Hypericin | SGX301 | CAS#548-04-9 | photosensitizer

MedKoo Cat#: 206623 | Name: Hypericin (SGX301)

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Hypericin, also known as SGX301, is a novel, first-in-class photodynamic therapy using a potent photosensitizer, synthetic hypericin, that is topically applied and activated by safe visible fluorescent light. This treatment avoids the risk of secondary malignancies (including melanoma) inherent with the frequently employed DNA-damaging chemotherapeutic drugs and other photodynamic therapies that are dependent on ultraviolet A (UVA) light exposure.

Chemical Structure

Hypericin (SGX301)

CAS#548-04-9

Theoretical Analysis

MedKoo Cat#: 206623

Name: Hypericin (SGX301)

CAS#: 548-04-9

Chemical Formula: C30H16O8

Exact Mass: 504.0845

Molecular Weight: 504.45

Elemental Analysis: C, 71.43; H, 3.20; O, 25.37

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks

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Related CAS #

No Data

Synonym

SGX301; SGX-301; SGX 301; NSC 407313; NSC 622946; hypericin.

IUPAC/Chemical Name

1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro(1,10,9,8-opqra)perylene-7,14-dione

InChi Key

BTXNYTINYBABQR-UHFFFAOYSA-N

InChi Code

InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3

SMILES Code

O=C1C2=C3C4=C5C1=C(O)C=C(C)C5=C6C(C)=CC(O)=C7C6=C4C8=C(C(O)=CC(O)=C8C3=C(O)C=C2O)C7=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 504.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Huang LF, Wang ZH, Chen SL. Hypericin: chemical synthesis and biosynthesis. Chin J Nat Med. 2014 Feb;12(2):81-8. doi: 10.1016/S1875-5364(14)60014-5. Review. PubMed PMID: 24636057. 2: Jiang B, Wang J, Ni Y, Chen F. Necrosis avidity: a newly discovered feature of hypericin and its preclinical applications in necrosis imaging. Theranostics. 2013 Aug 10;3(9):667-76. doi: 10.7150/thno.6650. eCollection 2013. Review. PubMed PMID: 24052807; PubMed Central PMCID: PMC3776218. 3: Krammer B, Verwanger T. Molecular response to hypericin-induced photodamage. Curr Med Chem. 2012;19(6):793-8. Review. PubMed PMID: 22214453. 4: Olivo M, Fu CY, Raghavan V, Lau WK. New frontier in hypericin-mediated diagnosis of cancer with current optical technologies. Ann Biomed Eng. 2012 Feb;40(2):460-73. doi: 10.1007/s10439-011-0462-7. Epub 2011 Nov 29. Review. PubMed PMID: 22124793; PubMed Central PMCID: PMC3281199. 5: Chopra A. (64)Cu-Labeled bis-1,4,7,10-tetraazacyclododecane-N,N',N,N'-tetraacetic acid conjugated hypericin. 2011 May 03 [updated 2011 May 26]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK55564/ PubMed PMID: 21656982. 6: Theodossiou TA, Hothersall JS, De Witte PA, Pantos A, Agostinis P. The multifaceted photocytotoxic profile of hypericin. Mol Pharm. 2009 Nov-Dec;6(6):1775-89. doi: 10.1021/mp900166q. Review. PubMed PMID: 19739671. 7: Olivo M, Du HY, Bay BH. Hypericin lights up the way for the potential treatment of nasopharyngeal cancer by photodynamic therapy. Curr Clin Pharmacol. 2006 Sep;1(3):217-22. Review. PubMed PMID: 18666746. 8: Saw CL, Heng PW, Olivo M. Potentiation of the photodynamic action of hypericin. J Environ Pathol Toxicol Oncol. 2008;27(1):23-33. Review. PubMed PMID: 18551893. 9: Lobban CS, Hallam SJ, Mukherjee P, Petrich JW. Photophysics and multifunctionality of hypericin-like pigments in heterotrich ciliates: a phylogenetic perspective. Photochem Photobiol. 2007 Sep-Oct;83(5):1074-94. Review. PubMed PMID: 17880503. 10: Vacek J, Klejdus B, Kubán V. [Hypericin and hyperforin: bioactive components of St. John's Wort (Hypericum perforatum). Their isolation, analysis and study of physiological effect]. Ceska Slov Farm. 2007 Apr;56(2):62-6. Review. Czech. PubMed PMID: 17619301. 11: Putnik K, Stadler P, Schäfer C, Koelbl O. Enhanced radiation sensitivity and radiation recall dermatitis (RRD) after hypericin therapy -- case report and review of literature. Radiat Oncol. 2006 Sep 1;1:32. Review. PubMed PMID: 16948841; PubMed Central PMCID: PMC1564402. 12: Kiesslich T, Krammer B, Plaetzer K. Cellular mechanisms and prospective applications of hypericin in photodynamic therapy. Curr Med Chem. 2006;13(18):2189-204. Review. PubMed PMID: 16918348. 13: Saw CL, Olivo M, Soo KC, Heng PW. Delivery of hypericin for photodynamic applications. Cancer Lett. 2006 Sep 8;241(1):23-30. Epub 2005 Nov 21. Review. PubMed PMID: 16303248. 14: Kubin A, Wierrani F, Burner U, Alth G, Grünberger W. Hypericin--the facts about a controversial agent. Curr Pharm Des. 2005;11(2):233-53. Review. PubMed PMID: 15638760. 15: Kamuhabwa A, Agostinis P, Ahmed B, Landuyt W, van Cleynenbreugel B, van Poppel H, de Witte P. Hypericin as a potential phototherapeutic agent in superficial transitional cell carcinoma of the bladder. Photochem Photobiol Sci. 2004 Aug;3(8):772-80. Epub 2004 Apr 2. Review. PubMed PMID: 15295634. 16: Miskovsky P. Hypericin--a new antiviral and antitumor photosensitizer: mechanism of action and interaction with biological macromolecules. Curr Drug Targets. 2002 Feb;3(1):55-84. Review. PubMed PMID: 11899265. 17: Agostinis P, Vantieghem A, Merlevede W, de Witte PA. Hypericin in cancer treatment: more light on the way. Int J Biochem Cell Biol. 2002 Mar;34(3):221-41. Review. PubMed PMID: 11849990. 18: Agostinis P, Assefa Z, Vantieghem A, Vandenheede JR, Merlevede W, De Witte P. Apoptotic and anti-apoptotic signaling pathways induced by photodynamic therapy with hypericin. Adv Enzyme Regul. 2000;40:157-82. Review. PubMed PMID: 10828351. 19: Lavie G, Mazur Y, Lavie D, Meruelo D. The chemical and biological properties of hypericin--a compound with a broad spectrum of biological activities. Med Res Rev. 1995 Mar;15(2):111-9. Review. Erratum in: Med Res Rev 1995 May;15(3):259. PubMed PMID: 7739292. 20: Durán N, Song PS. Hypericin and its photodynamic action. Photochem Photobiol. 1986 Jun;43(6):677-80. Review. PubMed PMID: 3529141.