Publication details

Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents

Authors

GILBERG Laura ZHANG Ben ZAVALIJ Peter Y. ŠINDELÁŘ Vladimír ISAACS Lyle

Year of publication 2015
Type Article in Periodical
Magazine / Source ORGANIC & BIOMOLECULAR CHEMISTRY
MU Faculty or unit

Faculty of Science

Citation
Web synthesis of a series of six new glycoluril derived molecular clips and acyclic CB[ n ]-type molecular containers
Doi http://dx.doi.org/10.1039/c5ob00184f
Field Organic chemistry
Keywords cucurbituruil; glycoluril; supramolecular chemistry
Description We present the synthesis of a series of six new glycoluril derived molecular clips and acyclic CB[n]-type molecular containers (1-3) that all feature SO3- solubilizing groups but differ in the number of glycoluril rings between the two terminal dialkoxyaromatic sidewalls. We report the X-ray crystal structure of 3b which shows that its dialkoxynaphthalene sidewalls actively define a hydrophobic cavity with high potential to engage in pi-pi interactions with insoluble aromatic guests. Compounds 1-3 possess very good solubility characteristics (>= 38 mM) and undergo only very weak self-association (K-s < 92 M-1) in water. The weak self-association is attributed to unfavorable SO3-center dot center dot center dot SO3- electrostatic interactions in the putative dimers 1(2)-4(2). Accordingly, we created phase solubility diagrams to study their ability to act as solubilizing agents for four water insoluble drugs (PBS-1086, camptothecin, beta-estradiol, and ziprasidone). We find that the containers 3a and 3b which feature three glycoluril rings between the terminal dialkoxy-o-xylylene and dialkoxynaphthalene sidewalls are less efficient solubilizing agents than 4a and 4b because of their smaller hydrophobic cavities. Containers 1 and 2 behave as molecular clip type receptors and therefore possess the ability to bind to and thereby solubilize aromatic drugs like camptothecin, ziprasidone, and PBS-1086.
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