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@article{1231958,
author = {Gilberg, Laura and Zhang, Ben and Zavalij, Peter Y. and Šindelář, Vladimír and Isaacs, Lyle},
article_location = {CAMBRIDGE (ENGLAND)},
article_number = {13},
doi = {http://dx.doi.org/10.1039/c5ob00184f},
keywords = {cucurbituruil; glycoluril; supramolecular chemistry},
language = {eng},
issn = {1477-0520},
journal = {ORGANIC & BIOMOLECULAR CHEMISTRY},
title = {Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents},
url = {http://pubs.rsc.org/en/content/articlelanding/2015/ob/c5ob00184f#!divAbstract},
volume = {13},
year = {2015}
}
TY - JOUR
ID - 1231958
AU - Gilberg, Laura - Zhang, Ben - Zavalij, Peter Y. - Šindelář, Vladimír - Isaacs, Lyle
PY - 2015
TI - Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents
JF - ORGANIC & BIOMOLECULAR CHEMISTRY
VL - 13
IS - 13
SP - 4041-4050
EP - 4041-4050
PB - ROYAL SOC CHEMISTRY
SN - 14770520
KW - cucurbituruil
KW - glycoluril
KW - supramolecular chemistry
UR - http://pubs.rsc.org/en/content/articlelanding/2015/ob/c5ob00184f#!divAbstract
L2 - http://pubs.rsc.org/en/content/articlelanding/2015/ob/c5ob00184f#!divAbstract
N2 - 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.
ER -
GILBERG, Laura, Ben ZHANG, Peter Y. ZAVALIJ, Vladimír ŠINDELÁŘ and Lyle ISAACS. Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents. \textit{ORGANIC \&{}amp; BIOMOLECULAR CHEMISTRY}. CAMBRIDGE (ENGLAND): ROYAL SOC CHEMISTRY, 2015, vol.~13, No~13, p.~4041-4050. ISSN~1477-0520. Available from: https://dx.doi.org/10.1039/c5ob00184f.
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