Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H19NO4 |
| Molecular Weight | 265.305 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)C=C1
InChI
InChIKey=YKJYKKNCCRKFSL-RDBSUJKOSA-N
InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1
| Molecular Formula | C14H19NO4 |
| Molecular Weight | 265.305 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Anisomycin (2-p-methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine) is an antibiotic isolated from cultures of various
Streptomyces. Anisomycin is a potent, structurally specific, and reversible inhibitor of protein biosynthesis in certain yeast and mammalian cells. The inhibition occurs subsequent to the formation of aminoacyl transfer ribonucleic acid but prior to the release of polypeptides from the polyribosome.
Anisomycin has unspecified effects that can produce temporary amnesia for a reactivated memory and they also could be responsible for any permanent effects that anisomycin produces. Anisomycin is known to cause apoptosis by activation of MAPK cascade.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Asbestos-induced disruption of calcium homeostasis induces endoplasmic reticulum stress in macrophages. | 2014-11-28 |
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| DON shares a similar mode of action as the ribotoxic stress inducer anisomycin while TBTO shares ER stress patterns with the ER stress inducer thapsigargin based on comparative gene expression profiling in Jurkat T cells. | 2014-01-30 |
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| BET inhibition as a single or combined therapeutic approach in primary paediatric B-precursor acute lymphoblastic leukaemia. | 2013-07-19 |
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| p38 Mitogen-activated protein kinase regulates nuclear receptor CAR that activates the CYP2B6 gene. | 2013-06 |
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| Wogonin inhibits H2O2-induced vascular permeability through suppressing the phosphorylation of caveolin-1. | 2013-03-08 |
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| In vitro antiviral activity of dehydroepiandrosterone, 17 synthetic analogs and ERK modulators against herpes simplex virus type 1. | 2012-07 |
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| Targets and intracellular signaling mechanisms for deoxynivalenol-induced ribosomal RNA cleavage. | 2012-06 |
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| A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells. | 2012-01-15 |
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| Chronic Nod2 stimulation potentiates activating transcription factor 3 and paradoxical superinduction of epithelial proinflammatory chemokines by mucoactive ribotoxic stressors via RNA-binding protein human antigen R. | 2012-01 |
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| Design and characterization of a potent and selective dual ATP- and substrate-competitive subnanomolar bidentate c-Jun N-terminal kinase (JNK) inhibitor. | 2011-09-22 |
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| Angiotensin II-induced vascular endothelial dysfunction through RhoA/Rho kinase/p38 mitogen-activated protein kinase/arginase pathway. | 2011-05 |
|
| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010-07 |
|
| Basolateral amygdala involvement in memory reconsolidation processes that facilitate drug context-induced cocaine seeking. | 2009-09 |
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| Epithelial cell survival by activating transcription factor 3 (ATF3) in response to chemical ribosome-inactivating stress. | 2009-03-15 |
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| Phosphorylation of Argonaute 2 at serine-387 facilitates its localization to processing bodies. | 2008-08-01 |
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| Molecular mechanism of apoptosis and gene expressions in human lymphoma U937 cells treated with anisomycin. | 2008-03-27 |
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| Translation of striatal-enriched protein tyrosine phosphatase (STEP) after beta1-adrenergic receptor stimulation. | 2007-10 |
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| Rapid down-regulation of Ret following exposure of dopaminergic neurons to neurotoxins. | 2007-09 |
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| Indomethacin induces apoptosis in 786-O renal cell carcinoma cells by activating mitogen-activated protein kinases and AKT. | 2007-06-01 |
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| p38 Mitogen-activated protein kinase mediates IL-8 induction by the ribotoxin deoxynivalenol in human monocytes. | 2006-06-15 |
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| Inhibition of ERK pathway or protein synthesis during reexposure to drugs of abuse erases previously learned place preference. | 2006-02-21 |
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| Arsenic trioxide inhibits nuclear receptor function via SEK1/JNK-mediated RXRalpha phosphorylation. | 2005-10 |
|
| Local proteins associated with methamphetamine-induced nigrostriatal dopaminergic neurotoxicity. | 2005-10 |
|
| Phosphorylation of the retinoid x receptor at the omega loop, modulates the expression of retinoic-acid-target genes with a promoter context specificity. | 2005-10 |
|
| Cultured embryonic hippocampal neurons deficient in glucocorticoid (GC) receptor: a novel model for studying nongenomic effects of GC in the neural system. | 2005-09 |
|
| Ribotoxic stress response to the trichothecene deoxynivalenol in the macrophage involves the SRC family kinase Hck. | 2005-06 |
|
| Complete inhibition of anisomycin and UV radiation but not cytokine induced JNK and p38 activation by an aryl-substituted dihydropyrrolopyrazole quinoline and mixed lineage kinase 7 small interfering RNA. | 2005-05-13 |
|
| Novel signaling stimulated by arsenite increases cholesterol metabolism through increases in unphosphorylated steroidogenic acute regulatory (StAR) protein. | 2005-02-28 |
|
| Superinduction of CYP1A1 in MCF10A cultures by cycloheximide, anisomycin, and puromycin: a process independent of effects on protein translation and unrelated to suppression of aryl hydrocarbon receptor proteolysis by the proteasome. | 2004-10 |
|
| Hypoxia-responsive growth factors upregulate periostin and osteopontin expression via distinct signaling pathways in rat pulmonary arterial smooth muscle cells. | 2004-10 |
|
| MAPK signaling pathways modulate IL-1beta expression in human keratinocytes. | 2004-04-01 |
|
| Estrogen and raloxifene induce apoptosis by activating p38 mitogen-activated protein kinase cascade in synthetic vascular smooth muscle cells. | 2003-09 |
|
| Selective activation of Src family kinases and JNK by low levels of chromium(VI). | 2003-08-01 |
|
| The activation of c-Jun NH2-terminal kinase (JNK) by DNA-damaging agents serves to promote drug resistance via activating transcription factor 2 (ATF2)-dependent enhanced DNA repair. | 2003-06-06 |
|
| Immediate-early gene induction by the stresses anisomycin and arsenite in human osteosarcoma cells involves MAPK cascade signaling to Elk-1, CREB and SRF. | 2003-03-27 |
|
| Cocaine treatment increases expression of a 40 kDa catecholamine-regulated protein in discrete brain regions. | 2003-01 |
|
| Phosphorylation is involved in the activation of metal-regulatory transcription factor 1 in response to metal ions. | 2001-11-09 |
|
| Transient activation of Jun N-terminal kinases and protection from apoptosis by the insulin-like growth factor I receptor can be suppressed by dicumarol. | 2001-06-01 |
|
| Vitamin D3 up-regulated protein 1 mediates oxidative stress via suppressing the thioredoxin function. | 2000-06-15 |
|
| Deficiency of the stress kinase p38alpha results in embryonic lethality: characterization of the kinase dependence of stress responses of enzyme-deficient embryonic stem cells. | 2000-03-06 |
|
| Quinone reductase inhibitors block SAPK/JNK and NFkappaB pathways and potentiate apoptosis. | 1999-10-29 |
|
| Cellular stress in xenopus kidney cells enhances the phosphorylation of eukaryotic translation initiation factor (eIF)4E and the association of eIF4F with poly(A)-binding protein. | 1999-09-15 |
|
| Rapid nucleolytic degradation of the small cytoplasmic Y RNAs during apoptosis. | 1999-08-27 |
|
| Activation of JNK pathway and induction of apoptosis by manganese in PC12 cells. | 1998-10 |
|
| Stress-induced immediate-early gene, egr-1, involves activation of p38/JNK1. | 1998-06-04 |
|
| The phosphorylation of eukaryotic initiation factor eIF4E in response to phorbol esters, cell stresses, and cytokines is mediated by distinct MAP kinase pathways. | 1998-04-17 |
|
| Protein synthesis inhibitors attenuate seizures induced in rats by lithium plus pilocarpine. | 1994-09 |
|
| Investigations into the neuropharmacological basis of temporal stages of memory formation in mice trained in an active avoidance task. | 1987-03 |
|
| Screening for new compounds with antiherpes activity. | 1984-10 |
Patents
Sample Use Guides
In order to make toxicological evaluation of Anisomycin, acute and four-week continuously intravenous toxicity studies were performed in mice. The calculated LD(50) for Anisomycin was 119.64 mg/kg. The mice were intravenously injected through mouse tail vein with a total dose of 5, 15, 30 and 60 mg/kg/mice of Anisomycin every other day for 4 weeks. Just in the high-dose mice, death of three mice happened and body weight of the mice was significantly decreased.
Route of Administration:
Intravenous
Treatment of U251 and U87 cells with anisomycin (0.01-8 μmol/L) inhibited the cell growth in time- and concentration-dependent manners (the IC(50) values at 48 h were 0.233±0.021 and 0.192±0.018 μmol/L, respectively). Anisomycin (4 μmol/L) caused 21.5%±2.2% and 25.3%±3.1% of apoptosis proportion, respectively, in U251 and U87 cells. In the two cell lines, anisomycin (4 μmol/L) activated p38 MAPK and JNK, and inactivated ERK1/2.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:35:57 GMT 2025
by
admin
on
Mon Mar 31 17:35:57 GMT 2025
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| Record UNII |
6C74YM2NGI
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C258
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ANISOMYCIN
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C95312
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6C74YM2NGI
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76712
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m1933
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D000841
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SALT/SOLVATE -> PARENT |
