Cycloheximide


Cycloheximide
Cycloheximide
Identifiers
CAS number 66-81-9 YesY
PubChem 6197
ChemSpider 5962 YesY
UNII 98600C0908 N
KEGG C06685 N
ChEBI CHEBI:27641 N
ChEMBL CHEMBL123292 N
RTECS number MA4375000
Jmol-3D images Image 1
Properties
Molecular formula C15H23NO4
Molar mass 281.35 g/mol
Appearance colourless crystals
Melting point

119.5–121 °C

Hazards
MSDS Oxford MSDS
EU classification Toxic (T)
R-phrases R26 R27 R28
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cycloheximide is an inhibitor of protein biosynthesis in eukaryotic organisms, produced by the bacterium Streptomyces griseus. Cycloheximide exerts its effect by interfering with the translocation step in protein synthesis (movement of two tRNA molecules and mRNA in relation to the ribosome) thus blocking translational elongation. Cycloheximide is widely used in biomedical research to inhibit protein synthesis in eukaryotic cells studied in vitro (i.e. outside of organisms). It is inexpensive and works rapidly. Its effects are rapidly reversed by simply removing it from the culture medium.

Due to significant toxic side effects, including DNA damage, teratogenesis, and other reproductive effects (including birth defects and toxicity to sperm[1]), cycloheximide is generally used only in in vitro research applications, and is not suitable for human use as a therapeutic compound. Although it has been used as a fungicide in agricultural applications, this application is now decreasing as the health risks have become better understood.

Cycloheximide is degraded by alkali (pH > 7), decontamination of work surfaces and containers can be achieved by washing with a non-harmful alkali solution such as soap.

Since cycloheximide is an effective inhibitor of protein biosynthesis in eukaryotes only, it may be used to distinguish between proteins translated in the mitochondria and proteins translated in the cytosol. mRNA translated in cytosol or ER from mRNA derived from the nucleus will not be expressed in the presence of cycloheximide. Conversely, translation using mitochondrial ribosomes is unaffected by cycloheximide, and mitochondrial genes will continue to be expressed.

Experimental applications

Cycloheximide can be used as an experimental tool in molecular biology to determine the half-life of a protein. Treating cells with cycloheximide in a time-course experiment followed by Western blotting of the cell lysates for the protein of interest can show differences in protein half-life. Cycloheximide treatment provides the ability to observe the half-life of a protein without confounding contributions from transcription or translation.

It is used as a plant growth regulator to stimulate ethylene production. It is used as a rodenticide and other animal pesticide. It is also used as a media to detect to unwanted bacteria by suppressing yeasts and molds in beer fermentation.

References

  1. ^ TOXNET

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Look at other dictionaries:

  • Cycloheximide — Général Nom IUPAC 4 {(2R) 2 [(1S,3S,5S) 3,5 dimethyl 2 oxocyclohexyl] 2 hydroxyethyl}piperidine 2,6 dione …   Wikipédia en Français

  • cycloheximide — cycloheximide. См. циклогексимид. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • cycloheximide — noun Etymology: cyclohexane + imide Date: 1950 an agricultural fungicide C15H23NO4 that inhibits protein synthesis and is obtained from a soil bacterium (Streptomyces griseus) …   New Collegiate Dictionary

  • cycloheximide — Antibiotic (MW 281) isolated from Streptomyces griseus. Blocks eukaryotic (but not prokaryotic) protein synthesis by preventing initiation and elongation on 80S ribosomes. Commonly used experimentally …   Dictionary of molecular biology

  • cycloheximide — /suy kloh hek seuh muyd , mid/, n. Pharm. an antibiotic substance, C15H23NO4, isolated from the bacterium Streptomyces griseus, used experimentally to block protein synthesis. [1945 50; CYCLOHEX(ANE) + IMIDE] * * * …   Universalium

  • cycloheximide — noun an agricultural fungicide …   Wiktionary

  • cycloheximide — An antibiotic obtained from certain strains of Streptomyces griseus; used in biochemical research to inhibit in vitro protein synthesis; also a fungicide and rat repellent. * * * cy·clo·hex·i·mide hek sə .mīd, məd n an agricultural fungicide… …   Medical dictionary

  • cycloheximide — cy·clo·hex·i·mide …   English syllables

  • cycloheximide — A molecule that inhibits protein synthesis in eukaryotes, but not in prokaryotes. It blocks peptide bond formation by binding to the large ribosomal subunits. Synonym: actidione …   Glossary of Biotechnology

  • cycloheximide — ˌ ̷ ̷ ̷ ̷ˈheksəˌmīd, mə̇d noun ( s) Etymology: cyclohexanone + imide : a colorless crystalline antibiotic C15H23NO4 isolated from streptomycin producing strains of a soil bacterium (Streptomyces griseus) that is effective against several yeasts… …   Useful english dictionary


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