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A4111

Sigma-Aldrich

2-AAPA hydrate

≥95% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C18H22N4O6S4
Peso molecular:
518.65
Código UNSPSC:
12352200
NACRES:
NA.25

Nivel de calidad

Análisis

≥95% (HPLC)

formulario

powder

solubilidad

DMSO: 10 mg/mL, clear

temp. de almacenamiento

2-8°C

Descripción general

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.

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

nwg

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


Certificados de análisis (COA)

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Determination of thiols and disulfides via HPLC quantification of 5-thio-2-nitrobenzoic acid
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
Jakob Morgenstern et al.
STAR protocols, 1(3), 100206-100206 (2020-12-31)
Aldo-keto reductases (AKRs) are responsible for the detoxification of harmful aldehydes. Due to the large number of isotypes, the physiological relevance of AKRs cannot be obtained using mRNA or protein quantification, but only through the use of enzymatic assays to

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