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Hypericin

AG-CN2-0449-M001 1 mg INQ
AG-CN2-0449-M005 5 mg INQ
AG-CN2-0449-M010 10 mg INQ
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Additional Information

Product Data
Synonyms Mycoporphyrin; NSC407313; Hypericum red
Properties
Formula C30H16O8
MW 504.5
Merck Index 14: 4863
CAS 548-04-9
Source/Host Isolated from Hypericum perforatum.
Purity ≥98% (HPLC)
Appearance Dark brown to black-red solid.
Solubility Soluble in 100% ethanol, methanol or DMSO. In pure water, hypericin forms aggregates which are non-soluble and non-fluorescent.
InChi Key BTXNYTINYBABQR-UHFFFAOYSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage +4°C
Handling Advice Keep cool and dry. Keep under inert gas. Protect from light. Protect from moisture and oxygen. Protect from light when in solution.
Use/Stability Stable for at least 2 years after receipt when stored at +4°C.
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Product Description

  • One of the principal active constituents of St. John's Wort (Hypericum perforatum).
  • Hypericin is a photosensitive pigment/chromophore with bright red fluorescence emission (λmax: 594nm).
  • Has a high triplet quantum yield and ability to produce considerable amounts of singlet oxygen and other ROS species when photoactivated.
  • Antiviral, anticancer and antidepressant agent.
  • Inactivates enveloped viruses (including HIV).
  • This photosensitizing agent has shown to induce apoptosis and necrosis in cancer cells during photodynamic therapy.
  • Selective inhibitor of protein kinase C (PKC). Has been shown to inhibit other kinases and targets such as EGFR-PTK, PI3K, CKII, MAPK and insulin receptor (IR).
  • Necrosis-avid contrast agent investigated for use in non-invasively targeting necrotic tissues, based on to be defined components in the phospholipid bilayer.

Product References

  1. On the absorption spectrum of hypericin: N. Pace & G. Mackinney; JACS 61, 3594 (1939)
  2. Hypericin and its photodynamic action: N. Duran & P.S. Song; Photochem. Photobiol. 43, 677 (1986) (Review)
  3. Hypericin and pseudohypericin specifically inhibit protein kinase C: possible relation to their antiretroviral activity: I. Takahashi, et al.; BBRC 165, 1207 (1989)
  4. Virucidal Activity of Hypericin Against Enveloped and Non-enveloped DNA and RNA Viruses: J. Tang, et al.; Antivir. Res. 13, 313 (1990)
  5. Agents for treating human immunodeficiency virus infection: E.P. Acosta & C.V. Fletcher; Am. J. Hosp. Pharm. 51, 2251 (1994) (Review)
  6. Photosensitized inhibition of growth factor-regulated protein kinases by hypericin: P. Agostinis, et al.; Biochem. Pharmacol. 49, 1615 (1995)
  7. The chemical and biological properties of hypericin - a compound with a broad spectrum of biological activities: G. Lavie, et al.; Med. Res. Rev. 15, 111 (1995) (Review)
  8. Natural products derived from plants as potential drugs for the photodynamic destruction of tumor cells: R. Ebermann, et al.; J. Photochem. Photobiol. B. 36, 95 (1996) (Review)
  9. Apoptotic and anti-apoptotic signaling pathways induced by photodynamic therapy with hypericin: P. Agostinis, et al.; Adv. Enzyme Regul. 40, 157 (2000) (Review)
  10. St John's wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties: J. Barnes, et al.; J. Pharm. Pharmacol. 53, 583 (2001) (Review)
  11. Hypericin in cancer treatment: more light on the way: P. Agostinis, et al.; Int. J. Biochem. Cell Biol. 34, 221 (2002) (Review)
  12. Hypericin - a new antiviral and antitumor photosensitizer: mechanism of action and interaction with biological macromolecules: P. Miskovsky; Curr. Drug Targets 3, 55 (2002) (Review)
  13. Mechanism of action of St John's wort in depression: what is known? V. Butterweck; CNS Drugs 17, 539 (2003) (Review)
  14. Cell death and growth arrest in response to photodynamic therapy with membrane-bound photosensitizers: J. Piette, et al.; Biochem. Pharmacol. 66, 1651 (2003) (Review)
  15. Hypericin - the facts about a controversial agent: A. Kubin, et al.; Curr. Pharm. Des. 11, 233 (2005)
  16. The multifaceted photocytotoxic profile of hypericin: T.A. Theodossiou, et al.; Mol. Pharm. 6, 1775 (2009) (Review)
  17. Molecular response to hypericin-induced photodamage: B. Krammer & T. Verwanger; Curr. Med. Chem. 19, 793 (2012) (Review)
  18. Necrosis avidity: a newly discovered feature of hypericin and its preclinical applications in necrosis imaging: B. Jiang, et al.; Theranostics 3, 667 (2013) (Review)
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