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Merck

C1988

Sigma-Aldrich

Cicloheximida

Biotechnology Performance Certified

Sinónimos:

3-[2-(3,5- Dimetil-2-oxociclohexil)-2-hidroxietil]glutarimida, Actidiona, Naramicina A

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About This Item

Fórmula empírica (notación de Hill):
C15H23NO4
Número de CAS:
Peso molecular:
281.35
Beilstein/REAXYS Number:
88868
EC Number:
MDL number:
UNSPSC Code:
51102829
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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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

Modo de acción: inhibición de la traducción en eucariotas que provoca la detención del crecimiento celular y la muerte celular. La CHX se utiliza ampliamente para la selección de cepas de levaduras y hongos resistentes a CHX, la inhibición controlada de la síntesis de proteínas para la detección de proteínas de vida corta y la súper-inducción de la expresión de proteínas, así como la inducción de la apoptosis o la facilitación de la inducción de la apoptosis por los receptores de muerte.

Espectro de actividad: activo contra levaduras y hongos como Candida, Aspergillus, Saccharomyces y 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.

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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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)
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.
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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