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Thiostrepton

Synonyms: Alaninamide, Bryamycin, Thiactin

Thiostrepton (Alaninamide, Bryamycin, Thiactin) is a natural cyclic oligopeptide antibiotic, derived from several strains of strepromycetes.

Thiostrepton Chemical Structure

Thiostrepton Chemical Structure

CAS: 1393-48-2

Selleck's Thiostrepton has been cited by 3 publications

Purity & Quality Control

Batch: Purity: 99.86%
99.86

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Biological Activity

Description Thiostrepton (Alaninamide, Bryamycin, Thiactin) is a natural cyclic oligopeptide antibiotic, derived from several strains of strepromycetes.
In vitro
In vitro Thiostrepton inhibits growth of the parasite in the micromolar range which is 10-fold below concentrations with observable effects on total protein synthesis. Thiostrepton results in disappearance of organellar-encoded RNA transcripts within 6 hours of treatment while transcripts of a nuclear-encoded mRNA remain constant for at least 8 hous of treatment. Thiostrepton directly interacts with two nucleotides in the GTPase domain of Escherichia coli. [1] Thiostrepton directly interacts the region around position 1067 in domain II of 23S rRNA inhibits GTP hydrolysis by elongation factor G (EF-G) on the ribosome at the conditions of multiple turnover. Thiostrepton interferes with EF-G footprints in the alpha-sarcin stem loop (A2660, A2662) located in domain VI of 23S rRNA. [2] Thiostrepton interacts with a 58-nucleotide domain of large subunit ribosomal RNA, and binds to the ribosome cooperatively with Ribosomal protein L11. Thiostrepton and RNA recognition cooperativity can be attributed to N- and C-terminal domains of L11, respectively. [3] Thiostrepton binds primarily to 23 S rRNA, thus probably inhibits peptide elongation by impeding a conformational change within protein L11 that is important for the function of the ribosomal GTPase centre. [4] Thiostrepton (10 μM) treatment reduces FOXM1 expression in a time- and dose-dependent manner, independent of de novo protein synthesis and predominantly at transcriptional and gene promoter levels. Thiostrepton (10 μM) induces cell cycle arrest at G(1) and S phases and cell death, concomitant with FOXM1 repression in breast cancer cells. Thiostrepton (10 μM) also shows efficacy in repressing breast cancer cell migration, metastasis, and transformation, which are all downstream functional attributes of FOXM1. [5]

Chemical lnformation & Solubility

Molecular Weight 1664.89 Formula

C72H85N19O18S5
CAS No. 1393-48-2 SDF Download Thiostrepton SDF
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
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