Beilstein J. Org. Chem.2020,16, 2007–2016, doi:10.3762/bjoc.16.167
chemistry tools to deliver into living cells has seen a shift of attention from counterion-mediated uptake of cell-penetrating peptides (CPPs) and their mimics, particularly the Schmuck cation, toward thiol-mediateduptake with cell-penetrating poly(disulfide)s (CPDs) and cyclic oligochalcogenides (COCs
; thiol-mediateduptake; Introduction
The effective delivery of substrates of free choice into cells with minimal endosomal capture on the one hand and a minimal toxicity on the other remains one of the grand challenges in science [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. This
depolymerization as soon as they reach the cytosol, and their endosomal capture is minimal because they enter cells by thiol-mediateduptake (Figure 4) [38][39][40][41][42][43][44][45][46][47][48]. This mechanism operates by dynamic covalent disulfide exchange on the cell surface and on the way into the cell
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Graphical Abstract
Figure 1:
Schematic representation of binding models between organic cations (simple ammonium, guanidinium, S...