N1-Acetyl-5-methoxykynuramine hydrochloride
Based on 1 Customer Validation
N1-Acetyl-5-methoxykynuramine hydrochloride (AMK hydrochloride) is an active metabolite of Melatonin (HY-B0075) with antioxidant activity and blood-brain barrier permeability. N1-Acetyl-5-methoxykynuramine hydrochloride inhibits LPS-induced activation of inducible nitric oxide synthase and COX-2, scavenges ROS, hydroxyl radicals, carbonate radicals and ABTS cation radicals, and protects bovine serum albumin from peroxyl radical-mediated damage. N1-Acetyl-5-methoxykynuramine hydrochloride reduces the increase in cytoplasmic and mitochondrial lipid peroxidation in the substantia nigra and striatum in MPTP (HY-15608)-induced mouse models of Parkinson's disease. N1-Acetyl-5-methoxykynuramine hydrochloride can be used in studies related to Parkinson's disease, metabolism-related diseases and oxidative stress.
For research use only. We do not sell to patients.
- CAS No.: 1215711-91-3
- Formula: C12H17ClN2O3
- Molecular Weight:272.73
-
Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
-
Biological Activity
-
Chemical Information
- Purity & Documentation
- References
-
Help & FAQs
Biological Activity
|
COX-2 |
iNOS |
nNOS |
N1-Acetyl-5-methoxykynuramine hydrochloride potently scavenges hydroxyl radicals and ABTS cation radicals in cell-free systems at pH 5.0 and 7.5, but only weakly scavenges superoxide anions. It significantly protects bovine serum albumin from damage by peroxyl radicals, yet is rapidly oxidized and degraded by hydroxyl and carbonate radicals in a heme-catalyzed system at pH 8.0[1].
N1-acetyl-5-methoxykynuramine (AMK) hydrochloride spontaneously oxidizes to form MQA, AMMC, and AMNK on silica gel thin-layer plates; it traps NO in a concentration-dependent manner to generate AMMC; it reacts with peroxynitrite to produce AMNK in the presence of pH 7.4 bicarbonate; and it scavenges ABTS cations and hydroxyl radicals in a concentration-dependent manner[3].
N1-Acetyl-5-methoxykynuramine (1-1000 μM; 18 h) hydrochloride specifically inhibits lipopolysaccharide-induced expression of cyclooxygenase-2 protein in RAW 264.7 mouse macrophages without affecting the level of cyclooxygenase-1[2].
N1-acetyl-5-methoxykynuramine (AMK) hydrochloride is converted from AFMK via an enzymatic reaction catalyzed by catalase, while AFMK is generated from the reaction of melatonin with singlet oxygen and hydrogen peroxide[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
-
Cell Line:RAW 264.7 murine macrophages
-
Concentration:1 μM, 10 μM, 100 μM, 500 μM, 1 mM
-
Incubation Time:18 h
-
Result:Prevented LPS-induced increases in COX-2 protein levels in a concentration-dependent manner.
Reduced LPS-induced COX-2 expression only at the 500 μM concentration; concentrations under 500 μM did not inhibit COX-2 upregulation.
Did not significantly alter constitutive COX-1 isoform expression at any tested concentration.
Showed comparable efficacy to melatonin and AFMK at preventing LPS-induced COX-2 upregulation at 1 mM.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
-
CAS No. 1215711-91-3
-
Molecular Weight 272.73
-
Formula C12H17ClN2O3
-
SMILES
O=C(C)NCCC(C1=CC(OC)=CC=C1N)=O.Cl
-
Synonyms
AMK hydrochloride
-
Shipping
Room temperature in continental US; may vary elsewhere.
-
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Ressmeyer AR, et al. Antioxidant properties of the melatonin metabolite N1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction. Redox report : communications in free radical research. 2003;8(4):205-13. [Content Brief]
[2]. Mayo JC, et al. Anti-inflammatory actions of melatonin and its metabolites, N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) and N1-acetyl-5-methoxykynuramine (AMK), in macrophages. Journal of neuroimmunology. 2005 Aug;165(1-2):139-49. [Content Brief]
[3]. Guenther AL, et al. Reactions of the melatonin metabolite AMK (N1-acetyl-5-methoxykynuramine) with reactive nitrogen species: formation of novel compounds, 3-acetamidomethyl-6-methoxycinnolinone and 3-nitro-AMK. Journal of pineal research. 2005 Oct;39(3):251-60. [Content Brief]
[4]. Manda K, et al. AFMK, a melatonin metabolite, attenuates X-ray-induced oxidative damage to DNA, proteins and lipids in mice. Journal of pineal research. 2007 Apr;42(4):386-93. [Content Brief]
[5]. Tapias V, et al. Melatonin and its brain metabolite N(1)-acetyl-5-methoxykynuramine prevent mitochondrial nitric oxide synthase induction in parkinsonian mice. J Neurosci Res. 2009 Oct;87(13):3002-10. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
N1-Acetyl-5-methoxykynuramine hydrochloride Related Classifications
HY-W587743 Related Classifications
Powered by Bioz
- N1-Acetyl-5-methoxykynuramine
- 1215711-91-3
- AMK
- Drug Metabolite
- NO Synthase
- COX
- Reactive Oxygen Species (ROS)
- cyclooxygenase
- cyclooxygenase-2
- RAW 264.7 murine macrophages
- inducible nitric oxide synthase
- peroxynitrite
- free radical scavenger
- Lingulodinium polyedrum
- bovine serum albumin
- antioxidant
- cyclooxygenase-1
- Inhibitor
- inhibitor
- inhibit