CycloheximideAn antibacterial protein synthesis inhibitor

Cycloheximide (CAS 66-81-9)

Cycloheximide | CAS 66-81-9 is rated 5.0 out of 5 by 4.
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Synonym: Naramycin A; Actidione; 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide
Application: Cycloheximide is a highly effective antibiotic. It inhitibs the synthesis of proteins and macromolecules.
CAS Number: 66-81-9
Purity: ≥98%
Molecular Weight: 281.35
Molecular Formula: C15H23NO4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Cycloheximide is a highly effective antibiotic with activity against mold, yeast, and phytopathogenic fungi, with lower activity against bacteria. It has been reported to inhibit the synthesis of both proteins and macromolecules, as well as affect apoptosis in eukaryotes. Inhibition of protein synthesis is believed to be mediated through DNA translation arrest, as demonstrated in rat thymocytes. Although cycloheximide has been reported to induce apoptosis in various cells, it has also been shown to inhibit or delay induced apoptosis. These observations suggest that cycloheximide's effect on apoptosis may not be solely through protein translation arrest and that other mechanisms may be involved. Cycloheximide has also been reported to inhibit FKBP12 (peptidylprolylisomerase hFKBP12, PPIase hFKBP12) via competitive inhibition.


References

1. Lotem, J. and Sachs, L. 1995. Cell Growth Differ. 6: 647-653. PMID: 7669718
2. Chow, S.C., et al. 1995. Exp. Cell Res. 216: 149-159. PMID: 7813615
3. Grand, R.J., et al. 1995. Exp. Cell Res. 218: 439-451. PMID: 7796880

Usage :
Recommended working concentration in literature is 1μg/mL
Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in water (20 mg/ml at 2° C), ethanol (50 mM), chloroform, and ether. Insoluble in saturated hydrocarbons. (Do not store aqueous solutions for more than one day)
Storage :
Store at 4° C
Melting Point :
110° C
Boiling Point :
491.8° C at 760 mmHg (Predicted)
Density :
1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.50 (Predicted)
IC50 :
Vero (Kidney cells): IC50 = 530 nM (chlorocebus aethiops); Saccharomyces cerevisiae: IC50 = 7420 nM; HeLa (Cervical adenocarcinoma cells): IC50 = 532.5 nM (human); Plasmodium falciparum: IC50 = 150 nM; CEM (T-cell leukemia): IC50 = 120 nM (human); 60S ribosomal protein L19-A: EC5050 = 644 nM (Saccharomyces cerevisiae S288c)
Ki Data :
PPIase hFKBP12: Ki= 3.4 µM; FK506 binding protein 14: Ki= 76.2 µM (human); FK506-binding protein 1A: Ki= 3.4 µM (human)
pK Values :
pKa: 11.61
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
MA4375000
PubChem CID :
6197
Merck Index :
14: 2728
MDL Number :
MFCD00082346
EC Number :
200-636-0
Beilstein Registry :
88868
SMILES :
C[C@H]1C[C@@H](C(=O)[C@@H](C1)[C@@H](CC2CC(=O)NC(=O)C2)O)C

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Cycloheximide  Product Citations

See how others have used Cycloheximide. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 60 total

PMID: # 30821592  Peng, M.|Wang, J.|Tian, Z.|Zhang, D.|Jin, H.|Liu, C.|Xu, J.|Li, J.|Hua, X.|Xu, J.|Huang, C.|Huang, C.| et al. 2019. Autophagy.

PMID: # 30696953  Knudsen, ES. et al. 2019. Oncogene. 490: 180-93.

PMID: # 31300553  Jo, S.|Lockridge, A.|Alejandro, EU.| et al. 2019. J. Biol. Chem.

PMID: # 31222373  Luo, Y. et al. 2019. Cell. Mol. Life Sci.

PMID: # 31278054  Episkopou, H.|Diman, A.|Claude, E.|Viceconte, N.|Decottignies, A.| et al. 2019. Mol. Cell.

PMID: # 28733990  Hoffmann, JHO.|Schaekel, K.|Hartl, D.|Enk, AH.|Hadaschik, EN.| et al. 2018. Br. J. Dermatol. 178: 207-214.

PMID: # 29715486  Rigalli, JP. et al. 2018. Cancer Lett. 428: 69-76.

PMID: # 29555469  Pappas, B. et al. 2018. Biochem. Pharmacol. 152: 34-44.

PMID: # 29535359  Zhang, L. et al. 2018. Nat Commun. 9: 1047.

PMID: # 29524606  Zhuang, H.|Li, Q.|Zhang, X.|Ma, X.|Wang, Z.|Liu, Y.|Yi, X.|Chen, R.|Han, F.|Zhang, N.|Li, Y.| et al. 2018. Free Radic. Biol. Med. 120: 1-12.

Citations 1 to 10 of 60 total

Is the material synthetic?

Asked by: chemsd02
Thank you for your question. sc-3508 (Cycloheximide, CAS 66-81-9) is not 100% synthetic. It's semi-fermented and semi-synthetic.
Answered by: Chemical Support 10
Date published: 2017-03-09

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. The compound, sc-3508, is provided as a white to off-white crystalline powder. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-17

What is the solubility of this product in DMSO?

Asked by: hawkeye11
Thank you for you question. Cycloheximide, sc-3508, is soluble in DMSO at 32mg/mL.
Answered by: TechService7
Date published: 2019-03-06

What is the country of origin of this compound?

Asked by: two2igm05
Thank you for your question. This particular chemical is from China. Please contact Technical Service if you have further questions concerning this product.
Answered by: Tech Service 9
Date published: 2018-11-02
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Rated 5 out of 5 by from Good quality This Cycloheximide gave us very consistent results in the past several years. Good quality.
Date published: 2017-10-09
Rated 5 out of 5 by from Saw good results in our experiments Saw good results in our experiments.
Date published: 2015-05-19
Rated 5 out of 5 by from Worked well in our experiments Worked well in our experiments, buy it routinely.
Date published: 2015-04-21
Rated 5 out of 5 by from Tang et Tang et. al. (PubMed ID 10066786) used cycloheximide to study the molecular mechanism behind CHX-induced cell death. -SCBT Publication Review
Date published: 2015-02-08
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