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3-Oxo-ß-sultam as a Sulfonylating Chemotype for Inhibition of Serine Hydrolases and Activity-Based Protein Profiling

2020-03-16Journal article Restricted access
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dc.contributor.authorCarvalho, Luís
dc.contributor.authorAlmeida, Vanessa Tavares
dc.contributor.authorBrito, José A.
dc.contributor.authorLum, Kenneth
dc.contributor.authorOliveira, Tânia F.
dc.contributor.authorGuedes, Rita C.
dc.contributor.authorGonçalves, Lídia
dc.contributor.authorLucas, Susana Dias
dc.contributor.authorCravatt, Benjamin
dc.contributor.authorArcher, Margarida
dc.contributor.authorMoreira, Rui
dc.date.accessioned2024-01-22T16:46:34Z
dc.date.available2024-01-22T16:46:34Z
dc.date.issued2020-03-16
dc.date.updated2023-02-27T18:33:22Z
dc.descriptionCopyright © 2020 American Chemical Societypt_PT
dc.description.abstract3-Oxo-β-sultams are four-membered ring ambident electrophiles that can react with nucleophiles either at the carbonyl carbon or at the sulfonyl sulfur atoms, and that have been reported to inhibit serine hydrolases via acylation of the active-site serine residue. We have developed a panel of 3-oxo-β-sultam inhibitors and show, through crystallographic data, that they are regioselective sulfonylating electrophiles, covalently binding to the catalytic serine of human and porcine elastases through the sulfur atom. Application of 3-oxo-β-sultam-derived activity-based probes in a human proteome revealed their potential to label disease-related serine hydrolases and proteasome subunits. Activity-based protein profiling applications of 3-oxo-β-sultams should open up new opportunities to investigate these classes of enzymes in complex proteomes and expand the toolbox of available sulfur-based covalent protein modifiers in chemical biology.pt_PT
dc.description.sponsorshipThis study was supported by Fundação para a Ciência e a Tecnologia (FCT, Portugal) through Project Nos. PTDC/BBB-BEP/2463/2014, SAICTPAC/0019/2015, and UID/DTP/04138/2019, Fellowship SFRH/BD/100400/2014 (to L.A.R.C.), Grant Nos. IF/00472/2014 (to S.D.L.) and IF/00656/2014 (to M.A.), and by European Union’s Structural & Investment Funds through COMPETE-POCI, under Programme Grant No. LISBOA-01-0145-FEDER-016405. This work was also supported by NIH R01 DA033760 (to B.F.C.), European Union’s Horizon 2020 Research and Innovation Programme (Grant No. 731005), MostMicro (Grant No. LISBOA-01-0145-FEDER-007660), and iNOVA4Health (Grant No. LISBOA-01-0145-FEDER-007344). J.A.B. was supported by Project LISBOA-01-0145-FEDER-007660 (Microbiologia Molecular, Estrutural e Celular) funded by FEDER funds through COMPETE2020-Programa Operacional Competitividade e Internacionalização (POCI) and by national funds through Fundação para a Ciência e a Tecnologia (FCT) within the framework of Article 23 of Decree-Law No. 57/2017 of August 29. L.A.R.C. was sponsored by an FCT-funded Fulbright Grant. Some of the experiments described herein were performed on beamlines ID23 and ID30A-3 at the European Synchrotron Radiation Facility (ESRF), Grenoble, France. We are grateful to the local contacts at these beamlines for providing assistance in using them. The authors would also like to thank Diamond Light Source for beamtime (Proposal No. MX20161), and the staff of beamlines I03 and I24 for assistance with crystal testing and data collection.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationCarvalho LAR, Almeida VT, Brito JA, Lum KM, Oliveira TF, Guedes RC, et al. 3-oxo-β-sultam as a sulfonylating chemotype for inhibition of serine hydrolases and activity-based protein profiling. ACS Chem Biol [Internet]. 17 de abril de 2020;15(4):878–83. Disponível em: https://pubs.acs.org/doi/10.1021/acschembio.0c00090pt_PT
dc.identifier.doi10.1021/acschembio.0c00090pt_PT
dc.identifier.issn1554-8929
dc.identifier.issn1554-8937
dc.identifier.slugcv-prod-2118937
dc.identifier.urihttp://hdl.handle.net/10451/62011
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.relationProbeCOPD. Protease activity-based probes for Chronic Obstructive Pulmonary Disease diagnostics
dc.relationResearch Institute for Medicines
dc.relationActiProbe: Activity-Based Probes as chemical tools for biomarker discovery in Chronic Obstructive Pulmonary Disease
dc.relationStructural biology of membrane proteins: promising candidates for drug development
dc.relationReleasing the full potential of Instruct to expand and consolidate infrastructure services for integrated structural life science research
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acschembio.0c00090pt_PT
dc.title3-Oxo-ß-sultam as a Sulfonylating Chemotype for Inhibition of Serine Hydrolases and Activity-Based Protein Profilingpt_PT
dc.typejournal article
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oaire.awardTitleProbeCOPD. Protease activity-based probes for Chronic Obstructive Pulmonary Disease diagnostics
oaire.awardTitleResearch Institute for Medicines
oaire.awardTitleActiProbe: Activity-Based Probes as chemical tools for biomarker discovery in Chronic Obstructive Pulmonary Disease
oaire.awardTitleStructural biology of membrane proteins: promising candidates for drug development
oaire.awardTitleReleasing the full potential of Instruct to expand and consolidate infrastructure services for integrated structural life science research
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oaire.citation.endPage883pt_PT
oaire.citation.issue4pt_PT
oaire.citation.startPage878pt_PT
oaire.citation.titleACS Chemical Biologypt_PT
oaire.citation.volume15pt_PT
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