Halide ions complex and deprotonate dipicolinamides and isophthalamides: assessment by mass spectrometry and UV-visible spectroscopy.

The F(-), Cl(-), and Br(-) binding selectivity of bis(p-nitroanilide)s of dipicolinic and isophthalic acids was studied by using competitive electrospray mass spectrometry and UV-Visible spectroscopy. Both hosts prefer binding Cl(-) over either F(-) or Br(-). Host deprotonation was observed to some extent in all experiments in which the host was exposed to halide ions. When F(-) was present, host deprotonation was often the major process, whereas little deprotonation was observed by Cl(-) or Br(-), which preferred complexation. A solution of either host changed color when mixed with a F(-), H(2)PO(4)(-), di- or triphenylacetate solution.

Dianilides of dipicolinic acid function as synthetic chloride channels.

We report that N(2),N(6)-bis(4-nitrophenyl)pyridine-2,6-dicarboxamide, which is related to known isophthalic acid dianilides, transports Cl(-) ions through phospholipid bilayer membranes and shows clear evidence of channel activity.

Transport of chloride and carboxyfluorescein through phospholipid vesicle membranes by heptapeptide amphiphiles.

Seven synthetic anion transporters (SAT) of the general form R(2)N-COCH(2)OCH(2)CO-(Gly)(3)-Pro-(Gly)(3)-OR' were prepared. Three pairs of compounds each contained twin n-hexyl, n-decyl, and n-octadecyl (R) groups at the N-terminus and one contained twin n-tetradecyl groups. Three of the compounds were C-terminated by benzyl and three by heptyl (R') residues. The ability of these compounds to mediate ion release from phospholipid vesicles was assessed. Chloride release was measured by ion selective electrode measurements and by chloride quenching of the fluorescent dye lucigenin. Transport of the anion carboxyfluorescein (CF) was measured by fluorescence dequenching. Differences in both the C- (R') and N-terminal (R) residues within the ionophores affected anion transport. The chloride release data acquired by ion selective electrode and fluorescence methods were similar but not identical. A possible carrier mechanism for Cl(-) transport was discredited. Both Cl(-) and CF anions were released from vesicles by these compounds. The results of CF and Cl(-) transport showed good consistency when the ionophore's N-terminal chains were either decyl or octadecyl but not when they were hexyl. The transport of CF and Cl(-) appears to be fundamentally different when R is C(6) compared to C(10) or C(18). Differences between the behavior of SATs with Cl(-) and CF were also reflected in negative ion mass spectrometric studies.