Literature DB >> 33642842

Discovery of sultam-containing small-molecule disruptors of the huntingtin-calmodulin protein-protein interaction.

Nicholas J Klus1, Khushboo Kapadia2, Peter McDonald3, Anuradha Roy3, Kevin J Frankowski1, Nancy A Muma2, Jeffrey Aubé1.   

Abstract

The aberrant protein-protein interaction between calmodulin and mutant huntingtin protein in Huntington's disease patients has been found to contribute to Huntington's disease progression. A high-throughput screen for small molecules capable of disrupting this interaction revealed a sultam series as potent small-molecule disruptors. Diversification of the sultam scaffold afforded a set of 24 analogs or further evaluation. Several structure-activity trends within the analog set were found, most notably a negligible effect of absolute stereochemistry and a strong beneficial correlation with electron-withdrawing aromatic substituents. The most promising analogs were profiled for off-target effects at relevant kinases and, ultimately, one candidate molecule was evaluated for neuroprotection in a neuronal cell model of Huntington's disease.

Entities:  

Keywords:  High-throughput screening; Huntington’s disease; Neurodegeneration; Structure—activity relationship studies

Year:  2020        PMID: 33642842      PMCID: PMC7906539          DOI: 10.1007/s00044-020-02583-8

Source DB:  PubMed          Journal:  Med Chem Res        ISSN: 1054-2523            Impact factor:   1.965


  24 in total

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Authors:  Lauren E Brown; Ken Chih-Chien Cheng; Wan-Guo Wei; Pingwei Yuan; Peng Dai; Richard Trilles; Feng Ni; Jing Yuan; Ryan MacArthur; Rajarshi Guha; Ronald L Johnson; Xin-zhuan Su; Melissa M Dominguez; John K Snyder; Aaron B Beeler; Scott E Schaus; James Inglese; John A Porco
Journal:  Proc Natl Acad Sci U S A       Date:  2011-04-15       Impact factor: 11.205

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Authors:  E G Puszkin; V Raghuraman
Journal:  J Biol Chem       Date:  1985-12-15       Impact factor: 5.157

3.  Tissue transglutaminase is increased in Huntington's disease brain.

Authors:  M Lesort; W Chun; G V Johnson; R J Ferrante
Journal:  J Neurochem       Date:  1999-11       Impact factor: 5.372

4.  Luminescent oxygen channeling immunoassay: measurement of particle binding kinetics by chemiluminescence.

Authors:  E F Ullman; H Kirakossian; S Singh; Z P Wu; B R Irvin; J S Pease; A C Switchenko; J D Irvine; A Dafforn; C N Skold
Journal:  Proc Natl Acad Sci U S A       Date:  1994-06-07       Impact factor: 11.205

Review 5.  The epsilon-(gamma-glutamyl)lysine crosslink and the catalytic role of transglutaminases.

Authors:  J E Folk; J S Finlayson
Journal:  Adv Protein Chem       Date:  1977

6.  Biology-oriented synthesis of a natural-product inspired oxepane collection yields a small-molecule activator of the Wnt-pathway.

Authors:  Sudipta Basu; Bernhard Ellinger; Stefano Rizzo; Céline Deraeve; Markus Schürmann; Hans Preut; Hans-Dieter Arndt; Herbert Waldmann
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-17       Impact factor: 11.205

7.  Expansion of polyglutamine repeat in huntingtin leads to abnormal protein interactions involving calmodulin.

Authors:  J Bao; A H Sharp; M V Wagster; M Becher; G Schilling; C A Ross; V L Dawson; T M Dawson
Journal:  Proc Natl Acad Sci U S A       Date:  1996-05-14       Impact factor: 11.205

8.  Protective effects of interrupting the binding of calmodulin to mutant huntingtin.

Authors:  Nichole L Dudek; Ying Dai; Nancy A Muma
Journal:  J Neuropathol Exp Neurol       Date:  2008-04       Impact factor: 3.685

9.  Calmodulin regulates transglutaminase 2 cross-linking of huntingtin.

Authors:  Gina M Zainelli; Christopher A Ross; Juan C Troncoso; John K Fitzgerald; Nancy A Muma
Journal:  J Neurosci       Date:  2004-02-25       Impact factor: 6.167

Review 10.  Molecular mechanisms of proteinopathies across neurodegenerative disease: a review.

Authors:  Alexander P Marsh
Journal:  Neurol Res Pract       Date:  2019-09-16
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