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W1628

Sigma-Aldrich

Wortmannin

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

Sinonimo/i:

KY 12420

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About This Item

Formula empirica (notazione di Hill):
C23H24O8
Numero CAS:
19545-26-7
Peso molecolare:
428.43
Beilstein:
67676
Numero MDL:
MFCD00133927
Codice UNSPSC:
12352207
ID PubChem:
24278777
NACRES:
NA.77

Origine biologica

Penicillium funiculosum

Livello qualitativo

300

Saggio

≥98% (HPLC and TLC)

Forma fisica

powder

Colore

off-white

Solubilità

DMSO: soluble
H2O: unstable

Temperatura di conservazione

2-8°C

Stringa SMILE

[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

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
QDLHCMPXEPAAMD-QAIWCSMKSA-N

Informazioni sul gene

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

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Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H300 + H310 + H330

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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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
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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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