Enzyme-Instructed CBT-Cys-like Click Cyclization Reactions for Bioimaging.

Content Provider	Europe PMC
Author	Yang, Yang Liu, Xiaoyang Wu, Xiaofeng Liang, Gaolin
Copyright Year	2023
Description	With high efficiency, mild conditions, and rapid reaction rate, click reactions have garnered much attention in the field of bioimaging since proposed by Sharpless et al. in 2001 (Angew. Chem., Int. Ed.2001, 40, 2004−2021). Inspired by the regenerative pathway of d-luciferin in fireflies, Liang et al. (Nat. Chem.2010, 2, 54−6021124381 ) raised a 2-cyanobenzothiazole (CBT)-cysteine (Cys) click condensation reaction in 2010, which exhibits a higher second-order reaction rate (9.19 M–1 s–1) and superior biocompatibility. As it has been developed in the past decade, remarkable progress has been made in the construction of enzyme-instructed CBT-Cys-based bioimaging probes. This review introduces the concept of the CBT-Cys click reaction, elucidates the mechanism of the CBT-Cys click reaction, and concerns the development progress of CBT-Cys reaction and its derived reactions [i.e., 2-cyano-6-hydroxyquinoline (CHQ)-Cys reaction and 2-pyrimidinecarbonitrile (PMN)-Cys reaction]. Furthermore, we give a comprehensive and up-to-date review of enzyme-instructed CBT-Cys-like click reaction-based probes with significantly enhanced imaging signal and contrast for various bioimaging modes, including fluorescence imaging, photoacoustic imaging, magnetic resonance imaging, and positron emission tomography. In the end, we discuss the possible challenges and opportunities that may arise in the future.
Abstract	With high efficiency, mild conditions,and rapid reaction rate,click reactions have garnered much attention in the field of bioimagingsince proposed by Sharpless et al. in 2001 (Angew. Chem., Int. Ed.2001, 40, 2004−2021). Inspired by the regenerative pathway of d-luciferin in fireflies, Liang et al. (Nat. Chem.2010, 2, 54−6021124381) raised a 2-cyanobenzothiazole (CBT)-cysteine (Cys) click condensationreaction in 2010, which exhibits a higher second-order reaction rate(9.19 M–1 s–1) and superior biocompatibility.As it has been developed in the past decade, remarkable progress hasbeen made in the construction of enzyme-instructed CBT-Cys-based bioimagingprobes. This review introduces the concept of the CBT-Cys click reaction,elucidates the mechanism of the CBT-Cys click reaction, and concernsthe development progress of CBT-Cys reaction and its derived reactions[i.e., 2-cyano-6-hydroxyquinoline (CHQ)-Cys reaction and 2-pyrimidinecarbonitrile(PMN)-Cys reaction]. Furthermore, we give a comprehensive and up-to-datereview of enzyme-instructed CBT-Cys-like click reaction-based probeswith significantly enhanced imaging signal and contrast for variousbioimaging modes, including fluorescence imaging, photoacoustic imaging,magnetic resonance imaging, and positron emission tomography. In theend, we discuss the possible challenges and opportunities that mayarise in the future.
Related Links	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC11504589&blobtype=pdf
Volume Number	2
DOI	10.1021/cbmi.3c00117
PubMed Central reference number	PMC11504589
Issue Number	2
PubMed reference number	39474483
Journal	Chemical & Biomedical Imaging [Chem Biomed Imaging]
e-ISSN	28323637
Language	English
Publisher	Nanjing University and American Chemical Society
Publisher Date	2023-12-31
Access Restriction	Open
Rights License	Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). © 2023 The Authors. Co-published by Nanjing University and American Chemical Society
Subject Keyword	Bioimaging CBT-Cys-like reactions Click chemistry Cyclization reaction Enzyme-instructed assembly
Content Type	Text
Resource Type	Article
Subject	Medicine