2.B.44. The Synthetic Indole-based Perenosin (SIP) Family
Prodigiosin (TC# 2.B.20) is one of the most potent anion transporters. Inspired by the structure of this natural product, Jowett et al. 2017 designed and synthesised a new class of H+/Cl- cotransporters named 'perenosins'. The described a library of indole-based perenosins and their anion transport properties. The new transporters showed superior transmembrane transport efficiency when compared to other indole-based transporters, due to favourable encapsulating effects from the substituents on the perenosin backbone. The compounds function as 'strict' HCl cotransporters. Cell viability studies showed that some compounds specifically trigger late-onset cell death after 72 h with a unique correlation to the position of alkyl chains on the perenosins. A combination of cell cycle arrest and apoptosis was responsible for the observed decrease in cell viability (Jowett et al. 2017).