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
PubChem	6197
ChemSpider	5962
UNII	98600C0908
KEGG	C06685
ChEBI	CHEBI:27641
ChEMBL	CHEMBL123292
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 ; Key: YPHMISFOHDHNIV-FSZOTQKASA-N 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
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/11/21 15:21:14」(JST)

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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[edit]

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 in media to detect unwanted bacteria by suppressing yeasts and molds in beer fermentation.

The translational elongation freezing properties of Cycloheximide are also used for ribosome profiling / translational profiling. Translation is halted via the addition of cycloheximide, and the DNA/RNA in the cell is then nuclease treated. The ribosome-bound parts of RNA can then be sequenced.

References[edit]

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UpToDate Contents

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English Journal

Puromycin resistance gene as an effective selection marker for ciliate Tetrahymena.

Iwamoto M1, Mori C1, Hiraoka Y2, Haraguchi T3.Author information 1Advanced ICT Research Institute Kobe, National Institute of Information and Communications Technology (NICT), Kobe 651-2492, Japan.2Advanced ICT Research Institute Kobe, National Institute of Information and Communications Technology (NICT), Kobe 651-2492, Japan; Graduate School of Frontier Biosciences, Osaka University, Suita 565-0871, Japan; Graduate School of Science, Osaka University, Toyonaka 560-0043, Japan.3Advanced ICT Research Institute Kobe, National Institute of Information and Communications Technology (NICT), Kobe 651-2492, Japan; Graduate School of Frontier Biosciences, Osaka University, Suita 565-0871, Japan; Graduate School of Science, Osaka University, Toyonaka 560-0043, Japan. Electronic address: tokuko@nict.go.jp.AbstractA puromycin-N-acetyltransferase gene (pac) is widely used as a selection marker for eukaryotic gene manipulation. However, it has never been utilized for molecular studies in the ciliate Tetrahymena thermophila, in spite of the limited number of selection markers available for this organism. To utilize pac as a maker gene for T. thermophila, the nucleotide sequence of the pac gene was altered to accord with the most preferred codon-usage in T. thermophila. This codon-optimized pac gene expressed in T. thermophila conferred a resistance to transformed cells against 2000μg/ml of puromycin dihydrochloride, whereas the growth of wild-type cells was completely inhibited by 200μg/ml. Furthermore, an expression cassette constructed with the codon-optimized pac and an MTT1 promoter was effectively utilized for experiments to tag endogenous proteins of interest by fusing the cassette into the target gene locus. These results indicate that pac can be used as a selection marker in molecular studies of T. thermophila.
Gene.Gene.2014 Jan 25;534(2):249-55. doi: 10.1016/j.gene.2013.10.049. Epub 2013 Nov 1.
A puromycin-N-acetyltransferase gene (pac) is widely used as a selection marker for eukaryotic gene manipulation. However, it has never been utilized for molecular studies in the ciliate Tetrahymena thermophila, in spite of the limited number of selection markers available for this organism. To util
PMID 24185080

Transcriptional repression of the Ahr gene by LHCGR signaling in preovulatory granulosa cells is controlled by chromatin accessibility.

Teino I, Matvere A, Kuuse S, Ingerpuu S, Maimets T, Kristjuhan A, Tiido T.Author information Department of Cell Biology, Institute of Molecular and Cell Biology, University of Tartu, Riia 23, 51010 Tartu, Estonia.AbstractRecent advances in establishing the role of the aryl hydrocarbon receptor (Ahr) in normophysiology have discovered its fundamental role, amongst others, in female reproduction. Considering previous studies suggesting the hormonal modulation of Ahr, we aimed to investigate whether in murine granulosa cells (GCs) the gonadotropins regulate Ahr expression and how this is mechanistically implemented. We found that the FSH-like substance - pregnant mare serum gonadotropin - led to stimulation of Ahr expression. More importantly hCG produced relatively rapid reduction of Ahr mRNA in GCs of preovulatory follicles. We show for the first time that LHCGR signaling in regulating the Ahr message involves protein kinase A pathway and is attributable to decreased transcription rate. Finally, we found that Ahr promoter accessibility was decreased by hCG, implicating chromatin remodeling in Ahr gene regulation by LH.
Molecular and cellular endocrinology.Mol Cell Endocrinol.2014 Jan 25;382(1):292-301. doi: 10.1016/j.mce.2013.10.011. Epub 2013 Oct 18.
Recent advances in establishing the role of the aryl hydrocarbon receptor (Ahr) in normophysiology have discovered its fundamental role, amongst others, in female reproduction. Considering previous studies suggesting the hormonal modulation of Ahr, we aimed to investigate whether in murine granulosa
PMID 24145128

Growth Factor Receptor-Bound Protein 2 Promotes Autophagic Removal of Amyloid-β Protein Precursor Intracellular Domain Overload in Neuronal Cells.

Roy K, Raychaudhuri M, Chakrabarti O, Mukhopadhyay D.Author information Biophysics and Structural Genomics Division, Saha Institute of Nuclear Physics, WB, Kolkata, India.AbstractThe ascertainment of elevated levels of amyloid-β protein precursor intracellular domain (AICD) in Alzheimer's disease (AD) brains and the fact that it contributes to AD-like pathology has geared the search toward a new paradigm. While studying endogenous as well as overexpressed Grb2-AICD interaction in AD cell models, it was found that Grb2 co-localized to compartments along with AICD. We report now that these vesicles form in a clathrin and dynamin independent manner. Both types of vesicles mature into autophagosomes, merge with lysosomes, and relieve the cells of AICD overload. Inhibiting autophagosome formation results in vesicle accumulation. AICD-level is reduced in Grb2 excess condition in Cycloheximide Chase setup. Reduced caspase activity and apoptosis point toward the fact that the cytotoxic effect of AICD is alleviated by its sequestration in autolysosomes. Hence we state that the entrapping of AICD in Grb2 vesicles and its clearance via autophagosomes is a survival contrivance on the part of the cell. This study unravels, for the first time, the roles of Grb2 in autophagy and in handling toxic protein overload in an AD-like scenario.
Journal of Alzheimer's disease : JAD.J Alzheimers Dis.2014 Jan 1;38(4):881-95. doi: 10.3233/JAD-130929.
The ascertainment of elevated levels of amyloid-β protein precursor intracellular domain (AICD) in Alzheimer's disease (AD) brains and the fact that it contributes to AD-like pathology has geared the search toward a new paradigm. While studying endogenous as well as overexpressed Grb2-AICD interact
PMID 24100123

Japanese Journal

Involvement of protein synthesis in recovery from refractory period of electrical depolarization induced by osmotic stimulation in Chara corallina

SHIMMEN Teruo
Journal of plant research 124(5), 639-644, 2011-09-01
NAID 10029563904

Biological safety of nasal thallium-201 administration: A preclinical study for olfacto-scintigraphy

WASHIYAMA Kohshin,SHIGA Hideaki,HIROTA Kyoko,TSUCHIDA Asuka,YAMAMOTO Junpei,YAGI Sayaka,YOSHIZAKI Tomokazu,FURUKAWA Mitsuru,AMANO Ryohei,MIWA Takaki
Journal of radiation research 52(4), 450-455, 2011-07-16
… We assessed the odor detection ability of normal mice (n = 8) following nasal administration of 201TlCl to both sides of the nasal cavity, by observing cycloheximide solution avoidance behavior. …
NAID 10029122142

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