Abstract
We report the discovery and optimization of a potent inhibitor against the papain-like protease (PLpro) from the coronavirus that causes severe acute respiratory syndrome (SARS-CoV). This unique protease is not only responsible for processing the viral polyprotein into its functional units but is also capable of cleaving ubiquitin and ISG15 conjugates and plays a significant role in helping SARS-CoV evade the human immune system. We screened a structurally diverse library of 50,080 compounds for inhibitors of PLpro and discovered a noncovalent lead inhibitor with an IC(50) value of 20 microM, which was improved to 600 nM via synthetic optimization. The resulting compound, GRL0617, inhibited SARS-CoV viral replication in Vero E6 cells with an EC(50) of 15 microM and had no associated cytotoxicity. The X-ray structure of PLpro in complex with GRL0617 indicates that the compound has a unique mode of inhibition whereby it binds within the S4-S3 subsites of the enzyme and induces a loop closure that shuts down catalysis at the active site. These findings provide proof-of-principle that PLpro is a viable target for development of antivirals directed against SARS-CoV, and that potent noncovalent cysteine protease inhibitors can be developed with specificity directed toward pathogenic deubiquitinating enzymes without inhibiting host DUBs.
MeSH Terms
Antiviral Agents/chemistry,classification,metabolism,pharmacology
Coronavirus 3C Proteases
Crystallography, X-Ray
Cysteine Endopeptidases/chemistry,metabolism
Endopeptidases/chemistry,metabolism
Enzyme Inhibitors/chemistry,classification,metabolism,pharmacology
Models, Molecular
Protein Binding
SARS Virus/drug effects,physiology
Substrate Specificity
Viral Proteins/antagonists & inhibitors,chemistry,metabolism
Virus Replication/drug effects
Chemicals
Antiviral Agents
Enzyme Inhibitors
Viral Proteins
Endopeptidases
Cysteine Endopeptidases
Coronavirus 3C Proteases
ubiquitin isopeptidase
Authors & Affiliations
13 authors, click to expand affiliations / ORCID
Ratia Kiira
Center for Pharmaceutical Biotechnology and Department of Medicinal Chemistry and Pharmacognosy, University of Illinois, Chicago, IL 60607, USA.
Pegan Scott
Takayama Jun
Sleeman Katrina
Coughlin Melissa
Baliji Surendranath
Chaudhuri Rima
Fu Wentao
Prabhakar Bellur S
Johnson Michael E
Baker Susan C
Ghosh Arun K
Mesecar Andrew D
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