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870601C

Avanti

Azelaoyl-PAF

Avanti Research™ - A Croda Brand 870601C

Synonym(s):

1-hexadecyl-2-azelaoyl-sn-glycero-3-phosphocholine

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About This Item

Empirical Formula (Hill Notation):
C33H66NO9P
CAS Number:
354583-69-0
Molecular Weight:
651.85
MDL number:
MFCD03412018
UNSPSC Code:
12352211
NACRES:
NA.25

form

liquid

packaging

pkg of 1 × 1 mL (870601C-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 870601C

concentration

1 mg/mL (870601C-1mg)

shipped in

dry ice

storage temp.

−20°C

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC(CCCCCCCC(O)=O)=O)COCCCCCCCCCCCCCCCC)=O

InChI

1S/C33H66NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-20-23-27-40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-17-18-21-24-32(35)36/h31H,5-30H2,1-4H3,(H-,35,36,38,39)/t31-/m1/s1

InChI key

ZDFOCDTXDPKJKA-WJOKGBTCSA-N

General description

1-hexadecyl-2-azelaoyl-sn-glycero-3-phosphocholine (Azelaoyl-PAF) Azelaoyl-PAF is an alkyl phosphatidylcholine and is a component of the lipid pool within oxidized low-density lipoprotein (oxLDL) particles. Azelaoyl-PAF is a low molecular weight phospholipid.

Application

Azelaoyl-PAF may be used in binding assay of anti-inflammatory peptides, 2F and 4F.[1]

Biochem/physiol Actions

1-hexadecyl-2-azelaoyl-sn-glycero-3-phosphocholine (Azelaoyl-PAF) acts as an agonist for peroxisome proliferator-activated receptors γ(PPAR-γ). It may be used as a therapeutic for Friedreich′s ataxia (FRDA).[2] At low concentrations azelaoyl-PAF may induce apoptosis.[1]

Packaging

5 mL Clear Glass Sealed Ampule (870601C-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system, Liver,Kidney

wgk_germany

WGK 3

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PPAR-gamma agonist azelaoyl PAF increases frataxin protein and mRNA expression. New implications for the friedreich?s ataxia therapy
Marmolino D, et al.
Cerebellum, 8(2), 98-103 (2009)
Anti-inflammatory peptides grab on to the whiskers of atherogenic oxidized lipids
Epand RF, et al.
Biochimica et Biophysica Acta - Biomembranes, 1788(9), 1967-1975 (2009)
S S Davies et al.
The Journal of biological chemistry, 276(19), 16015-16023 (2001-03-30)
Synthetic high affinity peroxisome proliferator-activated receptor (PPAR) agonists are known, but biologic ligands are of low affinity. Oxidized low density lipoprotein (oxLDL) is inflammatory and signals through PPARs. We showed, by phospholipase A(1) digestion, that PPARgamma agonists in oxLDL arise
P Tontonoz et al.
Cell, 93(2), 241-252 (1998-05-06)
The formation of foam cells from macrophages in the arterial wall is characterized by dramatic changes in lipid metabolism, including increased expression of scavenger receptors and the uptake of oxidized low-density lipoprotein (oxLDL). We demonstrate here that the nuclear receptor
Douglas S Watson et al.
Vaccine, 27(34), 4672-4683 (2009-06-13)
The membrane proximal region (MPR) of HIV-1 gp41 is a desirable target for development of a vaccine that elicits neutralizing antibodies since the patient-derived monoclonal antibodies, 2F5 and 4E10, bind to the MPR and neutralize primary HIV isolates. The 2F5

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