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SML1081

Sigma-Aldrich

Ezatiostat

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C27H35N3O6S
CAS Number:
168682-53-9
Molecular Weight:
529.65
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

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

InChI key

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

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
074M4721V

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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
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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