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

Organic & Biomolecular Chemistry Pub Date: 2011-09-27 DOI: 10.1039/C1OB06231J

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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