We have discovered a remarkable sensitivity of the synthetic GFP chromophores (Cros) to environment which makes then unique reporters for use in supramolecular photochemistry.1 In solutions the fluorescence of most Cros is quenched due to the very efficient photoisomerization-induced deactivation. Some Cros show a remarkable sensitivity to confinement in bilayers. We have done an initial screening of the representative compounds from all available Cro classes, but only mesogenic compounds demonstrate a remarkable (more than a 100-fold) fluorescence enhancement when solubilized in the suspension of DPPC vesicles at room temperature. The temperature dependence of the fluorescence in the solid-state (gel) phase demonstrates an enormous enthalpy of deactivation as compared to that in bulk ethanol solution. This effect vanishes upon the DPPC phase transition at 41 oC which leads to melting of the bilayer into a liquid crystalline phase, and dramatic fluorescence decrease. The effects of the lipid headgroup, the rates of bilayer melting, and the hysteresis were also studied. 1Tolbert, L. M.; Baldridge, A.; Kowalik, J.; Solntsev, K. M. Acc. Chem. Res. 2012 , 45, 171-181. 

Synthetic analogs of the GFP chromophores as fluorescent probes for lipid bilayers

245th National Meeting (2013)

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