Advanced search
Publication Cover
Journal of Enzyme Inhibition and Medicinal Chemistry Volume 35, 2020 - Issue 1
Submit an article Journal homepage
1,439
Views
14
CrossRef citations to date
0
Altmetric
Research Paper

Synthesis, in vitro inhibitory activity, kinetic study and molecular docking of novel N-alkyl–deoxynojirimycin derivatives as potential α-glucosidase inhibitors

Ping Lina Jiangxi Key Laboratory of Natural Products and Functional Foods, Jiangxi Agricultural University, Nanchang, ChinaView further author information
,
Jia-Cheng Zenga Jiangxi Key Laboratory of Natural Products and Functional Foods, Jiangxi Agricultural University, Nanchang, ChinaView further author information
,
Ji-Guang Chena Jiangxi Key Laboratory of Natural Products and Functional Foods, Jiangxi Agricultural University, Nanchang, ChinaView further author information
,
Xu-Liang Nieb College of Science, Jiangxi Agricultural University, Nanchang, ChinaView further author information
,
En Yuanc College of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang, ChinaView further author information
,
Xiao-Qiang Wangd State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin, ChinaView further author information
,
Da-Yong Pengb College of Science, Jiangxi Agricultural University, Nanchang, ChinaCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0003-2527-8714View further author information
ORCID Icon &
Zhong-Ping Yina Jiangxi Key Laboratory of Natural Products and Functional Foods, Jiangxi Agricultural University, Nanchang, ChinaCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-8802-4343View further author information
ORCID Icon show all
Pages 1879-1890 | Received 21 Nov 2019, Accepted 16 Sep 2020, Published online: 01 Oct 2020

References

  • Hirsh AJ, Yao SYM, Young JD, Cheeseman CI. Inhibition of glucose absorption in the rat jejunum: a novel action of alpha-D-glucosidase inhibitors. Gastroenterology 1997;113:205–11.
  • Ross SA, Gulve EA, Wang M. Chemistry and biochemistry of type 2 diabetes. Chem Rev 2004;104:1255–82.
  • Borges de Melo E, da Silveira Gomes A, Carvalho I. α- and β-Glucosidase inhibitors: chemical structure and biological activity. Tetrahedron 2006;62:10277–302.
  • Mehta A, Zitzmann N, Rudd PM, et al. Alpha-glucosidase inhibitors as potential broad based anti-viral agents . FEBS Letters 1998;430:17–22.
  • Clercq D. Erik Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J Med Chem 1995;38:2491–517.
  • Meneilly GS, Ryan EA, Radziuk J, et al. Effect of acarbose on insulin sensitivity in elderly patients with diabetes. Diabetes Care 2000;23:1162–7.
  • Liu Z, Ma S. Recent advances in synthetic α-glucosidase inhibitors. ChemMedChem 2017;12:819–29.
  • Compain P, Martin OR. Iminosugars: from synthesis to therapeutic applications. Chichester (UK): John Wiley and Sons; 2007.
  • Yagi M, Kouno T, Aoyagi Y, Murai H. The structure of moraoline, a piperidine alkaloid from Morus species. Nippon Nogeik Kaishi 1976;50:571–2.
  • Hatano A, Kanno Y, Kondo Y, et al. Use of a deoxynojirimycin-fluorophore conjugate as a cell-specific imaging probe targeting α-glucosidase on cell membranes. Bioorg Med Chem 2019;27:859–64.
  • Nishimura Y. Gem-diamine 1-N-iminosugars and related iminosugars, candidate of therapeutic agents for tumor metastasis. Curr Top Med Chem 2003;3:575–91.
  • Papandreou M-J. The alpha-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step. Mol Pharm 2001;61:186–93.
  • Wu H, Zeng W, Chen L, et al. Integrated multi-spectroscopic and molecular docking techniques to probe the interaction mechanism between maltase and 1-deoxynojirimycin, an α-glucosidase inhibitor. Int J Biol Macromol 2018;114:1194–202.
  • Butters TD, van den Broek LAGM, Fleet GWJ, et al. Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis. Tetrahedron Asymmetry 2000;11:113–24.
  • Nakagawa K, Kubota H, Kimura T, et al. Occurrence of orally administered mulberry 1-deoxynojirimycin in rat plasma. J Agric Food Chem 2007;55:8928–33.
  • Faber ED, Oosting R, Neefjes JJ, et al. Distribution and elimination of the glycosidase inhibitors 1-deoxymannojirimycin and N-methyl-1-deoxynojirimycin in the rat in vivo. Pharm Res-Dordr 1992;9:1442–50.
  • Ardes-Guisot N, Alonzi DS, Reinkensmeier G, et al. Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain. Org Biomol Chem 2011;9:5373–88.
  • Rawlings AJ, Lomas H, Pilling AW, et al. Synthesis and biological characterisation of novel N-alkyl-deoxynojirimycin alpha-glucosidase inhibitors. Chembiochem 2009;10:1101–5.
  • Zhang Y, Gao H, Liu R, et al. Quinazoline-1-deoxynojirimycin hybrids as high active dual inhibitors of EGFR and α-glucosidase. Bioorg Med Chem Lett 2017;27:4309–13.
  • Lesur B, Ducep JB, Lalloz MN, et al. New deoxynojirimycin derivatives as potent inhibitors of intestinal α-glucohydrolases. Cheminform 2010;28:355–60.
  • Trott O, Olson AJ. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61.
  • Andrew W, Martino B, Stefan B, et al. SWISS-MODEL: homology modelling of protein structures and complexes. Nucleic Acids Res 2018;46:W296–303.
  • Zeng F, Yin Z, Chen J, et al. Design, synthesis, and activity evaluation of novel N-benzyl deoxynojirimycin derivatives for use as α-glucosidase inhibitors. Molecules 2019;24:3309.
  • Shahzad D, Saeed A, Larik FA, et al. Novel C-2 symmetric molecules as α-glucosidase and α-amylase inhibitors: design, synthesis, kinetic evaluation, molecular docking and pharmacokinetics. Molecules 2019;24:1511–27.
  • Kiefer F, Arnold K, Künzli M, et al. The SWISS-MODEL Repository and associated resources. Nucleic Acids Res 2009;37:D387–92.
  • Wang G, Peng Z, Wang J, et al. Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors. Eur J Med Chem 2017;125:423–9.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.