Ceramide Phosphoethanolamines (bovine)
目录号 : GC43229
Ceramide phosphoethanolamine (CPE) is an analog of sphingomyelin that contains ethanolamine rather than choline as the head group.
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ceramide phosphoethanolamine (CPE) is an analog of sphingomyelin that contains ethanolamine rather than choline as the head group. It is the principal membrane phospholipid in invertebrates such as Drosophila, which lacks sphingomyelin. It is only produced in small amounts in mammalian cells, accounting for approximately 0.02 mol% of total phospholipids in mouse testis and brain. In Drosophila, CPE is biosynthesized by CPE synthase from ceramide and cytidine diphosphate-ethanolamine in the Golgi lumen. In mammals, it is biosynthesized by sphingomyelin synthase 2 (SMS2) in the plasma membrane and by sphingomyelin synthase-related protein (SMSr) in the endoplasmic reticulum (ER). In Drosophila, CPE has a role in glial ensheathment of axons. Disrupting CPE synthesis by depleting SMSr in vitro in mammalian cells leads to an accumulation of ER ceramides, which are then mislocalized to the mitochondria, inducing apoptosis. However, ceramide levels are not altered in transgenic mice lacking SMSr catalytic activity. CPEs (bovine) is a mixture of CPEs with variable N-acyl chain lengths.
| Cas No. | SDF | ||
| Canonical SMILES | [R]C(N[C@@H](COP(OCC[NH3+])([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC)=O | ||
| 分子式 | C43H87N2O6P (for tricosanoyl) | 分子量 | 759.2 |
| 溶解度 | Chloroform:Methanol:Water (2:1:0.1): Soluble | 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 | 1.3172 mL | 6.5859 mL | 13.1718 mL |
| 5 mM | 0.2634 mL | 1.3172 mL | 2.6344 mL |
| 10 mM | 0.1317 mL | 0.6586 mL | 1.3172 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。
Formation of tubules and helical ribbons by ceramide phosphoethanolamine-containing membranes
Sci Rep 2019 Apr 9;9(1):5812.PMID:30967612DOI:10.1038/s41598-019-42247-1.
Ceramide phosphoethanolamine (CPE), a major sphingolipid in invertebrates, is crucial for axonal ensheathment in Drosophila. Darkfield microscopy revealed that an equimolar mixture of bovine buttermilk CPE (milk CPE) and 1,2-dioleoyl-sn-glycero-3-phosphocholine (diC18:1 PC) tends to form tubules and helical ribbons, while pure milk CPE mainly exhibits amorphous aggregates and, at low frequency, straight needles. Negative staining electron microscopy indicated that helices and tubules were composed of multilayered 5-10 nm thick slab-like structures. Using different molecular species of PC and CPE, we demonstrated that the acyl chain length of CPE but not of PC is crucial for the formation of tubules and helices in equimolar mixtures. Incubation of the lipid suspensions at the respective phase transition temperature of CPE facilitated the formation of both tubules and helices, suggesting a dynamic lipid rearrangement during formation. Substituting diC18:1 PC with diC18:1 PE or diC18:1 PS failed to form tubules and helices. As hydrated galactosylceramide (GalCer), a major lipid in mammalian myelin, has been reported to spontaneously form tubules and helices, it is believed that the ensheathment of axons in mammals and Drosophila is based on similar physical processes with different lipids.
Efficient in vitro digestion of lipids and proteins in bovine milk fat globule membrane ingredient (MFGMi) and whey-casein infant formula with added MFGMi
J Dairy Sci 2023 May;106(5):3086-3097.PMID:36935237DOI:10.3168/jds.2022-22763.
The relative immaturity of the infant digestive system has the potential to affect the bioavailability of dietary lipids, proteins, and their digested products. We performed a lipidomic analysis of a commercial bovine milk fat globule membrane ingredient (MFGMi) and determined the profile of lipids and proteins in the bioaccessible fraction after in vitro digestion of both the ingredient and whey-casein-based infant formula without and with MFGMi. Test materials were digested using a static 2-phase in vitro model, with conditions simulating those in the infant gut. The extent of digestion and the bioaccessibility of various classes of neutral and polar lipids were monitored by measuring a wide targeted lipid profile using direct infusion-mass spectrometry. Digestion of abundant proteins in the ingredient and whey-casein infant formula containing the ingredient was determined by denaturing PAGE with imaging of Coomassie Brilliant Blue stained bands. Cholesterol esters, diacylglycerides, triacylglycerides, phosphatidylcholines, and phosphatidylethanolamines in MFGMi were hydrolyzed readily during in vitro digestion, which resulted in marked increases in the amounts of free fatty acids and lyso-phospholipids in the bioaccessible fraction. In contrast, sphingomyelins, ceramides, and gangliosides were largely resistant to simulated digestion. Proteins in MFGMi and the infant formulas also were hydrolyzed efficiently. The results suggest that neutral lipids, cholesterol esters, phospholipids, and proteins in MFGMi are digested efficiently during conditions that simulate the prandial lumen of the stomach and small intestine of infants. Also, supplementation of whey-casein-based infant formula with MFGMi did not appear to alter the profiles of lipids and proteins in the bioaccessible fraction after digestion.
Dithranol as a MALDI matrix for tissue imaging of lipids by Fourier transform ion cyclotron resonance mass spectrometry
Anal Chem 2012 Oct 2;84(19):8391-8.PMID:22931516DOI:10.1021/ac301901s.
To fill the unmet need for improved matrixes for matrix-assisted laser desorption ionization (MALDI) tissue imaging of small molecules, dithranol (DT)--a matrix mainly used for the analysis of synthetic polymers--was evaluated for detection of lipids in rat liver and bovine calf lens, using MALDI Fourier transform ion cyclotron resonance mass spectrometry (FTICR MS). The use of DT resulted in better detection of endogenous lipids than did two other commonly used matrixes, α-cyano-4-hydroxycinnamic acid (CHCA) and 2,5-dihydroxybenzoic acid (DHB), with >70 lipid entities (including phosphatidylcholines, phosphatidylethanolamines, sphingomyelins, phosphatidylserines, phosphatidylglycerol, phosphatidic acids, ceramide phosphates, sterol lipids, acyl carnitines, and glycerides) being detected in rat liver and bovine lens tissue sections, using positive-ion detection. Using saturated DT in chloroform/methanol (2:1, v/v), with 1% formic acid in the final mixture, 57 lipid entities were successfully imaged from bovine calf lens, with clear and distinct distribution patterns. In a section across the lens equatorial plane, all compounds showed concentric distributions around the lens nucleus and most showed specific abundance changes, which correlated with lens fiber cell age. As a novel finding, palmitoylcarnitine and oleoylcarnitine were found uniquely localized to the younger lens fiber cell cortex region. This work demonstrates the potential of DT as a new matrix for tissue imaging by MALDI-FTICR MS.
Experimental autoimmune encephalomyelitis. Augmentation of demyelination by different myelin lipids
Lab Invest 1984 Oct;51(4):416-24.PMID:6207382doi
Alterations in the effect of a known encephalitogenic dose of myelin basic protein (MBP) when inoculated in combination with various myelin lipids have been examined in guinea pigs. A previous study demonstrated that, when MBP was given with galactocerebroside, it produced an acute autoimmune encephalomyelitis similar to that induced by whole white matter in which both inflammation and demyelination were features of the central nervous system lesions. MBP alone, on the other hand, resulted in inflammation only, without demyelination. The present study examined combinations of MBP with the myelin lipids galactocerebroside, sulfatide, ethanolamine phosphoglycerides, and serine phosphoglycerides. The lipids were given with or without MBP, in the same ratio as in intact central nervous system myelin, and were emulsified with complete Freund's adjuvant. An additional group received galactocerebroside and bovine serum albumin in complete Freund's adjuvant. These groups were compared with animals receiving either bovine white matter or MBP in complete Freund's adjuvant. Clinical autoimmune encephalomyelitis was observed in animals receiving bovine white matter, MBP, and all lipid-MBP emulsions; the bovine white matter, galactocerebroside/MBP, sulfatide/MBP, and ethanolamine phosphoglycerides/MBP groups demonstrated central nervous system lesions with a similar picture consisting of inflammation with demyelination, whereas inflammation without demyelination was seen in the MBP and serine phosphoglycerides/MBP groups. Thus, the addition of myelin lipids to MBP leads to the augmentation of demyelination in autoimmune encephalomyelitis lesions in the guinea pig. This might suggest that the immune response against MBP is enhanced by other myelin components. The relevance of these findings to human demyelinating disorders is discussed.
Drug-biomolecule interactions: interaction of gentamicin with lipid monomolecular films
J Pharm Sci 1975 Mar;64(3):516-9.PMID:239194DOI:10.1002/jps.2600640343.
The interaction of gentamicin with monomolecular films of a series of biologically important lipids spread on an aqueous buffered subphase was studied. The surface pressure, pi, of these films was determined by the Wilhelmy plate method as a function of surface area, A, and pi-A curves were constructed. Changes in the pi-A characteristics in the presence of gentamicin were used as a measure of antibiotic-film interaction. No interaction was observed between gentamicin and films of cholesterol, egg lecithin, dipalmitoyl lecithin, phosphatidyl ethanolamine, stearyl alcohol, and bovine ceramides at all pH values studied. Stearic acid films showed no interaction with gentamicin at pH 5. At pH 7 and 8, a small increase in pressure (approximately 3 dynes/cm) was noted. A dramatic increase in surface pressure was observed in the presence of stearyl aldehyde films ranging from approximately 9 dynes/cm at pH 7,2 to 23 dynes/cm at pH 8.4. This effect was attributed to a Schiff-base reaction between the nonprotonated primary amino groups on the gentamicin molecule and the stearyl aldehyde. Further evidence was reported by the fact that the addition of glucose (which has been reported to participate in Schiff-base formation with amines) to the subphase inhibited the stearyl aldehyde-gentamicin interaction. Sucrose did not show a corresponding effect. The addition of sodium bisulfite, which reacts with aldehydes to form alpha-hydroxysulfonic acid, also inhibited the gentamicin-stearyl aldehyde interaction. It is postulated that Schiff-base formation is a step in the in vivo transport of gentamicin across the membrane of sensitive organisms.