A derivative of withaferin A with anticancer activity
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Product Categories

Product Type

Biochemicals

Research Area

Cancer
Cell Death
DNA Damage and Repair

4-oxo-27-TBDMS Withaferin A

Item No. 28323

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β,6β,22R)-27-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5,6-epoxy-22-hydroxy-1,4-dioxo-ergosta-2,24-dien-26-oic acid, δ-lactone
CAS Number
1214886-31-3
Molecular Formula
C34H50O6Si
Formula Weight
582.9
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 5mg/mLDMSO: 5mg/mLDMSO:PBS (pH 7.2) (1:1): 0.5mg/mL
λmax
224 nm
SMILES
O=C(C=C1)[C@@]2(C)[C@@]([C@H]3C[C@]4([H])[C@]2([H])CC[C@@]5(C)[C@@]4([H])CC[C@]5([H])[C@H](C)[C@@]6([H])CC(C)=C(CO[Si](C)(C)C(C)(C)C)C(O6)=O)(O3)C1=O
InChi Code
InChI=1S/C34H50O6Si/c1-19-16-26(39-30(37)22(19)18-38-41(8,9)31(3,4)5)20(2)23-10-11-24-21-17-29-34(40-29)28(36)13-12-27(35)33(34,7)25(21)14-15-32(23,24)6/h12-13,20-21,23-26,29H,10-11,14-18H2,1-9H3/t20-,21-,23+,24-,25-,26+,29+,32+,33-,34+/m0/s1
InChi Key
RZWFBNOFUAHADD-VTYRCZOESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $90

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    5 mg

    $262

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    10 mg

    $436

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    Product Description

    4-oxo-27-TBDMS Withaferin A is a derivative of the steroidal lactone withaferin A (Item No. 11352) that has anticancer activity.1 It is cytotoxic to A2780 ovarian cancer cells (IC50 = 17 µM) but not to carboplatin-resistant A2780 (A2780/CP70) cells (IC50 = >100 µM). It is selective for A2780 cells over non-cancerous ARPE19 cells (IC50 = 1,660 µM). 4-oxo-27-TBDMS Withaferin A induces DNA fragmentation in A2780 cells.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Perestelo, N.R., Llanos, G.G., Reyes, C.P., et al. Expanding the chemical space of withaferin A by incorporating silicon to improve its clinical potential on human ovarian carcinoma cells. J. Med. Chem. 62(9), 4571-4585 (2019).