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

Catalog No.GC17198 Copy One-Click Copy Product Info

Cycloheximide is an orally active antifungal antibiotic produced by Streptomyces griseus. Cycloheximide inhibits protein synthesis and RNA synthesis in vivo (IC50=532.5nM and 2880nM).

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Cycloheximide Chemical Structure

Cas No.: 66-81-9

Size Price Stock Qty
10mM (in 1mL DMSO)
$58.00
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200mg
$54.00
In stock
500mg
$108.00
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Sample solution is provided at 25 µL, 10mM.



Product has been cited by 58 publications

Description of Cycloheximide

Cycloheximide is an orally active antifungal antibiotic produced by Streptomyces griseus. Cycloheximide inhibits protein synthesis and RNA synthesis in vivo (IC50=532.5nM and 2880nM). Cycloheximide binds to the E site of the eukaryotic 60S ribosomal subunit to block eEF2-mediated translocation, thereby inhibiting protein synthesis. At the same time, Cycloheximide suppresses autophagy through activating the mTORC1 pathway. Cycloheximide can be used in studies related to protein half-life determination and translational regulation[1-4].

In vitro, Cycloheximide (10μg/ml) together with lipopolysaccharide (100ng/ml) acted on J774.1 macrophage-like cells for 4h. Cycloheximide induced apoptotic cell death. Cycloheximide blocked the production of p38 phosphatase through inhibiting protein synthesis, prolonged p38 phosphorylation signals, and triggered the death pathway[5]. Cycloheximide (0.35–100μM) treated human colon adenocarcinoma HT29-D4 cells for 48h. Cycloheximide dose-dependently increased the number of vasoactive intestinal peptide binding sites on the cell surface[6].

In vivo, Cycloheximide (10mg/kg; single injection) was subcutaneously injected into Swiss-Webster mice. Cycloheximide inhibited protein synthesis in the mouse brain and induced retention deficits of prior learning[7]. Cycloheximide (200mg/kg; single injection) was intraperitoneally injected into ICR mice. After 20min, kainic acid (0.1μg) was injected into the lateral ventricle. Cycloheximide significantly prevented kainic acid-induced memory impairment and hippocampal CA3 pyramidal cell death. Cycloheximide inhibited the elevation of p-ERK, p-JNK1, and p-CaMK II, the expression of c-Fos and c-Jun, and microglial activation caused by kainic acid[8].

References:

[1] Montes LF. Cycloheximide in dermatology. Acta Derm Venereol. 1997 May;77(3):240.

[2] Huerta-Bahena J, Villalobos-Molina R, García-Sáinz JA. Cycloheximide: an adrenergic agent. Life Sci. 1982 May 17;30(20):1757-62.

[3] Gail DB, Massaro GD, Massaro D. Influence of cycloheximide on the lung. J Appl Physiol. 1975 Apr;38(4):623-9.

[4] Borrelli MJ, Stafford DM, Rausch CM, et al. Cycloheximide protection against actinomycin D cytotoxicity. J Cell Physiol. 1992 Dec;153(3):507-17.

[5] Karahashi H, Amano F. Endotoxin-tolerance to the cytotoxicity toward a macrophage-like cell line, J774.1, induced by lipopolysaccharide and cycloheximide: Role of p38 MAPK in induction of the cytotoxicity. Biol Pharm Bull. 2003 Sep;26(9):1249-59.

[6] Luis J, Martin JM, El Battari A, et al. Cycloheximide induces accumulation of vasoactive intestinal peptide(VIP) binding sites at the cell surface of a human colonic adenocarcinoma cell line(HT29-D4): evidence for the presence of an intracellular pool of VIP receptors. Eur J Biochem. 1987 Sep;167(2):391-6.

[7] Nagelberg DB, Nagy ZM. Cycloheximide produces adult-like retention deficits of prior learning in infant mice. Pharmacol Biochem Behav. 1977;7(5):435-41.

[8] Lee HK, Choi SS, Han KJ, et al. Cycloheximide inhibits neurotoxic responses induced by kainic acid in mice. Brain Res Bull. 2003;61(1):99-107.

Protocol of Cycloheximide

Cell experiment [1]:

Cell lines

JA-4 cells (an LPS‑sensitive subline of murine macrophage‑like cell line J774.1)

Preparation Method

JA‑4 cells were maintained in Ham’s F‑10 medium supplemented with 10% heat‑inactivated fetal bovine serum, 50U/ml penicillin and 50μg/ml streptomycin at 37°C, 5% CO₂. Cells were seeded at 2×10⁵ cells/well in 24‑well plates overnight, then treated with or without 10ng/ml LPS for 90min, washed, and subsequently incubated with 100ng/ml LPS and 10μg/ml Cycloheximide for 4h.

Reaction Conditions

10μg/ml; 4h

Applications

Cycloheximide combined with LPS induced apoptotic cell death evidenced by PARP cleavage, DNA ladder formation, caspase‑3 activation, and LDH release. Sustained phosphorylation of p38 MAP kinase was observed and required for the cytotoxicity. Pretreatment with 10ng/ml LPS for 90min prevented the cytotoxicity, correlating with downregulated p38 phosphorylation.
Animal experiment [2]:

Animal models

Male ICR mice (20-25g)

Preparation Method

Male ICR mice were intraperitoneally administered Cycloheximide at 200mg/kg 20min prior to intracerebroventricular (i.c.v.) injection of kainic acid (0.1μg/5μl). A one-trial step-through passive avoidance test was performed 24h after kainic acid administration, and mice were sacrificed at 30min (for p-ERK and p-JNK1 detection), 2h (for c-Fos and c-Jun detection) or 24h (for hippocampal CA3 neuronal death and OX-42 immunoreactivity detection) post kainic acid injection.

Dosage form

200mg/kg; i.p.; single injection

Applications

Cycloheximide pretreatment prevented kainic acid-induced memory impairment in the passive avoidance test, blocked kainic acid-induced pyramidal cell death in the hippocampal CA3 region, attenuated kainic acid-elevated phosphorylation of ERK in dentate gyrus and mossy fiber, phosphorylation of JNK1 and CaMK II in hippocampus, inhibited kainic acid-induced upregulation of c-Fos and c-Jun expression in hippocampus, and reduced kainic acid-induced increase of OX-42 immunoreactivity in hippocampal CA3 region.

References:

[1] Karahashi H, Amano F. Endotoxin-tolerance to the cytotoxicity toward a macrophage-like cell line, J774.1, induced by lipopolysaccharide and cycloheximide: Role of p38 MAPK in induction of the cytotoxicity. Biol Pharm Bull. 2003 Sep;26(9):1249-59.

[2] Lee HK, Choi SS, Han KJ, et al. Cycloheximide inhibits neurotoxic responses induced by kainic acid in mice. Brain Res Bull. 2003;61(1):99-107.

Chemical Properties of Cycloheximide

Cas No. 66-81-9 SDF
Synonyms Naramycin A; Actidione; 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide
Chemical Name 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
Canonical SMILES CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C
Formula C15H23NO4 M.Wt 281.4
Solubility ≥ 100 mg/mL (355.87 mM) in DMSO, ≥ 57.6 mg/mL in EtOH, ≥ 14.05 mg/mL in Water with ultrasonic and warming Storage 4°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Cycloheximide

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1 mg 5 mg 10 mg
1 mM 3.5537 mL 17.7683 mL 35.5366 mL
5 mM 710.7 μL 3.5537 mL 7.1073 mL
10 mM 355.4 μL 1.7768 mL 3.5537 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 30 reference(s) in Google Scholar.)

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