Science Foundation of China 21778013Project 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)

Figures(6)

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.
- glycosidase inhibitor,
- self-assembly,
- multivalent,
- 1-deoxynojirimycin
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