ArticleBioconjugate chemistry2018
Vinylboronic Acids as Efficient Bioorthogonal Reactants for Tetrazine Labeling in Living Cells.
Article in Bioconjugate chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023Review
- Bioorthogonal Reactions in Activity-Based Protein Profiling.Molecules (Basel, Switzerland) · 2020Review
- Activation and Delivery of Tetrazine-Responsive Bioorthogonal Prodrugs.Molecules (Basel, Switzerland) · 2020Review
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
- Studies on the Stability and Stabilization ofTetrahedron · 2019Article
- Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks.Angewandte Chemie (International ed. in English) · 2019Article
- Factors Controlling the Diels-Alder Reactivity of Hetero-1,3-Butadienes.ChemistryOpen · 2018Article
- Highly Stable and Selective Tetrazines for the Coordination-Assisted Bioorthogonal Ligation with Vinylboronic Acids.Bioconjugate chemistry · 2018Article
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4 authors.
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Abstract
Bioorthogonal chemistry can be used for the selective modification of biomolecules without interfering with any other functionality present in the cell. The tetrazine ligation is very suitable as a bioorthogonal reaction because of its selectivity and high reaction rates with several alkenes and alkynes. Recently, we described vinylboronic acids (VBAs) as novel hydrophilic bioorthogonal moieties that react efficiently with dipyridyl- s-tetrazines and used them for protein modification in cell lysate. It is not clear, however, whether VBAs are suitable for labeling experiments in living cells because of the possible coordination with, for example, vicinal carbohydrate diols. Here, we evaluated VBAs as bioorthogonal reactants for labeling of proteins in living cells using an irreversible inhibitor of the proteasome and compared the reactivity to that of an inhibitor containing norbornene, a widely used reactant for the tetrazine ligation. No large differences were observed between the VBA and norbornene probes in a two-step labeling approach with a cell-penetrable fluorescent tetrazine, indicating that the VBA gives little or no side reactions with diols and can be used efficiently for protein labeling in living cells.
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