1.D.61.  The 4,4'-dinotropicolinanilide compound 28 (DNPA28) Family 

This compound, in contrast to some of its analogues which function as carriers (see 2.B.18 and 2.B.24), appears to function as an anion channel under physioloically relevant voltages.  Moreover, compound 28 exhibited "open-closed" conductance activity in planar bilayers with an apparent pore size of about 8 Å, similar to that of a Cl- anion (6.5 Å). Probably the pore forms by a self-assembly process via pi-pi interactions as suggested on the basis of several lines of evidence including x-ray structures revealing pi-pi stacks (Yamnitz et al. 2010; Gale et al. 2017).


 

References:

Gale, P.A., J.T. Davis, and R. Quesada. (2017). Anion transport and supramolecular medicinal chemistry. Chem Soc Rev 46: 2497-2519.

Yamnitz, C.R., S. Negin, I.A. Carasel, R.K. Winter, and G.W. Gokel. (2010). Dianilides of dipicolinic acid function as synthetic chloride channels. Chem Commun (Camb) 46: 2838-2840.