C3-triiodocyclotriveratrylene as a key intermediate to fluorescent probes: application to selective choline recognition.

Org Biomol Chem

Université de Bordeaux, Institut des Sciences Moléculaires UMR CNRS 5525, Groupe Nanosystèmes analytiques, Site ENSCBP, 16 Av. Pey Berland, 33607, Pessac, France.

Published: December 2011

AI Article Synopsis

  • A new method is introduced for creating fluorescent cyclotriveratrylene (CTV) probes, focusing on a key intermediate called triiodo CTV.
  • The synthesis of triiodo CTV is achieved in three steps with a 47% yield and requires just one purification step.
  • This intermediate is used to develop a fluorescent probe that selectively binds to choline over acetylcholine, enabling the rapid creation of a library of probes for further research.

Article Abstract

A new strategy to obtain fluorescent cyclotriveratrylene (CTV) probes is proposed. The key intermediate, a triiodo CTV, is prepared in 3 steps with 47% overall yield. The whole synthesis requires only one purification step. The potential of this triiodo CTV as an intermediate is illustrated through the synthesis of a fluorescent phosphorylated probe that is able to bind choline and acetylcholine in pseudo-physiological conditions, with selectivity towards choline. As a consequence, this intermediate should allow us to rapidly form a library of probes in order to highlight the most promising ones.

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Source
http://dx.doi.org/10.1039/c1ob06231jDOI Listing

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