Chloride anion transport and copper-mediated DNA cleavage by C-ring functionalized prodigiosenes

Abstract

A new class of prodigiosenes with stability-enhancing functionalities appended to the C-ring were found to transport chloride anions through liposomal membranes, as well as to induce copper-mediated DNA cleavage.

Calix[4]pyrrole-based anion transporters with tuneable transport properties

“…This trend in transporter efficiency may be an influence associated with partitioning of the carrier from the aqueous phase to the 55 lipid bilayer, mobility within the membrane, 'solubilising' the anion in the lipophilic portion of the membrane or a combination of all these factors. 21 The observed chloride transport activity for compounds 4-6 with vesicles loaded with NaCl suspended in a sulfate medium is low and therefore we 60 suggest that the compounds function as chloride-nitrate antiport agents and not sodium chloride co-transporters.…”

Using small molecules to facilitate exchange of bicarbonate and chloride anions across liposomal membranes

“…Prodigiosin appears to cause apoptosis of cancer cells selectively, 21 and the structural analogue obatoclax is currently in clinical trials for the treatment of cancer. 22 The origin of the biological activity has yet to be unambiguously established, although there is evidence that this class of compound facilitates the co-transport of HCl [23][24][25][26][27][28] and/or the anion exchange of chloride 29,30 across lipid bilayer membranes. Indeed, the antibiotic activity of prodigiosin-like molecules has been related to their activity as transmembrane Cl -carriers.…”

Aggregation Behavior and Dynamics of Synthetic Amphiphiles That Self‐Assemble to Anion Transporters

“…[1-6] Current, key challenges are to demonstrate the transport capabilities of a model channel system [7] and then to understand the structure and dynamics of the functioning transporter. [8,9] In this report, we bring to bear an array of analytical methods that have thus far been little used in this area.…”

“…The Cterminal ester group is either aromatic (benzyl, 6) or aliphatic (7)(8)(9)(10)(11). The alkyl groups in 7-11 are as follows: 7, ethyl; 8, isopropyl; 9, n-heptyl; 10, n-decyl; and 11, n-octadecyl.…”