Description
1-Deoxynojirimycin (1-DNJ) is an iminosugar that has been found in
M. alba (mulberry) leaves and has diverse biological activities. It inhibits the activities of α- and β-glucosidase (IC
50s = 35 and 71 μM, respectively). 1-DNJ (5 mM) reduces the formation of N-linked complex oligosaccharides in IEC-6 cells. It inhibits HIV-1 envelope-mediated membrane fusion in CEM cells when used at a concentration of 2 mM. 1-DNJ (1-100 μg/ml) reduces the invasion and migration of B16/F10 mouse melanoma cells. It improves glucose and insulin tolerance in
db/db mice when administered intravenously at doses ranging from 20 to 80 mg/kg per day for four weeks.
General Description
Specific glucosidase inhibitor, including trimming glucosidases I and II, that sequentially removes the three glucose residues from precursor Glc
3Man
9GlcNAc
2 in N-linked glycan biosynthesis.
References
[1] KUO GAO. 1-Deoxynojirimycin: Occurrence, Extraction, Chemistry, Oral Pharmacokinetics, Biological Activities and In Silico Target Fishing.[J]. Molecules, 2016, 21 1. DOI:
10.3390/molecules21111600[2] ANA I AHUJA-CASARíN. Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors.[J]. Journal of Enzyme Inhibition and Medicinal Chemistry, 2021: 138-146. DOI:
10.1080/14756366.2020.1847101[3] JULIAN A. CODELLI. Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry[J]. Journal of the American Chemical Society, 2008, 130 34: 11486-11493. DOI:
10.1021/ja803086r[4] MARIE-JEANNE PAPANDRéOU. The alpha-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step.[J]. Molecular Pharmacology, 2002, 61 1 1: 186-193. DOI:
10.1124/mol.61.1.186[5] RAN-JUH WANG Miao L H Chun Hung Yang. 1-Deoxynojirimycin Inhibits Metastasis of B16F10 Melanoma Cells by Attenuating the Activity and Expression of Matrix Metalloproteinases-2 and -9 and Altering Cell Surface Glycosylation[J]. Journal of Agricultural and Food Chemistry, 2010, 58 16: 8988-8993. DOI:
10.1021/jf101401b[6] QINGPU LIU. 1-Deoxynojirimycin Alleviates Insulin Resistance via Activation of Insulin Signaling PI3K/AKT Pathway in Skeletal Muscle of db/db Mice.[J]. Molecules, 2015, 20 1: 21700-21714. DOI:
10.3390/molecules201219794
