Thiostrepton, Streptomyces laurentii, 90+%

Description

Natural cyclic oligopeptide antibiotic | CAS: 1393-48-2 | C72H85N19O18S5 | 1664.89 g/mol

Thiostrepton exhibits antibiotic activity through blockade of ribosome turnover after an elongation step in protein synthesis by inhibiting both the dissociation of elongation factor G (EF-G) from the ribosome and the release of inorganic phosphate from EF-G following GTP hydrolysis. Thiostrepton is also described to show efficacy against cancer cell growth through downregulation of the forkhead box M1 (FOXM1) transcription factor, commonly overexpressed in many malignancies. Thiostrepton is an inhibitor of FOXM1. Thiostrepton has been used as a selectable marker for recombinant Streptomyces cultures.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Thiostrepton exhibits antibiotic activity through blockade of ribosome turnover after an elongation step in protein synthesis by inhibiting both the dissociation of elongation factor G (EF-G) from the ribosome and the release of inorganic phosphate from EF-G following GTP hydrolysis. Thiostrepton is also described to show efficacy against cancer cell growth through downregulation of the forkhead box M1 (FOXM1) transcription factor, commonly overexpressed in many malignancies. Thiostrepton is an inhibitor of FOXM1. Thiostrepton has been used as a selectable marker for recombinant Streptomyces cultures.

Solubility
Soluble in DMSO or chloroform

Notes
Store at -20°C. Incompatible with oxidizing agents. Protect from heat.

Specifications

• Type: Thiostrepton
• Physical Form: Powder
• CAS: 1393-48-2
• Color: White to Yellow
• Quantity: 1 g
• Molecular Formula: C72H85N19O18S5
• MDL Number: MFCD00135828,MFCD00135828
• Merck Index: 14,9364
• Synonym: Bryamycin; Thiactin
• Solubility Information: Soluble in DMSO or chloroform
• InChI Key: NSFFHOGKXHRQEW-DVRIZHICNA-N
• SMILES: CCC(C)C1NC2C=CC3=C(C=C(N=C3C2O)C(=O)OC(C)C2NC(=O)C3=CSC(=N3)C(NC(=O)C3CSC(=N3)\C(NC(=O)C(NC(=O)C3=CSC(=N3)C3(CCC(=NC3C3=CSC2=N3)C2=NC(=CS2)C(=O)NC(=C)C(=O)NC(=C)C(N)=O)NC(=O)C(C)NC(=O)C(=C)NC(=O)C(C)NC1=O)C(C)O)=C/C)C(C)(O)C(C)O)C(C)O
• IUPAC Name: 2-({2-[(11E)-37-(butan-2-yl)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,60-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-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2²⁹,³².1²,⁵.1¹²,¹⁵.1¹⁹,²².1³¹,³⁵.1⁵⁴,⁵⁷.0¹,⁵³]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazol-4-yl}formamido)-N-(1-carbamoyleth-1-en-1-yl)prop-2-enamide
• Molecular Weight (g/mol): 1664.89
• PubChem CID: 122173112
• Formula Weight: 1664.89
• Percent Purity: ≥90%
• Chemical Name or Material: Thiostrepton, Streptomyces laurentii

Safety and Handling

EINECSNumber	215-734-9
RTECSNumber	XN6300100
TSCA	No
Recommended Storage	Store at -20°C

SDS

RUO – Research Use Only