DPPC (129Y83)
(Synonyms: 二棕榈酰磷脂酰胆碱; 129Y83) 目录号 : GC33629
DPPC (129Y83) 是一种磷酸甘油酯，可用于制备脂质体。
Cas No.:63-89-8
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
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Cell lines |
Bovine embryos (IVPEs) |
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Preparation Method |
The effect of (DPPC (129Y83)-produced multilamellar vesicles (MLVs) on the lipid profile of the plasma membrane of IVP bovine embryos was also evaluated by matrix-assisted laser desorption/ionisation mass spectrometry (MALDI-MS). The MLVs were prepared by the lipid hydration method. Briefly, a DPPC chloroform solution (10-3 mol/L) was placed in a glass vial, followed by the chloroform evaporation under nitrogen flow. The MLVs were prepared by adding the appropriate aqueous solution to the DPPC film containing vial at 55℃, stirred for 1 h before cooling down to room temperature. MLV stability was investigated by measuring the vesicle size with different media and time intervals. The film was resuspended in ultrapure water and SOFaaci medium in the absence or presence of 2.5% foetal bovine serum (FBS; v/v), 5 mg/mL bovine serum albumin (BSA), and 13 mmol/L pyruvate. For each resuspension medium, three different lipid concentrations were used: 1.0, 1.5, or 2.0 mmol/L. In addition, the MLVs were evaluated immediately after production (refrigerated at 4℃) and after incubation at 38.5℃ in a controlled gas atmosphere (5% O2, 5% CO2, and 90% N2) for 24 and 48 h. |
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Reaction Conditions |
1.0 and 1.5 mmol/L DPPC (129Y83) for 24 h |
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Applications |
The largest MLVs were observed with 1.0 and 1.5 mmol/L DPPC (129Y83) (with or without incubation) in water compared with SOFaaci medium. After 24 h of incubation, MLVs with the largest diameter (approximately 1.5 µm) were obtained with 1.0 mmol/L DPPC (129Y83) in the culture medium. |
| Animal experiment [2]: | |
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Animal models |
Female BALB/c mice (6-wk-old) |
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Preparation Method |
Liposomes for liposome immune lysis assay (LILA) were prepared from a lipid mixture solution containing DMPC (0.5 μmol), Chol (0.5 μmol), DPPA (0.05 μmol) and GSLs (0.05 μmol) and used for detection of anti-GSL antibodies.Mice was intraperitoneally immunized as follows: group I, GSL alone (0.05 μmol); group II, liposome composed of DMPC, Chol , S. minnesota R595 LPS and GSL; group III, liposome composed of DPPC (129Y83) (0.5 μmol), Chol , S. minnesota R595 LPS and GSL (DPPC (129Y83)-liposome); group IV, liposome composed of DSPC, Chol, and S. minnesota R595 LPS and GSL. All were immunized with 0.5 ml of the immunogen per mouse. |
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Dosage form |
0.05 μmol DPPC (129Y83) |
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Applications |
DPPC (129Y83)-liposome would serve effectively as a delivery vehicle for inducing immune responses against GSL antigen. |
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References: [1]. De Rossi H, Bortoliero Costa C, et,al. Modulating the lipid profile of blastocyst cell membrane with DPPC multilamellar vesicles. Artif Cells Nanomed Biotechnol. 2022 Dec;50(1):158-167. doi: 10.1080/21691401.2022.2088545. PMID: 35713365. |
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DPPC (129Y83) is a phosphoglyceride that can be used in liposome preparation.
When to evaluate the effect of multilamellar vesicles (MLVs) of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC (129Y83)) in co-culture with in vitro-produced bovine embryos (IVPEs). Incubation (24 and 48 h) did not impair the MLV structure but affected the average diameter. The rate of blastocyst production was not reduced, demonstrating the nontoxicity of the MLVs even at 2.0 mmol/L[1]. The interactions in cholesterol/DPPC (129Y83)/APC films were found to be weaker than those in the cholesterol/DPPC (129Y83) system, serving as a model of healthy cell membranes, thus proving that the incorporation of APCs is, from a thermodynamic point of view, unfavorable for binary cholesterol/DPPC (129Y83) monolayers[2]. To elucidate the interaction of a cationic surfactant synthesized, investigations involving Nα-benzoyl-arginine decyl amide (Bz-Arg-NHC10), and model membranes composed by 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC (129Y83)) were done. As the concentration of Bz-Arg-NHC10 increased, the main transition temperature of DPPC (129Y83) slightly decreased[3]. MPOx copolymers are proved to modify both the size and lamellarity of DPPC (129Y83) liposomes. The gradient copolymer with higher hydrophilic content induces shrinkage of the uni- and bi-lamellar DPPC (129Y83) vesicles[4]. DPPC (129Y83) liposomes enhanced the pulmonary absorption of unencapsulated free insulin;although unencapsulated free insulin spreads throughout the alveolar mucus layer, the concentration of insulin released near the absorption surface is increased by the encapsulation of insulin into DPPC (129Y83) liposomes and the absorption efficiency is also increased[5]. When show how oppositely charged gold nanoparticles (Au-NPs) interact with monolayers of the zwitterionic DPPC (129Y83). For the zwitterionic DPPC (129Y83), on the other hand, significant effects only occurred for negatively charged NPs, including a decrease in elasticity[6].
DPPC (129Y83)-liposome would serve effectively as a delivery vehicle for inducing immune responses against GSL antigen[7].
References:
[1]. De Rossi H, Bortoliero Costa C, et,al. Modulating the lipid profile of blastocyst cell membrane with DPPC multilamellar vesicles. Artif Cells Nanomed Biotechnol. 2022 Dec;50(1):158-167. doi: 10.1080/21691401.2022.2088545. PMID: 35713365.
[2]. Wn?trzak A, L?tka K, et,al. Interactions of alkylphosphocholines with model membranes-the Langmuir monolayer study. J Membr Biol. 2013 Jun;246(6):453-66. doi: 10.1007/s00232-013-9557-4. Epub 2013 May 15. PMID: 23673723; PMCID: PMC3682106.
[3]. Hermet M, Elisa Fait M, et,al. Interaction of cationic surfactants with DPPC membranes: effect of a novel Nα-benzoylated arginine-based compound. Amino Acids. 2021 Apr;53(4):609-619. doi: 10.1007/s00726-021-02964-2. Epub 2021 Mar 12. PMID: 33710434.
[4]. Papagiannopoulos A, Pippa N, et,al. Lamellarity and size distributions in mixed DPPC/amphiphilic poly(2-oxazoline) gradient copolymer vesicles and their temperature response. Chem Phys Lipids. 2021 Jan;234:105008. doi: 10.1016/j.chemphyslip.2020.105008. Epub 2020 Nov 9. PMID: 33181095.
[5]. Chono S, Togami K, et,al. Aerosolized liposomes with dipalmitoyl phosphatidylcholine enhance pulmonary absorption of encapsulated insulin compared with co-administered insulin. Drug Dev Ind Pharm. 2017 Nov;43(11):1892-1898. doi: 10.1080/03639045.2017.1353521. Epub 2017 Jul 24. PMID: 28689439.
[6]. Torrano AA, Pereira ?S, et,al. Probing the interaction of oppositely charged gold nanoparticles with DPPG and DPPC Langmuir monolayers as cell membrane models. Colloids Surf B Biointerfaces. 2013 Aug 1;108:120-6. doi: 10.1016/j.colsurfb.2013.02.014. Epub 2013 Mar 5. PMID: 23528608.
[7]. Uemura A, Watarai S, et,al.Induction of immune responses against glycosphingolipid antigens: comparison of antibody responses in mice immunized with antigen associated with liposomes prepared from various phospholipids. J Vet Med Sci. 2005 Dec;67(12):1197-201. doi: 10.1292/jvms.67.1197. PMID: 16397376.
DPPC (129Y83)是一种磷酸甘油酯，可用于制备脂质体。
何时评估 1,2-二棕榈酰-sn-甘油-3-磷酸胆碱 (DPPC (129Y83)) 的多层囊泡 (MLV) 在与体外产生的牛胚胎 (IVPE) 共培养中的作用。孵化（24 和 48 小时）不会损害 MLV 结构，但会影响平均直径。即使在 2.0 mmol/L[1] 时，囊胚的产生率也没有降低，证明了 MLVs 的无毒性。发现胆固醇/DPPC (129Y83)/APC 膜中的相互作用弱于胆固醇/DPPC (129Y83) 系统中的相互作用，作为健康细胞膜的模型，从而证明 APC 的掺入是从热力学观点，对二元胆固醇/DPPC (129Y83) 单分子层不利[2]。为了阐明合成的阳离子表面活性剂的相互作用，研究涉及 Nα-苯甲酰基-精氨酸癸基酰胺 (Bz-Arg-NHC10)，以及由 1,2-二棕榈酰-sn-甘油-3-磷酸胆碱 (DPPC (129Y83)) 组成的模型膜) 完成了。随着Bz-Arg-NHC10浓度的增加，DPPC(129Y83)的主要转变温度略有下降[3]。 MPOx 共聚物被证明可以改变 DPPC (129Y83) 脂质体的大小和层状结构。具有较高亲水含量的梯度共聚物引起单层和双层 DPPC (129Y83) 囊泡的收缩[4]。 DPPC(129Y83)脂质体增强了未包封的游离胰岛素的肺部吸收；尽管未包封的游离胰岛素遍布肺泡粘液层，但由于胰岛素被包封到DPPC(129Y83)脂质体中，吸收面附近释放的胰岛素浓度增加效率也得到提高[5]。当显示带相反电荷的金纳米粒子 (Au-NP) 如何与两性离子 DPPC (129Y83) 的单层相互作用时。另一方面，对于两性离子 DPPC (129Y83)，仅带负电的 NP 会产生显着影响，包括弹性降低[6]。
DPPC (129Y83)-脂质体可有效作为诱导针对 GSL 抗原的免疫应答的递送载体[7]。
| Cas No. | 63-89-8 | SDF | |
| 别名 | 二棕榈酰磷脂酰胆碱; 129Y83 | ||
| Canonical SMILES | CCCCCCCCCCCCCCCC(O[C@H](COC(CCCCCCCCCCCCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O)=O | ||
| 分子式 | C40H80NO8P | 分子量 | 734.04 |
| 溶解度 | <30mg/ml in ethanol | 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 | 1.3623 mL | 6.8116 mL | 13.6232 mL |
| 5 mM | 0.2725 mL | 1.3623 mL | 2.7246 mL |
| 10 mM | 0.1362 mL | 0.6812 mL | 1.3623 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。
Conformational state diagram of DOPC/DPPCd62/cholesterol mixtures
Biochim Biophys Acta Biomembr 2022 Apr 1;1864(4):183869.PMID:35063400DOI:10.1016/j.bbamem.2022.183869.
Raman spectra of aqueous suspensions of vesicles composed of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), deuterated 1,2-dipalmitoyl-d62-sn-glycero-3-phosphocholine (DPPCd62), and cholesterol (Chol) were studied at room temperature to determine the conformational states of the phospholipid hydrocarbon chains. Deuteration of DPPCd62 allowed us to characterize the conformational states of DOPC and DPPCd62 independently. The parameters of Raman peaks, which are sensitive to the conformational order, were studied in a wide range of compositions. It was found that the DOPC molecules are conformationally disordered for all compositions. The conformational state of the DPPCd62 molecules changes with composition. Their conformational state is influenced by cholesterol-induced partial disordering and DOPC solvation, transforming the DPPC molecules into the disordered state. The conformational state diagram from the Raman experiment was compared with outcomes from the differential scanning calorimetry (DSC) experiment. The Raman spectra also revealed that the DPPC molecules coexist in the disordered and all-trans ordered states for the DOPC/DPPCd62/Chol mixtures except for the pure liquid-disordered phase.
Curcumin Accelerates the Lateral Motion of DPPC Membranes
Langmuir 2022 Aug 9;38(31):9649-9659.PMID:35878409DOI:10.1021/acs.langmuir.2c01250.
Curcumin, the main ingredient in turmeric, has attracted attention due to its potential anti-inflammatory, anticancer, wound-healing, and antioxidant properties. Though curcumin efficacy is related to its interaction with biomembranes, there are few reports on the effects of curcumin on the lateral motion of lipids, a fundamental process in the cell membrane. Employing the quasielastic neutron scattering technique, we explore the effects of curcumin on the lateral diffusion of the dipalmotylphosphatidylcholine (DPPC) membrane. Our investigation is also supported by Fourier transform infrared spectroscopy, dynamic light scattering, and calorimetry to understand the interaction between curcumin and the DPPC membrane. It is found that curcumin significantly modulates the packing arrangement and conformations of DPPC lipid, leading to enhanced membrane dynamics. In particular, we find that the presence of curcumin substantially accelerates the DPPC lateral motion in both ordered and fluid phases. The effects are more pronounced in the ordered phase where the lateral diffusion coefficient increases by 23% in comparison to 9% in the fluid phase. Our measurements provide critical insights into molecular mechanisms underlying increased lateral diffusion. In contrast, the localized internal motions of DPPC are barely altered, except for a marginal enhancement observed in the ordered phase. In essence, these findings indicate that curcumin is favorably located at the membrane interface rather than in a transbilayer configuration. Further, the unambiguous evidence that curcumin modulates the membrane dynamics at a molecular level supports a possible action mechanism in which curcumin can act as an allosteric regulator of membrane functionality.
Interaction of neutral and protonated Tamoxifen with the DPPC lipid bilayer using molecular dynamics simulation
Steroids 2023 Jun;194:109225.PMID:36948347DOI:10.1016/j.steroids.2023.109225.
Tamoxifen as an antiestrogen is successfully applied for the clinical treatment of breast cancer in pre- and post-menopausal women. Due to the side effects related to the oral administration of Tamoxifen (such as deep vein thrombosis, pulmonary embolism, hot flushes, ocular disturbances and some types of cancer), liposomal drug delivery is recommended for taking this drug. Drug encapsulation in a liposomal or lipid drug delivery system improves the pharmacokinetic and pharmacodynamic properties. In this regard, we carried out 200-ns molecular dynamics (MD) simulations for three systems (pure DPPC and neutral and protonated Tamoxifen-loaded DPPC). Here, DPPC is a model lipid bilayer to provide us with conditions like liposomal drug delivery systems to investigate the interactions between Tamoxifen and DPPC lipid bilayers and to estimate the preferred location and orientation of the drug molecule inside the bilayer membrane. Properties such as area per lipid, membrane thickness, lateral diffusion coefficient, order parameters and mass density, were surveyed. With insertion of neutral and protonated Tamoxifen inside the DPPC lipid bilayers, area per lipid and membrane thickness increased slightly. Also, Tamoxifen induce ordering of the hydrocarbon chains in DPPC bilayer. Analysis of MD trajectories shows that neutral Tamoxifen is predominantly found in the hydrophobic tail region, whereas protonated Tamoxifen is located at the lipid-water interface (polar region of DPPC lipid bilayers).
Dipalmitoylphosphatidylcholine (DPPC): Annealing Strategy to Mitigate Variability in Thermotropic and Moisture Sorption Behavior
J Pharm Sci 2018 Oct;107(10):2635-2642.PMID:29909027DOI:10.1016/j.xphs.2018.06.006.
Dipalmitoylphosphatidylcholine (DPPC) demonstrated complex differential scanning calorimetry (DSC) thermal behavior. Transitions below 100°C showed variability in their thermotropic reversibility. An experimental design employing a DSC heat-cool-heat-cool-heat cycle and modulated DSC were used to gain insight into the DPPC's complex thermal nature. An annealing strategy was developed to reduce DPPC's thermotropic variability, moisture uptake rate, and rate variability. Samples annealed at 110°C for 5 min provided a reproducible, thermally reversible material. The annealed material also exhibited an 8-fold decrease in moisture sorption rate and a statistically significant (p = 0.0233) 100-fold decrease in water sorption rate variability compared to DPPC "as is." An optimized validated stability-indicating high performance liquid chromatography with evaporative light scattering detection method was developed and showed no change in DPPC chemical stability under the annealing treatment conditions.
Interactions of DPPC with semitelechelic poly(glycerol methacrylate)s with perfluoroalkyl end groups
Langmuir 2012 Nov 6;28(44):15651-62.PMID:23046205DOI:10.1021/la3028226.
Semitelechelic poly(glycerol methacrylate)s having a perfluoroalkyl end group (PGMA(n)-F(9)) were synthesized by ATRP. The interactions of these polymers with different degrees of polymerization with chiral or racemic dipalmitoylphosphatidylcholine (l-DPPC, d-DPPC, or rac-DPPC) monolayers at the air/water interface were studied. Langmuir trough measurements coupled with epifluorescence microscopy allowed for the observation of domain formation within the coexistence region of liquid-expanded (LE) and liquid-condensed (LC) states of DPPC in mixed DPPC-polymer films prepared by spreading a solution of both compounds in the same organic solvent (cospread films). Because of the incorporation of PGMA(n)-F(9) polymers into the LE phase and their line-active behavior, a formation of novel types of domains could be observed. During compression, a thinning out of the tips of two- to six-lobed flowerlike domain structures and consecutive spiral formation appeared for l- and d-DPPC within the two-phase coexistence region (LE/LC) of the monolayer. When rac-DPPC was used, symmetrical stripe formation was induced at the vertices of the domains and fingerprint-like structures were created by convection-inducing movements of the domains at the air/water interface. Additional investigations of the interaction of PGMA(n)-F(9) with DPPC vesicles using differential scanning calorimetry (DSC) supported the finding on the monolayer system that the incorporation of the polymers into the lipid monolayers is not solely driven by the perfluoroalkyl chain but significantly by the hydrophilic polymer part. Apparently, interactions of the PGMA chain with the lipid headgroups are important as the interactions increase with the elongation of the polymer chain, indicating that the polymer also has hydrophobic character.