Literature DB >> 20471633

1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines.

Richard F G Fröhlich1, Richard H Furneaux, Don J Mahuran, Brigitte A Rigat, Arnold E Stütz, Michael B Tropak, Jacqueline Wicki, Stephen G Withers, Tanja M Wrodnigg.   

Abstract

Cyclization by double reductive amination of d-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl-1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of d-glucosidases and could also be shown to distinctly improve, at sub-inhibitory concentrations, the activity of beta-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20471633      PMCID： PMC3201982          DOI： 10.1016/j.carres.2010.04.015

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  10 in total

1.  Rational design and synthesis of highly potent beta-glucocerebrosidase inhibitors.

Authors:  Xiaoxiang Zhu; Kamlesh A Sheth; Shihong Li; Hui-Hwa Chang; Jian-Qiang Fan
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

2.  Isofagomine- and 2,5-anhydro-2,5-imino-D-glucitol-based glucocerebrosidase pharmacological chaperones for Gaucher disease intervention.

Authors:  Zhanqian Yu; Anu R Sawkar; Lisa J Whalen; Chi-Huey Wong; Jeffery W Kelly
Journal:  J Med Chem       Date:  2007-01-11       Impact factor: 7.446

3.  6-Amino-6-deoxy-5,6-di-N-(N'-octyliminomethylidene)nojirimycin: synthesis, biological evaluation, and crystal structure in complex with acid beta-glucosidase.

Authors:  Boris Brumshtein; Matilde Aguilar-Moncayo; M Isabel García-Moreno; Carmen Ortiz Mellet; José M García Fernández; Israel Silman; Yoseph Shaaltiel; David Aviezer; Joel L Sussman; Anthony H Futerman
Journal:  Chembiochem       Date:  2009-06-15       Impact factor: 3.164

4.  Development of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives as selective inhibitors of glucosylceramide metabolism in man.

Authors:  Tom Wennekes; Richard J B H N van den Berg; Wilma Donker; Gijsbert A van der Marel; Anneke Strijland; Johannes M F G Aerts; Herman S Overkleeft
Journal:  J Org Chem       Date:  2007-01-23       Impact factor: 4.354

5.  Glycosidase profiling with immobilised glycosidase-inhibiting iminoalditols--a proof-of-concept study.

Authors:  Andreas J Steiner; Arnold E Stütz; Tanja M Wrodnigg; Chris A Tarling; Stephen G Withers; Albin Hermetter; Hannes Schmidinger
Journal:  Bioorg Med Chem Lett       Date:  2008-02-07       Impact factor: 2.823

6.  Purification by affinity chromatography of glucosidase I, an endoplasmic reticulum hydrolase involved in the processing of asparagine-linked oligosaccharides.

Authors:  H Hettkamp; G Legler; E Bause
Journal:  Eur J Biochem       Date:  1984-07-02

7.  Identification and characterization of ambroxol as an enzyme enhancement agent for Gaucher disease.

Authors:  Gustavo H B Maegawa; Michael B Tropak; Justin D Buttner; Brigitte A Rigat; Maria Fuller; Deepangi Pandit; Liangiie Tang; Gregory J Kornhaber; Yoshitomo Hamuro; Joe T R Clarke; Don J Mahuran
Journal:  J Biol Chem       Date:  2009-07-03       Impact factor: 5.157

Review 8.  Glycosphingolipids--nature, function, and pharmacological modulation.

Authors:  Tom Wennekes; Richard J B H N van den Berg; Rolf G Boot; Gijsbert A van der Marel; Herman S Overkleeft; Johannes M F G Aerts
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Mechanism of Agrobacterium beta-glucosidase: kinetic studies.

Authors:  J B Kempton; S G Withers
Journal:  Biochemistry       Date:  1992-10-20       Impact factor: 3.162

10.  Iminoalditol-amino acid hybrids: synthesis and evaluation as glycosidase inhibitors.

Authors:  Andreas J Steiner; Arnold E Stütz; Chris A Tarling; Stephen G Withers; Tanja M Wrodnigg
Journal:  Carbohydr Res       Date:  2007-03-28       Impact factor: 2.104
  10 in total
  4 in total

Review 1.  Identification and characterization of pharmacological chaperones to correct enzyme deficiencies in lysosomal storage disorders.

Authors:  Kenneth J Valenzano; Richie Khanna; Allan C Powe; Robert Boyd; Gary Lee; John J Flanagan; Elfrida R Benjamin
Journal:  Assay Drug Dev Technol       Date:  2011-06       Impact factor: 1.738

Review 2.  Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2009-2010.

Authors:  David J Harvey
Journal:  Mass Spectrom Rev       Date:  2014-05-26       Impact factor: 10.946

3.  1-Deoxy-D-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines.

Authors:  Richard F G Fröhlich; Richard H Furneaux; Don J Mahuran; Robert Saf; Arnold E Stütz; Michael B Tropak; Jacqueline Wicki; Stephen G Withers; Tanja M Wrodnigg
Journal:  Carbohydr Res       Date:  2011-05-24       Impact factor: 2.104

4.  N-Alkylated Iminosugar Based Ligands: Synthesis and Inhibition of Human Lysosomal β-Glucocerebrosidase.

Authors:  Andreas Wolfsgruber; Martin Thonhofer; Patrick Weber; Seyed A Nasseri; Roland Fischer; Michael Schalli; Arnold E Stütz; Stephen G Withers; Tanja M Wrodnigg
Journal:  Molecules       Date:  2020-10-11       Impact factor: 4.411
  4 in total

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