Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids

Adams, Julian; Behnke, Mark; Chen, Shaowu; Cruickshank, Amy A.; Dick, Lawrence R.; Grenier, Louis; Klunder, Janice M.; Ma, Yu-Ting; Plamondon, Louis; Stein, Ross L.

doi:10.1016/s0960-894x(98)00029-8

Cited by 698Ubiquitin and proteasome pathwaysProtease and Inhibitor MechanismsProtein Degradation and Inhibitors

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Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids

Adams, Julian, Behnke, Mark, Chen, Shaowu, Cruickshank, Amy A., Dick, Lawrence R., Grenier, Louis, Klunder, Janice M., Ma, Yu-Ting, Plamondon, Louis, Stein, Ross L.·1998·Bioorganic & Medicinal Chemistry Letters

DOI 10.1016/s0960-894x(98)00029-8

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Abstract

Potent and selective dipeptidyl boronic acid proteasome inhibitors are described. As compared to peptidyl aldehyde compounds, boronic acids in this series display dramatically enhanced potency. Compounds such as 15 are promising new therapeutics for treatment of cancer and inflammatory diseases.

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Replacing an aldehyde electrophile with a boronic acid substantially increased proteasome inhibition potency.
“Exchange of the aldehyde electrophile for a boronic acid substantially increased the potency of proteasome inhibition121.”
From Advances in covalent drug discovery (2022) · cites this paper as [121]

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ChemInform Abstract: Potent and Selective Inhibitors of the Proteasome: Dipeptidyl Boronic Acids.
Adams, J., Behnke, M. L., CHEN, S., Cruickshank, A., Dick, L. R., Grenier, L., Klunder, J. M., MA, Y. ‐., Plamondon, L., & Stein, R. L. (1998) · ChemInform · doi:10.1002/chin.199821191 · Cited by 1
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Synthesis, in Vitro and in Vivo Biological Evaluation, and Comprehensive Understanding of Structure−Activity Relationships of Dipeptidyl Boronic Acid Proteasome Inhibitors Constructed from β-Amino Acids
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Authors: Adams, J., Behnke, M., Chen, S., Cruickshank, A. A., Dick, L. R., Grenier, L., Klunder, J. M., Ma, Y.-T., Plamondon, L., & Stein, R. L.
ORCID: Adams, Julian
Dick, Lawrence R.
Stein, Ross L.
Venue: Bioorganic & Medicinal Chemistry Letters
Publisher: Elsevier BV
Published: 1998-02
Volume: 8
Issue: 4
Pages: 333-338
ISSN: 0960-894X (ISSN-L)
DOI: 10.1016/s0960-894x(98)00029-8
OpenAlex: W1992978957
Cited by: 685
References: 20
Citations by year: 2026: 7 · 2025: 9 · 2024: 15 · 2023: 12 · 2022: 15 · 2021: 32 · 2020: 20 · 2019: 23 · 2018: 25 · 2017: 17 · 2016: 25 · 2015: 21 · 2014: 42 · 2013: 25 · 2012: 39
FWCI: 5.01
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: Bioorganic & Medicinal Chemistry Letters (publishedVersion)
PubMed (publishedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Ubiquitin and proteasome pathways
Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Protease and Inhibitor Mechanisms
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein Degradation and Inhibitors
Keywords: proteasome inhibitors, boronic acid, selective inhibitors, cancer therapeutics, inflammatory diseases
MeSH terms: Boronic Acids, Cysteine Endopeptidases, Multienzyme Complexes, Protease Inhibitors, Molecular Structure, Proteasome Endopeptidase Complex

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Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids

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