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

Lisa Peyrard (1) , Sabine Chierici (2) , Sandra Pinet (1) , Pinar Batat (3) , Gediminas Jonusauskas (3) , Noël Pinaud (1) , Pierre Meyrand (4) , Isabelle Gosse (1)

1 ISM - Institut des Sciences Moléculaires
2 DCM - Département de Chimie Moléculaire
3 LOMA - Laboratoire Ondes et Matière d'Aquitaine
4 IMN - Institut des Maladies Neurodégénératives [Bordeaux]

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.

Domaines: Chimie-Physique [physics.chem-ph]

Lisa Peyrard, Sabine Chierici, Sandra Pinet, Pinar Batat, Gediminas Jonusauskas, et al.. C3-triiodocyclotriveratrylene as a key intermediate to fluorescent probes: application to selective choline recognition. Organic & Biomolecular Chemistry, 2011, 9 (24), pp.8489-8494. ⟨10.1039/C1OB06231J⟩. ⟨hal-00673589⟩