The cellular membrane is a crucial dynamic structure made of lipids, which protects the cellular content and facilitates interactions of the cells with the outer environment. This thesis focused on two questions about the membrane: visualization of membrane tension and transmembrane thiol-mediated uptake (TMU). In the first part, a new scaffold of fluorescent membrane tension Flipper probes was synthesized and evaluated. The second part was dedicated to the development of new motifs for TMU and its inhibition. In the study, cyclic thiosulfonates arose as a new prominent scaffold, highlighted by its excelled reactivity with thiols over the less oxidized analogs. Furthermore, the reaction product, sulfinate, was shown to continue further exchange with disulfides in a unique, water-content-dependent manner. In the last part, the templated ring-opening oligomerization of cyclic disulfides was investigated. The use of oligo(p-phenyleneethynylene)s as rigid templates was shown effective for the formation of up to tri(disulfide) products.