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Merck

A9789

Anisomycin

from Streptomyces griseolus, ≥98% (HPLC), solid, protein synthesis inhibitor

Synonym(s):

(2R,3S,4S)-2-(4-Methoxybenzyl)-3,4-pyrrolidinediol-3-acetate, 2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate, Flagecidin

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About This Item

Empirical Formula (Hill Notation):
C14H19NO4
CAS Number:
22862-76-6
Molecular Weight:
265.30
NACRES:
NA.77
PubChem Substance ID:
24891496
UNSPSC Code:
12352200
EC Number:
245-269-7
MDL number:
MFCD00077650
Beilstein/REAXYS Number:
20705
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
300

Key Documents

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Product Name

Anisomycin from Streptomyces griseolus, ≥98% (HPLC), solid

Quality Level

300

assay

≥98% (HPLC)

form

solid

color

white to faint yellow

solubility

H2O: 2 mg/mL (Aqueous solutions are stable over a wide range of pH at room temperature.), DMSO: 20 mg/mL, methanol: 20 mg/mL

antibiotic activity spectrum

neoplastics

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

COc1ccc(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)cc1

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

InChI key

YKJYKKNCCRKFSL-RDBSUJKOSA-N

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Related Categories

Biochem/physiol Actions

Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes.
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.

Disclaimer

Hygroscopic

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000510740
0000510740
0000453631
0000453631
0000442830

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J Daubriac et al.
Cell death and differentiation, 16(8), 1146-1155 (2009-04-04)
Pleural fluid accumulation is a frequent clinical observation in diffuse malignant pleural mesothelioma (MPM). The cytological analysis of pleural fluid often reveals the presence of free spheroid aggregates of malignant cells, giving rise to the question of the ability of
Puromycin reactivity does not accurately localize translation at the subcellular level
Enam , Syed Usman et al.
eLife, 9, e60303-e60303 (2020)
Einar Ö Einarsson et al.
Learning & memory (Cold Spring Harbor, N.Y.), 19(10), 449-452 (2012-09-18)
It has been suggested that memories become more stable and less susceptible to the disruption of reconsolidation over weeks after learning. Here, we test this by targeting the anterior cingulate cortex (ACC) and test its involvement in the formation, consolidation
Tao Ma et al.
Nature neuroscience, 16(9), 1299-1305 (2013-08-13)
Expression of long-lasting synaptic plasticity and long-term memory requires protein synthesis, which can be repressed by phosphorylation of eukaryotic initiation factor 2 α-subunit (eIF2α). Elevated phosphorylation of eIF2α has been observed in the brains of Alzheimer's disease patients and Alzheimer's
Takeshi H Saito et al.
PloS one, 8(3), e57037-e57037 (2013-03-08)
A wide range of growth factors encode information into specific temporal patterns of MAP kinase (MAPK) and CREB phosphorylation, which are further decoded by expression of immediate early gene products (IEGs) to exert biological functions. However, the IEG decoding system
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