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Cycloalkyne reactive dyes can be used in copper-free click reactions.
Click chemistry is a way to quickly synthesize a large number of compounds. Click chemistry uses readily available chemical raw materials to realize the connection between carbon atoms and heteroatoms through fast, efficient, and highly selective modular chemical reactions. Click chemistry has the following characteristics: (1) The reaction has a wide range of applications. (2) The reaction conditions are simple, and the reaction process is not sensitive to water and oxygen. (3) The reaction yield is high, and there are almost no by-products. (4) The reaction has good stereoselectivity. (5) The product is easy to separate and purify and has high stability.
Classical click chemistry reactions include copper-catalyzed azide-alkyne cycloaddition reactions. Click chemistry of the azide-alkyne cycloaddition reaction is extensively used in organic chemistry, medicinal chemistry, chemical biology, molecular biology, cell biology, and other multidisciplinary fields.
The copper-catalyzed azide-alkyne click chemistry reaction is a kind of highly efficient bio-orthogonal reaction. However, the copper catalytic system has poor biocompatibility in biological systems. In addition, metal catalytic systems are potentially toxic. Therefore, more and more researchers have turned to click chemistry without metal catalysis.
The key to copper-free click chemistry is cycloalkynes. Cycloalkyne reactive dyes react with azides through copper-free click reactions to form stable triazoles. The stability of the triazole allows extensive washing to produce a high signal-to-noise ratio, which facilitates the detection of intracellular targets in fixed and permeabilized cells. This reaction can occur under mild conditions without copper catalysis, which makes it possible to study the surface of living cells, which greatly promotes the application of click chemistry in living biological systems. Cycloalkyne reactive dyes are an ideal substitute for fluorescent alkynes that require copper catalysis.