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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
Molecular Weight:
1664.89
MDL Number:
MFCD00135828
MOL File:
1393-48-2.mol
Last updated:2024-11-20 15:18:15

THIOSTREPTON Properties

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.
EWG's Food Scores 1
FDA UNII HR4S203Y18

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302+H312+H332
Precautionary statements  P271-P261-P280
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
NFPA 704
0
2 0

THIOSTREPTON price More Price(27)

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

THIOSTREPTON Chemical Properties,Uses,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

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

beta-adrenergic agonist

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

Global( 161)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8810 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578 sales@hbmojin.com China 12839 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 49374 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 32165 58
Hubei Ipure Biology Co., Ltd
+8613367258412 ada@ipurechemical.com China 10319 58
Career Henan Chemica Co
+86-0371-86658258 +8613203830695 laboratory@coreychem.com China 30240 58
HONG KONG IPURE BIOLOGY CO.,LIMITED
86 18062405514 18062405514 ada@ipurechemical.com CHINA 3461 58
HANGZHOU CLAP TECHNOLOGY CO.,LTD
86-571-88216897,88216896 13588875226 sales@hzclap.com CHINA 6312 58
ANHUI WITOP BIOTECH CO., LTD
+8615255079626 eric@witopchemical.com China 23541 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167 1026@dideu.com China 7724 58

View Lastest Price from THIOSTREPTON manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
THIOSTREPTON pictures 2024-11-20 THIOSTREPTON
1393-48-2
US $1.00 / kg 1kg 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
Thiostrepton pictures 2024-11-19 Thiostrepton
1393-48-2
US $55.00-39.00 / mg 99.57% 10g TargetMol Chemicals Inc.
THIOSTREPTON pictures 2023-08-30 THIOSTREPTON
1393-48-2
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
  • THIOSTREPTON pictures
  • THIOSTREPTON
    1393-48-2
  • US $1.00 / kg
  • 99%
  • Hebei Weibang Biotechnology Co., Ltd
  • Thiostrepton pictures
  • Thiostrepton
    1393-48-2
  • US $55.00-39.00 / mg
  • 99.57%
  • TargetMol Chemicals Inc.
  • THIOSTREPTON pictures
  • THIOSTREPTON
    1393-48-2
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd

THIOSTREPTON Spectrum

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 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 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,9,10,11,12,13,14,18,19,20,21,27,28,32a-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...