Literature DB >> 33054210

Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19.

Robert L Hoffman1, Robert S Kania1, Mary A Brothers1, Jay F Davies1, Rose A Ferre1, Ketan S Gajiwala1, Mingying He1, Robert J Hogan2, Kirk Kozminski1, Lilian Y Li1, Jonathan W Lockner1, Jihong Lou1, Michelle T Marra1, Lennert J Mitchell1, Brion W Murray1, James A Nieman1, Stephen Noell1, Simon P Planken1, Thomas Rowe2, Kevin Ryan1, George J Smith1, James E Solowiej1, Claire M Steppan1, Barbara Taggart2.   

Abstract

The novel coronavirus disease n class="Disease">COVID-19 that emerged in 2019 is caused by the virus SARS CoV-2 and named for its close genetic similarity to SARS CoV-1 that caused severe acute respiratory syndrome (SARS) in 2002. Both SARS coronavirus genomes encode two overlapping large polyproteins, which are cleaved at specific sites by a 3C-like cysteine protease (3CLpro) in a post-translational processing step that is critical for coronavirus replication. The 3CLpro sequences for CoV-1 and CoV-2 viruses are 100% identical in the catalytic domain that carries out protein cleavage. A research effort that focused on the discovery of reversible and irreversible ketone-based inhibitors of SARS CoV-1 3CLpro employing ligand-protease structures solved by X-ray crystallography led to the identification of 3 and 4. Preclinical experiments reveal 4 (PF-00835231) as a potent inhibitor of CoV-2 3CLpro with suitable pharmaceutical properties to warrant further development as an intravenous treatment for COVID-19.

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Year:  2020        PMID: 33054210      PMCID: PMC7571312          DOI: 10.1021/acs.jmedchem.0c01063

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  37 in total

1.  Crystal structures of reversible ketone-Based inhibitors of the cysteine protease cruzain.

Authors:  Lily Huang; Linda S Brinen; Jonathan A Ellman
Journal:  Bioorg Med Chem       Date:  2003-01-02       Impact factor: 3.641

2.  Solid-phase synthesis of a combinatorial array of 1,3-bis(acylamino)-2-butanones, inhibitors of the cysteine proteases cathepsins K and L.

Authors:  D S Yamashita; X Dong; H J Oh; C S Brook; T A Tomaszek; L Szewczuk; D G Tew; D F Veber
Journal:  J Comb Chem       Date:  1999 May-Jun

3.  In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease.

Authors:  A K Patick; S L Binford; M A Brothers; R L Jackson; C E Ford; M D Diem; F Maldonado; P S Dragovich; R Zhou; T J Prins; S A Fuhrman; J W Meador; L S Zalman; D A Matthews; S T Worland
Journal:  Antimicrob Agents Chemother       Date:  1999-10       Impact factor: 5.191

4.  A catalytic mechanism for caspase-1 and for bimodal inhibition of caspase-1 by activated aspartic ketones.

Authors:  K D Brady; D A Giegel; C Grinnell; E Lunney; R V Talanian; W Wong; N Walker
Journal:  Bioorg Med Chem       Date:  1999-04       Impact factor: 3.641

5.  P1 aspartate-based peptide alpha-((2,6-dichlorobenzoyl)oxy)methyl ketones as potent time-dependent inhibitors of interleukin-1 beta-converting enzyme.

Authors:  R E Dolle; D Hoyer; C V Prasad; S J Schmidt; C T Helaszek; R E Miller; M A Ator
Journal:  J Med Chem       Date:  1994-03-04       Impact factor: 7.446

6.  Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements.

Authors:  P S Dragovich; T J Prins; R Zhou; S E Webber; J T Marakovits; S A Fuhrman; A K Patick; D A Matthews; C A Lee; C E Ford; B J Burke; P A Rejto; T F Hendrickson; T Tuntland; E L Brown; J W Meador; R A Ferre; J E Harr; M B Kosa; S T Worland
Journal:  J Med Chem       Date:  1999-04-08       Impact factor: 7.446

7.  Peptidyl (acyloxy)methyl ketones and the quiescent affinity label concept: the departing group as a variable structural element in the design of inactivators of cysteine proteinases.

Authors:  A Krantz; L J Copp; P J Coles; R A Smith; S B Heard
Journal:  Biochemistry       Date:  1991-05-14       Impact factor: 3.162

8.  Synthesis and evaluation of tripeptidyl alpha-ketoamides as human rhinovirus 3C protease inhibitors.

Authors:  Shu-Hui Chen; Jason Lamar; Frantz Victor; Nancy Snyder; Robert Johnson; Beverly A Heinz; Mark Wakulchik; Q May Wang
Journal:  Bioorg Med Chem Lett       Date:  2003-10-20       Impact factor: 2.823

9.  Coronavirus main proteinase (3CLpro) structure: basis for design of anti-SARS drugs.

Authors:  Kanchan Anand; John Ziebuhr; Parvesh Wadhwani; Jeroen R Mesters; Rolf Hilgenfeld
Journal:  Science       Date:  2003-05-13       Impact factor: 47.728

10.  Tripeptide aldehyde inhibitors of human rhinovirus 3C protease: design, synthesis, biological evaluation, and cocrystal structure solution of P1 glutamine isosteric replacements.

Authors:  S E Webber; K Okano; T L Little; S H Reich; Y Xin; S A Fuhrman; D A Matthews; R A Love; T F Hendrickson; A K Patick; J W Meador; R A Ferre; E L Brown; C E Ford; S L Binford; S T Worland
Journal:  J Med Chem       Date:  1998-07-16       Impact factor: 7.446

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  106 in total

1.  The race for antiviral drugs to beat COVID - and the next pandemic.

Authors:  Elie Dolgin
Journal:  Nature       Date:  2021-04       Impact factor: 49.962

Review 2.  Inhibition of the main protease of SARS-CoV-2 (Mpro) by repurposing/designing drug-like substances and utilizing nature's toolbox of bioactive compounds.

Authors:  Io Antonopoulou; Eleftheria Sapountzaki; Ulrika Rova; Paul Christakopoulos
Journal:  Comput Struct Biotechnol J       Date:  2022-03-14       Impact factor: 7.271

3.  Diastereomeric Resolution Yields Highly Potent Inhibitor of SARS-CoV-2 Main Protease.

Authors:  Mark S Cooper; Linlin Zhang; Mohamed Ibrahim; Kaixuan Zhang; Xinyuanyuan Sun; Judith Röske; Matthias Göhl; Mark Brönstrup; Justin K Cowell; Lucie Sauerhering; Stephan Becker; Laura Vangeel; Dirk Jochmans; Johan Neyts; Katharina Rox; Graham P Marsh; Hannah J Maple; Rolf Hilgenfeld
Journal:  J Med Chem       Date:  2022-09-30       Impact factor: 8.039

Review 4.  A review of the latest research on Mpro targeting SARS-COV inhibitors.

Authors:  Huihui Yang; Jinfei Yang
Journal:  RSC Med Chem       Date:  2021-04-14

Review 5.  Improved SARS-CoV-2 Mpro inhibitors based on feline antiviral drug GC376: Structural enhancements, increased solubility, and micellar studies.

Authors:  Wayne Vuong; Conrad Fischer; Muhammad Bashir Khan; Marco J van Belkum; Tess Lamer; Kurtis D Willoughby; Jimmy Lu; Elena Arutyunova; Michael A Joyce; Holly A Saffran; Justin A Shields; Howard S Young; James A Nieman; D Lorne Tyrrell; M Joanne Lemieux; John C Vederas
Journal:  Eur J Med Chem       Date:  2021-05-30       Impact factor: 7.088

6.  Identifying SARS-CoV-2 antiviral compounds by screening for small molecule inhibitors of Nsp5 main protease.

Authors:  Jennifer C Milligan; Theresa U Zeisner; George Papageorgiou; Dhira Joshi; Christelle Soudy; Rachel Ulferts; Mary Wu; Chew Theng Lim; Kang Wei Tan; Florian Weissmann; Berta Canal; Ryo Fujisawa; Tom Deegan; Hema Nagaraj; Ganka Bineva-Todd; Clovis Basier; Joseph F Curran; Michael Howell; Rupert Beale; Karim Labib; Nicola O'Reilly; John F X Diffley
Journal:  Biochem J       Date:  2021-07-16       Impact factor: 3.857

7.  Report of the National Institutes of Health SARS-CoV-2 Antiviral Therapeutics Summit.

Authors:  Matthew D Hall; James M Anderson; Annaliesa Anderson; David Baker; Jay Bradner; Kyle R Brimacombe; Elizabeth A Campbell; Kizzmekia S Corbett; Kara Carter; Sara Cherry; Lillian Chiang; Tomas Cihlar; Emmie de Wit; Mark Denison; Matthew Disney; Courtney V Fletcher; Stephanie L Ford-Scheimer; Matthias Götte; Abigail C Grossman; Frederick G Hayden; Daria J Hazuda; Charlotte A Lanteri; Hilary Marston; Andrew D Mesecar; Stephanie Moore; Jennifer O Nwankwo; Jules O'Rear; George Painter; Kumar Singh Saikatendu; Celia A Schiffer; Timothy P Sheahan; Pei-Yong Shi; Hugh D Smyth; Michael J Sofia; Marla Weetall; Sandra K Weller; Richard Whitley; Anthony S Fauci; Christopher P Austin; Francis S Collins; Anthony J Conley; Mindy I Davis
Journal:  J Infect Dis       Date:  2021-07-15       Impact factor: 7.759

Review 8.  Time to 'Mind the Gap' in novel small molecule drug discovery for direct-acting antivirals for SARS-CoV-2.

Authors:  Colleen B Jonsson; Jennifer E Golden; Bernd Meibohm
Journal:  Curr Opin Virol       Date:  2021-06-29       Impact factor: 7.090

9.  Structure-Guided Design of Conformationally Constrained Cyclohexane Inhibitors of Severe Acute Respiratory Syndrome Coronavirus-2 3CL Protease.

Authors:  Chamandi S Dampalla; Yunjeong Kim; Naemi Bickmeier; Athri D Rathnayake; Harry Nhat Nguyen; Jian Zheng; Maithri M Kashipathy; Matthew A Baird; Kevin P Battaile; Scott Lovell; Stanley Perlman; Kyeong-Ok Chang; William C Groutas
Journal:  J Med Chem       Date:  2021-07-02       Impact factor: 7.446

Review 10.  Synthetic and computational efforts towards the development of peptidomimetics and small-molecule SARS-CoV 3CLpro inhibitors.

Authors:  Abhik Paul; Arnab Sarkar; Sanjukta Saha; Avik Maji; Pritha Janah; Tapan Kumar Maity
Journal:  Bioorg Med Chem       Date:  2021-07-03       Impact factor: 3.641

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