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

Research output: Contribution to journalArticle

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

Fingerprint

esters
Esters
Fluorophores
Quantum yield
chemistry
synthesis
Fluorescence
fluorescence
Time and motion study
phenylalanine
Molecular interactions
lysine
molecular interactions
compartments
cells
Fluorescein
Phenylalanine
Serine
Lysine
amino acids

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Li, Chun ; Henry, Etienne ; Mani, Naresh Kumar ; Tang, Jie ; Brochon, Jean Claude ; Deprez, Eric ; Xie, Juan. / Click chemistry to fluorescent amino esters : Synthesis and spectroscopic studies. In: European Journal of Organic Chemistry. 2010 ; No. 12. pp. 2395-2405.
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Click chemistry to fluorescent amino esters : Synthesis and spectroscopic studies. / Li, Chun; Henry, Etienne; Mani, Naresh Kumar; Tang, Jie; Brochon, Jean Claude; Deprez, Eric; Xie, Juan.

In: European Journal of Organic Chemistry, No. 12, 01.04.2010, p. 2395-2405.

Research output: Contribution to journalArticle

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