PGPC

Cayman Chemical Item Number 10044

(CAS 89947-79-5)

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Description

Oxidized low-density lipoprotein (oxLDL) particles contain low molecular weight species which promote the differentiation of monocytes and activate polymorphonuclear leukocytes.1 Many of these substances were recently isolated and purified from oxLDL, and identified as phosphatidylcholine species containing a fragmented, oxidized short-chain fatty acid remnant at the sn-2 position.2 One of these substances isolated from oxLDL and identified as azelaoyl PAF is a potent PPARγ agonist.3 1-Palmitoyl-2-glutaryl phosphatidylcholine (PGPC) and 1-(palmitoyl)-2-(5-oxovaleroyl) phosphatidylcholine (POV-PC) are closely related compounds with strikingly different activity.4 PGPC treatment of vascular endothelial cells induces the expression of both E-selectin and VCAM-1, and increases endothelial cell binding by both neutrophils and monocytes. This contrasts with POV-PC treatment, which stimulates only monocyte binding, and strongly inhibits the LPS-induced binding of neutrophils.4

1. Tontonoz, P., Nagy, L., Alvarez, J.G.A., et al. PPARγ promotes monocyte/macrophage differentiation and uptake of oxidized LDL. Cell 93 241-252 (1998).

2. Podrez, E.A., Batyreva, E., Shen, Z., et al. A novel family of atherogenic oxidized phospholipids promotes macrophage foam cell formation via the scavenger receptor CD36 and is enriched in atherosclerotic lesions. J Biol Chem 277 (41) 38517-38523 (2002).

3. Davies, S.S., Pontsler, A.V., Marathe, G.K., et al. Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor γ ligands and agonists. J Biol Chem 276 16015-16023 (2001).

4. Leitinger, N., Tyner, T.R., Oslund, L., et al. Structurally similar oxidized phospholipids differentially regulate endothelial binding of monocytes and neutrophils. Proc Natl Acad Sci USA 96(21) 12010-12015 (1999).

Formal Name 1-​palmitoyl-​2-​glutaryl phosphatidylcholine
CAS Number 89947-79-5
Molecular Formula C29H56NO10P
Formula Weight 609.7
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCCCCCCCCCCCCC(=O)​OC[C@H]​(COP(=O)​(O)​OCC[N]​(C)​(C)​C)​OC(=O)​CCCC(=O)​O
InCHI Code
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​1S/C29H56NO10P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-28(33)​37-24-26(40-29(34)​21-18-19-27(31)​32)​25-39-41(35,36)​38-23-22-30(2,3)​4/h26H,5-25H2,1-4H3,(H-,31,32,35,36)​/t26-/m1/s1
InCHI Key
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CDZVJFRXJAUXPP-AREMUKBSSA-N

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PGPC is available in the following screening library:

Size Price Quantity Subtotal
500 µg $18.00 $0.00
1 mg $34.00 $0.00
5 mg $144.00 $0.00
10 mg $252.00 $0.00
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Pricing updated 2015-04-27. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA

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