β-1,3-Glucan-complexed tetra(aminophenyl)porphyrin changed from ‘off-state’ to ‘on-state’ with respect of fluorescence and showed photodynamic activity by intracellular uptake.
A preparation of a lipid-membrane-incorporated tetraphenylporphyrin was achieved from the corresponding tetraphenylporphyrin·cyclodextrin complexes using an exchange method in both liposomes and cells.
β‐(1,3‐1,6)‐D‐Glucan, λ‐carrageenan, tamarind gum, and pullulan can dissolve various porphyrin derivatives via the formation of complexes in water using a high‐speed vibration milling method. The aqueous solutions of the resulting complexes exhibit long‐term stability. Despite the adverse effects of the self‐quenching process, notable fluorescence and improved photodynamic activity of the polysaccharide‐complexed porphyrin derivatives were observed in the presence of liposomes, micelles, cyclodextrins, and HeLa cells. It was noted that the type of porphyrins was more important than the type of polysaccharides present in the complex. Porphyrin self‐aggregates were monodispersed in the lipid membranes of the liposomes and lysosomes. The polysaccharide‐complexed porphyrin derivatives showed increased photodynamic activity toward HeLa cells under photoirradiation between 610 and 740 nm.
Polysaccharides, such as pullulan and λ‐carrageenan, can incorporate tetraphenylethylene derivatives through self‐aggregation in water by a high‐speed vibration milling method, which cannot be done by sonication and heating methods. Aggregation‐induced emission is observed from the tetraphenylethylene‐polysaccharide complexes. Furthermore, the tetraphenylethylene self‐assembled into polysaccharides is able to preserve the initial helical chirality (M‐ or P‐helicity) of the crystals in water after ball milling. Intracellular uptake of the polysaccharide‐complexed tetraphenylethylene derivative with a phenol unit by HeLa cells is enhanced compared with that without the phenol unit.
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