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A0737

Sigma-Aldrich

N-acetylcysteine amide

≥98% (HPLC), lyophilized powder, antioxidant

Synonyme(s) :

(R)- 2-(Acetylamino)-3-mercapto-Propanamide, AD4, N-Acetyl-L-cysteinamide, NACA, acetylcysteinamide

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About This Item

Formule empirique (notation de Hill):
C5H10N2O2S
Numéro CAS:
38520-57-9
Poids moléculaire :
162.21
Numéro MDL:
MFCD01696115
Code UNSPSC :
12352209
ID de substance PubChem :
329770626
Nomenclature NACRES :
NA.25

product name

N-acetylcysteine amide, ≥98% (HPLC)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

lyophilized powder

Conditions de stockage

desiccated

Couleur

white to off-white

Solubilité

H2O: ≥20 mg/mL
DMSO: >40 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

CC(=O)N[C@@H](CS)C(N)=O

InChI

1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1

Clé InChI

UJCHIZDEQZMODR-BYPYZUCNSA-N

Application

N-acetylcysteine amide has been used:
  • to protect retinal pigment epithelium (RPE) from oxidative stress
  • to show that increased expression of cell adhesion molecule 4 (CADM4) in oligodendrocytes inhibits myelination
  • to protect cells from apoptosis induced by shikonin plus erlotinib/gefitinib
  • as a component in various culture media

as an antioxidant to reduce oxidative stress in brains of homozygous Drosophila spermine synthase (dSms e/e) mutant flies and melanoma cells.

Actions biochimiques/physiologiques

N-acetylcysteine amide is a membrane penetrating antioxidant with antiinflamatory activity through regulation of activation of NF-κB and HIF-1α as well as modulation of ROS. The compound readily crosses cell membranes, replenishes intracellular GSH, and defends the cell from oxidative stress. In contrast to DTT, AD4 is able to directly reduce intracellularl GSSG to GSH without the involvement of glutathione peroxidase. Such direct thiol exchange might have a protective effect. This compound has a potential in research and exploration for treatment of neurodegeneration, radiation exposure, and other oxidation-mediated disorders.

Autres remarques

This product is hydroscopic and air sensitive.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Culture and establishment of self-renewing human and mouse adult liver and pancreas 3D organoids and their genetic manipulation
Broutier L, et al.
Nature Protocols, 11(9), 1724-1724 (2016)
Axoglial adhesion by cadm4 regulates CNS myelination
Elazar N, et al.
Neuron, 101(2), 224-231 (2019)
Oxidative stress-mediated NFkappaB phosphorylation upregulates p62/SQSTM1 and promotes retinal pigmented epithelial cell survival through increased autophagy
Song C, et al.
PLoS ONE, 12(2), e0171940-e0171940 (2017)
Spermine synthase deficiency causes lysosomal dysfunction and oxidative stress in models of Snyder-Robinson syndrome
Li C, et al.
Nature Communications, 8(1), 1257-1257 (2017)
Hui Chen et al.
STAR protocols, 1(1), 100043-100043 (2020-10-29)
WNT signaling is crucial for embryonic development, adult tissue homeostasis, and injury repair. The poor biophysical characteristics of WNTs and their lack of receptor selectivity have hindered their use as research tools or potential therapeutics. We have developed a platform
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