Ganglioside-Selective Mechanosensitive Fluorescent Membrane Probes

Article Article scientifique Article Ganglioside-Selective Mechanosensitive Fluorescent Membrane Probes eng 2018 author Strakova Karolina 854961 author Soleimanpour Saeideh 749283 author Diez Castellnou Marta 837259 author Sakai Naomi 0000-0002-9460-1944 131140 author Matile Stefan 0000-0002-8537-8349 129654 e1800019 10.1002/hlca.201800019 0018-019X The development of fluorescent probes to image forces in cells is an important challenge in chemistry and biology. Planarizable push‐pull probes have been introduced recently for this purpose. To provide most valuable information on forces in complex systems, these mechanosensitive ‘flipper' probes will have to be localized by molecular recognition of targets of interest. Here we report fluorescent flippers that selectively recognize gangliosides on the surface of lipid bilayer membranes by formation of dynamic covalent boronate esters. The original flipper probes were equipped with 2‐fluorophenyl boronic acids and benzoboroxoles using consecutive triazole and oxime ligation. Evaluation was done in large unilamellar vesicles composed of EYPC/SM/CL/GM 40:40‐x:20:x to obtain mixed membranes with separate liquid‐disordered (Ld) and ganglioside (GM) containing liquid‐ordered (Lo) domains. With increasing GM concentration, fluorescence intensities increased and excitation maximum shifted to the red. Deconvolution of the spectra confirmed that these changes originate from a migration of the flipper probes from Ld to Lo domains upon binding to the gangliosides and thus the planarization in the more ordered environment. Control mechanophores without boronic acids failed to show the same response, and fructose partially inhibited the ganglioside sensitivity. These results demonstrate that it is possible to selectively accumulate mechanosensitive flipper probes in Lo domains and, more generally, that probe localization in complex membranes is possible and matters. Dewey 540 36 Département de chimie organique 141 false 761 Groupe Matile Helvetica Chimica Acta 101 5 90c9c5eb-2c67-4fc9-8048-83bf3ba3937b Article (Published version) Restricted Strakova_et_al-2018-Helvetica_Chimica_Acta.pdf 4800325 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Ganglioside-Selective Mechanosensitive Fluorescent Membrane Probes	Helvetica Chimica Acta			2018	580	1

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Diez Castellnou, Marta