ChemicalBook > CAS DataBase List > THIOSTREPTON

THIOSTREPTON

Product Name
THIOSTREPTON
CAS No.
1393-48-2
Chemical Name
THIOSTREPTON
Synonyms
x146;a-8506;thiactin;bryamycin;hiostrepton;THIOSTREPTON;Thiostreptin;THIOSTREPTION;antibioticx146;(-)-Nuciferine
CBNumber
CB5204768
Molecular Formula
C72H85N19O18S5
Formula Weight
1664.89
MOL File
1393-48-2.mol
More
Less

THIOSTREPTON Property

Melting point:
248-257°C (dec.)
alpha 
D23 -98.5° (glacial acetic acid); -61° (dioxane); -20° (pyridine)
Density 
1.0824 (rough estimate)
refractive index 
1.6700 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Soluble in DMSO or chloroform
form 
Off-white powder
pka
10.43±0.46(Predicted)
color 
Off-white
Water Solubility 
0.24g/L(28 ºC)
Merck 
13,9440
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 week.
More
Less

Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
XN6300100
10-21
HS Code 
29419090
Toxicity
LD50 oral in mouse: > 1gm/kg
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
598226
Product name
Thiostrepton - CAS 1393-48-2 - Calbiochem
Purity
Thiostrepton, CAS 1393-48-2, is an antibiotic that inhibits protein synthesis by preventing binding of GTP to 50S ribosomal subunit.
Packaging
1g
Price
$130
Updated
2024/03/01
Sigma-Aldrich
Product number
598226
Product name
Thiostrepton - CAS 1393-48-2 - Calbiochem
Purity
Thiostrepton, CAS 1393-48-2, is an antibiotic that inhibits protein synthesis by preventing binding of GTP to 50S ribosomal subunit.
Packaging
10g
Price
$1010
Updated
2024/03/01
Alfa Aesar
Product number
J62332
Product name
Thiostrepton, Streptomyces laurentii, 90+%
Packaging
1g
Price
$201
Updated
2024/03/01
Alfa Aesar
Product number
J62332
Product name
Thiostrepton, Streptomyces laurentii, 90+%
Packaging
5g
Price
$705
Updated
2021/12/16
Cayman Chemical
Product number
19200
Product name
Thiostrepton
Purity
≥95%
Packaging
1g
Price
$96
Updated
2024/03/01
More
Less

THIOSTREPTON Chemical Properties,Usage,Production

Description

The mammalian transcription factor forkhead box M1 (FoxM1) is induced during G1 phase, with expression continuing through S phase and mitosis. Thiostrepton is a natural peptide thiazole antibiotic that inhibits FoxM1 in mammalian cells, preventing the expression of FoxM1-regulated genes, which includes FoxM1 itself. Through this mechanism, thiostrepton prevents proliferation and induces apoptosis in human cancer cells. These effects correlate with the ability of thiostrepton to act as a proteasome inhibitor.

Chemical Properties

Off-White Solid

Uses

beta-adrenergic agonist

Uses

Thiostrepton is a macrocyclic antibiotic incorporating thiazoles and other atypical amino acids. Patented in 1961, thiostrepton has been used as an antibiotic and acts by binding to ribosomes to prevent the binding of the EF-G elongation factor and GTP to the 50S ribosomal subunit. Thiostrepton is an inducer of tipA, a gene that controls the bacterial transcription regulators, TipAL and TipAS, that are central regulators in multidrug resistance. Thiostrepton is closely related to siomycin, a recently discovered inhibitor of oncogenic transcription factor, FoxM1.

Uses

A protein synthesis-inhibiting antibiotic

Uses

Natural antibiotic derived from Streptomyces.

Definition

ChEBI: A heterodetic cyclic peptide, in which the cyclisation step involves a formal lactonisation between the carboxy group of a quinaldic acid-based residue and a secondary alcohol. An antibiotic that inhibits bacterial protein synthesis. Also acts as an antitu or agent.

General Description

A thiazole-containing peptide antibiotic that inhibits protein synthesis by preventing binding of GTP to 50S ribosomal subunit. Inhibits the function of elongation factor G (EF-G) and the dissociation of EF-G from the ribosome. The thiostrepton-resistant gene is also commonly used as a selective marker for recombinant DNA/plasmid technologies.

Biochem/physiol Actions

Primary TargetEF-G

in vitro

thiostrepton inhibits the transcriptional activity and foxm1 expression, and induces strong apoptosis in human cancer cells of different origin that correlates with suppression of foxm1, including leukemia, neuroblastoma, liver cancer, melanoma and prostate cancer cells. thiostrepton binds foxm1 on the promoter site to inhibit transcriptional activity of foxm1 through the foxm1 autoregulation mechanism [1].

in vivo

thiostrepton suppressed tumor growth in a human breast cancer xenograft model. treatment with developed micelle-thiostrepton nanoparticles decreased xenograft tumor growth induced by the human mda-mb-231 breast and hepg2 liver cancer cell lines. these apoptosis activities in drug-treated tumors were correlated with in vivo suppression of oncogenic foxm1 [1].

References

1) Bowen et al. (2005), Interaction of thiostrepton and elongation factor-G with the ribosomal protein L11-binding domain; J. Biol. Chem., 280 2934 2) Gonzalez et al. (2007), Thiostrepton inhibition of tRNA delivery to the ribosome; RNA, 13 2091 3) Kwok et al. (2008), Thiostrepton selectively targets breast cancer cells through inhibition of forkhead box M1 expression; Mol. Cancer Ther., 7 2022

THIOSTREPTON Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

THIOSTREPTON Suppliers

Lingyuan Bebiansen Biological Technology Co., Ltd
Tel
18642120371
Email
2837458851@qq.com
Country
China
ProdList
7995
Advantage
58
Zhejiang Huida Biotech Co., LTD
Tel
0571-89903882 13626641628
Email
jiangnan@huidabiotech.com
Country
China
ProdList
3656
Advantage
58
SHANG HAI WEI LING BIOTECHNOLOGY CO.,LTD
Tel
13917490980
Email
81939905@qq.com
Country
China
ProdList
367
Advantage
58
Hangzhou Huiyi Biotechnology Co., LTD
Tel
0571-89918262 13357170655
Email
chenlingwei@hizyme.com
Country
China
ProdList
282
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8415
Advantage
55
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
More
Less

View Lastest Price from THIOSTREPTON manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
THIOSTREPTON 1393-48-2
Price
US $1.00/PCS
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-05-24
Hebei Mojin Biotechnology Co., Ltd
Product
THIOSTREPTON 1393-48-2
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-30
Zhuozhou Wenxi import and Export Co., Ltd
Product
Thiostrepton 1393-48-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

1393-48-2, THIOSTREPTONRelated Search:


  • Thiostrepton (200 mg)
  • BryaMycin, Thiactin, AlaninaMide, X 146, A 8506, 6761-31
  • Thiostrepton, froM StreptoMyces sp.
  • x146
  • THIOSTREPTON
  • Alaninamide, L-threonyl-(4S)-2-(1Z)-1-amino-1-propenyl-4,5-dihydro-4-thiazolecarbonyl-2-(1S,2S,3R)-1-amino-2,3-dihydroxy-2-methylbutyl-4-thiazolecarbonyl-2-(5R,6S)-6-2-(1S,2R)-1-amino-2-hydroxypropyl-4-thiazolyl-5-N-(7R,8S)-2-carboxy-7,8-dihydro-8-hydroxy
  • THIOSTREPTION
  • thiostrepton from streptomyces azureus
  • Thiostrepton, 96%, from Streptomyces sp.
  • Thiostrepton - CAS 1393-48-2 - Calbiochem
  • AlaninaMide,N-[(7R,8S)-2-carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-aMino-21-[(1S,2R)-1,2-dihydroxy-1-Methylpropyl]-14-ethylidene-3,4,4a,9,10,1
  • a-8506
  • antibiotic6761-31
  • antibiotica8506
  • antibioticx146
  • bryamycin
  • thiactin
  • Alaninamide, N-[(7R,8S)-2-carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahyd...
  • THIOSTREPTON USP/EP/BP
  • N-[(7R,8S)-2-Carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahydro-11,28-bis[(1R)-1-hydroxyethyl]-9,12,19,26-tetraoxo-17H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-4-thiazolecarbonyl-2,3-didehydroalanyl-2,3-didehydro-alaninamide,(1→528)-lactone
  • (-)-Nuciferine
  • hiostrepton
  • Thiostrepton, USP
  • Thiostreptin
  • N-[(7R,8S)-2-Carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahydro-11,28-bis[(1R)-1-hydroxyethyl]-9,12,19,26-tetraoxo-17H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-4-thiazolecarbonyl-2,3-didehydroala
  • 1393-48-2
  • C72H85N19O18S5
  • Antibiotics T-Z
  • Antibiotics
  • Antibiotics A to Z
  • BioChemical
  • Inhibitors
  • BETAPACE
  • antibiotic
  • Peptide Synthesis/Antibiotics
  • Amino Acids & Derivatives
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Antibacterial
  • Antibiotics
  • Antibiotics A to
  • Antibiotics by Application
  • Antibiotics T-ZAntibiotics
  • Chemical Structure Class
  • Gene Regulation and Expression
  • Genetic Marker SelectionAntibiotics
  • Interferes with Protein SynthesisSpectrum of Activity
  • L - ZAntibiotics
  • Mechanism of Action
  • PeptidesCell Signaling and Neuroscience
  • Organics
  • RNA-Protein Translation InhibitorsMore...Close...