A9789
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A9789
Sigma
Anisomycin from Streptomyces griseolus
~97% (TLC), solid
| Synonym: | (2R,3S,4S)-2-(4-Methoxybenzyl)-3,4-pyrrolidinediol-3-acetate, 2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate, Flagecidin |
| CAS Number: | 22862-76-6 |
| Linear Formula: | C14H19NO4 |
| Molecular Weight: | 265.30 |
| Beilstein Registry Number: | 20705 |
| EC Number: | 245-269-7 |
| MDL number: | MFCD00077650 |
| PubChem Substance ID: | 24891496 |
Description
| Caution | Hygroscopic |
| Biochem/physiol Actions | Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent. |
Properties
| assay | ~97% (TLC) |
| form | solid |
| color | white |
| solubility | ethanol: 12 mg/mL |
| H2O: 2 mg/mL Aqueous solutions are stable over a wide range of pH at room temperature. | |
| DMSO: 20 mg/mL | |
| storage temp. | 2-8°C |
Safety
| Personal Protective Equipment | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges |
| Hazard Codes | T |
| Risk Statements | 25 |
| Safety Statements | 45 |
| RIDADR | UN3462 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | BZ9800000 |
References
| reference | Alberts, B., et al., Basic genetic mechanisms in molecular biology of the cell. Cell 3rd ed., New York, NY , 240, (1994) |
| Polverino, A.J., Patterson, S.D., Selective activation of caspases during apoptotic induction in HL-60 cells. Effects of a tetrapeptide inhibitor. J. Biol. Chem. 272, 7013, (1997) Abstract | |
| Faris, M., et al., The c-Jun N-terminal kinase cascade plays a role in stress-induced apoptosis in Jurkat cells by up-regulating Fas ligand expression. J. Immunol. 160, 134-144, (1998) Abstract | |
| Zechner, D., et al., MKK6 activates myocardial cell NF-kappaB and inbibits apoptosis in a p38 mitogen-activated protein kinase-dependent manner. J. Biol. Chem. 273, 8232-8239, (1998) Abstract | |
| Liao, J., et al., Stress apoptosis and mitosis induce phosphorylation of human keratin 8 at Ser-73 in tissues and cultured cells. J. Biol. Chem. 272, 17565, (1997) Abstract | |
| Barros, L.F., et al., Evidence of two mechanisms for the activation of the glucose transporter GLUT1 by anisomycin: p38(MAP kinase) activation and protein synthesis inhibition in mammalian cells. J. Physiol. 504, 517-525, (1997) Abstract | |
| Barancik, M., et al., Okadaic acid and anisomycin are protective and stimulate the SAPK/JNK pathway. J. Cardiovasc. Pharmacol. 34, 182-190, (1999) Abstract | |
| Hoffman, M.E., et al., Inhibition of protein synthesis and amino acid transport by crystal violet in Trypanosoma cruz. J. Eukaryot. Microbiol. 42, 293-297, (1995) Abstract | |
| Merck | Merck 13,673 |
| Beilstein | Beil. 21,V,5,523 |
