W1628

Wortmannin

Name: Wortmannin
Brand: SIGMA

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 key

QDLHCMPXEPAAMD-QAIWCSMKSA-N

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

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

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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Bioactive Small Molecule Inhibitors

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Este artículo	681675	M9440	C2020
Sigma-Aldrich W1628 Wortmannin	Sigma-Aldrich 681675 Wortmannin	Sigma-Aldrich M9440 Methyl-3,4-dephostatin	Sigma-Aldrich C2020 α-Cyano-4-hydroxycinnamic acid
form powder	form solid	form powder	form powder
assay ≥98% (HPLC and TLC)	assay ≥98% (HPLC)	assay >98% (HPLC)	assay ≥98% (TLC)
Quality Level 300	Quality Level 100	Quality Level 100	Quality Level 300
storage temp. 2-8°C	storage temp. −20°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: soluble, H₂O: unstable	solubility DMSO: 25 mg/mL	solubility DMSO: soluble 18 mg/mL, H₂O: insoluble	solubility H₂O: slightly soluble, methanol: water: soluble, polar organic solvents: soluble
color off-white	color white to off-white	color red-brown	color yellow

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.

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Referencia del producto

Descripción

Precios

W3144

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

pictograms

GHS06

signalword

Danger

hcodes

H300 + H310 + H330

pcodes

P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310

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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Wortmannin, a microbial product inhibitor of myosin light chain kinase.

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

Synthesis of phosphatidylinositol 3-kinase (PI3K) inhibitory analogues of the sponge meroterpenoid liphagal.

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

Zebrafish bioassay-guided natural product discovery: isolation of angiogenesis inhibitors from East African medicinal plants.

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

Regulation of autotaxin expression and secretion by lysophosphatidate and sphingosine 1-phosphate.

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

The progenitor cell marker NG2/MPG promotes chemoresistance by activation of integrin-dependent PI3K/Akt signaling.

M Chekenya et al.

Oncogene, 27(39), 5182-5194 (2008-05-13)

Chemoresistance represents a major problem in the treatment of many malignancies. Overcoming this obstacle will require improved understanding of the mechanisms responsible for this phenomenon. The progenitor cell marker NG2/melanoma proteoglycan (MPG) is aberrantly expressed by various tumors, but its

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