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

被引：52

作者：

Chen, Zixin ^{[1
,2
]}

Chen, Min ^{[1
,2
]}

Cheng, Yunfeng ^{[1
,2
]}

Kowada, Toshiyuki ^{[3
]}

Xie, Jinghang ^{[1
,2
]}

Zheng, Xianchuang ^{[1
,2
]}

Rao, Jianghong ^{[1
,2
]}

机构：

[1] Stanford Univ, Sch Med, Mol Imaging Program Stanford, Dept Radiol, Stanford, CA 94305 USA

[2] Stanford Univ, Sch Med, Mol Imaging Program Stanford, Dept Chem, Stanford, CA 94305 USA

[3] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, 2-1-1 Katahira, Sendai, Miyagi 9808577, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 08期

关键词：

bioorthogonal reactions; enzyme activity imaging; fluorescent probes; nanoparticles; self-assembly; AZIDE-ALKYNE CYCLOADDITION; PHOTOCLICK-CHEMISTRY; CLICK CHEMISTRY; COPPER-FREE; PROTEIN; LIGATION; HYDROGELS; F-18-C-SNAT; ACTIVATION; SURFACES;

D O I：

10.1002/anie.201913314

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 beta-galactosidase activity in live cells. These results demonstrate the generality of this system for imaging hydrolytic enzymes.

引用

页码：3272 / 3279

页数：8

共 70 条

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