SDS
CofA
Description
A fungal metabolite that specifically inhibits phosphatidylinositol 3-kinase (PI-3), mitogen-activated protein kinase(MAPK) and myosin light-chain kinase (MLCK).Glycogen Synthase Kinase-3 Plays a Central Role in Mediating Glucocorticoid-Induced Apoptosis, Independent and sequential recruitment of NHEJ and HR factors to DNA damage sites in mammalian cells.Nongenotropic, Anti-Apoptotic Signaling of 1,25(OH)2-Vitamin D3 and Analogs through the Ligand Binding Domain of the Vitamin D Receptor in Osteoblasts and Osteocytes: MEDIATION BY Src, PHOSPHATIDYLINOSITOL 3-, AND JNK KINASES
Applications
• exhibits broad spectrum antifungal activity
• antitumor and antiinflammatory activity
• cell biology reagent in research to inhibit DNA repair
More Information
Alternate Name/Synonyms
Wartmannin; Penicillium wortmanni; KY 12420; SL-2052
SKU
W-1022
CAS #
19545-26-7
Chemical Name
[(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate
Chemical Formula
C23H24O8
Molecular Weight
428.4 Da
Appearance
White powder with yellow cast
Purity
>98% by HPLC
Solubility
DMSO (50 mg/ml), ethanol (25 mg/ml), methanol, 1:8 DMSO:PBS(pH 7.2) (~0.1 mg/ml), and DMF (~14 mg/ml)
Melting Point
240°C
Storage Temp
-20°C, desiccated
THERAPEUTIC AREA
Infectious Diseases
USE
Wortmannin is a commonly used cell biology reagent that has been used previously in research to inhibit DNA repair, receptor-mediated endocytosis and cell proliferation. It is a selective, irreversible inhibitor of phosphatidylinositol 3-kinase (PI3K), and PI3K is involved in Toll-like receptor (TLR) signaling. Inhibition of PI3K with wortmannin enhances TLR-mediated inducible nitric-oxide synthase (iNOS) expression, activates NF-κB and up-regulates cytokine mRNA production. Furthermore, PI3K is required for autophagy, which is a complex pathway in which cell material can be sequestered and delivered to the lysosome for degradation. Inhibition of PI3K with wortmannin can inhibit autophagic sequestration.
Merck Index
13.10110.2001
MDL NUMBER
MFCD00133927
CHEMACX
X1097086-6
INCHI
InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1
SMILES
CC(=O)O[C@@H]1C[C@]2([C@@H](CCC2=O)C3=C1[C@@]4(c5c(coc5C3=O)C(=O)O[C@@H]4COC)C)C
RTECS
CB9641000
UN #'S
UN 3462
PACKING GROUP
I
Handling
WARNING! Very TOXIC
PROTECT FROM LIGHT & MOISTURE!
Use only in area provided with appropriate exhaust ventilation. Keep away from heat and source of ignition. Empty containers pose a fire risk, evaporate residue under fume hood. Ground all equipment containing material. Do not breathe dust.
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3
| GHS PICTOGRAMS |  |
|---|---|
| Handling | WARNING! Very TOXIC PROTECT FROM LIGHT & MOISTURE! Use only in area provided with appropriate exhaust ventilation. Keep away from heat and source of ignition. Empty containers pose a fire risk, evaporate residue under fume hood. Ground all equipment containing material. Do not breathe dust. |
| UN #'S | UN 3462 |
| Packing Group | I |
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