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

Zixin Chen, Min Chen, Yunfeng Cheng, Toshiyuki Kowada, Jinghang Xie, Xianchuang Zheng, Jianghong Rao

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)3272-3279
Number of pages8
JournalAngewandte Chemie - International Edition
Volume59
Issue number8
DOIs
Publication statusPublished - 2020 Feb 17

Keywords

  • bioorthogonal reactions
  • enzyme activity imaging
  • fluorescent probes
  • nanoparticles
  • self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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