A napthodianthrone with anticancer activity
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Protohypericin

Item No. 36043

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,3,4,6,8,15-hexahydroxy-10,13-dimethyl-dibenzo[a,o]perylene-7,16-dione
CAS Number
548-03-8
Molecular Formula
C30H18O8
Formula Weight
506.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly Soluble: 1-10 mg/mlMethanol: Sparingly Soluble: 1-10 mg/ml
λmax
213, 215 nm
SMILES
O=C1C2=C(C=C(C)C=C2C(C(C3=CC(C)=CC(O)=C34)=C56)=C7C1=C(O)C=C(O)C7=C5C(O)=CC(O)=C6C4=O)O
InChi Code
InChI=1S/C30H18O8/c1-9-3-11-19(13(31)5-9)29(37)25-17(35)7-15(33)23-24-16(34)8-18(36)26-28(24)22(21(11)27(23)25)12-4-10(2)6-14(32)20(12)30(26)38/h3-8,31-36H,1-2H3
InChi Key
YLILOANQCQKPOD-UHFFFAOYSA-N
Origin
Plant/Hypericum perforatum L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Protohypericin is a naphthodianthrone that has been found in H. perforatum and has anticancer activity.1,2,3 It induces photocytotoxicity in HeLa cervical cancer cells in the presence of light with a 50% cytotoxic concentration (CC50) value of 0.21 µM.2 In vivo, protohypericin labeled with 131iodine (131I-protohypericin), in combination with combrestatin A4 3'-O-phosphate (Item No. 10007415), increases survival, decreases tumor volume, and induces tumor necrosis in an A549 lung cancer mouse xenograft model.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Piperopoulos, G., Lotz, R., Wixforth, A., et al. Determination of naphthodianthrones in plant extracts from Hypericum perforatum L. by liquid chromatography-electrospray mass spectrometry. J. Chromatogr. B Biomed. Sci. Appl. 695(2), 309-316 (1997).

    2. Delaey, E.M., Kamuhabwa, A.R., Vandenbogaerde, A.L., et al. Photocytotoxicity of protohypericin after photoconversion to hypericin. Planta Med. 65(8), 719-722 (1999).

    3. Liu, X., Jiang, C., Zhang, D., et al. Tumor necrosis targeted radiotherapy of non-small cell lung cancer using radioiodinated protohypericin in a mouse model. Oncotarget 6(28), 26400-26410 (2015).