| Source: | Wortmanin is produced by the fungus Talaromyces (Penicillium) wortmannii |
| Synonyms | Antibiotic 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
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| Description: | Wortmannin is an antifungal antibiotic, similar to viridin. |
| Canonical SMILES |
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| 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 point | 240oC +- 2oC. not a part of specification |
| Solubility | Clear colorless solution at 5 mg/ml Methanol. |
| Storage | -20°C .Hygroscopic. Protect from light and moisture. |
| Applications | Wortmannin 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. |
| Classification | chemical class:Androstadiene
phospholipase D inhibitor. Immunosupressor. Antifungal. |
| Related products | |
| | For Research use only. Not for Human or Drug use
GMP/API grade
 Wortmannin by Fermentek (starting with lot number W019) is not produced from or contains any ingredients from animal origin.
No genetically modified organisms are used. |
| Publications | Yuan 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 derivatesJournal 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 formationM 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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