| Identification | Back Directory | [Name]
THIOSTREPTON | [CAS]
1393-48-2 | [Synonyms]
x146
a-8506
thiactin
bryamycin
THIOSTREPTON
THIOSTREPTION
antibioticx146
antibiotica8506
antibiotic6761-31
Thiostrepton (200 mg)
THIOSTREPTON USP/EP/BP
Thiostrepton, froM StreptoMyces sp.
thiostrepton from streptomyces azureus
Thiostrepton, 96%, from Streptomyces sp.
Thiostrepton - CAS 1393-48-2 - Calbiochem
BryaMycin, Thiactin, AlaninaMide, X 146, A 8506, 6761-31
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
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
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... | [EINECS(EC#)]
215-734-9 | [Molecular Formula]
C72H85N19O18S5 | [MDL Number]
MFCD00135828 | [MOL File]
1393-48-2.mol | [Molecular Weight]
1664.89 |
| Chemical Properties | Back Directory | [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. |
| Hazard Information | Back Directory | [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.1,2 Through this mechanism, thiostrepton prevents proliferation and induces apoptosis in human cancer cells.1 These effects correlate with the ability of thiostrepton to act as a proteasome inhibitor.3 | [Chemical Properties]
Off-White Solid | [Uses]
A protein synthesis-inhibiting antibiotic | [Uses]
beta-adrenergic agonist | [Uses]
Natural antibiotic derived from Streptomyces. | [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. | [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 |
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