Wortmannin

AdipoGen Life Sciences
Product Code: AG-CN2-0023
CodeSizePrice
AG-CN2-0023-M0011 mg£50.00
Quantity:
AG-CN2-0023-M0055 mg£100.00
Quantity:
AG-CN2-0023-M02525 mg£370.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
KY 12420; BRN 0067676; NSC 627609; Antibiotic SL-2052
Appearance:
White to light yellow solid.
CAS:
19545-26-7
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Keep cool and dry.
Hazards:
H300, H310, H330
InChi:
1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1
InChiKey:
QDLHCMPXEPAAMD-QAIWCSMKSA-N
Long Description:
Chemical. CAS: 19545-26-7. Formula: C23H24O8. MW: 428.4. Isolated from Penicillium sp. Antibiotic. Potent anti-neutrophil agent with cardioprotective effects. mTOR, DNA-PK, phosphatidylinositol 4-kinases, myosin light chain kinase (MLCK) and mitogen-activated protein kinase (MAPK) inhibitor at high concentrations. Potent cell permeable and selective inhibitor of phosphatidyl-inositol 3-kinase (PI3K). Similar potency in vitro for the class I, II, and III PI3K. Antitumor compound. Radiosensitizing agent. Adipogenesis inhibitor. Angiogenesis inhibitor. Autophagy inhibitor, regardless of the nutrient status and thus is a more suitable autophagy inhibitor than 3-MA. DNA repair, receptor-mediated endocytosis and cell proliferation inhibitor. Potentiates the LPS-induced nitric oxide (NO) production from macrophages. Induces in vivo Alzheimer-like hyperphosphorylation in tau. Polo-like kinase family inhibitor. TRAIL sensitizer
MDL:
MFCD00133927
Molecular Formula:
C23H24O8
Molecular Weight:
428.4
Package Type:
Vial
PG:
III
Precautions:
P262, P280, P301, P310, P302, P350, P304, P340, P405
Product Description:
Antibiotic [1]. Potent anti-neutrophil agent with cardioprotective effects [1, 13]. mTOR, DNA-PK, phosphatidylinositol 4-kinases, myosin light chain kinase (MLCK) and mitogen-activated protein kinase (MAPK) inhibitor at high concentrations [2, 5, 14]. Potent cell permeable and selective inhibitor of phosphatidyl-inositol 3-kinase (PI3K) [3, 4]. Similar potency in vitro for the class I, II, and III PI3K. Antitumor compound. [6] Radiosensitizing agent [8]. Adipogenesis inhibitor [5, 7]. Angiogenesis inhibitor. [10] Autophagy inhibitor, regardless of the nutrient status and thus is a more suitable autophagy inhibitor than 3-MA [12,18]. DNA repair, receptor-mediated endocytosis and cell proliferation inhibitor [8, 9, 14]. Potentiates the LPS-induced nitric oxide (NO) production from macrophages [11]. Induces in vivo Alzheimer-like hyperphosphorylation in tau [15]. Polo-like kinase family inhibitor [16]. TRAIL sensitizer [19]
Purity:
>98% (HPLC)
Signal word:
Danger
SMILES:
[H][C@@]12CCC(=O)[C@@]1(C)C[C@@H](OC(C)=O)C1=C2C(=O)C2=C3C(=CO2)C(=O)O[C@H](COC)[C@]13C
Solubility Chemicals:
Soluble in DMSO methanol, ethanol or chloroform. Slightly soluble in water.
Source / Host:
Isolated from Penicillium sp.
Transportation:
Excepted Quantity
UN Nummer:
UN 3462
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

Demethoxyviridin and wortmannin block phospholipase C and D activation in the human neutrophil: R.W. Bonser, et al.; Br. J. Pharmacol. 103, 1237 (1991) | Wortmannin, a microbial product inhibitor of myosin light chain kinase: S. Nakanishi, et al.; J. Biol. Chem. 267, 2157 (1992) | Wortmannin is a potent phosphatidylinositol 3-kinase inhibitor: the role of phosphatidylinositol 3,4,5-trisphosphate in neutrophil responses: A. Arcaro & M.P. Wyman; Biochem. J. 296, 297 (1993) | Wortmannin, a potent and selective inhibitor of phosphatidylinositol-3-kinase: G. Powis, et al.; Cancer Res. 54, 2419 (1994) | Wortmannin inhibits the effects of insulin and serum on the activities of glycogen synthase kinase-3 and mitogen-activated protein kinase: G.I. Welsh, et al.; Biochem. J. 303, 15 (1994) | In vitro and in vivo antitumor activity of the phosphatidylinositol-3-kinase inhibitor, wortmannin: R.M. Schultz, et al.; Anticancer Res. 15, 1135 (1995) | Wortmannin, a specific phosphatidylinositol 3-kinase inhibitor, inhibits adipocytic differentiation of 3T3-L1 cells: K. Tomiyama, et al.; BBRC 212, 263 (1995) | The phosphatidylinositol 3-kinase inhibitor wortmannin sensitizes murine fibroblasts and human tumor cells to radiation and blocks induction of p53 following DNA damage: B.D. Price & M.B. Youmell; Cancer Res. 56, 246 (1996) | Wortmannin is a potent inhibitor of DNA double strand break but not single strand break repair in Chinese hamster ovary cells: S. Boulton, et al.; Carcinogenesis 17, 2285 (1996) | Potent inhibition of angiogenesis by wortmannin, a fungal metabolite: T. Oikawa & M. Shimamura; Eur. J. Pharmacol. 318, 93 (1996) | Wortmannin, a specific inhibitor of phosphatidylinositol-3-kinase, enhances LPS-induced NO production from murine peritoneal macrophages: Y.C. Park, et al.; BBRC 240, 692 (1997) | The phosphatidylinositol 3-kinase inhibitors wortmannin and LY294002 inhibit autophagy in isolated rat hepatocytes: E.F. Blommaart, et al.; Eur. J. Biochem. 243, 240 (1997) | Wortmannin, a potent antineutrophil agent, exerts cardioprotective effects in myocardial ischemia/reperfusion: L.H. Young, et al.; J. Pharmacol. Exp. Ther. 295, 37 (2000) | DNA-PK inhibitor wortmannin enhances DNA damage induced by bleomycin in V79 Chinese hamster cells: N.G. Oliveira, et al.; Teratog. Carcinog. Mutagen. 22, 343 (2002) | Alzheimer-like tau phosphorylation induced by wortmannin in vivo and its attenuation by melatonin: S.J. Liu & J.Z. Wang; Acta Pharmacol. Sin. 23, 183 (2002) | Wortmannin, a widely used phosphoinositide 3-kinase inhibitor, also potently inhibits mammalian polo-like kinase: Y. Liu, et al.; Chem. Biol. 12, 99 (2005) | Chemistry and biology of wortmannin: P. Wipf & R.J. Halter; Org. Biomol. Chem. 3, 2053 (2005) | Dual role of 3-methyladenine in modulation of autophagy via different temporal patterns of inhibition on class I and III phosphoinositide 3-kinase: YT. Wu, et al.; J. Biol. Chem. 285, 10850 (2010) | Novel HTS strategy identifies TRAIL-sensitizing compounds acting specifically through the Caspase-8 apoptotic axis: D. Finlay, et al.;PLoS One 5, e13375 (2010) | Insulin inhibits AMPK activity and phosphorylates AMPK Ser485/491 through Akt in hepatocytes, myotubes and incubated rat skeletal muscle: R.J. Valentine, et al.; Arch. Biochem. Biophys. 562, 62 (2014)

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