| Identification | Back Directory | [Name]
ANISOMYCIN | [CAS]
22862-76-6 | [Synonyms]
Nsc76712
Nsc147340
Aids031977
FLAGECIDIN
ANISOMYCIN
Aids-031977
Wuningmeisu C
4-beta))-alph
antibioticpa-106
ANISOMYCIN, STREPTOMYCES GRISEOLUS
ANISOMYCIN FROM STREPTOMYCES GRISEOLUS
2-(P-METHOXYBENZYL)-3,4-PYRROLIDINEDIOL-3-ACETATE
Anisomycin (from Streptomyces griseolus)≥ 98% (HPLC)
2-P-METHOXYPHENYLMETHYL-3-ACETOXY-4-HYDROXYPYRROLIDINE
(2R)-2α-(4-Methoxybenzyl)pyrrolidine-3α,4β-diol 3-acetate
NSC 76712 Anisomycin Flagecidin
Flagecidin, SA 3097C1, PA 106, Anhydroscopin A, NSC 76712
2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol-3-acetate
Anisomycin, Ready Made Solution from Streptomyces griseolus
2-(p-methoxybenzyl)-,3-acetate,(2s,3r,4r)-4-pyrrolidinediol
(2R,3S,4S)-2-(4-METHOXYBENZYL)-3,4-PYRROLIDINEDIOL-3-ACETATE
(2R,3S,4S)-2-(4-METHOXYBENZYL)-3,4-PYRROLIDINEDOIL-3-ACETATE
(2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate
(2R,3S,4S)-4-hydroxy-2-(4-Methoxybenzyl)pyrrolidin-3-yl acetate
(2S,3R,4R)-2-(4-methoxybenzyl)-4-hydroxypyrrolidin-3-yl acetate
(2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine
(2R,3S,4S)-2-[(4-METHOXYPHENYL)METHYL]-3,4-PYRROLIDINEDIOL 3-ACETATE
1,4-Imino-5-(4-methoxyphenyl)1,4,5-trideoxy-D-xylo-pentitol 3-acetate
Acetic acid (2R)-4β-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3α-yl ester
1,4,5-trideoxy-1,4-imino-5-(p-methoxyphenyl)-D-xylo-pentitol 3-acetate
3,4-Pyrrolidinediol, 2-(4-methoxyphenyl)methyl-, 3-acetate, (2R,3S,4S)-
2-((4-methoxyphenyl)methyl)-,3-acetate,(2r-(2-alpha,3-4-pyrrolidinediol
D-xylo-Pentitol, 1,4,5-trideoxy-1,4-imino-5-(4-methoxyphenyl)-, 3-acetate | [EINECS(EC#)]
245-269-7 | [Molecular Formula]
C14H19NO4 | [MDL Number]
MFCD00077650 | [MOL File]
22862-76-6.mol | [Molecular Weight]
265.3 |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
140-141 C | [alpha ]
D23 -30° (methanol) | [Boiling point ]
408.52°C (rough estimate) | [density ]
1.1356 (rough estimate) | [refractive index ]
1.5230 (estimate) | [Fp ]
87℃ | [storage temp. ]
2-8°C
| [solubility ]
methanol: 20 mg/mL, clear, colorless to faintly yellow
| [form ]
solid
| [pka]
7.9(at 25℃) | [color ]
white
| [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml | [λmax]
283nm(EtOH)(lit.) | [Merck ]
14,670 | [BRN ]
20705 | [InChIKey]
YKJYKKNCCRKFSL-RDBSUJKOSA-N |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline | [Uses]
Anisomycin is a phenylmethylenepyrrolidine first isolated from Streptomyces griseolus in 1954 as an antiprotozoan with antifungal activity. Anisomycin is an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. Interestingly, anisomycin has found use for the induction of amnesia in animal models. More recently, anisomycin has been demonstrated to induce apoptosis, to be a selective signalling agonist, to activate mitogen-activated protein (MAP) kinases and to be immunomodulatory via its action on T cells. | [Definition]
ChEBI: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. | [Biological Activity]
Protein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). | [Description]
Anisomycin (22862-76-6) activates JNK/SAPKs and reduces c-fos and c-jun. Protein synthesis inhibitor. Anisomycin induces apoptosis and sensitizes cells to anoikis. Cell permeable. | [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. | [Safety Profile]
Poison by ingestion,intraperitoneal, subcutaneous, and intravenous routes.When heated to decomposition it emits toxic fumes ofNOx. | [storage]
+4°C | [References]
1) Hazzalin?et al. (1998),?Anisomycin Selectively Desensitizes Signalling Components Involved in Stress Kinase Activation and fos and jun Induction; Mol. Cell. Bio.,?8?1844
2) Mawji?et al. (2007),?A Chemical Screen Identifies Anisomycin as an Anoikis Sensitizer That Functions by Decreasing FLIP Protein Synthesis; Cancer Res.,?67?8307 |
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