Porphyrins are widely applied for imaging, diagnosis, and treatment of diseases because of their excellent photophysical properties. However, porphyrins easily tend to aggregate driven by hydrophobic interaction and π-π stacking in an aqueous medium, which causes fluorescence quenching of the porphyrins as well as limitation of cell uptake and intracellular accumulation. Herein, cucurbit[10]uril (CB[10]) was used to fully encapsulate cationic porphyrin (CPor) in the large cavity with strong binding affinity in aqueous solutions, and the CPor aggregates were efficient disassembled, companying remarkable enhancing its fluorescence intensity. The CB[10]-based host-guest complex provided excellent protection to CPor, resulting in less susceptibility to oxidation and imparting higher photostability to CPor for cell imaging. In addition, by complexation with CB[10], it was found that the fluorescence signals and photostability of CPor were also effectively improved in cells with different reactive oxygen species levels. It is highly anticipated that the large macrocyclic host cavity-triggered large-guest encapsulation strategy in this work will provide a convenient and efficient method for designing supramolecular porphyrin dyes, thus broadening the diagnosis and imaging application in cells and microorganisms.
Keywords: cucurbit[10]uril; host−guest complex; photostability; porphyrin; supramolecular chemistry.