The surfaces of mammalian cells consist of a variety of membrane-bound receptors that possess selective, non-covalent molecular recognition mechanisms to control substrate transport. The use of synthetic receptors capable of �self-incorporation� in cellular membranes can mimic extracellular recognition. Deep cavitands are open-ended synthetic receptors that can selectively recognize small molecules of the correct size, shape and charge. They can be incorporated into supported lipid bilayers (SLBs), natural cellular membrane mimics, retaining their binding selectivity for substituted trimethylammonium (R-NMe3+) salts. The open-ended host can recognize a wide variety of species that contain R-NMe3+ groups at the bilayer:water interface, and the process is monitored by Surface Plasmon Resonance (SPR) spectroscopy. To study the scope of guests that can be recognized by cavitands embedded in biomimetic SLBs, several proteins of various sizes were functionalized with R-NMe3+ binding handles and the recognition event monitored by SPR. In the absence of cavitand, derivatized proteins show no affinity for SLBs. Shape-based molecular recognition with a synthetic host in living cells is far more challenging than in biomimetic membrane systems, due to the vast array of competitive species in a living cell. Despite the complexity of the environment, cavitandis capable of selective guest recognition and transmembrane transport in living cells. The cavitand was combined with fluorescent guest withR-NMe3+ binding handle in HeLa cells, and selective transport of the guest into the cells was observed. 

Extracellular non-covalent molecular recognition by self-folding synthetic receptors

248th National Meeting (2014)

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