1,2-Dioleoyl-sn-glycero-3-phosphocholine [4235-95-4]

1,2-Dioleoyl-sn-glycero-3-phosphocholine is a phospholipid that is extensively used in the field of biophysics and biochemistry for the study of membrane dynamics and structures. This particular phospholipid is a major component in the creation of liposomes and model cell membranes, which are essential for simulating biological membranes in research. It serves as a mimic of naturally occurring phospholipids, allowing for the examination of membrane fluidity, phase behavior, and protein-lipid interactions. Researchers employ this compound to investigate the delivery systems for various compounds by incorporating it into the liposome bilayer, thus understanding the encapsulation and release mechanisms. Its oleoyl chains are unsaturated, which provides fluidity to the bilayers, making them more similar to natural cell membranes. The study of 1,2-Dioleoyl-sn-glycero-3-phosphocholine also contributes to the understanding of lipid rafts and their role in cellular processes such as signaling and trafficking. It is particularly chosen for its ability to form stable bilayers, which can be used in a variety of experimental conditions, including NMR and X-ray crystallography to decipher structural intricacies.

References:

1. A rapid isocratic high-performance liquid chromatography method for determination of cholesterol and 1,2-dioleoyl-sn-glycero-3-phosphocholine in liposome-based drug formulations.  |  Singh, R., et al. 2005. J Chromatogr A. 1073: 347-53. PMID: 15909540
2. Behavior of 1,2-dioleoyl-sn-glycero-3-phosphocholine at the surface of 3-hydroxypropionitrile near the critical micelle concentration.  |  Pohl, H. and Morgner, H. 2010. J Phys Chem B. 114: 12847-50. PMID: 20849133
3. Interactions of biodegradable poly([R]-3-hydroxy-10-undecenoate) with 1,2-dioleoyl-sn-glycero-3-phosphocholine lipid: a monolayer study.  |  Jagoda, A., et al. 2011. Langmuir. 27: 10878-85. PMID: 21749038
4. Biophysical characterization of complexes of DNA with mixtures of the neutral lipids 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-hexanoylamine or 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-dodecanoylamine and 1,2-dioleoyl-sn-glycero-3-phosphocholine in the presence of bivalent metal cations for DNA transfection.  |  Pisani, M., et al. 2011. J Phys Chem B. 115: 10198-206. PMID: 21790167
5. FTIR spectroscopy study of the pressure-dependent behaviour of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1-palmitoyl-2-oleolyl-sn-glycero-3-phosphocholine (POPC) at low degrees of hydration.  |  Pfeiffer, H., et al. 2013. Chem Phys Lipids. 170-171: 33-40. PMID: 23524282
6. Liposomal spherical nucleic acids.  |  Banga, RJ., et al. 2014. J Am Chem Soc. 136: 9866-9. PMID: 24983505
7. Evaluation of matrix effects on TOF-SIMS data of leu-enkephalin and 1,2-dioleoyl-sn-glycero-3-phosphocholine mixed samples.  |  Nakano, S., et al. 2018. Biointerphases. 13: 03B403. PMID: 29351722
8. Effect of dehydrocholic acid conjugated with a hydrocarbon on a lipid bilayer composed of 1,2-dioleoyl-sn-glycero-3-phosphocholine.  |  Hayashi, K., et al. 2019. Colloids Surf B Biointerfaces. 181: 58-65. PMID: 31121382
9. The Cytotoxic Effect of alpha -Synuclein Aggregates.  |  Melo, F., et al. 2021. Chemphyschem. 22: 526-532. PMID: 33482036
10. Selective association of desmin intermediate filaments with a phospholipid layer in droplets.  |  Murakami, K., et al. 2021. Biochem Biophys Res Commun. 555: 109-114. PMID: 33813269
11. Conformational state diagram of DOPC/DPPCd62/cholesterol mixtures.  |  Zaytseva, YV., et al. 2022. Biochim Biophys Acta Biomembr. 1864: 183869. PMID: 35063400
12. Solid-Supported Assembly Composed of n-Octyl- beta -D-glucopyranoside and 1,2-Dioleoyl-sn-glycero-3-phosphocholine in Equilibrium with Its Ambient Aqueous Solution System Including Dispersed Assembly.  |  Ishiguro, R. and Kameyama, K. 2022. J Oleo Sci. 71: 223-233. PMID: 35110465
13. The effect of chitosan/TiO2/hyaluronic acid subphase on the behaviour of 1,2-dioleoyl-sn-glycero-3-phosphocholine membrane.  |  Ładniak, A., et al. 2022. Biomater Adv. 138: 212934. PMID: 35913237
14. Metabolism of liposomes prepared from a labelled ether analog of 1,2-dioleoyl-sn-glycero-3-phosphocholine in the rat.  |  Stein, Y., et al. 1984. Biochim Biophys Acta. 793: 354-64. PMID: 6712973