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Wortmannin

Catalog No.
A8544
PI3K inhibitor,selective and irreversible
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$90.00
In stock
5mg
$79.00
In stock
10mg
$119.00
In stock
20mg
$189.00
In stock

Tel: +1-832-696-8203

Email: [email protected]

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Background

Wortmannin is a selective and irreversible inhibitor of phosphatidylinositol-3-kinase with IC50 value of 1.9nM [1].

Wortmannin is a microbial product. It is produced by a fungal strain, Talaromyces wortmannin KY12420 and is screened out as a potent inhibitor of myosin light chain kina (MLCK). Wortmannin inhibits MLCK as directly interacting with the catalytic domain but not the calmodulin or the regulatory domains. It is found to be a non-competitive inhibitor. The IC50 value of wortmannin for MLCK is 1.9μM. Wortmannin inhibits the phosphorylation and contraction of myosin light chain in rat aort. As an inhibitor of MLCK, wortmannin is developed as vasodilators and anti-inflammatory agent [2].

Wortmannin is also found to be an inhibitor of PI3K with IC50 of 1.9nM in antiphosphotyrosine immunoprecipitates from Swiss 3T3 cells. The inhibition mode is noncompetitive with respect to ATP. Wortmannin is a highly selective inhibitor of PI3K. It has no inhibition effect on Ptdlns-4-kinase, protein kinase C, c-src protein tyrosine kinase and phosphoinositide-specific phospholipase C [1].

References:
[1] Powis G, Bonjouklian R, Berggren M M, et al. Wortmannin, a potent and selective inhibitor of phosphatidylinositol-3-kinase. Cancer Research, 1994, 54(9): 2419-2423.
[2] Nakanishi S, Kakita S, Takahashi I, et al. Wortmannin, a microbial product inhibitor of myosin light chain kinase. Journal of Biological Chemistry, 1992, 267(4): 2157-2163.

Product Citation

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt428.43
Cas No.19545-26-7
FormulaC23H24O8
Solubility≥21.42 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
Chemical Name(1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-3,6,6b,7,8,9,9a,10,11,11b-decahydro-1H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate
SDFDownload SDF
Canonical SMILESO=C1[[email protected]](C([H])([H])[[email protected]@]2([H])OC(C([H])([H])[H])=O)(C([H])([H])[H])[[email protected]](C([H])([H])C1([H])[H])([H])C(C3=O)=C2[[email protected]]4(C([H])([H])[H])C5=C3OC([H])=C5C(O[[email protected]]4([H])C([H])([H])OC([H])([H])[H])=O
Shipping ConditionEvaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tipsFor obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

Protocol

Cell experiment [1]:

Cell lines

v-sis NIH 3T3 cells

Preparation method

The solubility of this compound in DMSO is >21.4 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37°C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20°C for several months.

Reacting condition

1.3 μM

Applications

In PDGF-stimulated v-sis NIH 3T3 cells, Wortmannin almost completely inhibited the formation of Ptdlns-3-phosphates. However, in resting cells, Wortmannin showed no effect on the pattern of phospholipids.

Animal experiment [2]:

Animal models

Immunodeficient mice bearing orthotopic human pancreatic cancer xenografts

Dosage form

0-0.7 mg/kg; i.v.; 0-4 hrs

Applications

In orthotopic human pancreatic cancer xenografts, PKB/Akt phosphorylation was inhibited by Wortmannin in a time- and dose-dependent manner, and reached a plateau at 4 hrs and at 0.7 mg/kg. Meanwhile, the levels of PKB/Akt phosphorylation were decreased maximally by ~50%.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Powis G, Bonjouklian R, Berggren M M, et al. Wortmannin, a potent and selective inhibitor of phosphatidylinositol-3-kinase. Cancer Research, 1994, 54(9): 2419-2423.

[2]. Ng SS, Tsao MS, Nicklee T, Hedley DW. Wortmannin inhibits pkb/akt phosphorylation and promotes gemcitabine antitumor activity in orthotopic human pancreatic cancer xenografts in immunodeficient mice. Clin Cancer Res. 2001 Oct;7(10):3269-75.

Biological Activity

Description Wortmannin is an inhibitor of PI3K with an IC50 value of 3 nM.
Targets PI3K DNA-PK ATM MLCK ATR  
IC50 3 nM 16 nM 150 nM 170 nM 1.8 μM  

Quality Control

Chemical structure

Wortmannin

Related Biological Data

Wortmannin
In Western blot assay, we test whether Wortmannin and 3-Me could inhibit the effect of autophagy in 3T3 cells. The 1mM of inhibitors can suppress the cell survival of 3T3 cells. Due to the death of cell at the high concentration of Wortmannin and 3-Me, they are not fit to test in Western blot assay. The result has been shown that the low concentration of Wortmannin and 3-Me (1μM) significantly enhanced the P62 and inhibited the level of autophagy in 3T3 cells.
Method:Western blot; Cell Lines:3T3 cell lines; Concentrations:1μM~1mM; Incubation Time:24 h.

Related Biological Data

Wortmannin

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Wortmannin

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Wortmannin