Our group developed a new class of mechanosensitive membrane probes. To ensure the partitioning and the correct orientation inside the membrane, a charged "head" group was added to the design, generating an amphiphilic probe. Since the original design proven to show high mechanophoric properties the main focus was directed towards the hydrophilic part of the probe, the "head" group. A series of different linkers between the charged "head" group and the DTT core were tested resulting in the synthesis of a new probe which retained the mechanophoric properties of the original probe all while increasing its bio­compatibility and chemical and photo­ stability. Furthurmore, Dynamic covalent boronate ester was used in order to specifically target gangliosides on model membranes. The responsiveness of ganglioside recognition was tested by monitoring the incorporation of the probe inside large unilamellar vesicles containing different concentrations of ganglioside. pH­-dependence of this recognition was assessed.