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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
Molecular Weight:
428.43
MDL Number:
MFCD00133927
MOL File:
19545-26-7.mol
Last updated:2024-11-19 20:33:22

WORTMANNIN Properties

Melting point 234-240 °C
alpha +80.0~+105.0゜(20℃/D)(c=0.1,C2H5OH)
Boiling point 463.31°C (rough estimate)
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
FDA UNII XVA4O219QW

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300+H310+H330
Precautionary statements  P262-P280-P301+P310+P330-P302+P352+P310-P304+P340+P310
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
3-8-10
HazardClass  6.1
PackingGroup  I
HS Code  29322090
NFPA 704
0
4 0

WORTMANNIN price More Price(64)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W1628 Wortmannin from 19545-26-7 1mg $115 2024-03-01 Buy
Sigma-Aldrich W3144 Wortmannin, Ready Made Solution from Penicillium funiculosum, ≥95% (HPLC) 19545-26-7 250μL $132 2024-03-01 Buy
Sigma-Aldrich 681675 Wortmannin 19545-26-7 1mg $113 2024-03-01 Buy
TCI Chemical W0007 Wortmannin >98.0%(HPLC) 19545-26-7 20mg $215 2024-03-01 Buy
Alfa Aesar J63983 Wortmannin, Penicillium funiculosum, 99+% 19545-26-7 10mg $142 2023-06-20 Buy
Product number Packaging Price Buy
W1628 1mg $115 Buy
W3144 250μL $132 Buy
681675 1mg $113 Buy
W0007 20mg $215 Buy
J63983 10mg $142 Buy

WORTMANNIN Chemical Properties,Uses,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, 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

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 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.

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

22614-34-2
19545-26-7
Synthesis of WORTMANNIN from Androst-4-ene-3,17-dione, 9,11-epoxy-, (11α)-
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View Lastest Price from WORTMANNIN manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Wortmannin pictures 2024-11-19 Wortmannin
19545-26-7
US $32.00-72.00 / mg 99.76% 10g TargetMol Chemicals Inc.
WORTMANNIN pictures 2019-07-06 WORTMANNIN
19545-26-7
US $2.00 / kg 1kg 99% 100kg Career Henan Chemical Co
  • Wortmannin pictures
  • Wortmannin
    19545-26-7
  • US $32.00-72.00 / mg
  • 99.76%
  • TargetMol Chemicals Inc.
  • WORTMANNIN pictures
  • WORTMANNIN
    19545-26-7
  • US $2.00 / kg
  • 99%
  • Career Henan Chemical Co

WORTMANNIN Spectrum

antibioticsl-2052 sl-2052 [1S-(1ALPHA,6BALPHA,9ABETA,11ALPHA,11BBETA)]-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-BENZOPYRAN-3,6,9-TRIONE KY 1242 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)- Wortmannin KY 1242 Wortmannin (+)-Wortmannin Wortmannin, Ready Made Solution 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 (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 Wortmannin,98% Wortmammin WORTMANNIN FROM PENICILLIUM FUMICULASUM Wortmannin,KY 12420 WORTMANNINWORTMANN CS-731 SL-2052;KY-12420 Wortmannin - CAS 19545-26-7 - Calbiochem Wortmannin, a multi-target inhibitor of PI3K and MLCK 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 from Talaromyces (Penicillium) Wortmannin, 98%, a multi-target inhibitor of PI3K and MLCK 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