PGPC
(Synonyms: 1-Palmitoyl-2-glutaryl phosphatidylcholine) 目录号 : GC44616An oxidized phospholipid
Cas No.:89947-79-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
PGPC is an oxidized phospholipid that can be formed under conditions of oxidative stress. [1] It is found as a component in mildly oxidized LDL (MM-LDL) and in products formed from the oxidation of 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (Ox-PAPC). [2] PGPC activates peroxisome proliferator-activated receptor (PPARα) in a concentration-dependent manner in a cell-based ligand-binding assay. [3] It increases VCAM1 and E-selectin expression in human aortic endothelial cells (HAECs), as well as HAEC binding by monocytes and polymorphonuclear neutrophils (PMNs), in a concentration-dependent manner.[4] PGPC (37.5 μM) also increases total 5-lipoxygenase metabolites in murine resident peritoneal macrophages (RPMs) and induces apoptosis in A7r5 rat aortic smooth muscle cells in vitro when used at a concentration of 50 μM.[5][6] PGPC levels are increased in the serum, LDL, and peripheral blood mononuclear cells (PBMCs) of patients with coronary artery disease. [7] UVA irradiation increases PGPC levels in cultured human skin fibroblasts. [8]
Reference:
[1]. Fruhwirth, G.O., Loidl, A., and Hermetter, A. Oxidized phospholipids: From molecular properties to disease. Biochimica et Biophysica Acta 1772, 718-736 (2007).
[2]. Watson, A.D., Leitinger, N., Navab, M., et al. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo. The Journal of Biological Chemisty 272(21), 13597-13607 (1997).
[3]. Lee, H., Shi, W., Tontonoz, P., et al. Role for peroxisome proliferator-activated receptor α in oxidized phospholipid-induced synthesis of monocyte chemotactic protein-1 and interleukin-8 by endothelial cells. Circ. Res. 87(6), 516-521 (2000).
[4]. Leitinger, N., Tyner, T.R., Oslund, L., et al. Structurally similar oxidized phospholipids differentially regulate endothelial binding of monocytes and neutrophils. Proceedings of the National Academy of Sciences of the United States of America 96(21), 12010-12015 (1999).
[5]. Zemski Berry, K.A., and Murphy, R.C. Phospholipid ozonation products activate the 5-lipoxygenase pathway in macrophages. Chem. Res. Toxicol. 29(8), 1355-1364 (2016).
[6]. Fruhwirth, G.O., Moumtzi, A., Loidl, A., et al. The oxidized phospholipids POVPC and PGPC inhibit growth and induce apoptosis in vascular smooth muscle cells. Biochim. Biophys. Acta. 1761(9), 1060-1069 (2006).
[7]. Mozzini, C., Frata Pasini, A., Garbin, U., et al. Increased endoplasmic reticulum stress and Nrf2 repression in peripheral blood mononuclear cells of patients with stable coronary artery disease. Free Radic. Biol. Med. 68, 178-185 (2014).
[8]. Gruber, F., Bicker, W., Oskolkova, O.V., et al. A simplified procedure for semi-targeted lipidomic analysis of oxidized phosphatidylcholines induced by UVA irradiation. J. Lipid. Res. 53(6), 1232-1242 (2012).
| Cas No. | 89947-79-5 | SDF | |
| 别名 | 1-Palmitoyl-2-glutaryl phosphatidylcholine | ||
| 化学名 | 1-palmitoyl-2-glutaryl phosphatidylcholine | ||
| Canonical SMILES | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC[N](C)(C)C)OC(=O)CCCC(=O)O | ||
| 分子式 | C29H56NO10P | 分子量 | 609.7 |
| 溶解度 | 20mg/mL in ethanol, 1mg/mL in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.6402 mL | 8.2008 mL | 16.4015 mL |
| 5 mM | 0.328 mL | 1.6402 mL | 3.2803 mL |
| 10 mM | 0.164 mL | 0.8201 mL | 1.6402 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Mixing of oxidized and bilayer phospholipids
Biochim Biophys Acta 2015 Jul;1848(7):1472-80.PMID:25839354DOI:10.1016/j.bbamem.2015.03.027.
Composition and phase dependence of the mixing of 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC), with the oxidized phospholipid, 1-palmitoyl-2-glutaryl-sn-glycero-3-phosphocholine (PGPC) were investigated by characterizing the aggregation states of DPPC/PGPC and DOPC/PGPC using a fluorescence quenching assay, dynamic light scattering, and time-resolved fluorescence quenching in the temperature range 5-60°C. PGPC forms 3.5nm radii micelles of aggregation number 33. In the gel phase, DPPC and PGPC fuse to form mixed vesicles for PGPC molar fraction, XPGPC≤0.3 and coexisting vesicles and micelles at higher XPGPC. Data suggest that liquid phase DPPC at 50°C forms mixed vesicles with segregated or hemi fused DPPC and PGPC for XPGPC≤0.3. At 60°C, DPPC and PGPC do not mix, but form coexisting vesicles and micelles. DOPC and PGPC do not mix in any proportion in the liquid phase. Two dissimilar aggregates of the sizes of vesicles and PGPC micelles were observed for all XPGPC for T≥22°C. DOPC-PGPC and DPPC-PGPC mixing is non-ideal for XPGPC>0.3 in both gel and fluid phases resulting in exclusion of PGPC from the bilayer. Formation of mixed vesicles is favored in the gel phase but not in the liquid phase for XPGPC≤0.3. For XPGPC≤0.3, aggregation states change progressively from mixed vesicles in the gel phase to component segregated mixed vesicles in the liquid phase close to the chain melting transition temperature to separated coexisting vesicles and micelles at higher temperatures.
Lipid Organization in Mixed Lipid Membranes Driven by Intrinsic Curvature Difference
Biophys J 2020 Apr 21;118(8):1830-1837.PMID:32246900DOI:10.1016/j.bpj.2020.03.009.
Laurdan fluorescence, novel spectral fitting, and dynamic light scattering were combined to determine lateral lipid organization in mixed lipid membranes of the oxidized lipid, 1-palmitoyl-2-glutaryl-sn-glycero-3-phosphocholine (PGPC), and each of the three bilayer lipids, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), and 1-palmitoyl-2-oleoylphosphatidylcholine (POPC). Second harmonic spectra were computed to determine the number of elementary emissions present. All mixtures indicated two emissions. Accordingly, spectra were fit to two log-normal distributions. Changes with PGPC mole fraction, XPGPC, of the area of the shorter wavelength line and of dynamic light scattering-derived aggregate sizes show that: DPPC and PGPC form component-separated mixed vesicles for XPGPC ≤ 0.2 and coexisting vesicles and micelles for XPGPC > 0.2 in gel and liquid-ordered phases and for all XPGPC in the liquid-disordered phase; POPC and PGPC form randomly mixed vesicles for XPGPC ≤ 0.2 and component-separated mixed vesicles for XPGPC > 0.2. DOPC and PGPC separate into vesicles and micelles. Component segregation is due to unstable inhomogeneous membrane curvature stemming from lipid-specific intrinsic curvature differences between mixing molecules. PGPC is inverse cone-shaped because its truncated tail with a terminal polar group points into the interface. It is similar to and mixes with POPC, also an inverse cone because of mobility of its unsaturated tail. PGPC is least similar to DOPC because mobilities of both unsaturated tails confer a cone shape to DOPC, and PGPC separates form DOPC. DPPC and PGPC do not mix in the liquid-disordered phase because mobility of both tails in this phase renders DPPC a cone. DPPC is a cylinder in the gel phase and of moderate similarity to PGPC and mixes moderately with PGPC.
The oxidized phospholipids POVPC and PGPC inhibit growth and induce apoptosis in vascular smooth muscle cells
Biochim Biophys Acta 2006 Sep;1761(9):1060-9.PMID:16904371DOI:10.1016/j.bbalip.2006.06.001.
Oxidized phospholipids, including 1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphocholine (POVPC) and 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphocholine (PGPC) are typically present in oxidatively modified low density lipoprotein (oxLDL) and have been found in atherosclerotic lesions. These compounds are gaining increasing importance as inducers of different cellular responses like inflammation, proliferation, or cell death. The aim of this study was to elicit the type and outcome of the cellular response of vascular smooth muscle cells (VSMC) upon treatment with POVPC and PGPC. Both oxidized phospholipids led to inhibition of cell proliferation and showed cytotoxic effects in VSMC. Several morphological criteria, the presence of typical DNA fragments, and a phosphatidylserine shift towards the outer leaflet of the cell membrane revealed that apoptosis was the predominant mode of cell death. In all experiments, POVPC was found to be a more potent inducer of apoptosis than PGPC. Interestingly, in the presence of high levels of serum in the growth media the proapoptotic but not the antiproliferative effects of both oxidized phospholipids were abolished. Thus, we conclude that under low serum conditions both intact POVPC and PGPC are proapoptotic mediators. Under high serum conditions, these lipids are hydrolyzed and the resultant lipid mixture containing the degradation products is no longer apoptotic but antiproliferative. Thus, the direct and indirect effects of POVPC and PGPC on cell viability may account for the detrimental actions of oxLDL on VSMC.
Toxicity of oxidized phospholipids in cultured macrophages
Lipids Health Dis 2012 Sep 7;11:110.PMID:22958747DOI:10.1186/1476-511X-11-110.
Background: The interactions of oxidized low-density lipoprotein (LDL) and macrophages are hallmarks in the development of atherosclerosis. The biological activities of the modified particle in these cells are due to the content of lipid oxidation products and apolipoprotein modification by oxidized phospholipids. Results: It was the aim of this study to determine the role of short-chain oxidized phospholipids as components of modified LDL in cultured macrophages. For this purpose we investigated the effects of the following oxidized phospholipids on cell viability and apoptosis: 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphocholine (PGPC), 1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphocholine (POVPC) and oxidized alkylacyl phospholipids including 1-O-hexadecyl-2-glutaroyl-sn-glycero-3-phosphocholine (E-PGPC) and 1-O-hexadecyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphocholine (E-POVPC). We found that these compounds induced apoptosis in RAW264.7 and bone marrow-derived macrophages. The sn-2 carboxyacyl lipid PGPC was more toxic than POVPC which carries a reactive aldehyde function in position sn-2 of glycerol. The alkylacyl phospholipids (E-PGPC and E-POVPC) and the respective diacyl analogs show similar activities. Apoptosis induced by POVPC and its alkylether derivative could be causally linked to the fast activation of an acid sphingomyelinase, generating the apoptotic second messenger ceramide. In contrast, PGPC and its ether analog only negligibly affected this enzyme pointing to an entirely different mechanism of lipid toxicity. The higher toxicity of PGPC is underscored by more efficient membrane blebbing from apoptotic cells. In addition, the protein pattern of PGPC-induced microparticles is different from the vesicles generated by POPVC. Conclusions: In summary, our data reveal that oxidized phospholipids induce apoptosis in cultured macrophages. The mechanism of lipid toxicity, however, largely depends on the structural features of the oxidized sn-2 chain.
Effects of oxidized phospholipids on gene expression in RAW 264.7 macrophages: a microarray study
PLoS One 2014 Oct 21;9(10):e110486.PMID:25333283DOI:10.1371/journal.pone.0110486.
Oxidized phospholipids (oxPLs) are components of oxidized LDL (oxLDL). It is known that oxLDL activates expression of a series of atherogenic genes and their oxPLs contribute to their biological activities. In this study we present the effects of 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphocholine (PGPC) and 1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphocholine (POVPC) on gene expression in RAW 264.7 macrophages using cDNA microarrays. PGPC affected the regulation of 146 genes, whereas POVPC showed only very minor effects. PGPC preferentially influenced expression of genes related to cell death, angiogenesis, cholesterol efflux, procoagulant mechanisms, atherogenesis, inflammation, and cell cycle. Many of these effects are known from studies with oxLDL or oxidized 1-hexadecanoyl-2-eicosatetra-5',8',11',14'-enoyl-sn-glycero-3-phosphocholine (oxPAPC), containing PGPC in addition to other oxPL species. It is known that POVPC efficiently reacts with proteins by Schiff base formation, whereas PGPC only physically interacts with its biological targets. POVPC seems to affect cell physiology to a great extent on the protein level, whereas PGPC gives rise to both the modulation of protein function and regulation on the transcriptional level.