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Articles

Exploring substituent diversity of deoxynojirimycin–triazole hybrid iminosugars: Discovery of potent glucosidase inhibitors

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Pages 415-436 | Received 25 Aug 2020, Accepted 11 Oct 2020, Published online: 23 Oct 2020

References

  • Kitabchi, A. E.; Umpierrez, G. E.; Miles, J. M.; Fisher, J. N. Hyperglycemic crises in adult patients with diabetes. Diabetes Care. 2009, 32(7), 1335–1343. doi:10.2337/dc09-1431.
  • Hati, S.; Madurkar, S. M.; Bathula, C.; Thulluri, C.; Agarwal, R.; Siddiqui, F. A.; Dangi, P.; Adepally, U.; Singh, A.; Singh, S.; et al. Design, synthesis and biological evaluation of small molecules as potent glucosidase inhibitors. Eur. J. Med. Chem. 2015, 100, 188–196. doi:10.1016/j.ejmech.2015.04.059.
  • Borges de Melo, E.; da Silveira Gomes, A.; Carvalho, I. α- and β-Glucosidase inhibitors: Chemical structure and biological activity. Tetrahedron 2006, 62(44), 10277–10302. doi:10.1016/j.tet.2006.08.055.
  • Yoshikuni, Y. Inhibition of intestinal α-glucosidase activity and postprandial hyperglycemia by moranoline and its N-alkyl derivatives. Agric. Biol. Chem. 1988, 52(1), 121–128. doi:10.1080/00021369.1988.10868611.
  • Sugimoto, S.; Nakajima, H.; Kosaka, K.; Hosoi, H. Review: Miglitol has potential as a therapeutic drug against obesity. Nutr. Metab. 2015, 12(1), 51. doi:10.1186/s12986-015-0048-8.
  • Segal, P.; Feig, P.; Schernthaner, G.; Ratzmann, K.; Rybka, J.; Petzinna, D.; Berlin, C. The efficacy and safety of miglitol therapy compared with glibenclamide in patients with NIDDM inadequately controlled by diet alone. Diabetes Care. 1997, 20(5), 687–691. doi:10.2337/diacare.20.5.687.
  • Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents. J. Med. Chem. 1986, 29(6), 1038–1046. doi:10.1021/jm00156a023.
  • Meneilly, G. S.; Ryan, E. A.; Radziuk, J.; Lau, D. C.; Yale, J. F.; Morais, J.; Chiasson, J. L.; Rabasa-Lhoret, R.; Maheux, P.; Tessier, D.; et al. Effect of acarbose on insulin sensitivity in elderly patients with diabetes. Diabetes Care 2000, 23(8), 1162–1167. doi:10.2337/diacare.23.8.1162.
  • Kimura, T.; Nakagawa, K.; Kubota, H.; Kojima, Y.; Goto, Y.; Yamagishi, K.; Oita, S.; Oikawa, S.; Miyazawa, T. Food-grade mulberry powder enriched with 1-deoxynojirimycin suppresses the elevation of postprandial blood glucose in humans. J. Agric. Food Chem. 2007, 55(14), 5869–5874. doi:10.1021/jf062680g.
  • Kim, G.-N.; Kwon, Y.-I.; Jang, H.-D. Mulberry leaf extract reduces postprandial hyperglycemia with few side effects by inhibiting α-glucosidase in normal rats. J. Med. Food. 2011, 14(7–8), 712–717. doi:10.1089/jmf.2010.1368.
  • Hanefeld, M.; Fischer, S.; Schulze, J.; Spengler, M.; Wargenau, M.; Schollberg, K.; Fücker, K. Therapeutic potentials of acarbose as first-line drug in NIDDM insufficiently treated with diet alone. Diabetes Care. 1991, 14(8), 732–737. doi:10.2337/diacare.14.8.732.
  • Bols, M.; López, Ó.; Ortega-Caballero, F. 1.21 - Glycosidase inhibitors: Structure, activity, synthesis, and medical relevance. In Comprehensive Glycoscience; Kamerling, H., Ed. Elsevier: Oxford, UK, 2007, pp 815–884.
  • Ardes-Guisot, N.; Alonzi, D. S.; Reinkensmeier, G.; Butters, T. D.; Norez, C.; Becq, F.; Shimada, Y.; Nakagawa, S.; Kato, A.; Blériot, Y.; et al. Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain. Org. Biomol. Chem. 2011, 9(15), 5373–5388. doi:10.1039/c1ob05119a.
  • Wennekes, T.; Lang, B.; Leeman, M.; Marel, G.; Smits, E.; Weber, M.; van Wiltenburg, J.; Wolberg, M.; Aerts, J.; Overkleeft, H. Large-scale synthesis of the glucosylceramide synthase inhibitor N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin. Org. Process Res. Dev. 2008, 12(3), 414–423. doi:10.1021/op700295x.
  • Garlapati, R.; Pottabathini, N.; Gurram, V.; Kasani, K. S.; Gundla, R.; Thulluri, C.; Machiraju, P. K.; Chaudhary, A. B.; Addepally, U.; Dayam, R.; et al. Development of α-glucosidase inhibitors by room temperature C–C cross couplings of quinazolinones. Org. Biomol. Chem. 2013, 11(29), 4778–4791. doi:10.1039/c3ob40636a.
  • Hottin, A.; Wright, D. W.; Davies, G. J.; Behr, J.-B. Exploiting the hydrophobic terrain in fucosidases with aryl-substituted pyrrolidine iminosugars. ChemBioChem 2015, 16(2), 277–283. doi:10.1002/cbic.201402509.
  • Martinez-Bailen, M.; Carmona, A. T.; Patterson-Orazem, A. C.; Lieberman, R. L.; Ide, D.; Kubo, M.; Kato, A.; Robina, I.; Moreno-Vargas, A. J. Exploring substituent diversity on pyrrolidine-aryltriazole iminosugars: Structural basis of β-glucocerebrosidase inhibition. Bioorg. Chem. 2019, 86, 652–664. doi:10.1016/j.bioorg.2019.02.025.
  • Diot, J.; Garcia-Moreno, M. I.; Gouin, S. G.; Ortiz Mellet, C.; Haupt, K.; Kovensky, J. Multivalent iminosugars to modulate affinity and selectivity for glycosidases. Org. Biomol. Chem. 2009, 7(2), 357–363. doi:10.1039/b815408b.
  • Decroocq, C.; Joosten, A.; Sergent, R.; Mena Barragan, T.; Ortiz Mellet, C.; Compain, P. The multivalent effect in glycosidase inhibition: probing the influence of valency, peripheral ligand structure, and topology with cyclodextrin-based iminosugar click clusters. ChemBioChem 2013, 14 (15), 2038–2049. doi:10.1002/cbic.201300283.
  • Tiwari, V. K.; Mishra, B. B.; Mishra, K. B.; Mishra, N.; Singh, A. S.; Chen, X. Cu-catalyzed click reaction in carbohydrate chemistry. Chem. Rev. 2016, 116(5), 3086–3240. doi:10.1021/acs.chemrev.5b00408.
  • Laigre, E.; Hazelard, D.; Casas, J.; Serra-Vinardell, J.; Michelakakis, H.; Mavridou, I.; Aerts, J. M.; Delgado, A.; Compain, P. Investigation of original multivalent iminosugars as pharmacological chaperones for the treatment of Gaucher disease. Carbohydr. Res. 2016, 429, 98–104. doi:10.1016/j.carres.2016.03.007.
  • Diot, J. D.; Moreno, I. G.; Twigg, G.; Mellet, C. O.; Haupt, K.; Butters, T. D.; Kovensky, J.; Gouin, S. G. Amphiphilic 1-deoxynojirimycin derivatives through click strategies for chemical chaperoning in N370S Gaucher cells. J. Org. Chem. 2011, 76(19), 7757–7768. doi:10.1021/jo201125x.
  • Wang, L.; Liang, T.; Fang, Z. Chemical synthesis and preliminary biological evaluation of C-6-O-methyl-1-deoxynojirimycin as a potent α-glucosidase inhibitor. J. Carbohydr. Chem. 2020, 39(1), 36–49. doi:10.1080/07328303.2019.1700995.
  • Wang, W.; Wang, F.; Liang, T.; Fang, Z. Synthesis and preliminary biological evaluation of C-6 deutero DNJ. Chem. Res. Appl. 2017, 29(6), 793–798.
  • Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67(9), 3057–3064. doi:10.1021/jo011148j.
  • Ferhati, X.; Matassini, C.; Fabbrini, M. G.; Goti, A.; Morrone, A.; Cardona, F.; Moreno-Vargas, A. J.; Paoli, P. Dual targeting of PTP1B and glucosidases with new bifunctional iminosugar inhibitors to address type 2 diabetes. Bioorg. Chem. 2019, 87, 534–549. doi:10.1016/j.bioorg.2019.03.053.
  • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew. Chem. Int. Ed. 2002, 41(14), 2596–2599. doi:10.1002/chin.200243045.
  • Figueredo, A. S.; Zamoner, L. O. B.; Rejzek, M.; Field, R. A.; Carvalho, I. Cluster glycosides and heteroglycoclusters presented in alternative arrangements. Tetrahedron Lett. 2018, 59(50), 4405–4409. doi:10.1016/j.tetlet.2018.10.069.
  • Díez-González, S.; Correa, A.; Cavallo, L.; Nolan, S. P. (NHC)Copper(I)-catalyzed [3 + 2] cycloaddition of azides and mono- or disubstituted alkynes. Chemistry 2006, 12(29), 7558–7564. doi:10.1002/chem.200600961.
  • Marra, A.; Vecchi, A.; Chiappe, C.; Melai, B.; Dondoni, A. Validation of the copper(I)-catalyzed azide-alkyne coupling in ionic liquids. Synthesis of a triazole-linked C-disaccharide as a case study. J. Org. Chem. 2008, 73(6), 2458–2461. doi:10.1021/jo7026454.
  • Overkleeft, H. S.; Renkema, G. H.; Neele, J.; Vianello, P.; Hung, I. O.; Strijland, A.; van der Burg, A. M.; Koomen, G. J.; Pandit, U. K.; Aerts, J. M. Generation of specific deoxynojirimycin-type inhibitors of the non-lysosomal glucosylceramidase. J. Biol. Chem. 1998, 273(41), 26522–26527. doi:10.1074/jbc.273.41.26522.
  • Dong, W. L.; Jespersen, T.; Bols, M.; Skrydstrup, T.; Sierks, M. R. Evaluation of isofagomine and its derivatives as potent glycosidase inhibitors. Biochemistry 1996, 35(8), 2788–2795. doi:10.1021/bi9522514.
  • Panday, N.; Canac, Y.; Vasella, A. Very strong inhibition of glucosidases by C(2)-substituted tetrahydroimidazopyridines. Helvetica 2000, 83(1), 58–79. doi:10.1002/chin.200018145.
  • Compain, P.; Decroocq, C.; Iehl, J.; Holler, M.; Hazelard, D.; Mena Barragán, T.; Ortiz Mellet, C.; Nierengarten, J.-F. Glycosidase inhibition with fullerene iminosugar balls: a dramatic multivalent effect. Angew. Chem. Int. Ed. Engl. 2010, 49(33), 5753–5756. doi:10.1002/anie.201002802.

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