ArticleJournal of medicinal chemistry2013
Development and optimization of piperidyl-1,2,3-triazole ureas as selective chemical probes of endocannabinoid biosynthesis.
Article in Journal of medicinal chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
28 citing papers in PubMed, 55 citations in OpenAlex.
- Development of Oxadiazolone Activity-Based Probes Targeting FphE for Specific Detection ofbioRxiv : the preprint server for biology · 2023Article
- Activity-based probes in pathogenic bacteria: Investigating drug targets and molecule specificity.Current opinion in chemical biology · 2023Review
- Inhibition of DAGLβ as a therapeutic target for pain in sickle cell disease.Haematologica · 2023Article
- Identification of cell wall synthesis inhibitors active against Mycobacterium tuberculosis by competitive activity-based protein profiling.Cell chemical biology · 2022Article
- α/β-Hydrolase Domain (ABHD) Inhibitors as New Potential Therapeutic Options against Lipid-Related Diseases.Journal of medicinal chemistry · 2021Review
- Development and biological applications of sulfur-triazole exchange (SuTEx) chemistry.RSC chemical biology · 2021Article
- Piperidine based 1,2,3-triazolylacetamide derivatives induce cell cycle arrest and apoptotic cell death inJournal of advanced research · 2021Article
- Strategies for Tuning the Selectivity of Chemical Probes that Target Serine Hydrolases.Cell chemical biology · 2020Review
- DAGLα Inhibition as a Non-invasive and Translational Model of Episodic Headache.Frontiers in pharmacology · 2020Article
- Structure Kinetics Relationships and Molecular Dynamics Show Crucial Role for Heterocycle Leaving Group in Irreversible Diacylglycerol Lipase Inhibitors.Journal of medicinal chemistry · 2019Article
- Diacylglycerol Lipase-β Is Required for TNF-α Response but Not CD8Cell chemical biology · 2019Article
- Lipid-metabolizing serine hydrolases in the mammalian central nervous system: endocannabinoids and beyond.Biochimica et biophysica acta. Molecular and cell biology of lipids · 2019Review
- Fluorescent Triazole Urea Activity-Based Probes for the Single-Cell Phenotypic Characterization of Staphylococcus aureus.Angewandte Chemie (International ed. in English) · 2019Article
- N-Acyl pyrazoles: Effective and tunable inhibitors of serine hydrolases.Bioorganic & medicinal chemistry · 2019Article
- Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy.Frontiers in chemistry · 2019Article
- Chemoproteomic Discovery of a Ritanserin-Targeted Kinase Network Mediating Apoptotic Cell Death of Lung Tumor Cells.Molecular pharmacology · 2018Article
- Neuroprotection in Oxidative Stress-Related Neurodegenerative Diseases: Role of Endocannabinoid System Modulation.Antioxidants & redox signaling · 2018Review
- Isoform-selective activity-based profiling of ERK signaling.Chemical science · 2018Article
- Liposomal Delivery of Diacylglycerol Lipase-Beta Inhibitors to Macrophages Dramatically Enhances Selectivity and Efficacy in Vivo.Molecular pharmaceutics · 2018Article
- Deconstructing Lipid Kinase Inhibitors by Chemical Proteomics.Biochemistry · 2018Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
We have previously shown that 1,2,3-triazole ureas (1,2,3-TUs) act as versatile class of irreversible serine hydrolase inhibitors that can be tuned to create selective probes for diverse members of this large enzyme class, including diacylglycerol lipase-β (DAGLβ), a principal biosynthetic enzyme for the endocannabinoid 2-arachidonoylglycerol (2-AG). Here, we provide a detailed account of the discovery, synthesis, and structure-activity relationship (SAR) of (2-substituted)-piperidyl-1,2,3-TUs that selectively inactivate DAGLβ in living systems. Key to success was the use of activity-based protein profiling (ABPP) with broad-spectrum and tailored activity-based probes to guide our medicinal chemistry efforts. We also describe an expanded repertoire of DAGL-tailored activity-based probes that includes biotinylated and alkyne agents for enzyme enrichment coupled with mass spectrometry-based proteomics and assessment of proteome-wide selectivity. Our findings highlight the broad utility of 1,2,3-TUs for serine hydrolase inhibitor development and their application to create selective probes of endocannabinoid biosynthetic pathways.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.