Hypericin from Hypericum perforatum 

56690, Hypericin from Hypericum perforatum

The fluorescent properties of hypericin are useful for the endoscopic and cytoscopic detection of bladder cancers.

Hypericin is a photoreactive pigment from Hypericum that becomes highly cytotoxic when activated by light at 590-600 nm (A_max = 592 nm). It induces apoptosis in cancer cells in vitro and in vivo and is a potent antiviral agent. The activated compound inhibits protein kinase C, irreversibly damages sarco/endoplasmic reticulum and other cellular membranes, decreases cellular pH, and inhibits mitochondrial function.

≥85% (HPLC)

powder

black

1 M NaOH: 10 mg/mL

ethanol: 5 mg/mL with sonication

DMSO: soluble

Ritz, R., et al., Photodynamic therapy of malignant glioma with hypericin: comprehensive in vitro study in human glioblastoma cell lines. Int. J. Oncol. 30, 659-667, (2007)

Yamazaki, T., et al., Excited-state properties of hypericin: electronic spectra and fluorescence decay kinetics. J. Phys. Chem. 97, 7870-7875, (1993)

Buytaert, E., et al., Role of endoplasmic reticulum depletion and multidomain proapoptotic BAX and BAK proteins in shaping cell death after hypericin-mediated photodynamic therapy. FASEB J. 20, 756-758, (2006)

Theodossiou, T.A., et al., Mitochondria are a primary target of hypericin phototoxicity: synergy of intracellular calcium mobilisation in cell killing. Int. J. Biochem. Cell Biol. 38, 1946-1956, (2006)

Kocanova, S., et al., Characterization of the interaction of hypericin with protein kinase C in U-87 MG human glioma cells. Photochem. Photobiol. 82, 720-728, (2006)

Blank, M., et al., Antimetastatic activity of the photodynamic agent hypericin in the dark. Int. J. Cancer 111, 596-603, (2004)

Miskovsky, P., Hypericin--a new antiviral and antitumor photosensitizer: mechanism of action and interaction with biological macromolecules. Curr. Drug Targets 3, 55-84, (2002)

Merck 13,4889

Beil. 8,IV,3761

3