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A4111

Sigma-Aldrich

2-AAPA hydrate

≥95% (HPLC)

Sinonimo/i:

R,R′-2-Acetylamino-3-[4-(2-acetylamino-2-carboxyethylsulfanylthiocarbonylamino)phenylthiocarbamoylsulfanyl]propionic acid hydrate, S, S′-[1,4-Phenylenebis(iminocarbonothioyl)]bis[N-acetyl-L-Cysteine] hydrate

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About This Item

Formula empirica (notazione di Hill):
C18H22N4O6S4
Peso molecolare:
518.65
Codice UNSPSC:
12352200
NACRES:
NA.25

Livello qualitativo

Saggio

≥95% (HPLC)

Stato

powder

Solubilità

DMSO: 10 mg/mL, clear

Temperatura di conservazione

2-8°C

Descrizione generale

2-Acetylamino-3-[4-(2-acetylamino-2-carboxy-ethylsulfanylthiocarbonylamino)phenylthiocarbamoylsulfanyl]propionic acid (2-AAPA) can block reductase systems, thereby modulating peroxiredoxin oxidation and mitochondrial function in A172 glioblastoma cells.

Azioni biochim/fisiol

Abnormal thiol redox state (TRS) is involved in the pathogenesis of a variety of diseases, such as chronic heart disease and atherosclerosis, rheumatoid arthritis , AIDS , Parkinson disease, Alzheimer disease, etc. Thus there is a need for tools capable of regulating TRS. Glutathione reductase (GR) is a critical enzyme in the homeostasis of TRS. Thus selective GR inhibitor would be a valuable research tool in studying TRS-related processes. Carmustine (#C0400) an anticancer drug is commonly used as GR inhibitor (IC50~470 microM). 2-AAPA is novel, potent cell-penetrable GR inhibitor. The compound is quite selective. But small reduction of activity for GP and GST was observed at 0.1mM concentration of 2-AAPT.
Glutathione reductase (GR) is a critical enzyme in the homeostasis of cellular thiol redox state. 2-AAPA is potent, selective, cell-permeable GR inhibitor, a valuable research tool in studying processes related to thiol redox state. For example, it was used in a study of the relationship between thiol redox state and overall redox state. In addition to the expected decrease in GSH and increase in GSSG, 2-AAPA increased the ratios of NAD(P)H/NAD(P)+. Significant protein glutathionylation was also observed.
Potent cell-permeable irreversible glutathione reductase (GR) inhibitor

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

nwg

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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Chen W, et al.
Journal of Pharmaceutical and Biomedical Analysis, 48(5), 1375-1380 (2008)
Inhibition of reductase systems by 2-AAPA modulates peroxiredoxin oxidation and mitochondrial function in A172 glioblastoma cells
de S L F, et al.
Toxicology in vitro, 42(5), 273-280 (2017)
Luiz Felipe de Souza et al.
Toxicology in vitro : an international journal published in association with BIBRA, 42, 273-280 (2017-05-04)
Thiol homeostasis has a critical role in the maintenance of proper cellular functions and survival, being coordinated by the action of several reductive enzymes, including glutathione (GSH)/glutathione reductase (GR) and thioredoxin (Trx)/thioredoxin reductase (TrxR) systems. Here, we investigated the effects

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