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Exploring the Condensation Reaction between Aromatic Nitriles and Amino Thiols To Optimize In Situ Nanoparticle Formation for the Imaging of Proteases and Glycosidases in Cells
Author(s) -
Chen Zixin,
Chen Min,
Cheng Yunfeng,
Kowada Toshiyuki,
Xie Jinghang,
Zheng Xianchuang,
Rao Jianghong
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201913314
Subject(s) - chemistry , cysteine , linker , condensation reaction , substrate (aquarium) , nanoparticle , in situ , reactivity (psychology) , combinatorial chemistry , hydrolysis , proteases , enzyme , nanotechnology , organic chemistry , catalysis , materials science , pathology , computer science , operating system , medicine , oceanography , alternative medicine , geology
Abstract The condensation reaction between 6‐hydroxy‐2‐cyanobenzothiazole (CBT) and cysteine has been shown for various applications such as site‐specific protein labelling and in vivo cancer imaging. This report further expands the substrate scope of this reaction by varying the substituents on aromatic nitriles and amino thiols and testing their reactivity and ability to form nanoparticles for cell imaging. The structure–activity relationship study leads to the identification of the minimum structural requirement for the macrocyclization and assembly process in forming nanoparticles. One of the scaffolds made of 2‐pyrimidinecarbonitrile and cysteine joined by a benzyl linker was applied to design fluorescent probes for imaging caspase‐3/7 and β‐galactosidase activity in live cells. These results demonstrate the generality of this system for imaging hydrolytic enzymes.