137592-26-8Relevant articles and documents
Enhanced Production and Anticancer Properties of Photoactivated Perylenequinones
Al Subeh, Zeinab Y.,Raja, Huzefa A.,Monro, Susan,Flores-Bocanegra, Laura,El-Elimat, Tamam,Pearce, Cedric J.,McFarland, Sherri A.,Oberlies, Nicholas H.
, p. 2490 - 2500 (2020)
Hypocrellins and hypomycins are naturally occurring fungal perylenequinones with potential photodynamic activity against cancer and microbial diseases. This project pursued three lines of research. First, the production of perylenequinones was enhanced by investigating the effect of culture medium and light exposure on their biosynthesis. Solid-fermentation cultures on rice medium allowed for enhanced production of hypocrellins as compared to Cheerios or oatmeal medium. Alternatively, increased production of hypomycins, which are structurally related to the hypocrellins, was observed on oatmeal medium. In both cases, light exposure was an essential factor for the enhanced biosynthesis. In addition, this led to the discovery of two new perylenequinones, ent-shiraiachrome A (5) and hypomycin E (8), which were elucidated based on spectroscopic data. Finally, the photocytotoxic effects of both classes of compounds were evaluated against human skin melanoma, with EC50 values at nanomolar levels for hypocrellins and micromolar levels for hypomycins. In contrast, both classes of compounds showed reduced dark toxicity (EC50 values >100 μM), demonstrating promising phototherapeutic indices.
Hypocrellin B-based activatable photosensitizers for specific photodynamic effects against high H2O2-expressing cancer cells
Kitamura, Takashi,Nakata, Hirotaka,Takahashi, Daisuke,Toshima, Kazunobu
, p. 242 - 245 (2022/01/04)
A novel tumor-related biomarker, a H2O2-activatable photosensitizer4based on the 1,3-dicarbonyl enol moieties of hypocrellin B (3), was designed and synthesized. The photosensitizer4showed a blue-shifted absorption band compared with3, and showed negligible photosensitizing ability without H2O2. However, the release of3from4by the reaction with H2O2regenerated the photosensitizing ability. Furthermore,4exhibited selective and effective photo-cytotoxicity against high H2O2-expressing cancer cells upon photo-irradiation with 660 nm light, which is inside the phototherapeutic window.
