Inhibition mechanism of SARS-CoV-2 main protease by ebselen and its derivatives.

Amporndanai, Kangsa; Meng, Xiaoli; Shang, Weijuan; Jin, Zhenmig; Rogers, Michael; Zhao, Yao; Rao, Zihe; Liu, Zhi-Jie et al. · Nat Commun · 2021

basic_science · Level V

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Abstract

The SARS-CoV-2 pandemic has triggered global efforts to develop therapeutics. The main protease of SARS-CoV-2 (M<sup>pro</sup>), critical for viral replication, is a key target for therapeutic development. An organoselenium drug called ebselen has been demonstrated to have potent M<sup>pro</sup> inhibition and antiviral activity. We have examined the binding modes of ebselen and its derivative in M<sup>pro</sup> via high resolution co-crystallography and investigated their chemical reactivity via mass spectrometry. Stronger M<sup>pro</sup> inhibition than ebselen and potent ability to rescue infected cells were observed for a number of derivatives. A free selenium atom bound with cysteine of catalytic dyad has been revealed in crystallographic structures of M<sup>pro</sup> with ebselen and MR6-31-2 suggesting hydrolysis of the enzyme bound organoselenium covalent adduct and formation of a phenolic by-product, confirmed by mass spectrometry. The target engagement with selenation mechanism of inhibition suggests wider therapeutic applications of these compounds against SARS-CoV-2 and other zoonotic beta-corona viruses.

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