Peptide-Boronic Acid Inhibitors of Flaviviral Proteases: Medicinal Chemistry and Structural Biology

Christoph Nitsche, Linlin Zhang, Lena F. Weigel, Jonas Schilz, Dominik Graf, Ralf Bartenschlager, Rolf Hilgenfeld, Christian D. Klein*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

110 Citations (Scopus)

Abstract

A thousand-fold affinity gain is achieved by introduction of a C-terminal boronic acid moiety into dipeptidic inhibitors of the Zika, West Nile, and dengue virus proteases. The resulting compounds have Ki values in the two-digit nanomolar range, are not cytotoxic, and inhibit virus replication. Structure-activity relationships and a high resolution X-ray cocrystal structure with West Nile virus protease provide a basis for the design of optimized covalent-reversible inhibitors aimed at emerging flaviviral pathogens.

Original languageEnglish
Pages (from-to)511-516
Number of pages6
JournalJournal of Medicinal Chemistry
Volume60
Issue number1
DOIs
Publication statusPublished - 12 Jan 2017
Externally publishedYes

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