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Merck

M3315

Sigma-Aldrich

MJ33 lithium salt

powder, ≥90% (NMR)

Sinónimos:

1-Hexadecyl-3-(trifluoroethyl)-sn-glycero-2-phosphomethanol lithium

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About This Item

Fórmula empírica (notación de Hill):
C22H43F3O6PLi
Número de CAS:
Peso molecular:
498.48
Número MDL:
Código UNSPSC:
41106300
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

Ensayo

≥90% (NMR)

Formulario

powder

color

white to beige

solubilidad

H2O: ≥5 mg/mL (warmed at 60 °C)

temp. de almacenamiento

2-8°C

cadena SMILES

CCCCCCCCCCCCCCCCOCC(COCC(F)(F)F)OP(OC)([O-])=O.[Li+]

InChI

1S/C22H44F3O6P.Li/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-29-18-21(31-32(26,27)28-2)19-30-20-22(23,24)25;/h21H,3-20H2,1-2H3,(H,26,27);/q;+1/p-1

Clave InChI

GDLMLQJISATCEL-UHFFFAOYSA-M

Aplicación

MJ33 lithium salt has been used as a peroxiredoxin VI (Prdx6) inhibitor:
  • to study its specific Prdx6 peroxidase activity in vitro and in breast cancer cell line (MCF-7) cell lysates
  • to study its effects on a mouse model of acute lung injury associated with exposure to hyperoxia
  • to study its potential use as a therapeutic agent

Acciones bioquímicas o fisiológicas

MJ33 acts as a non-toxic and potent inhibitor of agonist-induced activation of nicotinamide adenine dinucleotide phosphate (NADPH) oxidase type 2 (NOX2). It also prevents lung injuries associated with lung inflammation in mice. MJ33 is a fluorinated lipid analog, which blocks the enzyme by mimicking the transition state of the substrate.
Novel, active site directed, specific, competitive and reversible inhibitor of phospholipase A2 (PLA2).

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Inhibition of the phospholipase A2 activity of peroxiredoxin 6 prevents lung damage with exposure to hyperoxia
Benipal B, et al.
Redox Biology, 4, 321-327 (2015)
Fisher, A.B. et al.
American Journal of Physiology. Cell Physiology, 280, 748-748 (2001)
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.
José Pablo Vázquez-Medina et al.
American journal of physiology. Lung cellular and molecular physiology, 316(4), L656-L668 (2019-02-01)
Peroxiredoxin 6 (Prdx6) is a multifunctional enzyme that serves important antioxidant roles by scavenging hydroperoxides and reducing peroxidized cell membranes. Prdx6 also plays a key role in cell signaling by activating the NADPH oxidase, type 2 (Nox2) through its acidic
J W Chen et al.
The Journal of biological chemistry, 275(37), 28421-28427 (2000-07-14)
This report provides definitive evidence that the protein 1-Cys peroxiredoxin is a bifunctional ("moonlighting") enzyme with two distinct active sites. We have previously shown that human, rat, and bovine lungs contain an acidic Ca(2+)-independent phospholipase A(2) (aiPLA(2)). The cDNA encoding

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