Rational Design of an Ultrasensitive and Highly Selective Chemodosimeter by a Dual Quenching Mechanism for Cysteine Based on a Facile Michael-Transcyclization Cascade Reaction

Xiangmin Li, Yongjun Zheng, Hongjuan Tong, Rui Qian, Lin Zhou, Guixia Liu, Yun Tang, Hao Li, Kaiyan Lou, Wei Wang

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Differentiation of biologically important thiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) is still a challenging task. Herein, we present a novel fluorescent chemodosimeter capable of selectively detecting Cys over other biothiols including Hcy and GSH and other amino acids by a facile thiol-Michael addition/transcyclization rearrangement cascade click process. The unique transcyclization step is critical for the selectivity as a result of the kinetically favorable formation of a six-membered ring with the Cys Michael adduct. Moreover, the probe adopts a distinctive dual quenching mechanism—photoinduced electron transfer (PET) and photoinduced intramolecular charge transfer (ICT) to deliver a drastic turn-on fluorescence response only at the Cys-selective transcylization step. The judicious selection of strong electron-withdrawing naphthalimide fluorophore with maleimide group enhances the electrophilicity and thus reactivity for the cascade process leading to fast detection and ultrasensitivity with a detection limit of 2.0 nm (S/N=3). The probe has demonstrated its practical utility potential in Cys imaging in live cells.

Original languageEnglish (US)
Pages (from-to)9247-9256
Number of pages10
JournalChemistry - A European Journal
Volume22
Issue number27
DOIs
StatePublished - Jun 27 2016
Externally publishedYes

Keywords

  • cascade reactions
  • chemodosimeter
  • click chemistry
  • cysteine
  • fluorescent probes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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