C1988

Sigma-Aldrich

Cycloheximide

Biotechnology Performance Certified

Synonym(s):
Actidione, 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, Naramycin A
Empirical Formula (Hill Notation):
C15H23NO4
CAS Number:
Molecular Weight:
281.35
Beilstein/REAXYS Number:
88868
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

grade

Biotechnology Performance Certified

form

powder

application(s)

cell culture | mammalian: suitable

impurities

endotoxin, tested

solubility

ethanol: 50 mg/mL

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

fungi
yeast

storage temp.

2-8°C

SMILES string

[H][C@]1(C[C@@H](C)C[C@H](C)C1=O)[C@H](O)CC2CC(=O)NC(=O)C2

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

InChI key

YPHMISFOHDHNIV-FSZOTQKASA-N

Gene Information

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Related Categories

Application

Cycloheximide is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors. It has been shown to selectively clear macrophages in atherosclerotic plaques and activate cumulus-free equine oocytes.

Packaging

1, 5 g in glass bottle

Biochem/physiol Actions

Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.
Cycloheximide (CHX) is an antibiotic produced by S. griseus that inhibits protein biosynthesis in eukaryotes. It inactivate transferase II enzyme that is involved in peptide chain elongation. More recent studies revealed that CHX binds the 60S ribosome and specifically prevents the translocation step in elongation.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN2811 - class 6.1 - PG 2 - EHS - Toxic solids, organic, n.o.s., HI: all

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Valerie Croons et al.
The Journal of pharmacology and experimental therapeutics, 320(3), 986-993 (2006-12-01)
Macrophages are an essential component of unstable atherosclerotic plaques and play a pivotal role in the destabilization process. We have demonstrated previously that local delivery of the mammalian target of rapamycin (mTOR) inhibitor everolimus selectively clears macrophages in rabbit plaques....
Y H Choi et al.
Reproduction (Cambridge, England), 122(1), 177-183 (2001-06-27)
Two different culture media (TCM-199 and follicular fluid), two activation treatments (10 and 50 micromol calcium ionophore l(-1)) and three culture periods with cycloheximide were evaluated to find effective culture conditions for activation of cumulus-free equine oocytes. Oocytes were collected...
Tilman Schneider-Poetsch et al.
Nature chemical biology, 6(3), 209-217 (2010-02-02)
Although the protein synthesis inhibitor cycloheximide (CHX) has been known for decades, its precise mechanism of action remains incompletely understood. The glutarimide portion of CHX is seen in a family of structurally related natural products including migrastatin, isomigrastatin and lactimidomycin...
Mechanism of cycloheximide inhibition of protein synthesis in a cell-free system prepared from rat liver.
B S Baliga et al.
The Journal of biological chemistry, 244(16), 4480-4489 (1969-08-25)
Nina Xue et al.
Cellular and molecular life sciences : CMLS, 76(17), 3433-3447 (2019-04-14)
Enhancement of insulin-like growth factor 1 receptor (IGF-IR) degradation by heat shock protein 90 (HSP90) inhibitor is a potential antitumor therapeutic strategy. However, very little is known about how IGF-IR protein levels are degraded by HSP90 inhibitors in pancreatic cancer...

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