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Merck
CN

M3315

MJ33 lithium salt

≥90% (NMR), phospholipase A2 (PLA2) inhibitor , powder

Synonym(s):

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

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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

Key Documents

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Product Name

MJ33 lithium salt, powder, ≥90% (NMR)

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

Related Categories

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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000421061
0000421061
0000229403
0000194820
0000194820

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Bavneet Benipal et al.
Redox biology, 4, 321-327 (2015-02-01)
Lung injury associated with hyperoxia reflects in part the secondary effects of pulmonary inflammation and the associated production of reactive oxygen species due to activation of NADPH oxidase, type 2 (NOX2). Activation of NOX2 requires the phospholipase A2 (PLA2) activity
Fisher, A.B. et al.
American Journal of Physiology. Cell Physiology, 280, 748-748 (2001)
Allelic variants of glutathione S-transferase P1-1 differentially mediate the peroxidase function of peroxiredoxin VI and alter membrane lipid peroxidation
Manevich Y, et al.
Free radical biology & medicine, 54, 62-70 (2013)
Y Manevich et al.
Free radical biology & medicine, 54, 62-70 (2012-11-13)
The dual-functioning antioxidant enzyme peroxiredoxin VI (Prdx6) detoxifies lipid peroxides particularly in biological membranes, and its peroxidase function is activated by glutathione S-transferase Pi (GSTP). The GSTP gene is polymorphic in humans, with the wild-type GSTP1-1A (Ile105, Ala114) and three
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)
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