Click chemistry to fluorescent amino esters: Synthesis and spectroscopic studies

Chun Li, Etienne Henry, Naresh Kumar Mani, Jie Tang, Jean Claude Brochon, Eric Deprez, Juan Xie

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28 Citations (Scopus)

Abstract

A new series of fluorescent amino esters have successfully been prepared by click chemistry by introducing different fluorophores (fluorescein, dansyl, 4-nitro-2,1,3-benzoxadiazole, coumarin and benzothiadlazole) into the side-chain of either serine, lysine or phenylalanine. The newly synthesized fluorescent amino esters displayed spectroscopic properties similar to their native fluorophores, with high quantum yields and fluorescence in the visible region (420-520 nm). Steadystate as well as time-resolved studies indicated, that benzothiadiazole derivatives 22-25 are promising probes for studying protein dynamics or molecular interactions, especially in the cell, due to their emissions in the visible region, their high, quantum yields and their relatively long lifetimes (14.7-18.3 ns). Moreover, the fluorescence of 7-hydroxycoumarinsubstituted amino ester 27 was very sensitive to the solvent proticity and pH value. This compound appears to be a suitable pH-sensitive amino acid for probing the local pH in cell compartments.

Original languageEnglish
Pages (from-to)2395-2405
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number12
DOIs
Publication statusPublished - 01-04-2010

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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