27-O-(tert-Butyldimethylsilyl)withaferin A

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27-O-(tert-Butyldimethylsilyl)withaferin A (compound 9a), a natural withanolide, is an apoptosis inducer. 27-O-(tert-Butyldimethylsilyl)withaferin A shows antiproliferative activity against HeLa, A-549 and MCF-7 human cancer cell lines, and against normal Vero cells.

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27-O-(tert-Butyldimethylsilyl)withaferin A Chemical Structure

CAS No. : 1392820-18-6

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Biological Activity
Purity & Documentation
References
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Description

Cellular Effect

Cell Line	Type	Value	Description	References
A2780	IC₅₀	47.5 nM Compound: 21	Antiproliferative activity against cisplatin-sensitive human A2780 cells measured after 96 hrs by MTT assay Antiproliferative activity against cisplatin-sensitive human A2780 cells measured after 96 hrs by MTT assay	[PMID: 31008605]
A549	IC₅₀	1.5 μM Compound: 54	Cytotoxicity against human A549 cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against human A549 cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
A549	IC₅₀	1.5 μM Compound: 9a	Cytotoxicity against human A549 cells assessed as cell viability after 48 hrs by MTT assay Cytotoxicity against human A549 cells assessed as cell viability after 48 hrs by MTT assay	[PMID: 22705001]
A549	IC₅₀	1.5 μM Compound: 9a	Cytotoxicity against human A549 cells assessed as cell viability after 72 hrs by MTT assay Cytotoxicity against human A549 cells assessed as cell viability after 72 hrs by MTT assay	[PMID: 22705001]
A549	IC₅₀	4 μM Compound: 54	Cytotoxicity against human A549 cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against human A549 cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
ARPE-19	IC₅₀	12.4 nM Compound: 21	Cytotoxicity against human ARPE19 cells measured after 96 hrs by MTT assay Cytotoxicity against human ARPE19 cells measured after 96 hrs by MTT assay	[PMID: 31008605]
HeLa	IC₅₀	0.9 μM Compound: 54	Cytotoxicity against human HeLa cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against human HeLa cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
HeLa	IC₅₀	0.9 μM Compound: 9a	Cytotoxicity against human HeLa cells assessed as cell viability after 48 hrs by MTT assay Cytotoxicity against human HeLa cells assessed as cell viability after 48 hrs by MTT assay	[PMID: 22705001]
HeLa	IC₅₀	1 μM Compound: 9a	Cytotoxicity against human HeLa cells assessed as cell viability after 72 hrs by MTT assay Cytotoxicity against human HeLa cells assessed as cell viability after 72 hrs by MTT assay	[PMID: 22705001]
HeLa	IC₅₀	3.1 μM Compound: 54	Cytotoxicity against human HeLa cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against human HeLa cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
MCF7	IC₅₀	0.7 μM Compound: 54	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
MCF7	IC₅₀	0.7 μM Compound: 9a	Cytotoxicity against human MCF7 cells assessed as cell viability after 48 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as cell viability after 48 hrs by MTT assay	[PMID: 22705001]
MCF7	IC₅₀	0.7 μM Compound: 9a	Cytotoxicity against human MCF7 cells assessed as cell viability after 72 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as cell viability after 72 hrs by MTT assay	[PMID: 22705001]
MCF7	IC₅₀	1.2 μM Compound: 54	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
Vero	IC₅₀	0.7 μM Compound: 54	Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
Vero	IC₅₀	0.7 μM Compound: 9a	Cytotoxicity against african green monkey Vero cells assessed as cell viability after 48 hrs by MTT assay Cytotoxicity against african green monkey Vero cells assessed as cell viability after 48 hrs by MTT assay	[PMID: 22705001]
Vero	IC₅₀	0.8 μM Compound: 54	Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay	[PMID: 28923386]
Vero	IC₅₀	0.9 μM Compound: 9a	Cytotoxicity against african green monkey Vero cells assessed as cell viability after 72 hrs by MTT assay Cytotoxicity against african green monkey Vero cells assessed as cell viability after 72 hrs by MTT assay	[PMID: 22705001]

In Vitro

27-O-(tert-Butyldimethylsilyl)withaferin A (compound 9a; 32 μM; 4-8 hours) inhibits caspase-3 activity in HeLa cells^[1].
27-O-(tert-Butyldimethylsilyl)withaferin A (48 hours) shows antiproliferative activity against HeLa, A-549, MCF-7, and Vero cells with IC₅₀ values of 0.9 μM, 1.5 μM, 0.7 μM, and 0.7 μM, respectively^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

584.86

Formula

C₃₄H₅₂O₆Si

CAS No.

1392820-18-6

SMILES

C[C@]12[C@@]3([C@H](C=CC2=O)O)[C@](C[C@]4([H])[C@]1([H])CC[C@]5([C@@]4([H])CC[C@]5([H])[C@@H]([C@@]6([H])CC(C)=C(C(O6)=O)CO[Si](C)(C)C(C)(C)C)C)C)([H])O3

Structure Classification

Steroids

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Gabriel G Llanos, et al. Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells. Eur J Med Chem. 2012 Aug;54:499-511. [Content Brief]