Anisomycin
Molecular Formula
C14H19NO4
M.W.
265.30
CAS number
22862-76-6
Source
Streptomyces griseolus
Fermentek product Code
ANI-001
Brand/grade
For research
Appearance
White powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
139°C-145°C
Solubility test
Clear colorless solution at 10mg/ml Ethyl Acetate
Names and identifiers

Synonyms : Flagecidin

IUPAC Name: [(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate

EU number
245-269-7
Description

Anisomycin is a protein synthesis inhibitor. It binds to the 60S ribosomal subunits and prevents the formation of peptide bond, and consequently, the chain elongation.

InChl Key
YKJYKKNCCRKFSL-RDBSUJKOSA-N
Canonical SMILES
CC(=O)OC1C(CNC1CC2=CC=C(C=C2)OC)O
Isomeric SMILES
CC(=O)O[C@@H]1[C@H](CN[C@@H]1CC2=CC=C(C=C2)OC)O
Solubility ( literature )

Anisomycin is soluble in DMSO, Ethyl-Acetate, Dichloromethane. Slightly soluble in water

Compound Classification

Biological action classification

  • Protein Synthesis Inhibitor
  • Nucleic Acid Synthesis Inhibitor

Chemical classification

  • Pyrrolinin class antibiotic
Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Use the original container to store the product.
Keep the lid tightly closed.
Avoid exposing to strong direct light.
Applications

Originally discovered by Sobin and Tanner in 1954, Anisomycin was identified as an antibiotic active against protozoa such as Trichomonas and fungi and yeasts, and was considered as a potential human anti-candidal and anti-amoebic drug. Sobin, B. A., and F. W. Tanner, Jr. 1954. Anisomycin, a new antiprotozoa antibiotic. J. Am. Chem. Soc. 76:4053. As such, Anisomycin was put by GONZALEZ CONSTANDSE to clinical trials in 1955: Anisomycin in intestinal amebiasis; study of 30 clinical casesPrensa Med Mex. 1956 Sep-Dec;21(7-10):114-5 Anisomycin is also proposed as a potential psychiatric drug, as it is shown to affect protein synthesis an Amygdala, a brain part involved in memory(1). The earliest usage of Anisomycin in research on memory biochemistry was made by Jonec and Walsterlain in 1979 . Again, this property of Anisomycin is ascribed to its ability to inhibit protein synthesis. Effect of inhibitors of protein synthesis on the development of kindled seizures in rats.Jonec V, Walsterlain CG.Exp Neurol. 1979 Dec;66(3):524-32 Recently, publications appear showing the immunomodulating properties on Anisomycin. This discovery leads to researches on the potential use of Anisomycin in transplantation: Anisomycin inhibits the behaviors of T cells and the allogeneic skin transplantation in mice.Xing F et al,J Immunother. 2008 Nov-Dec;31(9):858-70 In the field of cell-signaling research, Anisomycin is used as an activator of kinase cascades in mammalian cells, especially the stress-activated Protein Kinase (SAPK2/p38MAPK) and p46/54JNK Anisomycin is a selective ingredientof Martin Lewis Agar, a bacteriological solid medium used for isolation of pathogenic Neisseria species. Martin, J. E., Jr., and J. S. Lewis. 1977. Anisomycin: improved antimycotic activity in modified Thayer-Martin medium. Public Health Lab. 35:53-62

Disclaimer
For Research use only
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Available since
Title
Transport information
Value
PG III
Title
tse
Value
P
Signal to sort
A