Thiostrepton

Molecular Formula:

C72H85N19O18S5

CAS number:

1393-48-2

Fermentek product code:

Source:

Streptomyces laurentii

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 (dec.)

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.

Molecular weight:

1 664.89

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.

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. Antibiotic that 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). Antitumor agent; induces cell cycle arrest and apoptosis in breast cancer cells via downregulation of FOXM1 expression.

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

Supply related comments:

Customs: Laboratory reagents-38220000

Shipped at ambient temperature

Transport safety: not regulated.

Transport safety: Not Dangerous Goods; Not Regulated

Publications

Yang N, Zhou TC, Lei XX, WangC, Yan M, Wang ZF, Liu W, Wang J, Ming KH, Wang BC, Xu BL, Liu Q.

Inhibition of Sonic Hedgehog Signaling Pathway by Thiazole Antibiotic Thiostrepton Attenuates the CD44+/CD24-Stem-Like Population and Sphere-Forming Capacity in Triple-Negative Breast Cancer.

ACS Chem Biol. 2016 Oct 21;11(10):2673-2678.

PMID: 27560135

Other Fields

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