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The azide group in azide exists in the form of nitrogen nitrogen double bond (N= N), and its bond energy is 418 kJ / mol. The three nitrogen atoms in azide molecule are connected with each other by linear resonance structure, and its general structural formula is RNNN. Azides are extremely sensitive to light, heat, radiation and vibration, and are now developed for functional fluorescent materials. As we all know, we can connect the required active groups to different fluorescent dyes, such as NHS, amine, COOH, azide, alkyne, maleimide, etc. The azide functional group allows the fluorescence to combine with various biomolecules, small molecules and polymers through Cu AAC or SP ACC click chemical reaction, which is very reliable.
Characteristics of Azides
Among the many advantages of azide click reaction, there are three important characteristics that have unique attraction to the biomedical field.
- Firstly, azide groups and alkyne groups hardly react with biomolecules, and their polarity is relatively weak. It has no obvious effect on the properties of other groups connected to it, and can be easily introduced into the compound.
- Secondly, the click reaction can be carried out in aqueous solution medium, so the reaction can be carried out under physiological conditions. For example, azide and alkyne form covalent bonds, which have the advantages of high efficiency, stability and high specificity. The reaction is not affected by pH and can be carried out in water at room temperature, or even in living cells.
- More importantly, this reaction has very high chemical selectivity and can be used to modify highly functional biomolecules, such as peptides, nucleic acids, polysaccharides and so on. Moreover, the azazole group generated after click reaction has the stability of aromatic ring, is not easy to decompose, and can withstand strong acids and bases It can remain stable under a variety of redox conditions.
Application of Azides
Azide modified fluorescent probes have been widely used in biology, which provides help for biomedical experiments and some physical and chemical experiments. The azide group modified fluorescent probe can carry out specific fluorescent labeling through its multifunctional reactivity.
Azide is easily soluble in organic solvents (such as DMSO and DMF), and azide functional groups allow fluorescence to combine with various biomolecules, small molecules and polymers through Cu AAC or SP ACC click chemical reaction. Therefore, it is often used to connect fluorophores for labeling reaction. Such as common azide fluorescent probes Azide-BDP-FL, 5-FAM-Azide, Cy5-Azide,etc.
Azide compounds can react with hydrogen sulfide molecules under mild conditions and eventually be reduced to amine compounds. Before and after the reaction of azide group and hydrogen sulfide, the rigid surface of fluorophore changes, so that hydrogen sulfide can quickly reduce azide group to generate amino group, release the fluorescence of fluorophore and realize the detection of hydrogen sulfide.