1,732
Views
14
CrossRef citations to date
0
Altmetric
Research Paper

Design and synthesis of naphthalimide group-bearing thioglycosides as novel β-N-acetylhexosaminidases inhibitors

, , , , &
Pages 445-452 | Received 17 Aug 2017, Accepted 14 Dec 2017, Published online: 02 Feb 2018

References

  • Henrissat B, Daviest G. Structural and sequence-based classification of glycoside hydrolases. Curr Opin Struct Biol 1997;7:637–44.
  • Kong HC, Chen W, Lu HZ, et al. Synthesis of NAG-thiazoline-derived inhibitors for β-N-acetyl-D-hexosaminidases. Carbohyd Res 2015;413:135–44.
  • Hattie M, Cekic N, Aleksandra, et al. Modifying the phenyl group of PUGNAc: reactivity tuning to deliver selective inhibitors for N-acetyl-D-glucosaminidases. Org Biomol Chem 2016;14:3193–7.
  • Liu T, Yan J, Yang Q. Comparative biochemistry of GH3, GH20 and GH84 β-N-acetyl-D-hexosaminidases and recent progress in selective inhibitor discover. Curr Drug Targets 2012;13:512–25.
  • Zhou FX, Huo JW, Liu Y, et al. Elevated glucose levels impair the WNT/b-catenin pathway via the activation of the hexosamine biosynthesis pathway in endometrial cancer. J Steroid Biochem 2016;159:19–25.
  • Shikhman AR, Brinson DC, Lotz M, et al. Profile of glycosaminoglycan-degrading glycosidases and glycoside sulfatases secreted by human articular chondrocytes in homeostasis and inflammation. Arthritis Rheum 2000;43:1307–14.
  • Liu JJ, Shikhman AR, Lotz MK, Wong C-H. Hexosaminidase inhibitors as new drug candidates for the therapy of osteoarthritis. Chem Biol 2001;8:701--11.
  • Mahuran DJ. Biochemical consequences of mutations causing the GM2 gangliosidose. Biochim Biophys Acta 1999;1455:105–38.
  • Tropak MB, Mahuran D. Lending a helping hand, screening chemical libraries for compounds that enhance β-hexosaminidase A activity in GM2 gangliosidosis cells. Febs J 2007;274:4951–61.
  • Tropak MB, Reid SP, Guiral M, et al. Pharmacological enhancement of β-hexosaminidase activity in fibroblasts from adult Tay-Sachs and Sandhoff patients. J Biol Chem 2004;279:13478–87.
  • Arnold CS, Johnson GVW, Cole RN, et al. The microtubule-associated protein tau is extensively modified with O-linked N-acetylglucosamine. J Biol Chem 1996;271:28741–4.
  • Lim S, Haque MM, Nam G, et al. Monitoring of intracellular tau aggregation regulated by OGA/OGT inhibitors. Int J Mol Sci 2015;16:20212--24.
  • Bergeron-Brlek M, Goodwin-Tindall J, Cekic N, et al. A convenient approach to stereoisomeric iminocyclitols: generation of potent brain-permeable OGA inhibitors. Angew Chem Int Ed 2015;54:15429–33.
  • Kim EJ, Perreira M, Craig J, et al. An O-GlcNAcase-specific inhibitor and substrate engineered by the extension of the N-Acetyl moiety. J Am Chem Soc 2006;128:4234–5.
  • Horsch M, Hoesch L, Vasella A, et al. N-Acetylglucosaminono-1,5-lactone oxime and the corresponding (phenylcarbamoyl)oxime. Novel and potent inhibitors of beta-N-acetylglucosaminidase. Eur J Biochem 1991;197:815–8.
  • Aoyama T, Naganawa H, Suda H, et al. The structure of nagstatin, a new inhibitor of N-acetyl-beta-D-glucosaminidase. J Antibiot 1992;45:1557–8.
  • Knapp S, Vocadlo D, Gao ZN, et al. NAG-thiazoline, An N-acetyl-β-hexosaminidase inhibitor that implicates acetamido participation. J Am Chem Soc 1996;18:6804–5.
  • Maegawa GH, Tropak M, Buttner J, et al. Pyrimethamine as a potential pharmacological chaperone for late-onset forms of GM2 gangliosidosis. J Biol Chem 2007;282:9150–61.
  • Ayers BJ, Glawar AFG, Martínez RF, et al. Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitor. J Org Chem 2014;79:3398–409.
  • Crabtree EV, Martínez F, Nakagawa S, et al. Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-Nacetylamino-1,2,4-trideoxy-1,4-iminopentitols. Org Biomol Chem 2014;12:3932–43.
  • Tropak MB, Blanchard JE, Withers SG, et al. High-throughput screening for human lysosomal β-N-acetylhexosaminidase inhibitors acting as pharmacological chaperones. Chem Biol 2007;14:153–64.
  • Guo P, Chen Q, Xu L, et al. Development of unsymmetrical dyads as potent noncarbohydrate-based inhibitors against human β-N-acetyl-D-hexosaminidase. ACS Med Chem Lett 2013;4:527–31.
  • Liu T, Zhou Y, Wang J, et al. A crystal structure-guided rational design switching non-carbohydrate inhibitors’ specificity between two β-GlcNAcase homologs. Sci Rep 2014;4:6188–93.
  • Chen Q, Guo P, Xu L, et al. Exploring unsymmetrical dyads as efficient inhibitors against the insect b-N-acetyl-D-hexosaminidase OfHex2. Biochimie 2014;97:152–62.
  • Liu T, Chen L, Ma Q, et al. Structural insights into chitinolytic enzymes and inhibition mechanisms of selective inhibitors. Curr Drug Targets 2014;20:754–70.
  • Ho CW, Popat SD, Liu TW, et al. Development of GlcNAc-Inspired iminocyclitiols as potent and selective N-acetyl-Hexosaminidase Inhibitors. ACS Chem Biol 2010;5:489–97.
  • Floyd N, Vijayakrishnan B, Koeppe JR, et al. Thiyl glycosylation of olefinic proteins: S-linked glycoconjugate synthesis. Angew Chem Int Ed 2009;48:7789–802.
  • Paul B, Korytnyk W. S-, N-, and O-glycosyl derivatives of 2-acetamido-2-deoxy-D-glucose with hydrophobic aglycons as potential chemotherapeutic agents and N-acetyl-beta- D-glucosaminidase inhibitors. Carbohydr Res 1984;126:27–43.
  • Landeyálvarez MA, Ochoaterán A, Pinaluis G, et al. Novel naphthalimide–aminobenzamide dyads as OFF/ON fluorescent supramolecular receptors in metal ion binding. Supramol Chem 2016;28:892–906.
  • Ramchander J. Synthesis of 3(N(1,3dioxo 1H benzo[de]isoquinolin- 2(3H)-yl)alkyl)-2- (4-substituted) phenylthiazolidine-4- carboxylic acid. Chem Sci Trans 2016;5:163–70.
  • Kong HC, Chen W, Liu T, et al. Synthesis of NAM-thiazoline derivatives as novel O-GlcNAcase inhibitors. Carbohydr. Res 2016;429:54–61.
  • Jain AN. Scoring non-covalent protein–ligand interactions: acontinuous differentiable function tuned to compute binding. J Comput Aided Mol Des 1996;10:427–40.
  • Babu S, Nagarajan SK, Lee SH, et al. Structural characterization of human CRTh2: a combined homology modeling, molecular docking and 3D-QSAR-based in silico approach. Med Chem Res 2016;25:653–71.
  • Li DL, Du SQ, Tan WM, et al. Computational insight into the structure-activity relationship of novel N-substituted phthalimides with gibberellin-like activity. J Mol Model 2015;21:271–80.
  • Roth C, Chan S, Offen WA, et al. Structural and functional insight into human O-GlcNAcase. Nat Chem Bio 2017;13:610–14.
  • Bateman KS, Cherney MM, Mahuran DJ, et al. Crystal structure of β-hexosaminidase B in complex with pyrimethamine, a potential pharmacological chaperone. J Med Chem 2011; 54:1421–9.