ArticleJournal of the American Chemical Society2011
Structure-activity relationships in tripodal transmembrane anion transporters: the effect of fluorination.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 58 papers.
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Who cites it
58 citing papers in PubMed, 330 citations in OpenAlex.
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- Near-Infrared Triggered Anion Transport Induces Cancer Cell Death.Angewandte Chemie (International ed. in English) · 2026Article
- Transmembrane Transport of cAMP and AMP Using a Two Component Small Molecule Transport System.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis of Novel Anion Recognition Molecules as Quinazoline Precursors.International journal of molecular sciences · 2025Article
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- Anion Transport by Bambusuril-Bile Acid Conjugates: Drastic Effect of the Cholesterol Content.Angewandte Chemie (International ed. in English) · 2025Article
- Activity Control of a Synthetic Transporter by Photodynamic Modulation of Membrane Mobility and Incorporation.Journal of the American Chemical Society · 2024Article
- Off-On Photo- and Redox-Triggered Anion Transport Using an Indole-Based Hydrogen Bond Switch.ACS omega · 2024Article
- Synthetic cation channel: reconstructing the ion permeation pathway of TRPA1 in an artificial system.RSC advances · 2024Article
- In vivo therapy of osteosarcoma using anion transporters-based supramolecular drugs.Journal of nanobiotechnology · 2024Article
- Photocontrolled activation of doublyChemical science · 2023Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
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.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.