WORTMANNIN

PRODUCT IDENTIFICATION

19545-26-7

TOXICITY

Oral Rat LD50 : 4 mg/kg

H.S. CODE

Wortmannin;

(1alpha,11alpha)-11-(Acetyloxy)-1-(methoxymethyl)-2-oxaandrosta-5,8-dieno (6,5,4-bc)furan- 3,7,17- trione;

O1C(=O)c2c3[C@]([C@H]1COC)(C1=C(C(=O)c3oc2)[C@H]2[C@] (C[C@H] 1OC(=O)C)(C(=O)CC2)C)C

CLASSIFICATION

Antibiotic, Antifungal, Hormone antagonist, Immunosuppressive, Protein Kinase Inhibitor, Serotonin antagonist

EXTRA NOTES

A phospholipase D antagonist; also inhibits PI3-kinase; inhibits alloantigen-specific T cell activation and cytotoxic T cell responses in human tumor cell lines.

PHYSICAL AND CHEMICAL PROPERTIES

Insoluble

Soluble in methanol (5 mg/ml), ethanol

REFRACTIVE INDEX

NFPA RATINGS

Health hazard: 4, Fire: 0, Reactivity Hazard: 1

AUTOIGNITION

FLASH POINT

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Wortmannin

PubChem Compound Summary - Wortmannin

Drug Bank -  Wortmannin

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Wortmannin

http://www.ebi.ac.uk/ -  Wortmannin

http://www.ncbi.nlm.nih.gov/ -  Wortmannin

http://pubs.rsc.org/
Recent synthetic and biological studies of the viridin class of steroidal furans have revealed multiple opportunities for fundamental discoveries as well as advanced drug design. Wortmannin is a potent enzyme inhibitor that binds to the ATP site of important regulatory kinases such as PI-3 kinase and Polo-like kinase. The natural product shares a unique mechanism-based biological activation pathway with other viridins. Furthermore, while there have been several encouraging approaches toward the total synthesis of these compounds, there is still ample room for improvements in synthetic strategies and tactics, and the development of structurally simplified analogs that exert more specific biological effects and are devoid of toxicity issues that have thwarted the clinical development of the parent compounds.

http://www.sigmaaldrich.com/
Biochem/physiol Actions: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.

Local:

APPEARANCE

ASSAY

98.0% min

3462

HAZARD OVERVIEW

OSHA Hazards:Delayed target organ effects, Highly toxic by inhalation, Highly toxic by ingestion, Highly toxic by skin absorption. Target Organs: Hear

GHS

Danger

PICTOGRAMS

HAZARD STATEMENTS

H300-H310-H330

P STATEMENTS

P260-P264-P280-P284-P302 + P350-P310

RISK PHRASES

26/27/28

SAFETY PHRASES

28-36/37-45