Thiostrepton

Name: Thiostrepton
SKU: T3134
Availability: InStock

Product ID T3134

Cas No. 1393-48-2

Purity ≥97%, HPLC

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Description

Thiostrepton is a thiazole antibiotic that exhibits antibacterial and anticancer properties. Thiostrepton inhibits the proteasome, binding 23s rRNA; it inhibits phosphate release after GTP hydrolysis in the ribosome, preventing tRNA translocation and turnover and inhibiting elongation during protein synthesis. Thiostrepton also inhibits the expression of Forkhead box M1 (FOXM1), an oncogenic transcription factor involved in cell cycle progression and oxidative stress responses. This compound alters the electrophoretic mobility of peroxiredoxin 3 (PRX3), disabling mitochondrial antioxidative activities during oxidative stress.

Product Info

Cas No.	1393-48-2
Purity	≥97%, HPLC
Formula	C₇₂H₈₅N₁₉O₁₈S₅
Formula Wt.	1664.89
Chemical Name	N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(11E)-37-butan-2-yl-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,31-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
IUPAC Name	N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(11E)-37-butan-2-yl-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,31-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
Synonym	Alaninamide, Bryamycin, Thiactin
Melting Point	246-256°C dec.
Solubility	Practically insoluble in water. Soluble in chloroform, dichloromethane, DMF. DMSO solution (1 %) is unstable - should be freshly prepared.
Appearance	White to off white powder

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Store Temp	4°C
Ship Temp	Ambient

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MSDS	T3134 MSDS PDF
Info Sheet	T3134 Info Sheet PDF

References

Newick K, Cunniff B, Preston K, et al. Peroxiredoxin 3 is a redox-dependent target of thiostrepton in malignant mesothelioma cells. PLoS One. 2012;7(6):e39404. PMID: 22761781

Rodnina MV, Savelsbergh A, Matassova NB, et al. Thiostrepton inhibits the turnover but not the GTPase of elongation factor G on the ribosome. Proc Natl Acad Sci U S A. 1999 Aug 17;96(17):9586-90. PMID: 10449736.

Naaktgeboren N, Roobol K, Gubbens J, et al. The mode of action of thiostrepton in the initiation of protein synthesis. Eur J Biochem. 1976 Nov 1;70(1):39-47. PMID: 795651.

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Thiostrepton

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