Abstract
The emergence of bioorthogonal reactions has greatly broadened the scope of biomolecule labeling and detecting. Of all the bioorthogonal reactions that have been developed, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) is the most widely applied one, mainly because of its relatively fast kinetics and high efficiency. However, the introduction of copper species to in vivo systems raises the issue of potential toxicity. In order to reduce the copper-induced toxicity and further improve the reaction kinetics and efficiency, different strategies have been adopted, including the development of diverse copper chelating ligands to assist the catalytic cycle and the development of chelating azides as reagents. Up to now, the optimization of CuAAC has facilitated its applications in labeling and identifying either specific biomolecule species or on the omics level. Herein, we mainly discuss the efforts in the development of CuAAC to better fit the bioorthogonal reaction criteria and its bioorthogonal applications both in vivo and in vitro.
Highlights
For the better understanding of living systems, scientists have made every endeavor to monitor biomolecules in their native context
CuAAC, alkyne or azide chemical handles should firstly be inserted into the investigated biomolecules; the reactive probe molecules with the corresponding functional group will be added to the system, in the presence of a suitable ligand-Cu complex and reducing agent
Detection of nucleic acids including DNA and RNA is of great importance for monitoring Detection of nucleic acids including DNA and RNA is of great importance for monitoring different different biological processes (Figure 2). 5-Ethynyl-2-deoxyuridine (EdU) is a metabolic thymidine biological processes (Figure 2). 5-Ethynyl-2-deoxyuridine (EdU) is a metabolic thymidine analogue analogue that could be inserted in DNA during cell proliferation
Summary
For the better understanding of living systems, scientists have made every endeavor to monitor biomolecules in their native context. The second-order rate constant of this reaction was reported to be within the reactions (such as Michael addition, thiol-ene reaction, and so on), the ketone/aldehyde condensation, Lysine/cysteine modification reactions could achive the bioconjugation on specific amino acid residues of proteins. The applications of ketone/aldehyde condensation and Staudinger ligation were focused on labeling cell surface glycans [12,14,15,17,18,19] and purified proteins [20,21] This has already extended the monitoring scope beyond the limitation of proteins, and revealed the huge potential of or alkynes the fastest bioorthogonal reactions to date, with rate constants. M−1·s reactions have been exploited labelingforand detecting various kinds of and
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