Dianilides of dipicolinic acid function as synthetic chloride channels

Abstract

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.

Anion receptor chemistry: highlights from 2008 and 2009

“…Building on their work on the use of isophthalamides as anion transporters, 111 Gokel and co-workers have also illustrated the use of tris-arenes based on isophthalic acid and 2,6-dipicolinic acid (214-221) for transport of plasmid DNA into ampicillin resistant E. coli. 112 Transformation experiments using 2.6 kb plasmids showed isophthalamides with OCH 3 (214) and H (215) substituents give an enhancement in transformation of 2.3-and 2-fold respectively compared with DMSO and water controls, while the Cl (216) and CN (217) substituted species were less effective than the controls.…”

Membrane activity of 3-hydroxyglutarate diesters

“…In the long term, such practical applications will require relatively simple syntheses and relatively simple compounds, so one enduring motivation has been to identify 'minimalist' structures. Significant milestones in this regard are the ionpair systems reported by Kobuke and co-workers (14), linear oligoethyleneglycol esters reported by Schäfer, Neumann and co-workers (15), the isophthalate ethers we reported (16) and more recent reports of isophthalamides by the Yang group (8,9) and isopicolinamides by Gokel and co-workers (17). Underlying this series of papers are the puzzling and poorly reproducible channels formed by the detergent Triton X 100 (18,19).…”

Chromogenic amides of pyridine-2,6-dicarboxylic acid as anion receptors

“…Among all presented ligands, to the best our knowledge -on the basis of Chemical Abstracts, only L3 has been reported in literature until now. The reported method, where acetonitrile (25) was used as a solvent, gives a significantly lower yield (52% for L3) of the desired compounds.…”

“…Several of these compounds may act as both colorimetric and fluorescent anion chemosensors. For examples of different types of anion receptors, see Refs (18)(19)(20)(21)(22)(23)(24)(25)(26).…”