Issue 2, 2009
From the journal:

Organic & Biomolecular Chemistry

New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands

Silvio Aime,a   Eliana Gianolio,a   Francesca Arena,a   Alessandro Barge,b   Katia Martina,b   George Heropoulosc  and  Giancarlo Cravotto*b  

* Corresponding authors

a Dipartimento di Chimica IFM, Università di Torino, Via Giuria 7, Torino, Italy

b Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via Giuria 9, Torino, Italy
E-mail: giancarlo.cravotto@unito.it
Fax: +390116707687
Tel: +390116707684

c Institute of Organic and Pharmaceutical Chemistry, National Hellenic Res. Found., Vas. Constantinou Av. 48, Athens, Greece

Abstract

Bridged cyclodextrin dimers and trimers, in which respectively two and three hydrophobic cavities lie in close proximity, display much higher binding affinities and molecular selectivities than do parent cyclodextrins (CDs). By joining βCD units with links inserted at different positions (2-2′, 3-2′, 6-2′ or 6-2′-6″) and interposing spacers of different lengths and shapes, multicavity structures can be synthesized that are precisely tailored to fit specific guest molecules. This enzyme-mimicking strategy can also be used to generate stable supramolecular adducts. A series of CD dimers and trimers was prepared in good yields by carrying out the critical synthetic steps under power ultrasound (US) or microwave (MW) irradiation. Starting from azide and acetylenic CD derivatives, we exploited an efficient MW-promoted Huisgen 1,3-dipolar cycloaddition in the presence of Cu(I) salts. The resulting bridged CD derivatives gave stable adducts with magnetic-resonance-imaging contrast agents (MRI CAs) containing gadolinium(III) chelates. These inclusion complexes were found to be 2 to 3 orders of magnitude more stable than those formed by βCD and to be endowed with high relaxivity values.

Graphical abstract: New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands

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Article information

DOI
https://doi.org/10.1039/B812172A
Article type
Paper
Submitted
16 Jul 2008
Accepted
17 Oct 2008
First published
20 Nov 2008

Org. Biomol. Chem., 2009,7, 370-379

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New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands

S. Aime, E. Gianolio, F. Arena, A. Barge, K. Martina, G. Heropoulos and G. Cravotto, Org. Biomol. Chem., 2009, 7, 370 DOI: 10.1039/B812172A

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