A lignan with microtubule assembly inhibitory and anticancer activities
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Isomer(s)
283934'-Demethylepipodophyllotoxin
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4'-Demethylpodophyllotoxin

Item No. 36481

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,5aR,8aR,9R)-5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
CAS Number
40505-27-9
Molecular Formula
C21H20O8
Formula Weight
400.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 2 mg/mlEthanol: insolPBS (pH 7.2): insol
SMILES
O=C1[C@]2([H])[C@@](C3=CC(OC)=C(C(OC)=C3)O)([H])C4=CC(OCO5)=C5C=C4[C@@H]([C@@]2([H])CO1)O
InChi Code
InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19-/m0/s1
InChi Key
YVCVYCSAAZQOJI-BTINSWFASA-N
Origin
Plant/Dysosma versipellis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $48

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    10 mg

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    25 mg

    $190

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    50 mg

    $354

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    Product Description

    4'-Demethylpodophyllotoxin is a lignan that has been found in D. versipellis and has microtubule assembly inhibitory and anticancer activities.1,2 It inhibits the assembly of isolated chicken brain tubulin (IC50 = 0.5 µM) and the proliferation of LNCaP and PC3 prostate cancer cells (IC50s = 0.056 and 0.082 µM, respectively).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Loike, J.D., Brewer, C.F., Sternlicht, H., et al. Structure-activity study of the inhibition of microtubule assembly in vitro by podophyllotoxin and its congeners. Cancer Res. 38(9), 2688-2693 (1978).

    2. Jiang, R.-W., Zhou, J.-R., Hon, P.-M., et al. Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines. J. Nat. Prod. 70(2), 283-286 (2007).