The ability of deep cavitands to selectively recognize molecules of correct size, shape and charge, allows for their application as synthetic receptors. In particular, deep cavitands show significant affinity for trimethylammonium salts (NMe<sub>3</sub><sup>+</sup>) in aqueous environments through cation-p interactions. The cavitand’s hydrophobic, aromatic pocket allows for its incorporation into supported lipid bilayers while retaining its binding selectivity; incorporation into cell membranes is also possible. The rim and “feet” of the cavitand can be derivatized in order to impart properties such as solubility and charge as well as to better cater the desirable recognition interaction. Through derivatization, guests of multiple sizes can be immobilized by the cavitand, ranging from small molecules to proteins, even multivalent polymers which are grown in situ and have the ability to immobilize large structures such as cells. Complex binding events were studied by tailoring guests for specific cavitands. Furthermore, the cavitand, along with a fluorescent guest can be used as a fluorescence displacement sensor. Fluorescence displacement studies were also attempted inside live HeLa cells.

Molecular recognition in biomimetic membrane systems

255th National Meeting (2018)

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