Binding of toluidine blue-myristic acid derivative to cucurbit[7]uril and human serum albumin: computational and biophysical insights towards a biosupramolecular assembly.

A new toluidine blue-myristic acid photosensitizer derivate (TBOMyr) was investigated as a design molecule to bind simultaneously to cucurbit[7]uril (CB[7]) and human serum albumin (HSA) with the aim of constructing a biosupramolecular assembly. Molecular docking and dynamics calculations revealed the main supramolecular and bio-molecular interactions of TBOMyr with the macrocycle or the protein, respectively. The addition of the negatively charged myristic acid-like tail resulted in a unique conformation of the CB[7] complex where the phenothiazine core was included in the cavity of CB[7], leaving the fatty acid portion free to interact with the protein. A favorable ternary interaction between TBOMyr, CB[7] and HSA was suggested by the calculations, and an experimental binding affinity in the order of 105 M-1 was determined for the TBOMyr@CB[7] complex with HSA. The new TBOMyr derivative could find applications in photodynamic therapy benefiting from the biosupramolecular interactions as a transport system.