A4111

2-AAPA hydrate

≥95% (HPLC), Irreversible glutathione reductase inhibitor, powder

• 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
• Empirical Formula (Hill Notation): C₁₈H₂₂N₄O₆S₄
• Molecular Weight: 518.65
• UNSPSC Code: 12352200
• NACRES: NA.25
• Assay: ≥95% (HPLC)
• Form: powder

Properties

• Product Name: 2-AAPA hydrate, ≥95% (HPLC)
• Quality Segment: 100
• assay: ≥95% (HPLC)
• form: powder
• solubility: DMSO: 10 mg/mL, clear
• storage temp.: 2-8°C

Description

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.

Potent cell-permeable irreversible glutathione reductase (GR) inhibitor

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: nwg
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable