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Merck

681675

Wortmannin

≥98% (HPLC), solid, PI3-kinase inhibitor, Calbiochem

Synonym(s):

Wortmannin, KY 12420, MLCK Inhibitor II

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About This Item

Empirical Formula (Hill Notation):
C23H24O8
CAS Number:
19545-26-7
Molecular Weight:
428.43
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00133927

Product Name

Wortmannin, Wortmannin, CAS 19545-26-7, is a cell-permeable, potent, selective, and irreversible inhibitor of PI3-Kinase (IC50 = 5 nM). Does not affect any upstream signaling events.

SMILES string

[o]1c2c3c(c1)C(=O)O[C@@H]([C@@]3(C4=C([C@H]5[C@](C[C@H]4OC(=O)C)(C(=O)CC5)C)C2=O)C)COC

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

InChI key

QDLHCMPXEPAAMD-QAIWCSMKSA-N

description

Merck USA index - 14, 10053

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white to off-white

solubility

DMSO: 25 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: yes
Primary Target
phosphatidylinositol-3-kinase
Product does not compete with ATP.
Reversible: no
Target IC50: 5 nM against phosphatidylinositol 3-kinase; 5 nM against PDGF-mediated Ins(3,4,5)P3 formation; 200 nM against myosin light chain kinase

Disclaimer

Toxicity: Highly Toxic (H)

General description

A cell-permeable, fungal metabolite that acts as a potent, selective, and irreversible inhibitor of phosphatidylinositol 3-kinase in purified preparations and cytosolic fractions (IC50 = 5 nM). Blocks the catalytic activity of PI 3-kinase without affecting the upstream signaling events. Preincubation of fibroblasts with wortmannin abolishes PDGF-mediated Ins(3,4,5)P3 formation (IC50 = 5 nM). Also blocks the metabolic effects of insulin in isolated rat adipocytes without affecting the insulin receptor tyrosine kinase activity. Inhibits MAP kinase activation induced by platelet activating factor in guinea pig neutrophils (200 - 300 nM). Also inhibits other kinases such as myosin light chain kinase (IC50 = 200 nM) and PI 4-kinase at concentrations higher than that required for inhibition of PI 3-kinase. Also blocks phospholipase D. A 10 mM (1 mg/233 µl) solution of Wortmannin (Cat. No. 681676) in DMSO is also available.
A fungal metabolite that acts as a potent, selective, cell-permeable and irreversible inhibitor of phosphatidylinositol 3-kinase (PI 3-kinase) in purified preparations and cytosolic fractions (IC50 = 5 nM). Preincubation of fibroblasts with wortmannin abolishes PDGF-mediated Ins(3,4,5)P3 formation (IC50 = 5 nM). Blocks the catalytic activity of PI 3-kinase without affecting the upstream signaling events. Also blocks the metabolic effects of insulin in isolated rat adipocytes without affecting the insulin receptor tyrosine kinase activity. Inhibits MAP kinase activation induced by platelet activating factor in guinea pig neutrophils (0.2-0.3 µM). Inhibits osteoclastic bone resorption. Inhibits other kinases, such as myosin light chain kinase (IC50 = 200 nM) and PI 4-kinase at concentrations 100-fold higher than that required for the inhibition of PI 3-kinase. Also blocks phospholipase D.

Other Notes

Cross, M.J., et al. 1995. J. Biol. Chem. 270, 25352.
Nakamura, I., et al. 1995. FEBS Lett. 361, 79.
Ferby, I.M., et al. 1994. J. Biol. Chem. 269, 30485.
Okada, T., et al. 1994. J. Biol. Chem. 269, 3568.
Wymann, M.P. and Arcaro, A. 1994. Biochem. J.298, 517.
Arcaro, A. and Wymann, M.P. 1993. Biochem. J.296, 297.
Nakanishi, S., et al. 1992. J. Biol. Chem. 267, 2157.
Bonser, R.W., et al. 1991. Br. J. Pharmacol.103, 1237.
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Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Acute Tox. 2 Dermal

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Human Kinome & InhibitorSelect™ Libraries

Human Kinome Poster: The InhibitorSelect™ Protein Kinase Inhibitor Libraries provide broad coverage of the human kinome as shown here. The depicted human kinome dendrogram of 518 kinases are classified into five broad groups, 90 families, and 145 subfamilies. Inhibitor coverage was assigned based upon published data related to potency (IC50, EC50, Kd, etc.) for individual kinases harvested from the literature. Colored dots denote which library contains an inhibitor with demonstrated potent activity against the designated kinase and do not necessarily reflect known specificity of the inhibitor. Coverage of lipid and atypical kinases are depicted as a separate dendrogram. As shown, Calbiochem® Protein Kinase Inhibitor Libraries cover all major kinase families including TK, CMGC, CAMK, AGC, CK1, STE, TKL, as well as Lipid or Atypical kinase families.

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