Improved Hypericin solubility via β-cyclodextrin complexation: Photochemical and theoretical study for PDT...

Hypericin (HY) is a lipophilic photosensitizer (PS) extensively employed for photodynamic therapy (PDT), presenting high absorption in the visible region, chemical and photostability, as well as a good triplet quantum yield. Supramolecular complexation of photosensitizers into cyclodextrins (CD) is promising to improve their poor solubility, compromising their bioavailability and upcoming applications in PDT. This research produced an inclusion complex between HY and β-CD through the co-solvent method. HY became soluble after inclusion into β-CD cavities, besides retaining its fluorescent and singlet oxygen quantum yields (ϕ_f =0.115 and ϕ_Δ= 0.23, respectively), which are essential parameters for PDT uses and are not reported in the literature. By the theoretical analysis, since ΔG < 0, it was easy to conclude that HY inclusion into β-CD is a spontaneous process. Additionally, the complexes presented no changes in excited states after complexation. β-CDHY was 27% more phototoxic than free HY when tested in MCF7 cells using 3 J cm^-2 of irradiation, indicating a better cell uptake of HY. These outcomes suggest that the inclusion complex of HY into β-CD has the potential for use in PDT.