An inhibitor of tubulin polymerization
Related Products
Isomer(s)
364814'-Demethylpodophyllotoxin
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Product Categories

Product Type

Biochemicals
Microtubule Dynamics

Research Area

Cancer

4'-Demethylepipodophyllotoxin

Item No. 28393

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,5aR,8aR,9S)-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
6559-91-7
Synonyms
  • (−)-4′-Demethylepipodophyllotoxin
Molecular Formula
C21H20O8
Formula Weight
400.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5mg/mLDMSO: 10mg/mLDMSO:PBS (pH 7.2) (1:4): 0.2mg/mL
λmax
212, 285 nm
SMILES
O=C(OC1)[C@]([C@@]1([H])[C@@H]2O)([H])[C@@](C3=CC(OC)=C(O)C(OC)=C3)([H])C4=C2C=C(OCO5)C5=C4
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-JHQYFNNDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    10 g

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    25 g

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    Cayman Chemical
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    Product Description

    4'-Demethylepipodophyllotoxin is an inhibitor of tubulin polymerization (IC50 = 13 μM).1 It inhibits the growth of human HepG2 liver, HeLa cervical, A549 lung, and BGC-823 stomach cancer cells in vitro (IC50s = 18.74, 15.96, 52.08, and 21.26 μM, respectively).2 4'-Demethylepipodophyllotoxin also inhibits the growth of non-cancerous human HL-7702 liver cells (IC50 = 13.04 μM).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Daley, L., Guminski, Y., Demerseman, P., et al. Synthesis and antitumor activity of new glycosides of epipodophyllotoxin, analogues of etoposide, and NK 611. J. Med. Chem. 41(23), 4475-4485 (1998).

    2. Zhao, W., Chen, L., Li, H.-M., et al. A rational design strategy of the novel topoisomerase II inhibitors for the synthesis of the 4-O-(2-pyrazinecarboxylic)-4'-demethylepipodophyllotoxin with antitumor activity by diminishing the relaxation reaction of topoisomerase II-DNA decatenation. Bioorg. Med. Chem. 22(11), 2998-3007 (2014).