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Merck

W1628

Wortmannin

From Penicillium funiculosum, ≥98% (HPLC and TLC), phosphatidylinositol 3-kinase inhibitor, powder

Sinónimos:

KY 12420

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Fórmula empírica (notación de Hill):
C23H24O8
Número CAS:
19545-26-7
Peso molecular:
428.43
NACRES:
NA.77
PubChem Substance ID:
24278777
UNSPSC Code:
12352207
MDL number:
MFCD00133927
Beilstein/REAXYS Number:
67676

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Nombre del producto

Wortmannin, from Penicillium funiculosum, ≥98% (HPLC and TLC)

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

SMILES string

[H][C@@]12CCC(=O)[C@@]1(C)C[C@@H](OC(C)=O)C3=C2C(=O)c4occ5C(=O)O[C@H](COC)[C@@]3(C)c45

InChI key

QDLHCMPXEPAAMD-QAIWCSMKSA-N

biological source

Penicillium funiculosum

assay

≥98% (HPLC and TLC)

form

powder

color

off-white

solubility

DMSO: soluble
H2O: unstable

storage temp.

2-8°C

Quality Level

300

Gene Information

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

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Biochem/physiol Actions

Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM.
Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM. Inhibition of PI3-K/Akt signal transduction cascade enhances the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. Inhibition of PI3-K by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide and Kinase Phosphatase Biology research. Discover more featured Cyclic Nucleotide and Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the G Proteins (Heterotrimeric) and Phosphoinositide Kinases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Clase de almacenamiento

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
108M4006V
079M4044V
14171002
077M4083V
105M4020V

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Alban R Pereira et al.
Journal of medicinal chemistry, 53(24), 8523-8533 (2010-12-03)
Analogues of the sponge meroterpenoid liphagal have been synthesized and evaluated for inhibition of PI3Kα and PI3Kγ as part of a program aimed at developing new isoform-selective PI3K inhibitors. One of the analogues, compound 24, with IC₅₀ values of 66
S Nakanishi et al.
The Journal of biological chemistry, 267(4), 2157-2163 (1992-02-05)
We have found that a fungal strain, Talaromyces wortmannin KY12420, produces a potent inhibitor of smooth muscle myosin light chain kinase (MLCK). This active product, designated as MS-54, was isolated and purified from the culture broth of the fungus and
Alexander D Crawford et al.
PloS one, 6(2), e14694-e14694 (2011-03-08)
Natural products represent a significant reservoir of unexplored chemical diversity for early-stage drug discovery. The identification of lead compounds of natural origin would benefit from therapeutically relevant bioassays capable of facilitating the isolation of bioactive molecules from multi-constituent extracts. Towards
Inhibitory effect of wortmannin on phosphatidylinositol 3-kinase-mediated cellular events.
O Hazeki et al.
Journal of lipid mediators and cell signalling, 14(1-3), 259-261 (1996-09-01)
Matthew G K Benesch et al.
Journal of lipid research, 56(6), 1134-1144 (2015-04-22)
Autotaxin (ATX) is a secreted enzyme, which produces extracellular lysophosphatidate (LPA) from lysophosphatidylcholine (LPC). LPA activates six G protein-coupled receptors and this is essential for vasculogenesis during embryonic development. ATX is also involved in wound healing and inflammation, and in
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