Phototriggered Release of a Transmembrane Chloride Carrier from an o‐Nitrobenzyl‐Linked Procarrier

Abstract

While there have been many studies on synthetic chloride carriers and ar ecent application for apoptotic cell death, so far,t he proposed huge potential of these systems in targeting cancer has not been realized due to their cytotoxicity to healthy cells.H erein, we describe the development of an indole-2-carboxamide receptor as an efficient membrane chloride carrier while the corresponding o-nitrobenzyl-linked derivative is ap rocarrier of the ion. Photoirradiation of the procarrier in liposomes results in release of the active carrier with up to 90 %t ransport efficiency.S uch photorelease of the carrier also works within cancer cells,resulting in efficient cell killing.Suchphotocleavable procarriers have great potential as ap hotodynamic therapyt oc ombat various types of cancers.

Voltage‐Switchable HCl Transport Enabled by Lipid Headgroup–Transporter Interactions

“…[3] Thea nion transport and anti-cancer properties of prodigiosins have inspired supramolecular chemists to develop synthetic anion transporters for potential biomedical applications in both anticancer treatment and channel replacement therapy for conditions such as cysticf ibrosis. [4] Important progress has been made in recent years in the development of highly active transporters that can mediate anion transport in synthetic vesicles [5] and in cells, [6] and in elucidating biological activities including apoptosis induction [7] and autophagy inhibition. [8] Despite numerous efforts in this area of research, no synthetic transporters developed so far can match the H + /Cl À symport activity of the highly evolved natural product prodigiosin (Figure 1).…”

Esterase‐Activatable Synthetic M+/Cl− Channel Induces Apoptosis and Disrupts Autophagy in Cancer Cells

“…Very recently, considerable efforts have been invested in the design of stimuli‐responsive ion transporters aiming to target cancer cells selectively. In this regard pH, light, enzymes, glutathione, etc. have drawn significant attention.…”

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

“…Inspired with our recent ion transport studies with acyclic and cyclic fluorinated sugar derived peptides [13][14], we investigated the ion transport activity of 1 and 2a across lipid bilayer membrane. In this study, the collapse of the pH gradient (pHout = 7.8 and pHin = 7.0), created across egg yolk L-α-phosphatidylcholine (EYPC) vesicles with entrapped 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (HPTS) dye (i.e., EYPC-LUVsHPTS) [71][72][73][74][75][76][77][78] was monitored by measuring the fluorescence intensity of the dye at λem = 510 nm (λex = 450 nm) with time ( Figure S11). Thus, addition of 2a (10 µM) resulted in the significant increase in HPTS fluorescence within 200 s ( Figure 6B), while oxazolone pseudodi-peptide 1 was found to be lesser active ( Figure 6A).…”