Literature DB >> 24735644

Imidazole-derived 2-[N-carbamoylmethyl-alkylamino]acetic acids, substrate-dependent modulators of insulin-degrading enzyme in amyloid-β hydrolysis.

Julie Charton1, Marion Gauriot1, Qing Guo2, Nathalie Hennuyer3, Xavier Marechal1, Julie Dumont1, Malika Hamdane4, Virginie Pottiez1, Valerie Landry1, Olivier Sperandio5, Marion Flipo1, Luc Buee4, Bart Staels3, Florence Leroux1, Wei-Jen Tang2, Benoit Deprez6, Rebecca Deprez-Poulain7.   

Abstract

Insulin degrading enzyme (IDE) is a highly conserved zinc metalloprotease that is involved in the clearance of various physiologically peptides like amyloid-beta and insulin. This enzyme has been involved in the physiopathology of diabetes and Alzheimer's disease. We describe here a series of small molecules discovered by screening. Co-crystallization of the compounds with IDE revealed a binding both at the permanent exosite and at the discontinuous, conformational catalytic site. Preliminary structure-activity relationships are described. Selective inhibition of amyloid-beta degradation over insulin hydrolysis was possible. Neuroblastoma cells treated with the optimized compound display a dose-dependent increase in amyloid-beta levels.
Copyright © 2014 Elsevier Masson SAS. All rights reserved.

Entities:  

Keywords:  Amyloid-beta peptides; Enzymes; Inhibitors; Medicinal chemistry; Structure–activity relationships; X-ray diffraction

Mesh：

Substances：

Year:  2014        PMID： 24735644      PMCID： PMC4128174          DOI： 10.1016/j.ejmech.2014.04.009

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN： 0223-5234            Impact factor:   6.514


  38 in total

1.  Functional human insulin-degrading enzyme can be expressed in bacteria.

Authors:  V Chesneau; M R Rosner
Journal:  Protein Expr Purif       Date:  2000-06       Impact factor: 1.650

2.  Hydroxamates: relationships between structure and plasma stability.

Authors:  Marion Flipo; Julie Charton; Akila Hocine; Sandrine Dassonneville; Benoit Deprez; Rebecca Deprez-Poulain
Journal:  J Med Chem       Date:  2009-11-12       Impact factor: 7.446

3.  Functional relevance of a novel SlyX motif in non-conventional secretion of insulin-degrading enzyme.

Authors:  Konstantin Glebov; Sebastian Schütze; Jochen Walter
Journal:  J Biol Chem       Date:  2011-05-16       Impact factor: 5.157

4.  Insulin-degrading enzyme identified as a candidate diabetes susceptibility gene in GK rats.

Authors:  H Fakhrai-Rad; A Nikoshkov; A Kamel; M Fernström; J R Zierath; S Norgren; H Luthman; J Galli
Journal:  Hum Mol Genet       Date:  2000-09-01       Impact factor: 6.150

5.  Anion activation site of insulin-degrading enzyme.

Authors:  Nicholas Noinaj; Eun Suk Song; Sonia Bhasin; Benjamin J Alper; Walter K Schmidt; Louis B Hersh; David W Rodgers
Journal:  J Biol Chem       Date:  2011-11-02       Impact factor: 5.157

6.  Degradation of insulin-like growth factors I and II by a human insulin degrading enzyme.

Authors:  R A Roth; M L Mesirow; K Yokono; S Baba
Journal:  Endocr Res       Date:  1984       Impact factor: 1.720

7.  Alzheimer's beta-amyloid peptide specifically interacts with and is degraded by insulin degrading enzyme.

Authors:  I V Kurochkin; S Goto
Journal:  FEBS Lett       Date:  1994-05-23       Impact factor: 4.124

8.  Insulin inhibition of the proteasome is dependent on degradation of insulin by insulin-degrading enzyme.

Authors:  R G Bennett; J Fawcett; M C Kruer; W C Duckworth; F G Hamel
Journal:  J Endocrinol       Date:  2003-06       Impact factor: 4.286

9.  Peptidomics approach to elucidate the proteolytic regulation of bioactive peptides.

Authors:  Yun-Gon Kim; Anna Mari Lone; Whitney M Nolte; Alan Saghatelian
Journal:  Proc Natl Acad Sci U S A       Date:  2012-05-14       Impact factor: 11.205

10.  Identification of the allosteric regulatory site of insulysin.

Authors:  Nicholas Noinaj; Sonia K Bhasin; Eun Suk Song; Kirsten E Scoggin; Maria A Juliano; Luiz Juliano; Louis B Hersh; David W Rodgers
Journal:  PLoS One       Date:  2011-06-24       Impact factor: 3.240
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  12 in total

Review 1.  Targeting Insulin-Degrading Enzyme to Treat Type 2 Diabetes Mellitus.

Authors:  Wei-Jen Tang
Journal:  Trends Endocrinol Metab       Date:  2015-12-02       Impact factor: 12.015

2.  Catalytic Mechanism of Amyloid-β Peptide Degradation by Insulin Degrading Enzyme: Insights from Quantum Mechanics and Molecular Mechanics Style Møller-Plesset Second Order Perturbation Theory Calculation.

Authors:  Rui Lai; Wei-Jen Tang; Hui Li
Journal:  J Chem Inf Model       Date:  2018-09-06       Impact factor: 4.956

3.  Crystal Structure and Function of PqqF Protein in the Pyrroloquinoline Quinone Biosynthetic Pathway.

Authors:  Qiaoe Wei; Tingting Ran; Chencui Ma; Jianhua He; Dongqing Xu; Weiwu Wang
Journal:  J Biol Chem       Date:  2016-05-26       Impact factor: 5.157

4.  Structure-activity relationships of imidazole-derived 2-[N-carbamoylmethyl-alkylamino]acetic acids, dual binders of human insulin-degrading enzyme.

Authors:  Julie Charton; Marion Gauriot; Jane Totobenazara; Nathalie Hennuyer; Julie Dumont; Damien Bosc; Xavier Marechal; Jamal Elbakali; Adrien Herledan; Xiaoan Wen; Cyril Ronco; Helene Gras-Masse; Antoine Heninot; Virginie Pottiez; Valerie Landry; Bart Staels; Wenguang G Liang; Florence Leroux; Wei-Jen Tang; Benoit Deprez; Rebecca Deprez-Poulain
Journal:  Eur J Med Chem       Date:  2014-12-04       Impact factor: 6.514

Review 5.  Insulin-Degrading Enzyme, an Under-Estimated Potential Target to Treat Cancer?

Authors:  Laetitia Lesire; Florence Leroux; Rebecca Deprez-Poulain; Benoit Deprez
Journal:  Cells       Date:  2022-04-05       Impact factor: 6.600

6.  Catalytic site inhibition of insulin-degrading enzyme by a small molecule induces glucose intolerance in mice.

Authors:  Rebecca Deprez-Poulain; Nathalie Hennuyer; Damien Bosc; Wenguang G Liang; Emmanuelle Enée; Xavier Marechal; Julie Charton; Jane Totobenazara; Gonzague Berte; Jouda Jahklal; Tristan Verdelet; Julie Dumont; Sandrine Dassonneville; Eloise Woitrain; Marion Gauriot; Charlotte Paquet; Isabelle Duplan; Paul Hermant; François-Xavier Cantrelle; Emmanuel Sevin; Maxime Culot; Valerie Landry; Adrien Herledan; Catherine Piveteau; Guy Lippens; Florence Leroux; Wei-Jen Tang; Peter van Endert; Bart Staels; Benoit Deprez
Journal:  Nat Commun       Date:  2015-09-23       Impact factor: 14.919

7.  Structures of human CCL18, CCL3, and CCL4 reveal molecular determinants for quaternary structures and sensitivity to insulin-degrading enzyme.

Authors:  Wenguang G Liang; Min Ren; Fan Zhao; Wei-Jen Tang
Journal:  J Mol Biol       Date:  2015-01-28       Impact factor: 5.469

8.  Peptidic inhibitors of insulin-degrading enzyme with potential for dermatological applications discovered via phage display.

Authors:  Caitlin N Suire; Sarah Nainar; Michael Fazio; Adam G Kreutzer; Tara Paymozd-Yazdi; Caitlyn L Topper; Caroline R Thompson; Malcolm A Leissring
Journal:  PLoS One       Date:  2018-02-15       Impact factor: 3.240

Review 9.  Target Enzymes Considered for the Treatment of Alzheimer's Disease and Parkinson's Disease.

Authors:  Namdoo Kim; Hyuck Jin Lee
Journal:  Biomed Res Int       Date:  2020-11-09       Impact factor: 3.411

10.  Controllable preparation and performance of bio-based poly(lactic acid-iminodiacetic acid) as sustained-release Pb2+ chelating agent.

Authors:  Jian-Yun Lin; Xi-Ying Cao; Ying Xiao; Jin-Xin Wang; Shi-He Luo; Li-Ting Yang; Yong-Gan Fang; Zhao-Yang Wang
Journal:  iScience       Date:  2021-05-08
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