Thiostrepton
Molecular Formula
C72H85N19O18S5
M.W.
1 664.89
CAS number
1393-48-2
MSDS
Source
Streptomyces laurentii
Fermentek product Code
TIS-001
Brand/grade
For research
Appearance
White to off-white powder
slightly yellowish cast may be observed on the solid.
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
>210°C (decomposition, not melting.)
Solubility test
Clear colorless solution at 5mg/ml DMSO or Chloroform
Names and identifiers

Synonyms:  Alaninamide, Bryamycin , Thiactin
RTECS      :   XN6300100

EU number
215-734-9
Description

Thiostrepton is a broad spectrum polypeptide antibiotic which targets a wide range of gram positive and gram negative bacteria.

InChl Key
NSFFHOGKXHRQEW-DVRIZHICSA-N
Canonical SMILES
CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=NC2C4=CSC(=N4)C(C(OC(=O)C5=NC6=C(C=CC(C6O)N1)C(=C5)C(C)O)C)NC(=O)C7=CSC(=N7)C(NC(=O)C8CSC(=N8)C(=CC)NC(=O)C(NC(=O)C9=CSC3=N9)C(C)O)C(C)(C(C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
Isomeric SMILES
CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=NC2C4=CSC(=N4)C(C(OC(=O)C5=NC6=C(C=CC(C6O)N1)C(=C5)C(C)O)C)NC(=O)C7=CSC(=N7)C(NC(=O)C8CSC(=N8)/C(=C\C)/NC(=O)C(NC(=O)C9=CSC3=N9)C(C)O)C(C)(C(C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
Solubility ( literature )

Thiostrepton is 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. It 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.

Compound Classification

Polypeptide antibiotic
Antimicrobial

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Protect from moisture
Use the original container to store the product.
Keep the lid tightly closed.
Avoid exposing to strong direct light.
Other vendors may recommend higher temperatures for storage.
Applications

Thiostrepton is used as a reagent for both positive and negative selection of genes involved in nucleotide metabolism. Thiostrepton is highly active against gram-positive bacteria. In its crude form, Thiostrepton is used in veterinary medicine, in mastitis caused by gram-negative organisms and in dermatologic disorders. inhibits bacterial protein synthesis. Inhibits mRNA-tRNA translocation by GTPase elongation factor G (EF-G), EF-TU(GTP)-catalyzed aa-tRNA delivery and the activity of initiation factor 2 (IF-2).

As an antitumoragent Thiostrepton induces cell cycle arrest and apoptosis in breast cancer cells via downregulation of FOXM1 expression. Thiostrepton is a FoxM1 specific inhibitor.

Disclaimer
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Shipped at ambient temperature
Transport safety: Not Dangerous Goods; Not Regulated
Transport safety: not regulated.
Available since
Title
Change notif 23-Jule-2018
Value
Updated storage condition
Title
update 22-Jan-2019
Value
minor update, shipment conditions
Title
toxicity by RTECS
Value
LD50 oral mouse >1 gram/kg
Signal to sort
T