New “Cholapod” Anionophores; High-Affinity Halide Receptors Derived from Cholic Acid

Ayling, AJ; Pérez-Payán, M. Nieves; Davis, Anthony P.

doi:10.1021/ja016796z

Cited by 145 publications

(57 citation statements)

References 9 publications

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“…Two methods were used to detect the passage of chloride ions across the membranes. The first involved the use of lucigenin (18), a chloride-sensitive fluorescent dye, to detect inwardflowing chloride ions.…”

Section: Measurement Of Transport Rates and Binding Constants-methodomentioning

confidence: 99%

Structure–Activity Relationships in Cholapod Anion Carriers: Enhanced Transmembrane Chloride Transport through Substituent Tuning

McNally¹,

Koulov²,

Lambert³

et al. 2008

Chemistry A European J

119

111

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Chloride transport by a series of steroid-based "cholapod" receptors/carriers was studied in vesicles. The principal method involved preincorporation of the cholapods in the vesicle membranes, and the use of lucigenin fluorescence quenching to detect inward-transported Cl − . The results showed a partial correlation between anion affinity and transport activity, in that changes at the steroidal 7 and 12 positions affected both properties in concert. However, changes at the steroidal 3-position yielded irregular effects. Among the new steroids investigated the bis-p-nitrophenylthiourea 3 showed unprecedented activity, giving measurable transport through membranes with a transporter/lipid ratio of 1:250 000 (an average of <2 transporter molecules per vesicle). Increasing transporter lipophilicity had no effect, and positively charged steroids had low activity. The p-nitrophenyl monourea 25 showed modest but significant activity. Measurements using a second method, requiring the addition of transporters to preformed vesicle suspensions, implied that transporter delivery was problematic in some cases. A series of measurements employing membranes of different thicknesses provided further evidence that the cholapods act as mobile anion carriers.

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Section: Measurement Of Transport Rates and Binding Constants-methodomentioning

confidence: 99%

Structure–Activity Relationships in Cholapod Anion Carriers: Enhanced Transmembrane Chloride Transport through Substituent Tuning

McNally¹,

Koulov²,

Lambert³

et al. 2008

Chemistry A European J

119

111

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show abstract

“…More recently, redox systems based upon N,N 0 -tetramethyl-1,4-phenylenediamine (TMPD, 46, Wurster's blue) have been designed. 73 46 (L) undergoes a first reversible one-electron oxidation to the semiquinoid radical cation L + , 47, at a moderately negative potential vs. SCE, then a second one-electron oxidation at a more positive potential, to give the quinoid species L 2+ (48), as illustrated in Scheme 8.…”

Section: Fig 29mentioning

confidence: 99%

Anion recognition by hydrogen bonding: urea-based receptors

2010

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Since 1992 a variety of urea-based anion receptors have been synthesised, of varying complexity and sophistication. This critical review will focus on some distinctive aspects of anion recognition by urea derivatives, with a special reference to: (i) design and synthesis, (ii) methodologies for the investigation of the receptor-anion interaction in solution, (iii) the interpretation of the solution behaviour on the basis of the structural interplay between the receptor and the anion. It will be shown that the efficiency of urea as a receptor subunit depends on the presence of two proximate polarised N-H fragments, capable (i) of chelating a spherical anion or (ii) of donating two parallel H-bonds to the oxygen atoms of a carboxylate or of an inorganic oxoanion, a property which is shared with other diamides, e.g. squaramide. The wide use of urea in the design of neutral anion receptors seems to depends on the ease of its synthesis, in particular through the reaction of a primary amine group with an isocyanate, which allows the high-yield preparation of symmetrically and unsymmetrically substituted derivatives (83 references).

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“…These adverse and beneficial effects of fluoride prompted many scientists to develop chemosensors for fluoride recognition [15]. Fluoride ion receptors based on triarylboranes [21,22], desilyation [23,24], Pyrroles [25,26], amides [27][28][29][30], ureas [31,32], thioureas [33][34][35], or sulphonamides [36,37] are available in literature. Receptors based on NH and OH deprotonation or hydrogen bond formation by fluoride ion [38][39][40][41] failed to report the selectivity of F -ion over the other competitive anions.…”

mentioning

confidence: 99%

Aminobenzohydrazide based colorimetric and ‘turn-on’ fluorescence chemosensor for selective recognition of fluoride

Anand

Sivaraman

Iniya

et al. 2015

Analytica Chimica Acta

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New “Cholapod” Anionophores; High-Affinity Halide Receptors Derived from Cholic Acid

Cited by 145 publications

References 9 publications

Structure–Activity Relationships in Cholapod Anion Carriers: Enhanced Transmembrane Chloride Transport through Substituent Tuning

Structure–Activity Relationships in Cholapod Anion Carriers: Enhanced Transmembrane Chloride Transport through Substituent Tuning

Anion recognition by hydrogen bonding: urea-based receptors

Aminobenzohydrazide based colorimetric and ‘turn-on’ fluorescence chemosensor for selective recognition of fluoride

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