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17β-hydroxy Wortmannin Exclusive

Cayman Chemical Item Number 13812

17β-hydroxy Wortmannin

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Description

17β-hydroxy Wortmannin is an analog of wortmannin. It irreversibly binds phosphoinositide 3-kinase (PI3K) and potently blocks fMLP-stimulated respiratory burst in neutrophils (IC50 = 5 nM).1 17β-hydroxy Wortmannin inhibits recombinant PI3K and mTOR (IC50 = 2.7 and 193 nM, respectively) and prevents the growth of LNCap prostate cancer cells (IC50 = 1.46 μM).2 The 17-hydroxyl group has been used to further modify this compound, e.g., by pegylation and conjugation with rapamycin.3,4

1 Thelen, M., Wymann, M.P., and Langen, H. Wortmannin binds specifically to 1-phosphatidylinositol 3-kinase while inhibiting guanine nucleotide-binding protein-coupled receptor signaling in neutrophil leukocytes. Proc Natl Acad Sci USA 91 4960-4964 (1994).

2 Zask, A., Kaplan, J., Toral-Barza, L., et al. Synthesis and structure-activity relationships of ring-opened 17-hydroxywortmannins: Potent phosphoinositide 3-kinase inhibitors with improved properties and anticancer efficacy. J Med Chem 51 1319-1323 (2008).

3 Zhu, T., Gu, J., Yu, K., et al. Pegylated wortmannin and 17-hydroxywortmannin conjugates as phosphoinositide 3-kinase inhibitors active in human tumor xenograft models. J Med Chem 49 1373-1378 (2006).

4 Ayral-Kaloustian, S., Gu, J., Lucas, J., et al. Hybrid inhibitors of phosphatidylinositol 3-kinase (PI3K) and the mammalian target of rapamycin (mTOR): Design, synthesis, and superior antitumor activity of novel wortmannin-rapamycin conjugates. J Med Chem 53(1) 452-459 (2010).

Formal Name 17β-​hydroxy-​11-​(acetyloxy)-​1S,​6bR,​7,​8,​9aS,​10,​11R,​11bR-​octahydro-​1-​(methoxymethyl)-​9a,​11b-​dimethyl-​3H-​furo[4,​3,​2-​de]indeno[4,​5-​h]-​2-​benzopyran-​3,​6,​9-​trione
Molecular Formula C23H26O8
Formula Weight 430.4
Formulation A crystalline solid
Purity ≥98%
λmax 259, 292 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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COC[C@H]​1OC(=O)​c2coc3C(=O)​C4=C([C@H]​(OC(=O)​C)​C[C@]​5(C)​[C@@H]​(O)​CCC45)​[C@]​1(C)​c23

Background Reading

Zhu, T., Gu, J., Yu, K., et al. Pegylated wortmannin and 17-hydroxywortmannin conjugates as phosphoinositide 3-kinase inhibitors active in human tumor xenograft models. J Med Chem 49 1373-1378 (2006).

Thelen, M., Wymann, M.P., and Langen, H. Wortmannin binds specifically to 1-phosphatidylinositol 3-kinase while inhibiting guanine nucleotide-binding protein-coupled receptor signaling in neutrophil leukocytes. Proc Natl Acad Sci USA 91 4960-4964 (1994).

Ayral-Kaloustian, S., Gu, J., Lucas, J., et al. Hybrid inhibitors of phosphatidylinositol 3-kinase (PI3K) and the mammalian target of rapamycin (mTOR): Design, synthesis, and superior antitumor activity of novel wortmannin-rapamycin conjugates. J Med Chem 53(1) 452-459 (2010).

Zask, A., Kaplan, J., Toral-Barza, L., et al. Synthesis and structure-activity relationships of ring-opened 17-hydroxywortmannins: Potent phosphoinositide 3-kinase inhibitors with improved properties and anticancer efficacy. J Med Chem 51 1319-1323 (2008).

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Size Price Quantity Subtotal
500 µg $46.00 $0.00
1 mg $87.00 $0.00
5 mg $368.00 $0.00
10 mg $644.00 $0.00
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Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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