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Anisomycin information


Anisomycin[1]
Names
Preferred IUPAC name
(2R,3S,4S)-4-Hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate
Other names
Flagecidin
Identifiers
CAS Number
  • 22862-76-6 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:338412 ☒N
ChEMBL
  • ChEMBL423192 ☒N
ChemSpider
  • 29260 checkY
ECHA InfoCard 100.041.139 Edit this at Wikidata
PubChem CID
  • 31549
UNII
  • 6C74YM2NGI checkY
CompTox Dashboard (EPA)
  • DTXSID5040966 Edit this at Wikidata
InChI
  • 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+/m0/s1 checkY
    Key: YKJYKKNCCRKFSL-BFHYXJOUSA-N checkY
  • InChI=1/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+/m0/s1
    Key: YKJYKKNCCRKFSL-BFHYXJOUBQ
SMILES
  • O=C(O[C@@H]1[C@@H](NC[C@H]1O)Cc2ccc(OC)cc2)C
Properties
Chemical formula
C14H19NO4
Molar mass 265.309 g·mol−1
Melting point 139 to 143 °C (282 to 289 °F; 412 to 416 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Anisomycin, also known as flagecidin, is an antibiotic produced by Streptomyces griseolus which inhibits eukaryotic protein synthesis. Partial inhibition of DNA synthesis occurs at anisomycin concentrations that effect 95% inhibition of protein synthesis.[2] Anisomycin can activate stress-activated protein kinases, MAP kinase and other signal transduction pathways.

  1. ^ Anisomycin Archived January 19, 2012, at the Wayback Machine from Sigma Aldrich
  2. ^ Grollman, Arthur P. (1967). "Inhibitors of protein biosynthesis. II. Mode of action of anisomycin". The Journal of Biological Chemistry. 242 (13): 3226–33. doi:10.1016/S0021-9258(18)95953-3. PMID 6027796.

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Anisomycin

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amygdala has been shown to prevent long-term memory for fear conditioning. Anisomycin inhibits the production of proteins. In tests where it is delivered to...

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injected with anisomycin, an antibiotic that restricts protein synthesis, at different points in time. The rats that were injected with anisomycin after consolidation...

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adapted for research purposes. In research, commonly used PSI's include anisomycin, cycloheximide, and puromycin - although the use of puromycin has stopped...

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List of biomolecules

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α-amylase) Anabolic steroid Anandamide (ANA) Androgen Anethole Angiotensinogen Anisomycin Antidiuretic hormone (ADH) Anti-Müllerian hormone (AMH) Arabinose Arginine...

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Streptomyces halstedii

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oligomycins (oligomycin A, oligomycin B, oligomycin C) and the antibiotics anisomycin and sinefungin. Tohyama, Shigehiro; Kakinuma, Katsumi; Eguchi, Tadashi...

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MTORC1

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and JNK activation are not required for cell death induced by anisomycin and anisomycin analogues". Biochemical and Biophysical Research Communications...

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Azotobacter chroococcum

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specifically fungi that are susceptible to "fungicidal substances of the anisomycin group".[citation needed] This bacterium can also be used to determine...

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Peter Jaffrey Wheatley

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where he published a paper with John P. Schaefer on the structure of anisomycin. Wheatley’s last position was in the Department of Physical Chemistry...

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C14H19NO4

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C14H19NO4 (molar mass: 265.31 g/mol, exact mass: 265.1314 u) may refer to: Anisomycin, also known as flagecidin Filenadol This set index page lists chemical...

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Animal cognition

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retention of olfactory memories in honeybees is impaired by actinomycin D and anisomycin". The European Journal of Neuroscience. 10 (8): 2742–5. doi:10.1046/j...

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Synaptic tagging

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synthesis within the particular dendritic spine, as proven by injecting anisomycin into a dendritic spine and observing the resulting absence of late LTP...

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Hippocampal memory encoding and retrieval

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post-retrieval an intra-amygdalar infusion of a known amnesic agent, anisomycin, rats failed to recall a rapidly learned fear memory. Hippocampal lesions...

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Fermentek

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Haloferax larsenii

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acetate, propionate, and citrate. Sensitivity to novobiocin, bacitracin, anisomycin, aphidicolin, and rifampicin have been observed. However, no sensitivity...

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P53 upregulated modulator of apoptosis

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the cytokine TGFβ, the death effector TRAIL or chemical drugs such as anisomycin. PUMA protein is degraded in a proteasome dependent manner and its degradation...

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ZAK

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PMID 15684425. Wang X, Mader MM, Toth JE, et al. (2005). "Complete inhibition of anisomycin and UV radiation but not cytokine induced JNK and p38 activation by an...

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Halobacterium noricense

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antibiotics, including Vancomycin and Tetracycline, but can be killed by Anisomycin. This organism does not produce the enzymes gelatinase or amylase, so...

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MAPK13

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response to interleukin-1 cellular response to sorbitol cellular response to anisomycin cellular response to sodium arsenite MAPK cascade intracellular signal...

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ELK3

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(2000). "The net repressor is regulated by nuclear export in response to anisomycin, UV, and heat shock". Mol. Cell. Biol. 19 (10): 7076–87. doi:10.1128/mcb...

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Jun dimerization protein

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various stress conditions such as UV irradiation, oxidative stress, and anisomycin treatment or JDP2 is also regulated by other kinases such as p38 MAPK...

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