Literature DB >> 21250698

Evaluation of quinazoline analogues as glucocerebrosidase inhibitors with chaperone activity.

Juan J Marugan1, Wei Zheng, Omid Motabar, Noel Southall, Ehud Goldin, Wendy Westbroek, Barbara K Stubblefield, Ellen Sidransky, Ronald A Aungst, Wendy A Lea, Anton Simeonov, William Leister, Christopher P Austin.   

Abstract

Gaucher disease is a lysosomal storage disorder (LSD) caused by deficiency in the enzyme glucocerebrosidase (GC). Small molecule chaperones of protein folding and translocation have been proposed as a promising therapeutic approach to this LSD. Most small molecule chaperones described in the literature contain an iminosugar scaffold. Here we present the discovery and evaluation of a new series of GC inhibitors with a quinazoline core. We demonstrate that this series can improve the translocation of GC to the lysosome in patient-derived cells. To optimize this chemical series, systematic synthetic modifications were performed and the SAR was evaluated and compared using three different readouts of compound activity: enzymatic inhibition, enzyme thermostabilization, and lysosomal translocation of GC.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21250698      PMCID: PMC3103057          DOI: 10.1021/jm1008902

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  29 in total

Review 1.  The cell biology of lysosomal storage disorders.

Authors:  Anthony H Futerman; Gerrit van Meer
Journal:  Nat Rev Mol Cell Biol       Date:  2004-07       Impact factor: 94.444

2.  Impaired trafficking of mutants of lysosomal glucocerebrosidase in Gaucher's disease.

Authors:  Martina Schmitz; Marwan Alfalah; Johannes M F G Aerts; Hassan Y Naim; Klaus-Peter Zimmer
Journal:  Int J Biochem Cell Biol       Date:  2005-11       Impact factor: 5.085

3.  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

4.  Thermodynamic stability of carbonic anhydrase: measurements of binding affinity and stoichiometry using ThermoFluor.

Authors:  Daumantas Matulis; James K Kranz; F Raymond Salemme; Matthew J Todd
Journal:  Biochemistry       Date:  2005-04-05       Impact factor: 3.162

5.  Gaucher disease-associated glucocerebrosidases show mutation-dependent chemical chaperoning profiles.

Authors:  Anu R Sawkar; Sara L Adamski-Werner; Wei-Chieh Cheng; Chi-Huey Wong; Ernest Beutler; Klaus-Peter Zimmer; Jeffery W Kelly
Journal:  Chem Biol       Date:  2005-11

6.  Chemical chaperones increase the cellular activity of N370S beta -glucosidase: a therapeutic strategy for Gaucher disease.

Authors:  Anu R Sawkar; Wei-Chieh Cheng; Ernest Beutler; Chi-Huey Wong; William E Balch; Jeffery W Kelly
Journal:  Proc Natl Acad Sci U S A       Date:  2002-11-14       Impact factor: 11.205

Review 7.  Imino sugar inhibitors for treating the lysosomal glycosphingolipidoses.

Authors:  Terry D Butters; Raymond A Dwek; Frances M Platt
Journal:  Glycobiology       Date:  2005-05-18       Impact factor: 4.313

8.  Replacement therapy for inherited enzyme deficiency--macrophage-targeted glucocerebrosidase for Gaucher's disease.

Authors:  N W Barton; R O Brady; J M Dambrosia; A M Di Bisceglie; S H Doppelt; S C Hill; H J Mankin; G J Murray; R I Parker; C E Argoff
Journal:  N Engl J Med       Date:  1991-05-23       Impact factor: 91.245

9.  Improvement in hematological, visceral, and skeletal manifestations of Gaucher disease type 1 with oral eliglustat tartrate (Genz-112638) treatment: 2-year results of a phase 2 study.

Authors:  Elena Lukina; Nora Watman; Elsa Avila Arreguin; Marta Dragosky; Marcelo Iastrebner; Hanna Rosenbaum; Mici Phillips; Gregory M Pastores; Ravi S Kamath; Daniel I Rosenthal; Mathilde Kaper; Tejdip Singh; Ana Cristina Puga; M Judith Peterschmitt
Journal:  Blood       Date:  2010-08-16       Impact factor: 22.113

10.  Characterization of human saposins by NMR spectroscopy.

Authors:  Michael John; Michaela Wendeler; Markus Heller; Konrad Sandhoff; Horst Kessler
Journal:  Biochemistry       Date:  2006-04-25       Impact factor: 3.162

View more
  18 in total

1.  Binding of 3,4,5,6-tetrahydroxyazepanes to the acid-β-glucosidase active site: implications for pharmacological chaperone design for Gaucher disease.

Authors:  Susan D Orwig; Yun Lei Tan; Neil P Grimster; Zhanqian Yu; Evan T Powers; Jeffery W Kelly; Raquel L Lieberman
Journal:  Biochemistry       Date:  2011-11-14       Impact factor: 3.162

2.  Discovery, structure-activity relationship, and biological evaluation of noninhibitory small molecule chaperones of glucocerebrosidase.

Authors:  Samarjit Patnaik; Wei Zheng; Jae H Choi; Omid Motabar; Noel Southall; Wendy Westbroek; Wendy A Lea; Arash Velayati; Ehud Goldin; Ellen Sidransky; William Leister; Juan J Marugan
Journal:  J Med Chem       Date:  2012-06-08       Impact factor: 7.446

3.  Non-iminosugar glucocerebrosidase small molecule chaperones.

Authors:  Juan Jose Marugan; Wenwei Huang; Omid Motabar; Wei Zheng; Jingbo Xiao; Samarjit Patnaik; Noel Southall; Wendy Westbroek; Wendy A Lea; Anton Simeonov; Ehud Goldin; Maria A Debernardi; Ellen Sidransky
Journal:  Medchemcomm       Date:  2011-10-24       Impact factor: 3.597

4.  Chaperone therapy for Krabbe disease: potential for late-onset GALC mutations.

Authors:  Mohammad Arif Hossain; Katsumi Higaki; Seiji Saito; Kazuki Ohno; Hitoshi Sakuraba; Eiji Nanba; Yoshiyuki Suzuki; Keiichi Ozono; Norio Sakai
Journal:  J Hum Genet       Date:  2015-06-25       Impact factor: 3.172

5.  Design and Synthesis of Potent Quinazolines as Selective β-Glucocerebrosidase Modulators.

Authors:  Jianbin Zheng; Long Chen; Michael Schwake; Richard B Silverman; Dimitri Krainc
Journal:  J Med Chem       Date:  2016-09-06       Impact factor: 7.446

6.  β-Glucocerebrosidase Modulators Promote Dimerization of β-Glucocerebrosidase and Reveal an Allosteric Binding Site.

Authors:  Jianbin Zheng; Long Chen; Owen S Skinner; Daniel Ysselstein; Jonathan Remis; Peter Lansbury; Renato Skerlj; Michael Mrosek; Ursula Heunisch; Stephan Krapp; Joel Charrow; Michael Schwake; Neil L Kelleher; Richard B Silverman; Dimitri Krainc
Journal:  J Am Chem Soc       Date:  2018-04-30       Impact factor: 15.419

Review 7.  Progress and potential of non-inhibitory small molecule chaperones for the treatment of Gaucher disease and its implications for Parkinson disease.

Authors:  Olive Jung; Samarjit Patnaik; Juan Marugan; Ellen Sidransky; Wendy Westbroek
Journal:  Expert Rev Proteomics       Date:  2016-04-21       Impact factor: 3.940

8.  Discovery of a novel noniminosugar acid α glucosidase chaperone series.

Authors:  Jingbo Xiao; Wendy Westbroek; Omid Motabar; Wendy A Lea; Xin Hu; Arash Velayati; Wei Zheng; Noel Southall; Ann Marie Gustafson; Ehud Goldin; Ellen Sidransky; Ke Liu; Anton Simeonov; Rafael J Tamargo; Antonia Ribes; Leslie Matalonga; Marc Ferrer; Juan J Marugan
Journal:  J Med Chem       Date:  2012-08-17       Impact factor: 7.446

Review 9.  Recent developments in the use of differential scanning fluorometry in protein and small molecule discovery and characterization.

Authors:  Anton Simeonov
Journal:  Expert Opin Drug Discov       Date:  2013-06-06       Impact factor: 6.098

10.  Organic chemistry. Strain-release amination.

Authors:  Ryan Gianatassio; Justin M Lopchuk; Jie Wang; Chung-Mao Pan; Lara R Malins; Liher Prieto; Thomas A Brandt; Michael R Collins; Gary M Gallego; Neal W Sach; Jillian E Spangler; Huichin Zhu; Jinjiang Zhu; Phil S Baran
Journal:  Science       Date:  2016-01-15       Impact factor: 47.728

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.