| Identification | Back Directory | [Name]
17β-hydroxy Wortmannin | [CAS]
58053-83-1 | [Synonyms]
17β-hydroxy Wortmannin
XLJORQYAOTYVQS-OGCOKEDGSA-N
17.beta.-hydroxy Wortmannin
17β-hydroxy Wortmannin Exclusive
17β-hydroxy Wortmannin Exclusive
PI 3-K Inhibitor XI, HWT - CAS 58053-83-1 - Calbiochem
3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6(1H)-dione, 11-(acetyloxy)-6b,7,8,9,9a,10,11,11b-octahydro-9-hydroxy-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9S,9aS,11R,11bR)- | [Molecular Formula]
C23H26O8 | [MDL Number]
MFCD00939536 | [MOL File]
58053-83-1.mol | [Molecular Weight]
430.45 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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