Thiostrepton

Molecular Formula

C72H85N19O18S5

M.W.

1 664.89

CAS number

1393-48-2

MSDS

Download

Details

Source

Streptomyces laurentii

Fermentek product Code

TIS-001

Brand/grade

For research

Specifications

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

Chemical identification

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

Further Information

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.

Retest time

3 Years

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

Composition

Ingredient type

Fermentek product

Supply related information

Shipped at ambient temperature

Transport safety: Not Dangerous Goods; Not Regulated

Transport safety: not regulated.

Special Info