N-acetyl-L-Cysteine amide (Synonyms: N-Acetylcysteine amide, NACA) |
| Catalog No.GC44301 |
N-acetyl-L-Cysteine amide (NACA) is a novel antioxidant, the amide form of N-acetylcysteine (NAC), due to its permeability through both cellular and mitochondrial membranes.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 38520-57-9
Sample solution is provided at 25 µL, 10mM.
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N-acetyl-L-Cysteine amide (NACA) is a novel antioxidant, the amide form of N-acetylcysteine (NAC), due to its permeability through both cellular and mitochondrial membranes [1]. N-acetylcysteine amide permeates cellular and mitochondrial membranes, crosses the blood-brain barrier [1,2] and has higher radical scavenging ability, metal chelating activity and reducing power than NAC [3].
N-acetyl-L-Cysteine amide protects neurons and dopaminergic cells from oxidative stress in tissue cultures and lipid peroxidation in neuronal cell lines [4,5]. N-acetyl-L-Cysteine amide (750 µM) protected the PC12 cells from glutamate toxicity by slightly decreasing the bleb formation on neurites, and increased the PC12 cell GSH level [5]. N-acetyl-L-Cysteine amide protected PC12 cells against glutamate cytotoxicity by decreasing the glutamate-induced ROS accumulation [5]. N-acetylcysteine amide (1 mM) prevents METH-induced oxidative stress in human brain microvascular endothelial (HBMVEC) cells [6].
In moderate TBI, N-acetyl-L-Cysteine amide treatment improves mitochondrial bioenergetics, cognitive function, cortical tissue sparing and reduces lipid peroxidation product 4-hydroxynonenal compared to NAC or vehicle treated rats [7]. In acute spinal cord injury, N-acetyl-L-Cysteine amide (150 or 300 mg/kg/day) treatment improves mitochondrial bioenergetics, maintains mitochondrial glutathione and improves tissue sparing and hind limb function [8].
References:
[1]. Grinberg L, Fibach E, Amer J, et al. N-acetylcysteine amide, a novel cell-permeating thiol, restores cellular glutathione and protects human red blood cells from oxidative stress[J]. Free Radical Biology and Medicine, 2005, 38(1): 136-145.
[2]. Offen D, Gilgun‐Sherki Y, Barhum Y, et al. A low molecular weight copper chelator crosses the blood-brain barrier and attenuates experimental autoimmune encephalomyelitis[J]. Journal of neurochemistry, 2004, 89(5): 1241-1251.
[3]. Ates B, Abraham L, Ercal N. Antioxidant and free radical scavenging properties of N-acetylcysteine amide (NACA) and comparison with N-acetylcysteine (NAC)[J]. Free radical research, 2008, 42(4): 372-377.
[4]. Bahat‐Stroomza M, Gilgun‐Sherki Y, Offen D, et al. A novel thiol antioxidant that crosses the blood brain barrier protects dopaminergic neurons in experimental models of Parkinson's disease[J]. European Journal of Neuroscience, 2005, 21(3): 637-646.
[5]. Penugonda S, Mare S, Goldstein G, et al. Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12[J]. Brain research, 2005, 1056(2): 132-138.
[6]. Zhang X, Banerjee A, Banks W A, et al. N-Acetylcysteine amide protects against methamphetamine-induced oxidative stress and neurotoxicity in immortalized human brain endothelial cells[J]. Brain research, 2009, 1275: 87-95.
[7]. Pandya J D, Readnower R D, Patel S P, et al. N-acetylcysteine amide confers neuroprotection, improves bioenergetics and behavioral outcome following TBI[J]. Experimental neurology, 2014, 257: 106-113.
[8]. Patel S P, Sullivan P G, Pandya J D, et al. N-acetylcysteine amide preserves mitochondrial bioenergetics and improves functional recovery following spinal trauma[J]. Experimental neurology, 2014, 257: 95-105.
| Cell experiment [1]: | |
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Cell lines |
PC12 cells |
|
Preparation Method |
PC12 cells were plated at a density of 25 × 103 cells/well in a 24-well collagen-coated plate for morphological assessment. The plate was divided into five groups in triplicate: (1) control: no glutamate, no N-acetyl-L-Cysteine amide (NACA); (2) Nerve growth factor (NGF) control: NGF (100 ng/ml), no glutamate, no NACA; (3) NACA only: NGF (100 ng/ml), no glutamate, NACA (750 µM); (4) glutamate only: NGF (100 ng/ml), glutamate (10 mM), no NACA; and (5) Glu + NACA: NGF (100 ng/ml), glutamate (10 mM), NACA (750 µM). All wells received 100 ng/ml NGF every other day, except Group I. After 1 week, cells were treated or not (control) with 10 mM glutamate, with or without NACA, for 24 h. Twenty-four hours later, the cells were fixed with 0.5% (v/v) glutaraldehyde in PBS and micropictures were taken. |
|
Reaction Conditions |
750 µM for 24 h |
|
Applications |
The addition of N-acetyl-L-Cysteine amide protected the PC12 cells from glutamate toxicity by slightly decreasing the bleb formation on neurites. |
| Animal experiment [2]: | |
|
Animal models |
Adult male Sprague-Dawley rats |
|
Preparation Method |
In order to access tissue sparing following Traumatic brain injury (TBI), rats were randomly divided into three groups: (I.) N-acetyl-L-Cysteine amide (NACA) loaded pump (18.5 mg/kg/hr) and a single 150 mg/kg bolus intraperitoneal (IP) injection of NACA given (30 min post-injury) (II.) N-acetylcysteine (NAC) (18.5 mg/kg/hr) loaded pump and a single 150 mg/kg bolus injection of NAC given IP (30 min post-injury) (III.) Vehicle loaded pump and single vehicle bolus injection given IP (30 min post-injury). Following random distribution of all animals into one of the three previous groups, experimenters were blinded to treatment group. |
|
Dosage form |
loaded pump (18.5 mg/kg/hr) and a single 150 mg/kg, IP |
|
Applications |
N-acetyl-L-Cysteine amide treatment improved cognitive outcome following TBI as demonstrated by the significant improvements in distance traveled to goal as measured using the Morris Water Maze task. |
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References: [1]: Penugonda S, Mare S, Goldstein G, et al. Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12[J]. Brain research, 2005, 1056(2): 132-138. | |
| Cas No. | 38520-57-9 | SDF | |
| Synonyms | N-Acetylcysteine amide, NACA | ||
| Canonical SMILES | SC[C@H](NC(C)=O)C(N)=O | ||
| Formula | C5H10N2O2S | M.Wt | 162.2 |
| Solubility | DMF: 50 mg/mL,DMSO: 50 mg/mL,Ethanol: 50 mg/mL,PBS (pH 7.2): 30 mg/mL | 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.1652 mL | 30.8261 mL | 61.6523 mL |
| 5 mM | 1.233 mL | 6.1652 mL | 12.3305 mL |
| 10 mM | 0.6165 mL | 3.0826 mL | 6.1652 mL |
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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 40 reference(s) in Google Scholar.)
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