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C1988

Sigma-Aldrich

Cycloheximide

Biotechnology Performance Certified

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

grade

Biotechnology Performance Certified

form

powder

technique(s)

cell culture | mammalian: suitable

impurities

endotoxin, tested

solubility

ethanol: 50 mg/mL

antibiotic activity spectrum

fungi
yeast

Mode of action

protein synthesis | interferes

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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This Item
C769801810K1377
Cycloheximide Biotechnology Performance Certified

Sigma-Aldrich

C1988

Cycloheximide

-
Cycloheximide from microbial, ≥94% (TLC)

Sigma-Aldrich

C7698

Cycloheximide

-
Cycloheximide ≥90% (HPLC)

Sigma-Aldrich

01810

Cycloheximide

-
form

powder

form

powder

form

powder or crystals

form

powder

technique(s)

cell culture | mammalian: suitable

technique(s)

-

technique(s)

-

technique(s)

cell culture | mammalian: suitable, cell culture | plant: suitable

impurities

endotoxin, tested

impurities

-

impurities

-

impurities

≤5% kanamycin B

solubility

ethanol: 50 mg/mL

solubility

ethanol: soluble, clear to hazy

solubility

-

solubility

H2O: 10-50 mg/mL (As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 5 days.)

antibiotic activity spectrum

fungi, yeast

antibiotic activity spectrum

fungi, yeast

antibiotic activity spectrum

fungi, yeast

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria, mycoplasma

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.

Biochem/physiol Actions

Mode of Action: Translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for the 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.

Activity Spectrum: Active against yeast and fungi like Candida, Aspergillus, Saccharomyces, Penicillium
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

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Chronic 2 - Muta. 2 - Repr. 1B

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

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.
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)
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
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
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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