Laure-Lise Chapellet

Structural modifications of the cryptophanes: towards new types of biosensors
Laure-Lise Chapellet

Cryptophanes are known to be good hosts for xenon [1] and thus cryptophane-based biosensors have been developed exploiting the highly sensitive chemical shift of xenon depending on its environment [2].
Structural modifications of the cryptophane host could allow to broaden the scope of this study. We will present here two possible modifications either targeting the aromatic entity of the cyclotriveratrylene (CTV) unit by replacing the benzenic entity by a pyrrolic one or inserting a hydroxyl group on one of the arm in a way to create a new anchor point for a recognition side-chain.
Cyclononatripyrroles (CNTPs) can be considered as pyrrolic cyclotriveratrylene (CTV) analogues, and as such should present similar binding properties, especially towards xenon.
Different syntheses of CNTPs have been reported to date [3,4,5]  among which the rapid and simple method designed by J. Sessler seems particularly suited to our purposes.

[1]    A. Fogarty, P. Berthault, T. Brotin*, G. Huber, H. Desvaux and J.-P. Dutasta*, J. Am. Chem. Soc.  129 (2007) 10332-10333.
[2]    V. Roy, T. Brotin, J.-P. Dutasta, M.-H. Charles, T. Delair, F. Mallet, G. Huber, H. Desvaux, Y. Boulard and P. Berthault ChemPhysChem, 8 (2007) 2082-2085.
[3]    Treibs, A.; Kreuzer, F. H.; Häberle, N. Justus Liebigs Ann. Chem. 1970, 733, 37.
[4]    Treibs, A.; Kreuzer, F. H.; Häberle, N. Justus Liebigs Ann. Chem. 1970, 733, 37.
[5]    Fumoto, Y.; Uno, H.; Ito, S.; Tsugumi, Y.; Sasaki, M.; Kitawaki, Y.; Ono, N. J. Chem. Soc., Perkin Trans. 1 2000, 2977.