17β-hydroxy Wortmannin

Product Name17β-hydroxy Wortmannin
CAS58053-83-1
MFC23H26O8
MW430.45
EINECS
MOL File58053-83-1.mol

Chemical Properties

Boiling point	615.4±55.0 °C(Predicted)
Density	1.39±0.1 g/cm3(Predicted)
storage temp.	+2C to +8C
solubility	DMF: 3 mg/ml; DMF:PBS (pH 7.2) (1:9): 0.1 mg/ml; DMSO: 2.5 mg/ml; Ethanol: 0.15 mg/ml
form	Off-white solid
pka	14.49±0.70(Predicted)
color	off-white

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

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). 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). The 17-hydroxyl group has been used to further modify this compound, e.g., by pegylation and conjugation with rapamycin.

Uses

17β-Hydroxywortmannin (Wortmannin-17β-ol) is an orally active inhibitor for phosphatidylinositol-3-kinase (PI-3-kinase) with an IC50 of 0.5 nM, suppresses the osteoclast resorption with an IC50 of 10 nM[1]. 17β-Hydroxywortmannin exhibits antitumor activity[2].

in vivo

17β-Hydroxywortmannin (0.1 μg/kg, p.o. for 5 weeks) exhibits activity in osteoclast differentation and prevent an estrogen-deficiency induced bone loss in ovafiectomized OVX rats^[1].
17β-Hydroxywortmannin (2.5 mg/kg/week, i.v. for 2 weeks) exhibits antitumor efficacy towards U87MG glioma with a therapeutic index of 2⁶ in human tumor xenografted nude mice^[2].

Animal Model:	ovafiectomized rat^[1]
Dosage:	0.1 μg/kg/day
Administration:	p.o. for 5 weeks
Result:	Reduced the bone loss without significant toxicity.

Animal Model:	U87MG glioma xenografted nude mice^[2]
Dosage:	2.5 mg/kg/week
Administration:	i.v. for 2 weeks
Result:	Inhibited tumor growth.

IC 50

PI3K: 0.5 nM (IC₅₀)

References

[1] Hall TJ, et al., Wortmannin, a potent inhibitor of phosphatidylinositol 3-kinase, inhibits osteoclastic bone resorption in vitro. Calcif Tissue Int. 1995 Apr;56(4):336-8. DOI:10.1007/BF00318056
[2] Zask A, 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. 2008 Mar 13;51(5):1319-23. DOI:10.1021/jm7012858

Preparation Products And Raw materials

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