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WORTMANNIN

Product Name
WORTMANNIN
CAS No.
19545-26-7
Chemical Name
WORTMANNIN
Synonyms
CS-731;KY 1242;sl-2052;KY 12420;WORTMANNIN;Wortmammin;Wortmannin,98%;WORTMANNINTOXIN;SL-2052;KY-12420;antibioticsl-2052
CBNumber
CB7241293
Molecular Formula
C23H24O8
Formula Weight
428.43
MOL File
19545-26-7.mol
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WORTMANNIN Property

Melting point:
234-240 °C
Boiling point:
463.31°C (rough estimate)
alpha 
+80.0～+105.0゜(20℃/D)(c=0.1,C2H5OH)
Density 
1.2454 (rough estimate)
refractive index 
1.4480 (estimate)
Flash point:
2℃
storage temp. 
-20°C
solubility 
DMSO: soluble
form 
powder
color 
off-white
Sensitive 
Light Sensitive
λmax
296nm(lit.)
Merck 
14,10053
BRN 
67676
Stability:
Stable for 1 year from date of purchase as supplied. Dried aliquots evaporated from ethanol may be stored at -20° for several months. Solutions however are not stable and must be used within one working day. Note
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Safety

Hazard Codes 
T+,T,Xi,Xn,F
Risk Statements 
26/27/28-36/37/38-36-20/21/22-11
Safety Statements 
28-36/37-45-37/39-26-16
RIDADR 
UN 3462 6.1/PG 1
WGK Germany 
3
RTECS 
CB9641000
F 
3-8-10
HazardClass 
6.1
PackingGroup 
I
HS Code 
29322090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P262Do not get in eyes, on skin, or on clothing.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W1628
Product name
Wortmannin
Purity
from
Packaging
1mg
Price
$115
Updated
2024/03/01
Sigma-Aldrich
Product number
W3144
Product name
Wortmannin, Ready Made Solution
Purity
from Penicillium funiculosum, ≥95% (HPLC)
Packaging
250μL
Price
$132
Updated
2024/03/01
Sigma-Aldrich
Product number
681675
Product name
Wortmannin
Packaging
1mg
Price
$113
Updated
2024/03/01
TCI Chemical
Product number
W0007
Product name
Wortmannin
Purity
>98.0%(HPLC)
Packaging
20mg
Price
$215
Updated
2024/03/01
Alfa Aesar
Product number
J63983
Product name
Wortmannin, Penicillium funiculosum, 99+%
Packaging
10mg
Price
$142
Updated
2023/06/20
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WORTMANNIN Chemical Properties,Usage,Production

Description

Wortmannin (19545-26-7) is a potent and selective inhibitor of PI3-kinase which acts via covalent modification of Lys-802.2?Inhibits autophagy in rat hepatocytes.3?Inhibits adipocyte differentiation of 3T3-L1 cells.4?Wortmannin is useful tool for probing PI3-K-mediated cellular events.5

Chemical Properties

White to pale yellow powder

Uses

Wortmannin is a steroidal metabolite belonging to the viridin group, isolated from Penicillium wortmannii in 1957. The structure was finally solved in 1968. Wortmannin exhibits broad spectrum antifungal activity, together with antitumour and antiinflammatory activity. Wortmannin is a potent inhibitor of phosphoinositide 3-kinase and myosin light chain kinase. Wortmannin also activates neutrophil and formyl-Met-Leu-Phe-mediated phospholipase D, inhibits autophagy, potentiates LPS-induced NO production and induces Alzheimer-like hyperphosphorylation in tau in vivo.

Uses

Wortmannin is used as inhibitor of phosphatidylinositol 3-kinase, used cell biology reagent that has been used previously in research to inhibit DNA repair, receptor-mediated endocytosis and cell proliferation. It inhibits fMLP induced PIP3 and superoxide anion production in guinea pig neutrophils. It blocks insulin metabolic effects in rat adipocytes without affecting the insulin receptor tyrosine kinase activity.

Uses

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

Definition

ChEBI: Wortmannin is an organic heteropentacyclic compound, a delta-lactone, an acetate ester and a cyclic ketone. It has a role as an EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor, an anticoronaviral agent, a geroprotector, an autophagy inhibitor, a Penicillium metabolite, a radiosensitizing agent and an antineoplastic agent.

Biological Activity

Potent, selective, cell-permeable and irreversible inhibitor of phosphatidylinositol 3-kinase (PI 3-kinase) (IC 50 = 2-4 nM). Also potently inhibits polo-like kinase 1 (PLK1) (IC 50 = 5.8 nM).

Biochem/physiol Actions

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.

storage

-20°C (desiccate)

References

1) Holleran et al. (2003), Use of high-performance liquid chromatography to characterize the rapid decomposition of wortmannin in tissue culture media; Anal. Biochem., 323 19 2) Wymann et al. (1996), Wortmannin inactivates phosphoinositide 3-kinase by covalent modification of Lys-802, a residue involved in the phosphate transfer reaction; Mol. Cell. Biol., 16 1722 3) Blommaart et al. (1997), The phosphatidylinositol 3-kinase inhibitors wortmannin and LY294002 inhibit autophagy in isolated rat hepatocytes; Eur. J. Biochem., 243 240 4) Tomiyama et al. (1995), Wortmannin, a specific phosphatidylinositol 3-kinase inhibitor, inhibits adipocytic differentiation of 3T3-L1 cells; Biochem. Biophys. Res. Commun., 212 263 5) Ui et al. (1995), Wortmannin as a unique probe from an intracellular signaling protein, phosphoinositide 3-kinase; Trends Biochem. Sci., 20 303

WORTMANNIN Preparation Products And Raw materials

Raw materials

Preparation Products

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WORTMANNIN Suppliers

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View Lastest Price from WORTMANNIN manufacturers

Career Henan Chemical Co
Product
WORTMANNIN 19545-26-7
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-24

19545-26-7, WORTMANNINRelated Search:

TRIPLAL 2-HEXYLFURAN 1-(2-FURYL)BUTAN-1-ONE Methyl furan-3-carboxylate 2-PROPIONYLFURAN 1-(2-FURYL)HEPTAN-1-ONE 4-Methyl-3-decen-5-ol 2,6-Dimethyl-5-heptenal 1-(2-FURYL)PENTAN-1-ONE 3-(2-OXOPROPYL)-2-PENTYLCYCLOPENTANONE 2,5-DIMETHYL-2-OCTEN-6-ONE 2-HEXANOYLFURAN WORTMANNIN 2-N-HEPTYLFURAN 3-Furoic acid 2-METHYL-2-CYCLOHEXEN-1-OL 3-Methylfuran-2-carboxaldehyde 97% 11-desacetoxywortmannin

  • antibioticsl-2052
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  • Wortmannin KY 1242
  • Wortmannin (+)-Wortmannin
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  • Wortmannin solution
  • Wortmannin, Penicillium funiculosum
  • (1S,6BR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-3,6,6b,7,8,9,9a,10,11,11b
  • Wortmannin, 98%, a multi-target inhibitor of PI3K and MLCK
  • (1S,6BR,9AS,11R,11BR) 11-(ACETYLOXY)-1,6B,7,8,9A,10,11,11B-OCTAHYDRO-1-(METHOXYMETHYL)-9A,11B-DIMETHYL-3H-FURO[4,3,2-DE]INDENO[[4,5-H]-2-H]-2-BENZOPYRAN-3,6,9-TRIONE
  • WORTMANNIN FROM PENICILLIUM FUMICULOSUM
  • KY 12420
  • PI 3-KINASE INHIBITOR
  • WORTMANNIN, PENICILLIUM WORTMANNI
  • WORTMANNIN
  • Wortmannin,Penicilliumwortmannin
  • 3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)- (9CI)
  • WORTMANNINTOXIN
  • WORTMANNIN, FROM PENICILLIUM FUNICULOSUM
  • (1S,6br,9aS,11R,11bR) 11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo[4,3,2-de]indeno[4,5,-h]-2-h]-2-benzopyran-3,6,9-trione
  • (1S)-1,6bβ,7,8,9a,10,11,11b-Octahydro-11β-acetyloxy-1-(methoxymethyl)-9aα,11bα-dimethyl-3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione
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  • WORTMANNINWORTMANN
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  • SL-2052;KY-12420
  • Wortmannin - CAS 19545-26-7 - Calbiochem
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  • WORTMANNIN USP/EP/BP
  • (1S,6bR,9aS,11R,11bR)-1-(Methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate
  • Wortmannin (SL-2052
  • Wortmannin (99.5%)
  • Wortmannin (BR, 99%)
  • (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-3,6,6b,7,8,9,9a,10,11,11b-decahydro-1H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate
  • Wortmannin in Acetonitrile
  • 19545-26-7
  • C23H24O8
  • Enzymes, Inhibitors, and Substrates
  • Enzyme Inhibitors by Type
  • Enzyme Inhibitors
  • Kinase/Phosphatase Biology
  • Serine/Threonine Kinase Inhibitors
  • Phosphatidylinositol 3-kinase (PI3K)
  • Other
  • Cell Signaling and Neuroscience
  • Cell Biology
  • Biochemicals and Reagents
  • BioChemical
  • Anti-cancer&immunity
  • inhibitor
  • Inhibitors
  • Signalling