pH-Responsive Fluorescent Switches through Intramolecular Conjugate Addition Reactions and Application in Fluorogenic Bioimaging.

Org Lett

The Key Laboratory of Biomedical Information Engineering of Ministry of Education, School of Life Science and Technology, Xi'an Jiaotong University, No. 28 West Xianning Road, Xi'an, 710049, People's Republic of China.

Published: October 2024

AI Article Synopsis

  • New photoluminescent switching systems were developed that respond to pH changes through specific chemical reactions.
  • The study measured how these systems' absorption and fluorescence emissions varied with pH, identifying certain pseudo p values based on the substituents' nature.
  • A novel fluorescent probe was created, enabling the differentiation between cancer cells and normal cells during live imaging experiments.

Article Abstract

We report new photoluminescent switching systems achieved through pH-induced intramolecular oxa-Michael conjugate addition reactions. Ratiometric absorbance and fluorescence emission were observed across conjugate acceptors triggered by pH, resulting in specific pseudo p values. The effect of substituents on the pseudo p's was investigated, showing increased values from electron-withdrawing to electron-donating groups. Inspired by the physiologically related p, a fluorescent probe was designed, successfully distinguishing cancer cells from normal cells through live cellular imaging.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c03197DOI Listing

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