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Literature DB >> 27604065

Bicyclic isoureas derived from 1-deoxynojirimycin are potent inhibitors of β-glucocerebrosidase.

Alen Sevšek¹, Maša Čelan, Bibi Erjavec, Linda Quarles van Ufford, Javier Sastre Toraño, Ed E Moret, Roland J Pieters, Nathaniel I Martin.

Abstract

A series of bicyclic isourea derivatives were prepared from 1-deoxynojirimycin using a concise synthetic protocol proceeding via a guanidino intermediate. Inhibition assays with a panel of glycosidases revealed that these deoxynojirimycin-derived bicyclic isoureas display very potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range.

Entities: Chemical Gene Species

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Year: 2016 PMID： 27604065 DOI： 10.1039/c6ob01735e

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

6 in total

1. sp²-Iminosugars targeting human lysosomal β-hexosaminidase as pharmacological chaperone candidates for late-onset Tay-Sachs disease.

Authors: Manuel González-Cuesta; Irene Herrera-González; M Isabel García-Moreno; Roger A Ashmus; David J Vocadlo; José M García Fernández; Eiji Nanba; Katsumi Higaki; Carmen Ortiz Mellet
Journal: J Enzyme Inhib Med Chem Date: 2022-12 Impact factor: 5.756

2. Orthoester functionalized N-guanidino derivatives of 1,5-dideoxy-1,5-imino-d-xylitol as pH-responsive inhibitors of β-glucocerebrosidase.

Authors: Alen Sevšek; Javier Sastre Toraño; Linda Quarles van Ufford; Ed E Moret; Roland J Pieters; Nathaniel I Martin
Journal: Medchemcomm Date: 2017-10-10 Impact factor: 3.597

3. Probing the Inhibitor versus Chaperone Properties of sp²-Iminosugars towards Human β-Glucocerebrosidase: A Picomolar Chaperone for Gaucher Disease.

Authors: Teresa Mena-Barragán; M Isabel García-Moreno; Alen Sevšek; Tetsuya Okazaki; Eiji Nanba; Katsumi Higaki; Nathaniel I Martin; Roland J Pieters; José M García Fernández; Carmen Ortiz Mellet
Journal: Molecules Date: 2018-04-17 Impact factor: 4.411

Bicyclic isoureas derived from 1-deoxynojirimycin are potent inhibitors of β-glucocerebrosidase.

1. sp²-Iminosugars targeting human lysosomal β-hexosaminidase as pharmacological chaperone candidates for late-onset Tay-Sachs disease.

2. Orthoester functionalized N-guanidino derivatives of 1,5-dideoxy-1,5-imino-d-xylitol as pH-responsive inhibitors of β-glucocerebrosidase.

3. Probing the Inhibitor versus Chaperone Properties of sp²-Iminosugars towards Human β-Glucocerebrosidase: A Picomolar Chaperone for Gaucher Disease.

4. Thiol-ene "Click" Synthesis and Pharmacological Evaluation of C-Glycoside sp²-Iminosugar Glycolipids.

5. Synthesis of novel seven-membered carbasugars and evaluation of their glycosidase inhibition potentials.

Review 6. GCase Enhancers: A Potential Therapeutic Option for Gaucher Disease and Other Neurological Disorders.

Bicyclic isoureas derived from 1-deoxynojirimycin are potent inhibitors of β-glucocerebrosidase.

1. sp2-Iminosugars targeting human lysosomal β-hexosaminidase as pharmacological chaperone candidates for late-onset Tay-Sachs disease.

2. Orthoester functionalized N-guanidino derivatives of 1,5-dideoxy-1,5-imino-d-xylitol as pH-responsive inhibitors of β-glucocerebrosidase.

3. Probing the Inhibitor versus Chaperone Properties of sp²-Iminosugars towards Human β-Glucocerebrosidase: A Picomolar Chaperone for Gaucher Disease.

4. Thiol-ene "Click" Synthesis and Pharmacological Evaluation of C-Glycoside sp2-Iminosugar Glycolipids.

5. Synthesis of novel seven-membered carbasugars and evaluation of their glycosidase inhibition potentials.

Review 6. GCase Enhancers: A Potential Therapeutic Option for Gaucher Disease and Other Neurological Disorders.

1. sp²-Iminosugars targeting human lysosomal β-hexosaminidase as pharmacological chaperone candidates for late-onset Tay-Sachs disease.

4. Thiol-ene "Click" Synthesis and Pharmacological Evaluation of C-Glycoside sp²-Iminosugar Glycolipids.