Detailed Information on Publication Record
2015
Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents
GILBERG, Laura, Ben ZHANG, Peter Y. ZAVALIJ, Vladimír ŠINDELÁŘ, Lyle ISAACS et. al.Basic information
Original name
Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents
Authors
GILBERG, Laura (276 Germany, belonging to the institution), Ben ZHANG (156 China), Peter Y. ZAVALIJ (840 United States of America), Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution) and Lyle ISAACS (840 United States of America)
Edition
ORGANIC & BIOMOLECULAR CHEMISTRY, CAMBRIDGE (ENGLAND), ROYAL SOC CHEMISTRY, 2015, 1477-0520
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Field of Study
10401 Organic chemistry
Country of publisher
United Kingdom of Great Britain and Northern Ireland
Confidentiality degree
není předmětem státního či obchodního tajemství
Impact factor
Impact factor: 3.559
RIV identification code
RIV/00216224:14310/15:00080727
Organization unit
Faculty of Science
UT WoS
000351597700023
Keywords in English
cucurbituruil; glycoluril; supramolecular chemistry
Tags
International impact, Reviewed
Změněno: 28/4/2016 14:04, Ing. Andrea Mikešková
V originále
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.
In Czech
V této publikaci prezentujeme syntézu série šesti nových glykolurilových derivátůmolekulárních klips a acyklických molekulárních kontejnerů vycházejících z cucurbiturilů. Všechny tyto deriváty mají na svých krajích zavedené skupiny zvyšující jejich rozpustnost ve vodě, ale odlišují se počtem glykolurilových jednotek.
Links
| EE2.3.30.0009, research and development project |
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| GA13-15576S, research and development project |
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| LM2011028, research and development project |
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| LO1214, research and development project |
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