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Chemical Structure| 19545-26-7 Chemical Structure| 19545-26-7

Structure of Wortmannin
CAS No.: 19545-26-7

Chemical Structure| 19545-26-7

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Wortmannin (SL-2052; KY-12420) is a potent, selective, and irreversible PI3K inhibitor with an IC50 of 3 nM. It also blocks autophagy formation and strongly inhibits Polo-like kinase 1 (PlK1) and Plk3 with IC50s of 5.8 nM and 48 nM, respectively.

Synonyms: SL-2052; KY 12420; NSC 627609

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Product Details of Wortmannin

CAS No. :19545-26-7
Formula : C23H24O8
M.W : 428.43
SMILES Code : CC(O[C@@H](C1=C2C(C3=C4C(C(O[C@H](COC)[C@]14C)=O)=CO3)=O)C[C@]5(C)C(CC[C@]52[H])=O)=O
Synonyms :
SL-2052; KY 12420; NSC 627609
MDL No. :MFCD00133927
InChI Key :QDLHCMPXEPAAMD-QAIWCSMKSA-N
Pubchem ID :312145

Safety of Wortmannin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H332
Precautionary Statements:P261-P271

Related Pathways of Wortmannin

DNA
PI3K-AKT

Isoform Comparison

Biological Activity

Target
  • PI3K

    PI3K, IC50:3 nM

  • ATM

    ATM, IC50:150 nM

In Vitro:

Cell Line
Concentration Treated Time Description References
Rat vascular smooth muscle cells (VSMCs) 20 µM 24 h Inhibit PI3-kinase and block PDGF-induced downregulation of miR-145 PMC3886745
Rat vascular smooth muscle cells (VSMCs) 20 µM 24 h To investigate the effect of PI3-kinase inhibitor LY294002 on PDGF-induced downregulation of miR-145 expression. Results showed that LY294002 inhibited PDGF-induced downregulation of miR-145 expression. PMC3886745
NPCs 1μM 1 h To simulate the phosphorylation profile of CFC NPCs and test whether these pathways are associated with accelerated cell cycle exit. Wortmannin treatment decreased phosphorylation of AKT and ERK1/2, mimicking the phenotype of CFC NPCs. PMC5962360
HepG2 cells 1 µM 30 min Wortmannin was used to inhibit PI3K activity to study its effect on LLO-induced bead internalization. The results showed that wortmannin significantly inhibited LLO-induced bead internalization. PMC3207921
MDA-MB-231 cells 0.3 µM 6 h To evaluate the effect of Wortmannin on the internalization of MDA-MB-231 cells, results showed that Wortmannin significantly decreased cellular uptake, indicating that the internalization process is PI3K-dependent. PMC9963437
THP-1 cells 10 μM 60 min Wortmannin, as a PI3K inhibitor, was used to study the EMR2 activation-induced IL-8 and MMP-9 production. The results showed that Wortmannin significantly inhibited the production of IL-8 and MMP-9. PMC5376562
HepG2 cells 100 nM 30 min Inhibition of PI 3-kinase, blocking insulin-induced upregulation of Snail1 PMC6048127

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Rat Rat carotid artery balloon injury model Intraperitoneal injection 30 µg/kg Once daily for 3 days Inhibit PI3-kinase and block balloon injury-induced downregulation of miR-145 PMC3886745
Rats and mice Rat carotid artery balloon injury model and mouse atherosclerosis model Intraperitoneal injection 30 µg/kg Once daily for 3 days To investigate the effect of PI3-kinase inhibitor Wortmannin on balloon injury-induced downregulation of miR-145 expression. Results showed that Wortmannin significantly blocked balloon injury-induced downregulation of miR-145. PMC3886745
Mice Cav-3 overexpressing mice Intravenous injection 15 μg/kg Single dose, lasting 15 minutes Wortmannin treatment attenuated the endogenous cardiac protection observed in Cav-3 OE mice, reduced phosphorylation of Akt and GSK3β, and increased infarct size and cardiac troponin-I levels PMC2676165
Mice Ovariectomized mice Subcutaneous injection 14 µg/mouse Single injection Inhibit E2-induced AKT phosphorylation, thereby interfering with the induction of EGR1 and ADAMTS-1 PMC8336340

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.33mL

0.47mL

0.23mL

11.67mL

2.33mL

1.17mL

23.34mL

4.67mL

2.33mL

References

[1]Carter AN, Born HA, et al. Wortmannin Attenuates Seizure-Induced Hyperactive PI3K/Akt/mTOR Signaling, Impaired Memory, and Spine Dysmorphology in Rats. eNeuro. 2017 Jun 12;4(3). pii: ENEURO.0354-16.2017. .

[2]Nakanishi S, Kakita S, et al. Wortmannin, a microbial product inhibitor of myosin light chain kinase. J Biol Chem. 1992 Feb 5;267(4):2157-63.

[3]Yano H, Nakanishi S, Kimura K, Hanai N, Saitoh Y, Fukui Y, Nonomura Y, Matsuda Y. Inhibition of histamine secretion by wortmannin through the blockade of phosphatidylinositol 3-kinase in RBL-2H3 cells. J Biol Chem. 1993 Dec 5;268(34):25846-56.

[4]Quast SA, Berger A, Eberle J. ROS-dependent phosphorylation of Bax by wortmannin sensitizes melanoma cells for TRAIL-induced apoptosis. Cell Death Dis. 2013 Oct 10;4(10):e839.

[5]Ko JC, Chiu HC, Syu JJ, Chen CY, Jian YT, Huang YJ, Wo TY, Jian YJ, Chang PY, Wang TJ, Lin YW. Down-regulation of MSH2 expression by Hsp90 inhibition enhances cytotoxicity affected by tamoxifen in human lung cancer cells. Biochem Biophys Res Commun. 2015 Jan 2;456(1):506-12.

[6]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.

[7]Walker EH, Pacold ME, Perisic O, Stephens L, Hawkins PT, Wymann MP, Williams RL. Structural determinants of phosphoinositide 3-kinase inhibition by wortmannin, LY294002, quercetin, myricetin, and staurosporine. Mol Cell. 2000 Oct;6(4):909-19.

 

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