ABSTRACT
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.
Subject(s)
Hydrocarbons, Halogenated/chemistry , Ions/chemistry , Phthalic Acids/chemistry , Picolinic Acids/chemistry , Mass Spectrometry , Molecular Structure , Phenylacetates/chemistry , Protons , Spectrophotometry, UltravioletABSTRACT
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.
Subject(s)
Anilides/chemistry , Chloride Channels/chemistry , Picolinic Acids/chemistry , Chloride Channels/chemical synthesis , Models, Molecular , Molecular StructureABSTRACT
The compelling chemical goal of modeling protein channel behavior has led to synthetic compounds that are true ion channels. Although they largely lack the selectivity and sophistication of highly evolved proteins, they successfully perform a variety of biological functions. This tutorial review describes these novel structures and their activity in living systems. Different channel structures show antibacterial to anticancer activity when tested against a variety of cell types.
