@article{826f7ce8b1e5449eb79b1e5c7acfe5b1,
title = "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",
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.",
keywords = "bioorthogonal reactions, enzyme activity imaging, fluorescent probes, nanoparticles, self-assembly",
author = "Zixin Chen and Min Chen and Yunfeng Cheng and Toshiyuki Kowada and Jinghang Xie and Xianchuang Zheng and Jianghong Rao",
note = "Funding Information: J.X. thanks the Molecular Imaging Program at Stanford for the Molecular Imaging Young Investigator (MIYI) Award. M.C. acknowledges the support by the Stanford Cancer Translational Nanotechnology Training grant (T32CA196585) funded by the National Cancer Institute (NCI). The work was supported by a grant from NCI, Stanford CCNE-TD (U54CA199075) and the Stanford Bio-X Interdisciplinary Initiatives Seed Grants Program (IIP) award. Funding Information: J.X. thanks the Molecular Imaging Program at Stanford for the Molecular Imaging Young Investigator (MIYI) Award. M.C. acknowledges the support by the Stanford Cancer Translational Nanotechnology Training grant (T32CA196585) funded by the National Cancer Institute (NCI). The work was supported by a grant from NCI, Stanford CCNE‐TD (U54CA199075) and the Stanford Bio‐X Interdisciplinary Initiatives Seed Grants Program (IIP) award. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2020",
month = feb,
day = "17",
doi = "10.1002/anie.201913314",
language = "English",
volume = "59",
pages = "3272--3279",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "8",
}
