Cycloleucine |
| Katalog-Nr.GC61751 |
Cycloleucin ist ein spezifischer Inhibitor der S-Adenosyl-Methionin-vermittelten Methylierung.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 52-52-8
Sample solution is provided at 25 µL, 10mM.
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Cycloleucine is a specific inhibitor of S-adenosylmethionine-mediated methylation, which blocks the methylation modification process of various biological molecules by competitively binding to the active site of methyltransferases[1]. Cycloleucine is an antagonist of the glycine allosteric site of the N-methyl-D-aspartate (NMDA) receptor with a Ki value of 600μM and has an anxiolytic effect[2, 3]. Cycloleucine is also a competitive inhibitor of ATP:L-methionine-S-adenosyltransferase in vitro, which can interfere with the biosynthesis of S-adenosylmethionine (SAM), thereby affecting the supply of methyl donors[4]. Cycloleucine can significantly inhibit plant growth, resulting in the disappearance of plant apical dominance, a significant decrease in plant height and dry weight, the retardation of leaf hair development on the back, and the inhibition of net photosynthetic rate and the activity of key enzymes in the Calvin cycle[5].
In vitro, treatment of rat hepatocytes with Cycloleucine (20mM) for 24 or 48h significantly reduced intracellular S-adenosyl-L-methionine (SAM) levels and induced hepatocyte cytotoxicity[6]. Treatment of RAW cells with Cycloleucine (40 mM) for 2h depleted intracellular SAM[7].
In vivo, intracerebroventricular administration of Cycloleucine (0.5, 1, 2, 4µg) to rats with bilateral nucleus accumbens (NAS) cannulation increased the time the rats spent in the open arm, the time they entered the open arm, and the time they reached the extreme end of the arm in the elevated plus maze test[8].
References:
[1] Ma C, Xu A, Zuo L, et al. Methionine Dependency and Restriction in Cancer: Exploring the Pathogenic Function and Therapeutic Potential[J]. Pharmaceuticals, 2025, 18(5): 640.
[2] Hershkowitz N, Rogawski M A. Cycloleucine blocks NMDA responses in cultured hippocampal neurones under voltage clamp: antagonism at the strychnine‐insensitive glycine receptor[J]. British journal of pharmacology, 1989, 98(3): 1005-1013.
[3] Gottlieb A, Stein G Y, Ruppin E, et al. PREDICT: a method for inferring novel drug indications with application to personalized medicine[J]. Molecular systems biology, 2011, 7(1): 496.
[4] Caboche M, Hatzfeld J. Methionine metabolism in BHK cells: preliminary characterization of the physiological effects of cycloleucine, an inhibitor of S‐adenosylmethionine biosynthesis[J]. Journal of Cellular Physiology, 1978, 97(3): 361-370.
[5] Niu T, Zhang J, Li J, et al. Effects of exogenous glycine betaine and cycloleucine on photosynthetic capacity, amino acid composition, and hormone metabolism in Solanum melongena L[J]. Scientific Reports, 2023, 13(1): 7626.
[6] Zhuge J, Cederbaum A I. Depletion of S-adenosyl-l-methionine with cycloleucine potentiates cytochrome P450 2E1 toxicity in primary rat hepatocytes[J]. Archives of biochemistry and biophysics, 2007, 466(2): 177-185.
[7] Song Z, Chen T, Deaciuc I V, et al. Modulation of endotoxin stimulated interleukin-6 production in monocytes and Kupffer cells by S-adenosylmethionine (SAMe)[J]. Cytokine, 2004, 28(6): 214-223.
[8] Gargiulo A P I, Acuña A, Gargiulo M M L, et al. Effects of cycloleucine in the nucleus accumbens septi on the elevated plus maze test in rats[J]. Neuropsychobiology, 2020, 79(3): 191-197.
| Cell experiment [1]: | |
Cell lines | Hepatocytes |
Preparation Method | 5×106 hepatocytes were seeded in 15cm culture dishes and treated with 0 or 20mM Cycloleucine for 24 or 48h. The hepatocytes were washed twice with PBS and scraped, centrifuged at 80×g for 10min, and the cell pellet was dispersed with 120μL of 0.1M KPi (pH 7.4). 5μL was used for protein concentration analysis, and the remaining cell suspension was added to 120μL of 0.4M HClO4, mixed thoroughly, and centrifuged at 12,000rpm for 10min at 4°C. The supernatant was filtered and S-Adenosyl-L-methionine (SAM) levels were measured by high-performance liquid chromatography. |
Reaction Conditions | 20mM; 24, 48h |
Applications | Treatment with 20mM Cycloleucine for 24 or 48h dramatically decreased SAM levels to 30% those of non-treated control hepatocytes. |
| Animal experiment [2]: | |
Animal models | Rats of a Holtzman-derived colony |
Preparation Method | The elevated plus maze test was used. Male rats bilaterally cannulated into the nucleus accumbens septi (NAS) were employed. Rats were divided into 5 groups that received either 1µL injections of saline or Cycloleucine (0.5, 1, 2, or 4µg) 15min before testing. After testing completion, rats were injected with saturated methylene blue solution (1µL). They were sacrificed with an excess of ether 15min later. Brains were removed from the skull. Afterwards, they were fixed in 20% formalin solution. |
Dosage form | 0.5, 1, 2, 4µg; 1µL; i.c.v. |
Applications | Treatment with Cycloleucine produced increases in the time spent in the open arm. Open arm entries were increased by the higher dose, and extreme arrivals were increased by all doses. Time spent in the open arm is recognized as the most classical parameter of an anxiolytic effect. |
References: | |
| Cas No. | 52-52-8 | SDF | |
| Canonical SMILES | O=C(O)C1(CCCC1)N | ||
| Formula | C6H11NO2 | M.Wt | 129.16 |
| Löslichkeit | Water: 50 mg/mL (387.12 mM); DMSO: < 1 mg/mL (ultrasonic) (insoluble or slightly soluble) | Storage | Store at -20°C |
| 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. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 7.7423 mL | 38.7117 mL | 77.4234 mL |
| 5 mM | 1.5485 mL | 7.7423 mL | 15.4847 mL |
| 10 mM | 774.2 μL | 3.8712 mL | 7.7423 mL |
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Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Quality Control & SDS
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- Purity: >98.00%
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Average Rating: 5 (Based on Reviews and 35 reference(s) in Google Scholar.)
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