Issue 24, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Lisa Peyrard,a   Sabine Chierici,b   Sandra Pinet,a   Pinar Batat,c   Gediminas Jonusauskas,c   Noël Pinaud,d   Pierre Meyrande  and  Isabelle Gosse*a  

* Corresponding authors

a Université de Bordeaux, Institut des Sciences Moléculaires UMR CNRS 5525, Groupe Nanosystèmes analytiques, Site ENSCBP, 16 Av. Pey Berland, Pessac, France
E-mail: gosse@enscbp.fr
Fax: +33 5 4000 2717
Tel: +33 5 4000 6273

b Université Joseph Fourier, Département de Chimie Moléculaire UMR 5250, Grenoble, France
E-mail: sabine.chierici@ujf-grenoble.fr
Fax: +33 4 5652 0803
Tel: +33 4 5652 0804

c Université de Bordeaux, Centre de Physique Moléculaire Optique et Hertzienne, UMR 5798, 351 cours de la libération, Talence, France
E-mail: pinar.batat@etu.u-bordeaux1.fr
Fax: +33 5 4000 6970
Tel: +33 5 4000 6198

d Université de Bordeaux, Institut des Sciences Moléculaires UMR CNRS 5525, Centre d'Etude Structurale et d'Analyse des Molécules Organiques, 351 cours de la libération, Talence, France
E-mail: n.pinaud@ism.u-bordeaux1.fr
Fax: +33 5 4000 2623
Tel: +33 5 4000 6992

e Université de Bordeaux, Institut des Maladies Neurodégénératives UMR 5293, 351 cours de la libération, Talence, France
E-mail: p.meyrand@cnic.u-bordeaux1.fr
Fax: +33 5 5690 142
Tel: +33 5 4000 2562

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.

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

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Article information

DOI
https://doi.org/10.1039/C1OB06231J
Article type
Paper
Submitted
22 Jul 2011
Accepted
27 Sep 2011
First published
27 Sep 2011

Org. Biomol. Chem., 2011,9, 8489-8494

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

L. Peyrard, S. Chierici, S. Pinet, P. Batat, G. Jonusauskas, N. Pinaud, P. Meyrand and I. Gosse, Org. Biomol. Chem., 2011, 9, 8489 DOI: 10.1039/C1OB06231J

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