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C1988

Sigma-Aldrich

Cycloheximide

Biotechnology Performance Certified

Synonym(s):

3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, Actidione, Naramycin A

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About This Item

Empirical Formula (Hill Notation):
C15H23NO4
CAS Number:
66-81-9
Molecular Weight:
281.35
Beilstein:
88868
EC Number:
200-636-0
MDL number:
MFCD00082346
UNSPSC Code:
51102829
PubChem Substance ID:
24892457
NACRES:
NA.85
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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

human ... FKBP1A(2280) , PIN1(5300)

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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[1] and activate cumulus-free equine oocytes.[2]

Biochem/physiol Actions

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.[3] More recent studies revealed that CHX binds the 60S ribosome and specifically prevents the translocation step in elongation.[4]
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

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research
Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Signal Word

Danger

Hazard Statements

H300,H341,H360D,H411

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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Certificates of Analysis (COA)

Lot/Batch Number
0000406818
0000384107
0000355367
0000355366
0000361754

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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
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)
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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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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