Docking study and biological evaluation of pyrrolidine-based iminosugars as pharmacological chaperones for Gaucher disease

Docking study and biological evaluation of pyrrolidine-based iminosugars as pharmacological chaperones for Gaucher disease

We report on the synthesis and biological evaluation of a series of α-1-C-alkylated 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) derivatives as pharmacological chaperones for Gaucher disease. The parent compound, DAB, did not show inhibition of human β-glucocerebrosidase but showed moderate intestinal α...

書目詳細資料
Main Authors:	Kato, A, Nakagome, I, Sato, K, Yamamoto, A, Adachi, I, Nash, R, Fleet, G, Natori, Y, Watanabe, Y, Imahori, T, Yoshimura, Y, Takahata, H, Hirono, S
格式:	Journal article
語言:	English
出版:	Royal Society of Chemistry 2016

相似書籍

Cystic fibrosis and diabetes: isoLAB and isoDAB, enantiomeric carbon-branched pyrrolidine iminosugars
由: Best, D, et al.
出版: (2010)

Multivalent Pyrrolidine Iminosugars: Synthesis and Biological Relevance
由: Yali Wang, et al.
出版: (2022-08-01)

The L-enantiomers of D-sugar-mimicking iminosugars are noncompetitive inhibitors of D-glycohydrolase?
由: Asano, N, et al.
出版: (2005)

Design of a New α-1-C-Alkyl-DAB Derivative Acting as a Pharmacological Chaperone for β-Glucocerebrosidase Using Ligand Docking and Molecular Dynamics Simulation
由: Izumi Nakagome, et al.
出版: (2018-10-01)

Iminosugars as therapeutic agents: recent advances and promising trends.
由: Nash, R, et al.
出版: (2011)

Isolation and SAR studies of bicyclic iminosugars from Castanospermum australe as glycosidase inhibitors
由: Kato, A, et al.
出版: (2015)

Isolation and SAR studies of bicyclic iminosugars from Castanospermum australe as glycosidase inhibitors.
由: Kato, A, et al.
出版: (2015)

4-C-Me-DAB and 4-C-Me-LAB-enantiomeric alkyl-branched pyrrolidine iminosugars-are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group
由: Cruz, F, et al.
出版: (2010)

Strategy for Designing Selective Lysosomal Acid α-Glucosidase Inhibitors: Binding Orientation and Influence on Selectivity
由: Atsushi Kato, et al.
出版: (2020-06-01)

Looking-glass synergistic pharmacological chaperones: DGJ and L-DGJ from the enantiomers of tagatose.
由: Jenkinson, S, et al.
出版: (2011)

4-C-Me-DAB and 4-C-Me-LAB - enantiomeric alkyl-branched pyrrolidine iminosugars - are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group.
由: da Cruz, F, et al.
出版: (2011)

General synthesis of sugar-derived azepane nitrones: precursors of azepane iminosugars.
由: Zhao, W, et al.
出版: (2013)

Polyhydroxylated pyrrolidine and pyrrolizidine alkaloids from Hyancinthoides non-scripta and Scilla campanulata.
由: Kato, A, et al.
出版: (1999)

Isolation from Stevia rebaudiana of DMDP acetic acid, a novel iminosugar amino acid: synthesis and glycosidase inhibition profile of glycine and β-alanine pyrrolidine amino acids
由: Jenkinson, S, et al.
出版: (2019)

Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars
由: Qian, B, et al.
出版: (2016)

Mechanistic Insights into Dibasic Iminosugars as pH-Selective Pharmacological Chaperones to Stabilize Human α‑Galactosidase
由: Huang-Yi Li, et al.
出版: (2024-02-01)

3-fluoroazetidinecarboxylic acids and trans,trans-3,4-difluoroproline as peptide scaffolds: inhibition of pancreatic cancer cell growth by a fluoroazetidine iminosugar
由: Liu, Z, et al.
出版: (2015)

Potent aminocyclitol glucocerebrosidase inhibitors are subnanomolar pharmacological chaperones for treating gaucher disease.
由: Trapero, A, et al.
出版: (2012)

Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: the search for new therapeutic agents against Gaucher disease
由: Boucheron, C, et al.
出版: (2005)

Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics
由: Marco Marradi, et al.
出版: (2012-06-01)

Iminosugar Amino Acid idoBR1 Reduces Inflammatory Responses in Microglia
由: Olumayokun A. Olajide, et al.
出版: (2022-05-01)

New polyhydroxylated pyrrolidine, piperidine, and pyrrolizidine alkaloids from Scilla sibirica.
由: Yamashita, T, et al.
出版: (2002)

Polyhydroxylated pyrrolidine and piperidine alkaloids from Adenophora triphylla var. japonica (Campanulaceae).
由: Asano, N, et al.
出版: (2000)

Chaperoning glucocerebrosidase: a therapeutic strategy for both Gaucher disease and Parkinsonism
由: Benjamin McMahon, et al.
出版: (2016-01-01)

sp2-Iminosugars targeting human lysosomal β-hexosaminidase as pharmacological chaperone candidates for late-onset Tay-Sachs disease
由: Manuel González-Cuesta, et al.
出版: (2022-12-01)

THE IDENTIFICATION OF A HYDROXYLATED PYRROLIDINE DERIVATIVE FROM CASTANOSPERMUM-AUSTRALE
由: Nash, R, et al.
出版: (1985)

N- and C-alkylation of seven-membered iminosugars generates potent glucocerebrosidase inhibitors and F508del-CFTR correctors.
由: Désiré, J, et al.
出版: (2014)

Synthesis of N-substituted ε-hexonolactams as pharmacological chaperones for the treatment of N370S mutant Gaucher disease.
由: Wang, G, et al.
出版: (2012)

Rational design and synthesis of highly potent pharmacological chaperones for treatment of N370S mutant Gaucher disease.
由: Wang, G, et al.
出版: (2009)

Glycosidase-inhibiting pyrrolidine alkaloids from Hyacinthoides non-scripta
由: Watson, A, et al.
出版: (1997)

SYNTHESIS OF POLYHYDROXYLATED PYRROLIDINES, PIPERIDINES, AND OCTAHYDROINDOLIZINES AS GLYCOSIDASE INHIBITORS
由: Fleet, G
出版: (1989)

Antiviral effects of an iminosugar derivative on flavivirus infections.
由: Wu, S, et al.
出版: (2002)

Small Molecule Chaperones for the Treatment of Gaucher Disease and GBA1-Associated Parkinson Disease
由: Tae-Un Han, et al.
出版: (2020-05-01)

Cellular and biochemical response to chaperone versus substrate reduction therapies in neuropathic Gaucher disease
由: Margarita M. Ivanova, et al.
出版: (2021-01-01)

Iminosugar for treatment of tumors
由: Dwek, R, et al.
出版: (2008)

Amphiphilic 1-deoxynojirimycin derivatives through click strategies for chemical chaperoning in N370S Gaucher cells.
由: Diot, J, et al.
出版: (2011)

Crystal structures of complexes of N-butyl- and N-nonyl-deoxynojirimycin bound to acid beta-glucosidase: insights into the mechanism of chemical chaperone action in Gaucher disease.
由: Brumshtein, B, et al.
出版: (2007)

Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: the search for new therapeutic agents against Gaucher disease (vol 16, pg 1747, 2005)
由: Boucheron, C, et al.
出版: (2005)

Synthesis of iminosugars possessing galactofuranosyl stereochemistry as potential inhibitors of mycobacterial cell wall biosynthesis.
由: Lee, R, et al.
出版: (1998)

Iminosugar idoBR1 Isolated from Cucumber Cucumis sativus Reduces Inflammatory Activity
由: Robert J. Nash, et al.
出版: (2020-06-01)