C3-triiodocyclotriveratrylene as a key intermediate to fluorescent probes: application to selective choline recognition.
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.
Université de Bordeaux, Institut des Sciences Moléculaires UMR CNRS 5525, Groupe Nanosystèmes analytiques, Site ENSCBP, 16 Av. Pey Berland, 33607, Pessac, France.
Lisa
L
Peyrard
Sabine
S
Chierici
Sandra
S
Pinet
Pinar
P
Batat
Gediminas
G
Jonusauskas
Noël
N
Pinaud
Pierre
P
Meyrand
Isabelle
I
Gosse
D002794:Choline / Q000032:analysis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D005456:Fluorescent Dyes; D011083:Polycyclic Compounds; C483859:cyclotriveratrylene; D002794:Choline