1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine
(Synonyms: 1,2-二油酰-SN-甘油-3-磷酰乙醇胺,DOPE) 目录号 : GC39468
1,2-Dioleoyl-sn-glycero-3-PE (1,2-DOPE) 是天然存在的 PE 的合成类似物，在sn-1 和sn-2 位置含有 18:1 脂肪酸。1,2-DOPE 可用作乳化剂以促进 DNA-脂质体复合物跨膜转运。它与阳离子磷脂结合使用以提高 DNA 转染研究期间的效率，作为一种非病毒基因传递方法。
Cas No.:4004-05-1
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
1,2-
1.MacDonald, R.C., Rakhmanova, V.A., Choi, K.L., et al.O-ethylphosphatidylcholine: A metabolizable cationic phospholipid which is a serum-compatible DNA transfection agentJ. Pharm. Sci.88(9)896-904(1999) 2.Misra, S.K., Biswas, J., Kondaiah, P., et al.Gene transfection in high serum levels: Case studies with new cholesterol based cationic gemini lipidsPLoS One8(7)e68305(2013) 3.Chen, Y., Sun, J., Lu, Y., et al.Complexes containing cationic and anionic pH-sensitive liposomes: Comparative study of factors influencing plasmid DNA gene delivery to tumorsInt. J. Nanomedicine81573-1593(2013)
| Cas No. | 4004-05-1 | SDF | |
| 别名 | 1,2-二油酰-SN-甘油-3-磷酰乙醇胺,DOPE | ||
| Canonical SMILES | O=P(OC[C@H](OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)(OCCN)O | ||
| 分子式 | C41H78NO8P | 分子量 | 744.03 |
| 溶解度 | DMSO: 31.25 mg/mL (42.00 mM) | 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 | 1.344 mL | 6.7202 mL | 13.4403 mL |
| 5 mM | 0.2688 mL | 1.344 mL | 2.6881 mL |
| 10 mM | 0.1344 mL | 0.672 mL | 1.344 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。
The interaction energies of cholesterol and 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine in spread mixed monolayers at the air-water interface
J Phys Chem B 2009 Jul 23;113(29):9811-20.PMID:19569618DOI:10.1021/jp902748s.
The interaction of cholesterol with 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) was investigated in insoluble miscible mixed monolayers at the air-water interface using a Langmuir balance technique. The strong condensation effects observed at all compositions were quantified on the basis of excess thermodynamic properties of the system. It was found that partial molar areas and work of compression of cholesterol in the mixed monolayers were greatly reduced and increased, respectively, at xDOPE of 0.8, while, in accord with the "umbrella model", the character of cholesterol monolayers was drastically affected even at mole fractions of DOPE as low as 0.2. Calculated Gibbs free energies of mixing were shown to be symmetric about equimolar lipid quantities and considerably decreased at high surface pressures. Interaction energy parameters calculated from values of excess Gibbs energy are found to decrease linearly with surface pressure at a rate of 100 kT m.N(-1), regardless of composition. All evidence points out that cholesterol-DOPE molecular interactions can be adequately simulated using a simple regular mixture model.
Selective association of desmin intermediate filaments with a phospholipid layer in droplets
Biochem Biophys Res Commun 2021 May 28;555:109-114.PMID:33813269DOI:10.1016/j.bbrc.2021.03.131.
Desmin, an intermediate filament protein expressed in muscle cells, plays a key role in the integrity and regulation of the contractile system. Furthermore, the distribution of desmin in cells and its interplay with plasma and organelle membranes are crucial for cell functions; however, the fundamental properties of lipid-desmin interactions remain unknown. Using a water-in-oil method for a limited space system in vitro, we examined the distribution of desmin in three types of phospholipid droplets: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), and 1,2-dioleoyl-sn-glycero-3-phosphoserine (DOPS). When fluorescent-labeled desmin was observed for 60 min after desmin assembly was initiated by adding 25 mM KCl, desmin accumulated on both the DOPE and DOPS layers; however, it did not accumulate on the DOPC layer of droplets. An increase in salt concentration did not moderate the accumulation. The initial form of either oligomer or mature filament affected the accumulation on each lipid layer. When liposomes were included in the droplets, desmin was associated with DOPE but not on DOPC liposomes. These results suggest that desmin has the potential for association with phospholipids concerning desmin form and lipid shape. The behavior and composition of living membranes may affect the distribution of desmin networks.
Peptide-based targeted polymeric nanoparticles for siRNA delivery
Nanotechnology 2019 Oct 11;30(41):415604.PMID:31295734DOI:10.1088/1361-6528/ab313d.
The development of polymer-based nanoparticulate delivery systems for siRNA is important for the clinical success of gene therapy. However, there are some major drawbacks that need to be overcome. Short interfering RNA (siRNA) has been investigated as a potential therapeutic drug to silence disease-associated genes, but its usage is limited due to the lack of effective and safe nanocarriers. In this study, DOPE-PEI, a nanoparticle consisting of the fusogenic lipid 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) conjugated with low-molecular-weight, 600 Da, branched polyethylenimine (PEI) was produced and optimized for siRNA delivery. This delivery system was modified with other components such as 1,2-dioleoyl-sn-glycerol-3-phosphoethanolamine-N-[methoxy(polyethyleneglycol)2000] (DOPE-PEG2K), DOPE-PEG3.4K-bombesin and 1,2-dioleoyl-sn-glycerol-3-phosphoethanolamine/1,2-dioleoyl-3-trimethylammonium-propane (DOPE/DOTAP) and tested on PC-3 cells. The conjugation of DOPE to PEI polymer (DOPE-PEI) improved the efficiency of PEI to deliver siRNA into the cytosol and knockdown genes, but demonstrated high toxicity. The addition of DOPE-PEG2K reduced cellular toxicity by masking the surface positive charge of the DOPE-PEI/siRNA complex, with the incorporation of a gastrin-releasing peptide receptor (GRPR) targeting peptide and DOPE/DOTAP components improving the cellular uptake of siRNA into targeted cells and the siRNA knockdown efficiency.
Interactions of Cinnamycin-Immobilized Gold Nanorods with Biomimetic Membranes
J Membr Biol 2020 Feb;253(1):37-42.PMID:31754751DOI:10.1007/s00232-019-00103-3.
The behavior of the cinnamycin immobilized on the gold nanorod(AuNR) was investigated using surface plasmon resonance(SPR). For the comparison of the immobilized cinnamycin, the study for the free cinnamycin was also conducted. The bilayer was fabricated by tethering 1,2-dipalmitoyl-sn-glycero-3-phosphothioethanols on a gold surface to form a monolayer and then using liposomes to adsorb an outer layer on the tethered-monolayer. The liposomes were prepared with a desired ratio of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine to 1,2-dioleoyl-sn-glycero-3-phosphocholine (0:100, 5:95, 10:90, 20:80, and 30:70). After the cinnamycin was injected on the bilayers, the specific binding between the cinnamycin and the bilayer was monitored with SPR. The inclusion of DOPE in the outer layer clearly led to the specific binding of the cinnamycin on the membranes. Specifically, the binding behavior of the immobilized was different from that of the free. For the free cinnamycin, the binding amount of cinnamycin at 10% was two times more than that at 5%. For the immobilized cinnamycin, the amounts were identical for both compositions. However, the rate was much faster for the immobilized cinnamycin at 10% than 5%, compared to that for the free at both compositions. This difference was attributed to the mean-molecular areas of the cinnamycin and DOPE, and the steric effect of the AuNR. For the effects of the heat and storage, the immobilized enzyme showed less decrease in the relative binding amount than the free one.
Gastrin-releasing peptide receptor-targeted hybrid peptide/phospholipid pDNA/siRNA delivery systems
Nanomedicine (Lond) 2019 May;14(9):1153-1171.PMID:31050581DOI:10.2217/nnm-2018-0380.
Aim: To develop a peptide/phospholipid hybrid system for gastrin-releasing peptide receptor (GRPR)-targeted delivery of pDNA or siRNA. Materials & methods: A multifunctional GRPR-targeted peptide R9-K(GALA)-BBN(6-14) was combined with a phospholipid oligonucleotide delivery system (1:1 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine and 1,2-dioleoyl-3-trimethylammonium-propane) and evaluated for pDNA and siRNA delivery in terms of complex size, toxicity, receptor-targeted delivery and gene expression or knockdown efficiency. Results: By combining peptide and phospholipid delivery systems, synergistic improvements in gene expression and knockdown were observed when compared with either system alone. The optimized formulation demonstrated high levels of EGFP expression and EGFP knockdown, GRPR-targeted delivery, enhanced endosomal release and minimal toxicity. Conclusion: The peptide/phospholipid hybrid system provides efficient GRPR-targeted DNA/siRNA delivery.