Cart
Article
Structure–Activity Relationships in Tripodal Transmembrane Anion Transporters: The Effect of Fluorination
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Section:Abstract
A series of easy-to-make fluorinated tripodal anion transporters containing urea and thiourea groups have been prepared and their anion transport properties studied. Vesicle anion transport assays using ion-selective electrodes show that this class of compound is capable of transporting chloride through a lipid bilayer via a variety of mechanisms, including chloride/H+ cotransport and chloride/nitrate, chloride/bicarbonate, and to a lesser extent an unusual chloride/sulfate antiport process. Calculations indicate that increasing the degree of fluorination of the tripodal transmembrane transporters increases the lipophilicity of the transporter and this is shown to be the major contributing factor in the superior transport activity of the fluorinated compounds, with a maximum transport rate achieved for clog P = 8. The most active transporter 5 contained a urea functionality appended with a 3,5-bis(trifluoromethyl)phenyl group and was able to mediate transmembrane chloride transport at receptor to lipid ratios as low as 1:250000. Proton NMR titration and single crystal X-ray diffraction revealed the ability of the tripodal receptors to bind different anions with varying affinities in a 1:1 or 2:1 stoichiometry in solution and in the solid state. We also provide evidence that the most potent anion transporters are able to induce apoptosis in human cancer cells by using a selection of in vitro viability and fluorescence assays.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 1 ACS Journal articles (1 most recent appear below).
Oxyanion-Encapsulated Caged Supramolecular Frameworks of a Tris(urea) Receptor: Evidence of Hydroxide- and Fluoride-Ion-Induced Fixation of Atmospheric CO2 as a Trapped CO32– Anion
Sandeep Kumar Dey, Romen Chutia, and Gopal DasInorganic Chemistry2012 51 (3), 1727-1738Oxyanion-Encapsulated Caged Supramolecular Frameworks of a Tris(urea) Receptor: Evidence of Hydroxide- and Fluoride-Ion-Induced Fixation of Atmospheric CO2 as a Trapped CO32– Anion
Sandeep Kumar Dey, Romen Chutia, and Gopal DasInorganic Chemistry2012 51 (3), 1727-1738A tris(2-aminoethyl)amine-based tris(urea) receptor, L, with electron-withdrawing m-nitrophenyl terminals has been established as a potential system that can efficiently capture and fix atmospheric CO2 as air-stable crystals of a CO32–-encapsulated ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue September 07, 2011
- Article ASAPAugust 16, 2011
- Received: June 29, 2011
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
