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cancer research reagents

Wortmannin

MSDSSample CoA
 
Source: Wortmanin is produced by the fungus  Talaromyces (Penicillium) wortmannii
SynonymsAntibiotic SL-2052
Wartmannin
Wortmannin
Systematic Name
(1alpha,11alpha)-11-(Acetyloxy)-1-(methoxymethyl)-2-oxaandrosta-5,8-dieno(6,5,4-bc)furan-3,7,17-trione
 
Description: Wortmannin is an antifungal antibiotic, similar to viridin.
Canonical SMILES  
CAS number: 19545-26-7
Merck index: 12, 10188
Molecular weight: 428.44
Structure:

Molecular Formula: C23H24O8
Canonical SMILES: CC(=O)OC1CC2(C(CCC2=O)C3=C1C4(C(OC(=O)C5=COC(=C54)C3=O)COC)C)C
Solubility
information:
DMSO, Methanol. Unstable in aqueous and ethanolic solutions.
Specifications  
Appearance: Off-white to pale yellow powder
Purity: At least 97.5% by TLC, HPLC
λmax:210-220, 256, 293 (not a part of specification)
Melting point240oC +- 2oC. not a part of specification
SolubilityClear colorless solution at 5 mg/ml Methanol.
Storage-20°C .Hygroscopic. Protect from light and moisture.
ApplicationsWortmannin is an inhibitor of phosphatidyl-inositol 3-kinase
Wortmannin inhibits the growth of mammary tumors despite the existence of a novel wortmannin-insensitive phosphatidylinositol-3-kinase.
Wortmannin inhibits repair of DNA double-strand breaks in irradiated normal human cells.

Wortmannin was shown to have enhancing influence on memory and impair learning abilities.

Warnings TOXIC.
POTENTIALLY FATAL IF SWALLOWED, INHALLED OR ABSORBED THROUGH SKIN.
Classificationchemical class:Androstadiene
phospholipase D inhibitor. Immunosupressor. Antifungal.
Related products 
 For Research use only. Not for Human or Drug use
GMP/API grade

Animal Free productWortmannin by Fermentek (starting with lot number W019) is not produced from or contains any ingredients from animal origin.

No genetically modified organisms are used.
 PublicationsYuan H, Luo J, Weissleder R, Cantley L, Josephson L.
Wortmannin-C20 conjugates generate wortmannin.
J Med Chem. 2006 Jan 26;49(2):740-7.
 Nakipova OV, Andreeva LA, Zakharova NM, Semenova TP, Solomonov NG.
Influence of wortmannin on the inotropic effect of insulin in papillary muscles of Siberian ground squirrel heart.
Dokl Biochem Biophys. 2006 Mar-Apr;407:91-3
 Zhu T, Gu J, Yu K, Lucas J, Cai P, Tsao R, Gong Y, Li F, Chaudhary I, Desai P, Ruppen M, Fawzi M, Gibbons J, Ayral-Kaloustian S, Skotnicki J, Mansour T, Zask A.
Pegylated wortmannin and 17-hydroxywortmannin conjugates as phosphoinositide 3-kinase inhibitors active in human tumor xenograft models.
J Med Chem. 2006 Feb 23;49(4):1373-8.
 Hazeki K, Kinoshita S, Matsumura T, Nigorikawa K, Kubo H, Hazeki O.
Opposite effects of wortmannin and 2-(4-morpholinyl)-8-phenyl-1(4H)-benzopyran-4-one hydrochloride on toll-like receptor-mediated nitric oxide production: negative regulation of nuclear factor-{kappa}B by phosphoinositide 3-kinase.
Mol Pharmacol. 2006 May;69(5):1717-24.
 Giner JL, Kehbein KA, Cook JA, Smith MC, Vlahos CJ, Badwey JA.
Synthesis of fluorescent derivatives of wortmannin and demethoxyviridin as probes for phosphatidylinositol 3-kinase.
Bioorg Med Chem Lett. 2006 May 1;16(9):2518-21.
 Sullivan JA, Grummer MA, Yi FX, Bird IM.
Pregnancy-enhanced endothelial nitric oxide synthase (eNOS) activation in uterine artery endothelial cells shows altered sensitivity to Ca2+, U0126, and wortmannin but not LY294002--evidence that pregnancy adaptation of eNOS activation occurs at multiple levels of cell signaling.
Endocrinology. 2006 May;147(5):2442-57

Talaromyces sp.



Wortmannin on Wikipedia

Preclinical potential of
Wortmannin derivates

Journal of medicinal chemistry
2006, vol. 49, no4, pp. 1373-1378

Tianmin Zhu et al

Pegylated wortmannin and 17-hydroxy- wortmannin conjugates as phosphoinositide 3-kinase inhibitors active in human tumor xenograft models

...Wortmannin and its analogues are potent PI3K inhibitors whose thera-peutic use has been impeded by inherent defects such as instability and toxicity. Pegylation of wortmannin and 17-hydroxy- wortmannin gives rise to conjugates with improved properties, including a higher therapeutic index. ...


Wortmannin Enhances Long-Term Spatial and Contextual Memories

Pramod K. Dash et al

...post-training infusion of wortmannin, ..., into the dorsal hippocampi improved long-term memory in two hippocampus-dependent tasks, the Morris water maze and contextual fear conditioning...


Phosphatidylinositol 3-kinase: a molecule mediating BDNF-dependent spatial memory formation

M Mizuno et al

...When spatial learning was inhibited by antisense BDNF oligodeoxynucleotide, the activation was diminished. Chronic treatment with PI3-K inhibitor wortmannin impaired spatial learning...



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  Wortmannin for sale. Delivered immediately from stock. Wortmannin is only intended to be used by trained professionals. wortmannin is0 not iintended for household use.