Skip to Content
MilliporeSigma
All Photos(1)

Documents

M3315

Sigma-Aldrich

MJ33 lithium salt

powder, ≥90% (NMR)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C22H43F3O6PLi
CAS Number:
199106-13-3
Molecular Weight:
498.48
MDL number:
MFCD03787978
UNSPSC Code:
41106300
PubChem Substance ID:
24278549
NACRES:
NA.77

Quality Level

100

assay

≥90% (NMR)

form

powder

color

white to beige

solubility

H2O: ≥5 mg/mL (warmed at 60 °C)

storage temp.

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

InChI key

GDLMLQJISATCEL-UHFFFAOYSA-M

Application

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 Actions

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).

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service