- Thiostrepton
chembox new
Reference= ["Merck Index ", 11th Edition, 9295.]
ImageFile=Thiostrepton.png
IUPACName=
OtherNames=Alaninamide, Bryamycin, Thiactin
Section1=Chembox Identifiers
CASNo=1393-48-2
PubChem=16130278
SMILES=C [C@@H] (O) [C@@] (C)(O) [C@@H] (C2=NC6=CS2)NC(C1CSC(/C(NC( [C@@H] (NC(C3=CS [C@] ( [C@] 4(NC( [C@@H] (NC(C(NC( [C@H] (C)NC%10=O)=O)=C)=O)C)=O)C(C5=CSC( [C@H] ( [C@@H] (C)OC(C8=CC( [C@H] (C)O)=C(C=CC(N [C@] ( [H] )%10 [C@H] (CC)C) [C@@H] 9O)C9=N8)=O)NC6=O)=N5)N=C(C7=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS7)CC4)=N3)=O) [C@@H] (C)O)=O)=C/C)=N1)=O
Section2=Chembox Properties
Formula=C72H85N19O18S5
MolarMass=1664.83 g/mol
Appearance=White to off-white powder
Density=
MeltingPt=246-256 °C
BoilingPt=
Solubility= Insoluble
SolubleOther = 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. [ [http://www.fermentek.co.il/Thiostrepton.htm Thiostrepton product page] atFermentek ]
Solvent = other solvents
Section3=Chembox Hazards
MainHazards=
FlashPt=
Autoignition=Thiostrepton is a natural cyclic
oligopeptide antibiotic , derived from several strains of strepromycetes, such as "Streptomyces azureus " and "Streptomyces laurentii ".History
Thiostrepton was discovered by Donovick "et al." who desribed its antibacterial properties in 1955. [cite journal | author = Donovick R, Pagano JF, Stout HA, Weinstein MJ | journal =
Antibiot Annu | year = 1955 | volume = 3 | pages =554–9] Dorothy Crowfoot Hodgkin solved the structure of thiostrepton in 1970. [cite journal | author = Anderson B, Crowfoot Hodgkin D, Viswamitra MA | journal = Nature | year = 1970 | volume = 225 | pages = 223–235 | doi = 10.1038/225233a0 | title = The Structure of Thiostrepton]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 topicalsteroid s. 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. [cite journal |author=Kwok JM, Myatt SS, Marson CM, Coombes RC, Constantinidou D, Lam EW |title=Thiostrepton selectively targets breast cancer cells through inhibition of forkhead box M1 expression |journal=Mol. Cancer Ther. |volume=7 |issue=7 |pages=2022–32 |year=2008 |month=July |pmid=18645012 |doi=10.1158/1535-7163.MCT-08-0188 |url=]
Thiostrepton is used in molecular biology as a reagent for both positive and negative selection of genes involved in nucleotide metabolism.
References
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