Azapeptide activity-based probes for the SARS-CoV-2 main protease enable visualization of inhibition in infected cells.


Journal

Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951

Informations de publication

Date de publication:
15 Feb 2023
Historique:
received: 25 07 2022
accepted: 02 01 2023
entrez: 23 2 2023
pubmed: 24 2 2023
medline: 24 2 2023
Statut: epublish

Résumé

The COVID-19 pandemic has revealed the vulnerability of the modern, global society. With expected waves of future infections by SARS-CoV-2, treatment options for infected individuals will be crucial in order to decrease mortality and hospitalizations. The SARS-CoV-2 main protease is a validated drug target, for which the first inhibitor has been approved for use in patients. To facilitate future work on this drug target, we designed a solid-phase synthesis route towards azapeptide activity-based probes that are capped with a cysteine-reactive electrophile for covalent modification of the active site of M

Identifiants

pubmed: 36819852
doi: 10.1039/d2sc04147b
pii: d2sc04147b
pmc: PMC9931053
doi:

Types de publication

Journal Article

Langues

eng

Pagination

1666-1672

Informations de copyright

This journal is © The Royal Society of Chemistry.

Déclaration de conflit d'intérêts

The authors declare no conflicts of interest.

Références

Chembiochem. 2020 Dec 1;21(23):3383-3388
pubmed: 32717117
Cell Res. 2020 Aug;30(8):678-692
pubmed: 32541865
N Engl J Med. 2012 Nov 8;367(19):1814-20
pubmed: 23075143
J Med Chem. 2022 Oct 27;65(20):13852-13865
pubmed: 36229406
RSC Med Chem. 2021 Apr 14;12(7):1026-1036
pubmed: 34355175
Bioorg Med Chem. 2019 May 15;27(10):2066-2074
pubmed: 30975501
Nat Rev Immunol. 2022 May;22(5):267-269
pubmed: 35414124
Science. 2020 Apr 24;368(6489):409-412
pubmed: 32198291
Angew Chem Int Ed Engl. 2021 Apr 26;60(18):10423-10429
pubmed: 33655614
J Mol Biol. 2005 Nov 11;353(5):1137-51
pubmed: 16219322
Science. 2020 Jun 19;368(6497):1331-1335
pubmed: 32321856
Lancet. 2003 Jul 26;362(9380):263-70
pubmed: 12892955
Nat Med. 2022 May;28(5):1063-1071
pubmed: 35189624
Nat Commun. 2020 Oct 20;11(1):5409
pubmed: 33082353
Lancet. 1966 Jan 8;1(7428):76-7
pubmed: 4158999
Science. 2021 Dec 24;374(6575):1586-1593
pubmed: 34726479
Bioorg Med Chem Lett. 2020 Sep 1;30(17):127377
pubmed: 32738988
J Med Chem. 2022 Feb 24;65(4):2905-2925
pubmed: 34242027
J Med Chem. 2002 Nov 7;45(23):4958-60
pubmed: 12408706
ChemMedChem. 2022 Jan 5;17(1):e202100576
pubmed: 34651447
Proc Soc Exp Biol Med. 1966 Jan;121(1):190-3
pubmed: 4285768
Nat Chem Biol. 2021 Feb;17(2):222-228
pubmed: 33093684
Nature. 2020 Jun;582(7811):289-293
pubmed: 32272481
J Am Chem Soc. 2021 Dec 15;143(49):20697-20709
pubmed: 34860011
Bioorg Med Chem. 2020 Apr 1;28(7):115357
pubmed: 32081630
Org Lett. 2005 Dec 8;7(25):5649-52
pubmed: 16321013
Angew Chem Int Ed Engl. 2021 Mar 15;60(12):6799-6806
pubmed: 33350010
J Am Chem Soc. 2019 Jun 5;141(22):8951-8968
pubmed: 31060360
Mol Cell Proteomics. 2002 Jan;1(1):60-8
pubmed: 12096141
Cell Death Differ. 2007 Apr;14(4):727-32
pubmed: 17170749
ACS Infect Dis. 2021 Jun 11;7(6):1457-1468
pubmed: 33570381

Auteurs

Roeland Vanhoutte (R)

Department of Cellular and Molecular Medicine, Laboratory of Chemical Biology, KU Leuven Herestraat 49 box 802 3000 Leuven Belgium steven.verhelst@kuleuven.be.

Marta Barniol-Xicota (M)

Department of Cellular and Molecular Medicine, Laboratory of Chemical Biology, KU Leuven Herestraat 49 box 802 3000 Leuven Belgium steven.verhelst@kuleuven.be.

Winston Chiu (W)

Laboratory of Virology and Chemotherapy, Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, KU Leuven Herestraat 49, Box 1043 3000 Leuven Belgium.

Laura Vangeel (L)

Laboratory of Virology and Chemotherapy, Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, KU Leuven Herestraat 49, Box 1043 3000 Leuven Belgium.

Dirk Jochmans (D)

Laboratory of Virology and Chemotherapy, Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, KU Leuven Herestraat 49, Box 1043 3000 Leuven Belgium.

Steven De Jonghe (S)

Laboratory of Virology and Chemotherapy, Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, KU Leuven Herestraat 49, Box 1043 3000 Leuven Belgium.

Hadeer Zidane (H)

Maurice and Vivienne Wohl Institute for Drug Discovery, The Nancy and Stephen Grand Israel National Center for Personalized Medicine, The Weizmann Institute of Science Rehovot 7610001 Israel.

Haim M Barr (HM)

Maurice and Vivienne Wohl Institute for Drug Discovery, The Nancy and Stephen Grand Israel National Center for Personalized Medicine, The Weizmann Institute of Science Rehovot 7610001 Israel.

Nir London (N)

Department of Chemical and Structural Biology, Weizmann Institute of Science Rehovot 7610001 Israel.

Johan Neyts (J)

Laboratory of Virology and Chemotherapy, Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, KU Leuven Herestraat 49, Box 1043 3000 Leuven Belgium.

Steven H L Verhelst (SHL)

Department of Cellular and Molecular Medicine, Laboratory of Chemical Biology, KU Leuven Herestraat 49 box 802 3000 Leuven Belgium steven.verhelst@kuleuven.be.
AG Chemical Proteomics, Leibniz Institute for Analytical Sciences ISAS Otto-Hahn-Str. 6b 44227 Dortmund Germany.

Classifications MeSH