Withaferin A

Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Withaferin A is an inhibitor of endothelial protein C receptor (EPCR) shedding.

Product information

CAS Number: 5119-48-2

Molecular Weight: 470.60

Formula: C28H38O6

Chemical Name: (1S, 2R, 6S, 7R, 9R, 11S, 12S, 15R, 16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3, 6-dihydro-2H-pyran-2-yl]ethyl]-2, 16-dimethyl-8-oxapentacyclo[9.7.0.0, .0, .0, ]octadec-4-en-3-one

Smiles: CC1C[C@@H](OC(=O)C=1CO)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@@]54[C@@H](O)C=CC(=O)[C@]5(C)[C@H]3CC[C@@]21C

InChiKey: DBRXOUCRJQVYJQ-CKNDUULBSA-N

InChi: InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 100 mg/mL (212.49 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Withaferin A has antiinflammatory activity, and potently inhibits NF-kB activation by preventing the TNF-induced activation of Ik-B kinase beta via a thioalkylation-sensitive redox mechanism. Withaferin A also has anticancer activity. Withaferin A targets the IF protein vimentin, causes aggregation of vimentin filaments in bovine aortic endothelial cells (BAECs) at 3 μM, and induces vimentin fragmentation in endothelial cells at 10 μM. Withaferin A (0.5, 1.5 μM) alone or incombination with cisplatin (CIS) dose-dependently reduces tumorigenic potential of ALDH1 positive cancer stem cells (CSCs).

In Vivo:

Withaferin A (2 mg/kg, i.p.) shows potent angiogenesis inhibitory activity via vimentin in mice. Withaferin A (2 mg/kg) combined with cisplatin (CIS) regulates the expression of ALDH1 marker, and downregulates the expression of securin in tumors collected from mice.

References:

1. Kaileh M, et al. Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity. J Biol Chem. 2007 Feb 16;282(7):4253-64. Epub 2006 Dec 6.
2. Bargagna-Mohan P, et al. The tumor inhibitor and antiangiogenic agent withaferin A targets the intermediate filament protein vimentin. Chem Biol. 2007 Jun;14(6):623-34.
3. Kakar SS, et al. Withaferin A (WFA) inhibits tumor growth and metastasis by targeting ovarian cancer stem cells. Oncotarget. 2017 Aug 10;8(43):74494-74505.

Products are for research use only. Not for human use.