Cyclodextrins dimers and trimers

Figure 6 Examples of supramolecular multicavity cyclodextrin dimer and trimer scaffolds.

S. Aime, E. Gianolio, F. Arena, A. Barge, K. Martina, G. Heropoulos, and G. Cravotto, New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands, Org. Biomol Chem., 7 (2), 370-379,2009. 

Moore, S., Askew, J.A., Gibson, G.L., Aborgrein, A., El-Agnaf, O., Allsop, D., Leung, D.K. and Breslow, R., Novel cyclodextrin dimers and trimers as inhibitors of amyloid peptide aggregation, Neurohiol Aging, 2002, 23, S105. 

Figure J4.12 Supramolecular polymers obtained by Harada and coworkers, (a) Self-inclusion complex (cyclic monomer) formed as a result of the flexibility of the linker between the hydrophobic guest and yS-cyclodextrin (CD) [47] (b) Cyclic dimer and trimer formed when more rigid linkers were applied [48] (c) Supramolecular...

The concept of cyclodextrin guest inclusion has been extended to the synthesis of a library of multicavity dimers and trimers of cyclodextrin that can bind specific guest molecules to mimic enzymes (Figure 6) Such supramolecular structures were tested with mono-, di-, and tri-substituted Gd + complexes bearing hydrophobic cyclohexyl moieties for interaction with the cyclodextrin cavities. The relaxivity enhancement increased with the number of cyclohexyl groups on the Gd + chelate. Further, the cyclodextrin trimer host-guest supramolecule with the tri-substituted Gd " " complex exhibited the greatest relaxivity... 

Sequence-selective binding of peptides and small proteins is of considerable interest. We saw that some cyclodextrin dimers could selectively doubly bind peptides in water with appropriately placed hydrophobic side chains. This built on our earlier collaborative work on the selective binding of peptides by simple cydodextrin. We then showed that we could break up a protein dimer and a protein tetramer with appropriate cydodextrin dimers in water, since such protein aggregation ordinarily involved hydrophobic side chains that our dimers could bind to. In perhaps the most striking example, our cydodextrin dimers and trimers were able to inhibit the protein aggregation involved in the formation of Alzheimer s plaques. ... 

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