Skip to Content
Merck
All Photos(1)

Key Documents

Safety Information

A4111

Sigma-Aldrich

2-AAPA hydrate

≥95% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C18H22N4O6S4
Molecular Weight:
518.65
UNSPSC Code:
12352200
NACRES:
NA.25

Quality Level

100

Assay

≥95% (HPLC)

form

powder

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

General description

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.

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

A4111-VAR:
A4111-5MG:
A4111-BULK:
A4111-IP:
A4111-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service