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Merck

W3144

Wortmannin

from Penicillium funiculosum, ≥95% (HPLC), solution, PI3-kinase inhibitor

Synonym(s):

Antibiotic SL-2052

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About This Item

Empirical Formula (Hill Notation):
C23H24O8
CAS Number:
19545-26-7
Molecular Weight:
428.43
NACRES:
NA.77
UNSPSC Code:
12352200
Assay:
≥95% (HPLC)
Quality level:
200
Storage condition:
protect from light

Key Documents

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Product Name

Wortmannin, Ready Made Solution, from Penicillium funiculosum, ≥95% (HPLC)

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

biological source

Penicillium funiculosum

assay

≥95% (HPLC)

storage condition

protect from light

concentration

10 mM in DMSO (0.2 μm filtered)

shipped in

wet ice

storage temp.

−20°C

Quality Level

200

Gene Information

human ... PIK3CD(5293), PIK3CG(5294), PIK3R1(5295)

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Application

Wortmannin, Ready Made Solution has been used:
  • as a phosphoinositide 3-kinase (PI3K) pathway inhibitor
  • as an endoderm-inducing agent in stem cell selection and differentiation
  • as a autophagy inhibitor

Wortmannin, a low molecular weight membrane permeable hydrophobic fungal metabolite, is widely used to study and verify the involvement of phosphoinosidite 3-kinase (PI3K)/Akt in cell signaling cascades that regulate key processes such as cell survival and apoptosis. Wortmannin may also be used to block and study the functional roles of polo-like kinases involved in the regulation of mitosis.

Biochem/physiol Actions

Wortmannin is a low-molecular-weight hydrophobic fungal metabolite with a sterol-like structure produced by Penicillium funiculosum. It is a selective inhibitor of phosphoinosidite 3-kinase. It interferes with Akt signal transduction cascade, enhancing the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. Wortmannin is membrane-permeable, thus facilitating whole-cell studies of G-protein-coupled receptor and receptor tyrosine kinase signalling pathways. PI3K inhibition by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation. Research has demonstrated that wortmannin inhibits two mitotic enzymes, key regulators in the Polo-like kinase (Plk) family, Plk1 and Plk3.
Wortmannin is a hydrophobic fungal metabolite with a sterol-like structure. Inhibition of PI3K/Akt signal transduction cascade by wortmannin enhances apoptotic effects.
Wortmannin is a low molecular weight; hydrophobic fungal metabolite with a sterol-like structure produced by Penicilium fumiculosum. Inhibition of PI3K/Akt signal transduction cascade by wortmannin, enhances the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. PI3K inhibition by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation. Research has demonstrated that wortmannin inhibits two enzymes from mitotical division, key regulators Polo-like kinase (Plk) family, Plk1 and Plk3.
Wortmannin possesses anti-inflammatory properties. This mold metabolite is capable of preventing an intermediate step in transcytosis. In fisher rat thyroid (FRT) cells, wortmannin helps to block bidirectional transcytosis of ricin.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Physical form

Wortmannin Ready Made Solution supplied as a 10 mM 0.2 μm-filtered solution in DMSO.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 3 petroleums + Hazardous rank III + Water insoluble liquid

fsl

W3144-VAR: + W3144-250UL-PW: + W3144-BULK: + W3144-250UL:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
039M4134V
11181139
038M4102V
11170923
116M4067V

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Generation and selection of pluripotent stem cells for robust differentiation to insulin-secreting cells capable of reversing diabetes in rodents
Southard SM, et al.
Testing, 13(9), e0203126-e0203126 (2018)
Inhibiting the RAS-PI3K Pathway in Cancer Therapy
The Enzymes, 34, 107-136 (2013)
Rac1 targeting suppresses p53 deficiency-mediated lymphomagenesis
Bosco EE, et al.
Blood, 115(16), 3320-3328 (2010)
Inhibition of autophagy blocks cathepsins-tBid-mitochondrial apoptotic signaling pathway via stabilization of lysosomal membrane in ischemic astrocytes
Zhou XY, et al.
Cell Death & Disease, 8(2), e2618-e2618 (2017)
Wortmannin, an inhibitor of phosphoinositide 3-kinase, inhibits transcytosis in polarized epithelial cells
Hansen SH, et al.
The Journal of biological chemistry, 270(47), 28425-28432 (1995)
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