ArticleJournal of the American Chemical Society2017
Spirohexene-Tetrazine Ligation Enables Bioorthogonal Labeling of Class B G Protein-Coupled Receptors in Live Cells.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed, 67 citations in OpenAlex.
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- In vitro dynamic and quantitative monitoring of strigolactone-signaling complex formation by time-resolved FRET.The Plant journal : for cell and molecular biology · 2025Article
- Strategies to Expand the Genetic Code of Mammalian Cells.Chemical reviews · 2025Review
- Noncanonical Amino Acid Tools and Their Application to Membrane Protein Studies.Chemical reviews · 2024Review
- Cannabinoid Receptor Signaling is Dependent on Sub-Cellular Location.bioRxiv : the preprint server for biology · 2024Article
- Minimalist TetrazineJournal of the American Chemical Society · 2024Article
- Detecting and measuring of GPCR signaling - comparison of human induced pluripotent stem cells and immortal cell lines.Frontiers in endocrinology · 2023Review
- Quantitative Analysis and Optimization of Site-Specific Protein Bioconjugation in Mammalian Cells.Bioconjugate chemistry · 2022Article
- Dual fluorescent labeling of GLP-1R in live cellsRSC chemical biology · 2022Article
- Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells.Journal of the American Chemical Society · 2022Article
- Arylethynyltrifluoroborate Dienophiles for on Demand Activation of IEDDA Reactions.Bioconjugate chemistry · 2021Article
- Intracellular bioorthogonal labeling of glucagon receptor via tetrazine ligation.Bioorganic & medicinal chemistry · 2021Article
- IEDDA: An Attractive Bioorthogonal Reaction for Biomedical Applications.Molecules (Basel, Switzerland) · 2021Review
- Photoclick Chemistry: A Bright Idea.Chemical reviews · 2021Review
- Clicking of organelle-enriched probes for fluorogenic imaging of autophagic and endocytic fluxes.Chemical science · 2021Article
- Bioorthogonal chemistry.Nature reviews. Methods primers · 2021Article
- Predicting reactivity for bioorthogonal cycloadditions involving nitrones.RSC advances · 2020Article
- Bioorthogonal Ligations and Cleavages in Chemical Biology.ChemistryOpen · 2020Review
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
A new bioorthogonal reactant pair, spiro[2.3]hex-1-ene (Sph) and 3,6-di(2-pyridyl)-s-tetrazine (DpTz), for the strain-promoted inverse electron-demand Diels-Alder cycloaddition, that is, tetrazine ligation, is reported. As compared to the previously reported strained alkenes such as trans-cyclooctene (TCO) and 1,3-disubstituted cyclopropene, Sph exhibits balanced reactivity and stability in tetrazine ligation with the protein substrates. A lysine derivative of Sph, SphK, was site-selectively incorporated into the extracellular loop regions (ECLs) of GCGR and GLP-1R, two members of class B G protein-coupled receptors (GPCRs) in mammalian cells with the incorporation efficiency dependent on the location. Subsequent bioorthogonal reactions with the fluorophore-conjugated DpTz reagents afforded the fluorescently labeled GCGR and GLP-1R ECL mutants with labeling yield as high as 68%. A multitude of functional assays were performed with these GPCR mutants, including ligand binding, ligand-induced receptor internalization, and ligand-stimulated intracellular cAMP accumulation. Several positions in the ECL3s of GCGR and GLP-1R were identified that tolerate SphK mutagenesis and subsequent bioorthogonal labeling. The generation of functional, fluorescently labeled ECL3 mutants of GCGR and GLP-1R should allow biophysical studies of conformation dynamics of this important class of GPCRs in their native environment in live cells.
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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.