Abstract
Recently, click chemistry has provided important advances in biomedical research fields. Particularly, copper-free click chemistry including strain-promoted azide-alkyne cycloaddition (SPAAC) and inverse-electron-demand Diels-Alder (iEDDA) reactions enable fast and specific chemical conjugation under aqueous conditions without the need for toxic catalysts. Click chemistry has resulted in a change of paradigm, showing that artificial chemical reactions can occur on cell surfaces, in cell cytosol, or within the body, which is not easy with most other chemical reactions. Click chemistry in vitro allows specific labelling of cellular target proteins and studying of drug target engagement with drug surrogates in live cells. Furthermore, cellular membrane lipids and proteins could be selectively labelled with click chemistry in vitro and cells could be adhered together using click chemistry. Click chemistry in vivo enables efficient and effective molecular imaging and drug delivery for diagnosis and therapy. Click chemistry ex vivo can be used to develop molecular tools to understand tissue development, diagnosis of diseases, and therapeutic monitoring. Overall, the results from research to date suggest that click chemistry has emerged as a valuable tool in biomedical fields as well as in organic chemistry.
Highlights
Click chemistry has been broadly used for chemical reactions that have orthogonality, high yields, and fast kinetic second aDepartment of Molecular Science and Technology, Ajou University, Suwon 16499, Republic of Korea bDepartment of Medical Life Sciences, College of Medicine, The Catholic University of Korea, 222 Banpo-daero, Seocho-gu, Seoul, 06591, Republic of Korea
Click chemistry has resulted in a change of paradigm, showing that artificial chemical reactions can occur on cell surfaces, in cell cytosol, or within the body, which is not easy with most other chemical reactions
We have introduced important researches based on copper-free click chemistry in vitro, in vivo and ex vivo for biomedical applications
Summary
Click chemistry has been broadly used for chemical reactions that have orthogonality, high yields, and fast kinetic second aDepartment of Molecular Science and Technology, Ajou University, Suwon 16499, Republic of Korea bDepartment of Medical Life Sciences, College of Medicine, The Catholic University of Korea, 222 Banpo-daero, Seocho-gu, Seoul, 06591, Republic of Korea. Minireview being carried out on cell surfaces, in cell cytosol, or in the body.[3] organic chemists have attempted to remove the toxic copper catalyst from the representative click reaction, coppercatalyzed [3 + 2] azide–alkyne cycloaddition (CuAAC) Their trials resulted in ‘copper-free’ click chemistry which is highly attractive to biological or biomedical researchers.[4,5,6]. Bevilacqua et al and Kennedy et al demonstrated cell labelling by CuAAC using similar bis(tert-butyltriazoly) ligand and Cu(II)–bis-L-histidine complex, respectively.[15,16] To overcome this limitation fundamentally and increase the convenience, other chemists have increased the reactivity of alkynes using ringstrain which enables an azide–alkyne reaction without the need for a cytotoxic copper catalyst These strain-promoted azide– alkyne cycloaddition reactions (SPAAC) have favourable second order reaction rate constants (approximately 0.1 MÀ1 sÀ1) under aqueous conditions without a catalyst.[17]. If a new photoclick reaction using visible or NIR light is proposed in the future, it will be more useful for biomedical applications
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