Potent Inhibition of SARS-CoV-2 nsp14 N7-Methyltransferase by Sulfonamide-Based Bisubstrate Analogues
Potent Inhibition of SARS-CoV-2 nsp14 N7-Methyltransferase by Sulfonamide-Based Bisubstrate Analogues
Enzymes involved in RNA capping of SARS-CoV-2 are essential for the stability of viral RNA, translation of mRNAs, and virus evasion from innate immunity, making them attractive targets for antiviral agents. In this work, we focused on the design and synthesis of nucleoside-derived inhibitors against the SARS-CoV-2 nsp14 (N7-guanine)-methyltransferase (N7-MTase) that catalyzes the transfer of the methyl group from the S-adenosyl-l-methionine (SAM) cofactor to the N7-guanosine cap. Seven compounds out of 39 SAM analogues showed remarkable double-digit nanomolar inhibitory activity against the N7-MTase nsp14. Molecular docking supported the structure-activity relationships of these inhibitors and a bisubstrate-based mechanism of action. The three most potent inhibitors significantly stabilized nsp14 (ΔTm ≈ 11 °C), and the best inhibitor demonstrated high selectivity for nsp14 over human RNA N7-MTase.
S-Adenosylmethionine, Sulfonamides, [CHIM.ANAL] Chemical Sciences/Analytical chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, SARS-CoV-2, [CHIM.THER] Chemical Sciences/Medicinal Chemistry, 610, COVID-19, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Methyltransferases, Viral Nonstructural Proteins, 540, [CHIM.ORGA] Chemical Sciences/Organic chemistry, COVID-19 Drug Treatment, Molecular Docking Simulation, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, [CHIM] Chemical Sciences, Exoribonucleases, [CHIM]Chemical Sciences, Humans, RNA, Viral
S-Adenosylmethionine, Sulfonamides, [CHIM.ANAL] Chemical Sciences/Analytical chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, SARS-CoV-2, [CHIM.THER] Chemical Sciences/Medicinal Chemistry, 610, COVID-19, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Methyltransferases, Viral Nonstructural Proteins, 540, [CHIM.ORGA] Chemical Sciences/Organic chemistry, COVID-19 Drug Treatment, Molecular Docking Simulation, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, [CHIM] Chemical Sciences, Exoribonucleases, [CHIM]Chemical Sciences, Humans, RNA, Viral
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