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Sigma-Aldrich

Thiostrepton

≥98% (HPLC), powder, FOXM1 inhibitor, Calbiochem®

Synonym(s):

Thiostrepton, FOXM1 Inhibitor I

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About This Item

Empirical Formula (Hill Notation):
C72H85N19O18S5
CAS Number:
1393-48-2
Molecular Weight:
1664.89
MDL number:
MFCD00135828
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Thiostrepton, Thiostrepton, CAS 1393-48-2, is an antibiotic that inhibits protein synthesis by preventing binding of GTP to 50S ribosomal subunit.

Quality Level

100

assay

≥98% (HPLC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated
protect from light

color

off-white

solubility

DMSO: 10 mg/mL
chloroform: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15+

InChI key

NSFFHOGKXHRQEW-DVRIZHICSA-N

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.
A thiazole-containing polypeptide antibiotic isolated from Streptomyces azureus. Inhibits bacterial protein synthesis and ribosomal GTPase activity by binding noncovalently, but virtually irreversibly, to the 23S rRNA in the GTPase center of the 50S subunit. Thiostrepton binding directly prevents binding to the ribosome of elongation factor G (EF-G), which also binds specifically to the 23S rRNA. Thiostrepton has proved useful in elucidating the molecular mechanisms of translation, particularly of ribosomal translocation. It is also used for selection, in bacteria of Streptomyces sp., of vectors containing the tsr gene (S. azureus), which encode a 23S rRNA methylase whose action prevents thiostrepton from binding to ribosomes.

Biochem/physiol Actions

Primary Target
EF-G

Warning

Toxicity: Standard Handling (A)

Other Notes

Rodnina, M.V., et al. 1999. Proc. Natl. Acad. Sci USA96, 9586.
Rosendahl, G. and Douthwaite, S. 1994. Nucleic Acids Res.22, 357.
Saarma, U. and Remme, J. 1992. Nucleic Acids Res.20, 3147.
Malina, H. and Robert-Gero, M. 1992. Appl. Environ. Microbiol.58, 895.
Blanco, G., et al. 1992. Gene112, 59.
Miller, S.P. and Bodley, J.W. 1991. Nucleic Acids Res.19, 1657.
Ryan, P.C., et al. 1991. J. Mol. Biol.221, 1257.
Kutay, U.R., et al. 1990. Biochim. Biophys. Acta1050, 193.
Smokvina, T., et al. 1990. Gene94, 53.
Garrett, R. 1983. Trends Biochem. Sci.8, 189.
Bodley, J.W., et al. 1970. Biochem. Biophys. Res. Commun.41, 1406.
Thompson, J. and Cundliffe, E. 1970. Biochimie 73, 1131.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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