W3144

Wortmannin

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

• Synonym(s): Antibiotic SL-2052
• Empirical Formula (Hill Notation): C₂₃H₂₄O₈
• CAS Number: 19545-26-7
• Molecular Weight: 428.43
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Product Name: Wortmannin, Ready Made Solution, from Penicillium funiculosum, ≥95% (HPLC)
• biological source: Penicillium funiculosum
• Quality Level: 200
• 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
• 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
• Gene Information: human ... PIK3CD(5293) , PIK3CG(5294) , PIK3R1(5295)

Description

Application

Wortmannin, Ready Made Solution has been used:

• as a phosphoinositide 3-kinase (PI3K) pathway inhibitor[1]
• as an endoderm-inducing agent in stem cell selection and differentiation[2]
• as a autophagy inhibitor[3]

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.[4] Wortmannin may also be used to block and study the functional roles of polo-like kinases involved in the regulation of mitosis.[5]

Biochem/physiol Actions

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 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 possesses anti-inflammatory properties.[6] This mold metabolite[6] is capable of preventing an intermediate step in transcytosis. In fisher rat thyroid (FRT) cells, wortmannin helps to block bidirectional transcytosis of ricin.[7]

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302 + H332
• pcodes: P261 - P264 - P270 - P271 - P301 + P312 - P304 + P340 + P312
• Hazard Classifications: Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 2
• flash_point_f: 188.6 °F - closed cup
• flash_point_c: 87 °C - closed cup