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Thiostrepton

Name: Thiostrepton
Brand: MM

≥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

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00135828

Assay:

≥98% (HPLC)

Form:

powder

Storage condition:

OK to freeze, desiccated, protect from light

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Properties

Product Name

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

description

Merck USA index - 14, 9364

Quality Segment

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

Description

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

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

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c