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SML1081

Sigma-Aldrich

Ezatiostat

≥98% (HPLC)

Synonyme(s) :

γ-Glu-S-BzCys-PhGly diethyl ester, (2S)-2-Amino-5-[[(2R)-3-benzylsulfanyl-1-[[(1R)-2-ethoxy-2-oxo-1-phenylethyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoate, TER 199, TER199, TLK199, Terrapin 199

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About This Item

Formule empirique (notation de Hill):
C27H35N3O6S
Numéro CAS:
168682-53-9
Poids moléculaire :
529.65
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 5 mg/mL, clear (warmed)

Température de stockage

2-8°C

InChI

1S/C27H35N3O6S/c1-3-35-26(33)21(28)15-16-23(31)29-22(18-37-17-19-11-7-5-8-12-19)25(32)30-24(27(34)36-4-2)20-13-9-6-10-14-20/h5-14,21-22,24H,3-4,15-18,28H2,1-2H3,(H,29,31)(H,30,32)/t21-,22-,24+/m0/s1

Clé InChI

GWEJFLVSOGNLSS-WPFOTENUSA-N

Application

Ezatiostat has been used as glutathione S-transferase P1 (GSTP1) inhibitor:
  • to study its effects on peroxiredoxin 6 (PRDX6) inhibition in neonatal rat testicular gonocytes
  • for the incubation of bronchial epithelial cells in proteolysis assay
  • to study its effects on the cystine-glutamate antiporter xCT (SLC7A11) expression in tumor cells

Actions biochimiques/physiologiques

Ezatiostat is an inhibitor of glutathione S-transferase P1-1 (GSTP1-1) with hematopoiesis-stimulating activity. After intracellular de-esterification, the active form of ezatiostat binds to and inhibits GST P1-1, leading to activation of Jun kinase (JNK), a key regulator of cellular growth and differentiation of blood precursor cells, thereby restoring JNK and MAPK pathway activities and promoting MAPK-mediated cellular proliferation and differentiation. Ezatiostat promotes the proliferation and maturation of hematopoietic precursor cells, granulocytes, monocytes, erythrocytes and platelets. Ezatiostat has recently been given orphan drug designation for it for the treatment of myelodysplastic syndrome.

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

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Consulter la Bibliothèque de documents

Juan Carlos López-Rodríguez et al.
Redox biology, 26, 101256-101256 (2019-06-24)
Environmental proteases have been widely associated to the pathogenesis of allergic disorders. Der p 1, a cysteine-protease from house dust mite (HDM) Dermatophagoides pteronyssinus, constitutes one of the most clinically relevant indoor aeroallergens worldwide. Der p 1 protease activity depends
Sander Bekeschus et al.
Redox biology, 30, 101423-101423 (2020-01-14)
Cold physical plasma is a partially ionized gas investigated as a new anticancer tool in selectively targeting cancer cells in monotherapy or in combination with therapeutic agents. Here, we investigated the intrinsic resistance mechanisms of tumor cells towards physical plasma
Cristian O'Flaherty et al.
Antioxidants (Basel, Switzerland), 9(1) (2020-01-08)
Peroxiredoxins (PRDXs) are antioxidant enzymes that protect cells from oxidative stress and play a role in reactive oxygen species (ROS)-mediated signaling. We reported that PRDXs are critical for human fertility by maintaining sperm viability and regulating ROS levels during capacitation.

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