Cycloheximide

Cycloheximide
IUPAC name 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
Other names naramycin a, hizarocin actidione, actispray kaken, U-4527
Identifiers
CAS number	66-81-9 Y
PubChem	6197
ChemSpider	5962 Y
UNII	98600C0908 N
KEGG	C06685 N
ChEBI	CHEBI:27641 N
ChEMBL	CHEMBL123292 N
RTECS number	MA4375000
Jmol-3D images	Image 1
SMILES O=C2NC(=O)CC(C[C@@H](O)[C@H]1C(=O)[C@@H](C)C[C@H](C)C1)C2
InChI InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1 Y Key: YPHMISFOHDHNIV-FSZOTQKASA-N Y InChI=1/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1 Key: YPHMISFOHDHNIV-FSZOTQKABD
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: Y/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