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M3315

Sigma-Aldrich

MJ33 lithium salt

powder, ≥90% (NMR)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C22H43F3O6PLi
CAS-Nummer:
Molekulargewicht:
498.48
MDL-Nummer:
UNSPSC-Code:
41106300
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥90% (NMR)

Form

powder

Farbe

white to beige

Löslichkeit

H2O: ≥5 mg/mL (warmed at 60 °C)

Lagertemp.

2-8°C

SMILES String

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

InChIKey

GDLMLQJISATCEL-UHFFFAOYSA-M

Anwendung

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

Biochem./physiol. Wirkung

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).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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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