Fig. 1: 1,2-dithiolanes in chemical biology. | Nature Communications

Fig. 1: 1,2-dithiolanes in chemical biology.

From: Cyclic 5-membered disulfides are not selective substrates of thioredoxin reductase, but are opened nonspecifically

Fig. 1

a Linear disulfide-based cellular delivery: irreversible cleavage of linear disulfides after cell entry leads to intracellular cargo release (Pr-SH: intracellular protein thiol). b From linear, to cyclic 6-membered, to increasingly ring-strained 5-membered disulfides, to ETPs. c Strained 1,2-dithiolanes in natural products. d Fast, irreversible and nonspecific thiol-disulfide interchange of 1,2-dithiolanes by exofacial thiols, followed by dynamic transmembrane exchange cascades, enhances cellular uptake and intracellular delivery. [a:data from Matile et al.30]. e Some of the 1,2-dithiolane-based “TRFS” probes and prodrugs that have been reported as selective cellular substrates of thioredoxin reductase [TRFS = “Thioredoxin Reductase Fluorogenic Substrate“16,18,45].

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