Thiostrepton

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Thiostrepton is a natural cyclic oligopeptide antibiotic, derived from several strains of strepromycetes, such as Streptomyces azureus, Streptomyces laurentii.

Properties

  • Synonyms: Alaninamide, Bryamycin , Thiactin
  • CAS number: 1393-48-2
  • Merck index: 14: 9364
  • Molecular weight: 1664.89
  • Molecular Formula: C72H85N19O18S5
  • Melting point: decomposes at 246-256oC
  • Solubility information: Soluble in chloroform, dichloromethane, dioxane, pyridine, glacial acetic acid, DMF. Practically insoluble in water, the lower alcohols, nonpolar organic solvents, diluted aqeous acids or bases. May be dissolved by methanolic acid or base, but with decomposition. Working solution of 1% in DMSO is unstable and should be freshly prepared and protected from light.
  • Appearance: White to off-white powder

History

Thiostrepton was discovered by DONOVICK R, PAGANO JF, STOUT HA, WEINSTEIN MJ. in 1955 (Antibiot Annu. 1955-1956;3:554-9), who desribed its antibacterial properties.

Dorothy Crowfoot Hodgkin solved the structure of Thiostrepton in 1970.

Applications

Thiostrepton has been used in veterinary medicine in mastitis caused by gram-negative organisms and in dermatologic disorders. It is mostly used in complex ointments containing Neomycin, Nystatin, Thiostrepton and topical steroides. It is also active against gram-positive bacteria.

Recently, Thiostrepton has been reported to exhibit antimalarial and anticancer activities

Thiostrepton is used in molecular biology as a reagent for both positive and negative selection of genes involved in nucleotide metabolism.

References

Physicochemical data copied with permission from Thiostrepton product page from Fermentek




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