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| Thiostrepton[1] | |
|---|---|
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| Other names | Alaninamide, Bryamycin, Thiactin |
| Identifiers | |
| CAS number | [1393-48-2] |
| PubChem | |
| SMILES |
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| Properties | |
| Molecular formula | C72H85N19O18S5 |
| Molar mass | 1664.83 g/mol |
| Appearance | White to off-white powder |
| Melting point |
246-256 °C |
| Solubility in water | Insoluble |
| Solubility in other solvents | Soluble in CHCl3, CH2Cl2, dioxane, pyridine, glacial acetic acid, DMF. Practically insoluble in the lower alcohols, nonpolar organic solvents, diluted aqueous acids or bases. May be dissolved by methanolic acid or base, but with decomposition.[2] |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Thiostrepton is a natural cyclic oligopeptide antibiotic, derived from several strains of strepromycetes, such as Streptomyces azureus and Streptomyces laurentii.
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History
Thiostrepton was discovered by Donovick et al. who desribed its antibacterial properties in 1955.[3] Dorothy Crowfoot Hodgkin solved the structure of thiostrepton in 1970.[4]
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 steroids. It is also active against gram-positive bacteria.
Recently, thiostrepton has been reported to exhibit activity against breast cancer cells through targeting the transcription factor forkhead box M1. [5]
Thiostrepton is used in molecular biology as a reagent for both positive and negative selection of genes involved in nucleotide metabolism.
References
- ^ Merck Index, 11th Edition, 9295.
- ^ Thiostrepton product page at Fermentek
- ^ DONOVICK R, PAGANO JF, STOUT HA, WEINSTEIN MJ. Antibiot Annu. 1955-1956; 3:554-9
- ^ ANDERSON B, CROWFOOT HODGKIN D, VISWAMITRA MA. Nature. 1970; 225: 223-235
- ^ Thiostrepton selectively targets breast cancer cells through inhibition of forkhead box M1 expression. Kwok JM et al Molecular Cancer Therapeutics July 2008
External links
Wikipedia content modification information:
- This page was last modified on 12 August 2008, at 11:07.
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