Synonym
PON-PC; PON PC; PONPC; 16:0/9:0-PC; PC(16:0/9:0);
IUPAC/Chemical Name
(R)-2-((9-oxononanoyl)oxy)-3-(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
InChi Key
PPTNNIINSOQWCE-WJOKGBTCSA-N
InChi Code
InChI=1S/C33H64NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-24-32(36)40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-16-17-20-23-27-35/h27,31H,5-26,28-30H2,1-4H3/t31-/m1/s1
SMILES Code
O=C(OC[C@H](COP([O-])(OCC[N+](C)(C)C)=O)OC(CCCCCCCC=O)=O)CCCCCCCCCCCCCCC
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
PON-PC is an oxidized phospholipid containing a truncated 9-carbon fatty acyl chain terminating in an aldehyde at the sn-2 position.
PON-PC decreases the production of TNF-α, nitric oxide (NO), and NADP+ in primary mouse alveolar macrophages, as well as reduces the bactericidal activity of RAW 264.7 cells, when used at a concentration of 40 µM.
In vitro activity:
In contrast to the priming effect of POPC on AM activity, a harmful immune response, induced on incubation with PONPC, improved prostaglandin E2 (PGE2) formation, resulting in diminished bacterial phagocytosis. Additionally, PONPC induced production of CXCL1/KC, which potentially mediates neutrophil recruitment and enhances tissue inflammation. These results disclosed another dynamic mechanism by which pulmonary surfactant lipids (natural or oxidized) primed macrophage activity, thus affecting lung host defense.
Reference: Mol Immunol. 2020 Apr 30;122:163-172. https://pubmed.ncbi.nlm.nih.gov/32361419/
In vivo activity:
The levels of PON-GPC in BALF of mice exposed to CS were significantly elevated, compared with those of control mice. PON-GPC attenuated TNF-α, NO, and NADP(+) production in macrophages on stimulation with LPS plus IFN-γ. PON-GPC treatment attenuated the phosphorylation of p38 mitogen-activated protein kinase (MAPK). In addition, PON-GPC reduced the bactericidal activity of RAW264.7 cells.
Reference: Lung. 2012 Apr;190(2):169-82. https://pubmed.ncbi.nlm.nih.gov/21986851/
|
Solvent |
mg/mL |
mM |
Solubility |
Ethanol |
10.0 |
15.40 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
649.85
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. da Costa Loureiro L, da Costa Loureiro L, Gabriel-Junior EA, Zambuzi FA, Fontanari C, Sales-Campos H, Frantz FG, Faccioli LH, Sorgi CA. Pulmonary surfactant phosphatidylcholines induce immunological adaptation of alveolar macrophages. Mol Immunol. 2020 Apr 30;122:163-172. doi: 10.1016/j.molimm.2020.04.010. Epub ahead of print. PMID: 32361419.
2. Kimura T, Shibata Y, Yamauchi K, Igarashi A, Inoue S, Abe S, Fujita K, Uosaki Y, Kubota I. Oxidized phospholipid, 1-palmitoyl-2-(9'-oxo-nonanoyl)-glycerophosphocholine (PON-GPC), produced in the lung due to cigarette smoking, impairs immune function in macrophages. Lung. 2012 Apr;190(2):169-82. doi: 10.1007/s00408-011-9331-2. Epub 2011 Oct 11. PMID: 21986851.
3. Kimura T, Shibata Y, Yamauchi K, Igarashi A, Inoue S, Abe S, Fujita K, Uosaki Y, Kubota I. Oxidized phospholipid, 1-palmitoyl-2-(9'-oxo-nonanoyl)-glycerophosphocholine (PON-GPC), produced in the lung due to cigarette smoking, impairs immune function in macrophages. Lung. 2012 Apr;190(2):169-82. doi: 10.1007/s00408-011-9331-2. Epub 2011 Oct 11. PMID: 21986851.
In vitro protocol:
1. da Costa Loureiro L, da Costa Loureiro L, Gabriel-Junior EA, Zambuzi FA, Fontanari C, Sales-Campos H, Frantz FG, Faccioli LH, Sorgi CA. Pulmonary surfactant phosphatidylcholines induce immunological adaptation of alveolar macrophages. Mol Immunol. 2020 Apr 30;122:163-172. doi: 10.1016/j.molimm.2020.04.010. Epub ahead of print. PMID: 32361419.
2. Kimura T, Shibata Y, Yamauchi K, Igarashi A, Inoue S, Abe S, Fujita K, Uosaki Y, Kubota I. Oxidized phospholipid, 1-palmitoyl-2-(9'-oxo-nonanoyl)-glycerophosphocholine (PON-GPC), produced in the lung due to cigarette smoking, impairs immune function in macrophages. Lung. 2012 Apr;190(2):169-82. doi: 10.1007/s00408-011-9331-2. Epub 2011 Oct 11. PMID: 21986851.
In vivo protocol:
1. Kimura T, Shibata Y, Yamauchi K, Igarashi A, Inoue S, Abe S, Fujita K, Uosaki Y, Kubota I. Oxidized phospholipid, 1-palmitoyl-2-(9'-oxo-nonanoyl)-glycerophosphocholine (PON-GPC), produced in the lung due to cigarette smoking, impairs immune function in macrophages. Lung. 2012 Apr;190(2):169-82. doi: 10.1007/s00408-011-9331-2. Epub 2011 Oct 11. PMID: 21986851.
1: Ravandi A, Leibundgut G, Hung MY, Patel M, Hutchins PM, Murphy RC, Prasad A, Mahmud E, Miller YI, Dennis EA, Witztum JL, Tsimikas S. Release and capture of bioactive oxidized phospholipids and oxidized cholesteryl esters during percutaneous coronary and peripheral arterial interventions in humans. J Am Coll Cardiol. 2014 May 20;63(19):1961-71. doi: 10.1016/j.jacc.2014.01.055. Epub 2014 Mar 5. PMID: 24613321; PMCID: PMC4629781.
2: Karki P, Zhang CO, Promnares K, Li Y, Ke Y, Birukova AA, Birukov KG. Truncated oxidized phospholipids exacerbate endothelial dysfunction and lung injury caused by bacterial pathogens. Cell Signal. 2023 Sep;109:110804. doi: 10.1016/j.cellsig.2023.110804. Epub 2023 Jul 10. PMID: 37437826; PMCID: PMC10544726.
3: Karki P, Li Y, Zhang CO, Ke Y, Promnares K, Birukova AA, Eggerman TL, Bocharov AV, Birukov KG. Amphipathic Helical Peptide L37pA Protects against Lung Vascular Endothelial Dysfunction Caused by Truncated Oxidized Phospholipids via Antagonism with CD36 Receptor. Am J Respir Cell Mol Biol. 2024 Jan;70(1):11-25. doi: 10.1165/rcmb.2023-0127OC. PMID: 37725486; PMCID: PMC10768836.