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.
First synthesis of methylated hypocrellin and its fluorescent excited state: A cautionary tale
Xu, Shangjie,Chen, Shen,Zhang, Manhua,Shen, Tao
, p. 2048 - 2050 (2003)
Methylated hypocrellins were obtained and characterized by satisfactory 1HNMR, UV-vis, IR, and mass data, and their absorption and fluorescence emission spectra were studied. A previous report of methylated hypocrellin (J. Phys. Chem. A 1999, 103, 7949) appears to be in error.
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.
Quantitative and site-directed chemical modification of hypocrellins toward direct drug delivery and effective photodynamic activity
Deng, Hong,Liu, Xin,Xie, Jie,Yin, Rong,Huang, Naiyan,Gu, Ying,Zhao, Jingquan
body text, p. 1910 - 1919 (2012/05/20)
For photodynamic therapy (PDT) treatment of microvascular diseases, drugs are delivered via blood circulation and the targets are vasculature endothelial cells, for which the contradictory requirements of hydrophilicity and lipophilicity of the drugs have been achieved by liposome preparations. Herein, it is demonstrated that the drug delivery and target affinity are achieved by a single chemical compound, hypocrellin B (HB) derivative 6 selected from three novel aminoalkanesulfonic acid HB derivatives, 5-7. 6 exhibits a much higher PDT activity (IC50 = 22 nM) on human gastric carcinoma BGC823 cells than HB, while it has no cellular toxicity in the dark. On the basis of estimation of the clinically required concentration according to relative PDT activity and clinical criteria, it can be predicted that 6 is directly deliverable to and PDT effective on target cells. The enhanced red absorption and superhigh photoactivity suggest that 6 is more powerful for PDT of tumors than HB.
