Chloride Transport Across Vesicle and Cell Membranes by Steroid‐Based Receptors

Koulov, Atanas V.; Lambert, Timothy N.; Shukla, R. C.; Jain, Mahim; Boon, J. Middleton; Smith, Bradley D.; Li, Hongyu; Sheppard, David N.; Joos, Jean‐Baptiste; Clare, John P.; Davis, Anthony P.

doi:10.1002/ange.200351957

Cited by 44 publications

(29 citation statements)

References 21 publications

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“…52 The steroid scaffold is known to pre-organize two or three anion-binding motifs, resulting in powerful Cl À ionophores (''cholapods''). [53][54][55] We subjected several reported and new cholapod-based urea anionophores to the selectivity test. Compound 15 53 showed modest selectivity of 3-fold, which was eliminated when a trifluoroacetamide group, 54 as an additional hydrogen-bond donor, was introduced (compound 16), likely because of its high acidity (Table 2).…”

Section: Supplemental Information For Synthesis Of New Compounds) Thmentioning

confidence: 99%

“…[53][54][55] We subjected several reported and new cholapod-based urea anionophores to the selectivity test. Compound 15 53 showed modest selectivity of 3-fold, which was eliminated when a trifluoroacetamide group, 54 as an additional hydrogen-bond donor, was introduced (compound 16), likely because of its high acidity (Table 2). However, remarkable selectivity was achieved by 17 and 18, which feature binding-site enclosure ( Table 2).…”

Section: Supplemental Information For Synthesis Of New Compounds) Thmentioning

confidence: 99%

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Nonprotonophoric Electrogenic Cl− Transport Mediated by Valinomycin-like Carriers

Judd

Howe

et al. 2016

Chem

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Synthetic anion transporters can facilitate H + transport via deprotonation, or OH À transport via hydrogen bonding to OH À , thus allowing dissipation of transmembrane pH gradients, an undesired side-effect for biomedical applications as Cl À ionophores. To address this limitation, Gale and colleagues have developed two anionophores that show high Cl À > H + /OH À selectivity. Preliminary cellular studies support the biological relevance of the selectivity.

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Section: Supplemental Information For Synthesis Of New Compounds) Thmentioning

confidence: 99%

Section: Supplemental Information For Synthesis Of New Compounds) Thmentioning

confidence: 99%

Nonprotonophoric Electrogenic Cl− Transport Mediated by Valinomycin-like Carriers

Judd

Howe

et al. 2016

Chem

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154

202

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“…[13] The vesicles were loaded with a solution of NaCl (500 mm) and then diluted to produce a 1 mm suspension in a solution of NaNO 3 (500 mm). The integrity of the liposome membranes was established according to reported procedures.…”

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confidence: 99%

Synthesis, Anion‐Binding Properties, and In Vitro Anticancer Activity of Prodigiosin Analogues

et al. 2005

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“…This trend was consistent with but not exclusive for an ion carrier mechanism. [2,15,18] The presence of anionic lipids in the bilayer did not influence efficiencies much ( Figure S5). This insensitivity of polyanionic DNA to anionic phospholipids was in meaningful contrast to the strong dependence of polycationic CPPs and K + channels, in which anionic lipids in the membrane can act as intrinsic counterion activators.…”

Section: Dna As Transporters In Lipid Bilayer Membranesmentioning

confidence: 96%

Amphiphilic Counterion Activators for DNA: Stimuli‐Responsive Cation Transporters and Biosensors in Bulk and Lipid Bilayer Membranes

et al. 2009

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We report that amphiphilic counterions can enable DNA to act as cation carrier, enzyme detector and biosensor. Calf thymus DNA is used as example throughout the study. Evaluation of a series of counterion activators suggests that strong amphiphilicity, alkyl or calix[4]arene tails and guanidinium cations give best results, whereas weak amphiphilicity, bola-amphiphilicity, planar aryl tails and ammonium cations are less satisfactory for various reasons. In the U-tube, DNA-counterion complexes can carry cations such as safranin O or p-xylene-bis-pyridinium bromide (DPX) across bulk chloroform membranes, whereas anions such as carboxyfluorescein (CF) and (8-Hydroxy-1,3,6-pyrenetrisulfonate (HPTS) are not transported. Uptake of DNA-counterion complexes into intact vesicles is demonstrated by DNA trapping experiments with internal polylysine. Comparison of results from different assays suggests that DNA-counterion complexes act as cation carriers under mild conditions, whereas pore formation and lysis dominate at higher concentrations. Applicability of DNA-counterion transporters for the detection of enzyme activity is demonstrated with phytate as an inactivating substrate and phytase as a reactivating enzyme. Compatibility with biosensing is exemplified with the fluorometric monitoring of phytate levels in almond extracts. The conceptual significance of these findings is briefly discussed, as are promising perspectives such as the application of DNA chemistry to multianalyte sensing in fluorogenic vesicles.

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Chloride Transport Across Vesicle and Cell Membranes by Steroid‐Based Receptors

Cited by 44 publications

References 21 publications

Nonprotonophoric Electrogenic Cl− Transport Mediated by Valinomycin-like Carriers

Nonprotonophoric Electrogenic Cl− Transport Mediated by Valinomycin-like Carriers

Synthesis, Anion‐Binding Properties, and In Vitro Anticancer Activity of Prodigiosin Analogues

Amphiphilic Counterion Activators for DNA: Stimuli‐Responsive Cation Transporters and Biosensors in Bulk and Lipid Bilayer Membranes

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