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DMPC

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DMPC (1,2-Dimyristoyl-sn-glycero-3-phosphocholine) is a synthetic phospholipid utilized in liposomes and lipid bilayers for the study of biological membranes.

Category
Peptide Synthesis Reagents
Catalog number
BAT-006374
CAS number
18194-24-6
Molecular Formula
C36H72NO8P
Molecular Weight
677.93
DMPC
IUPAC Name
[(2R)-2,3-di(tetradecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
Synonyms
1,2-Dimyristoyl-sn-glycero-3-PC; 1,2-Ditetradecanoyl-sn-glycero-3-phosphocholine; (R)-2,3-Bis(tetradecanoyloxy)propyl [2-(Trimethylammonio)ethyl] Phosphate
Appearance
Crystalline solid.
Purity
> 97.0% (T) (HPLC)
Melting Point
219-220 °C
Boiling Point
> 300.0 °C
Storage
Store at -20°C.
Solubility
Ethanol: 25 mg/ml
InChI
InChI=1S/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3/t34-/m1/s1
InChI Key
CITHEXJVPOWHKC-UUWRZZSWSA-N
Canonical SMILES
CCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC
1.Comparative evaluation of proliposomes and self micro-emulsifying drug delivery system for improved oral bioavailability of nisoldipine.
Nekkanti V1, Rueda J2, Wang Z2, Betageri GV3. Int J Pharm. 2016 Mar 31;505(1-2):79-88. doi: 10.1016/j.ijpharm.2016.03.065. [Epub ahead of print]
The objective of this study was to develop proliposomal formulation and self micro-emulsifying drug delivery system (SMEDDS) for a poorly bioavailable drug, nisoldipine and to compare their in vivo pharmacokinetics. Proliposomes were prepared by thin film hydration method using different lipids such as Soy phosphatidylcholine (SPC), Hydrogenated Soy phosphatidylcholine (HSPC), Dimyristoylphosphatidylcholine (DMPC) and Dimyristoyl phosphatidylglycerol sodium (DMPG), Distearyl phosphatidylcholine (DSPC), and Cholesterol in various ratios. SMEDDS formulations were prepared using varying concentrations of Capmul MCM, Labrasol, Cremophor EL and Tween 80. Both proliposomes and SMEDDS were evaluated for particle size, zeta potential, in vitro drug release, in vitro permeability and in vivo pharmacokinetics. In vitro drug release was carried out in purified water using USP type II dissolution apparatus. In vitro drug permeation was studied using parallel artificial membrane permeation assay (PAMPA) and everted rat intestinal perfusion techniques.
2.Extending the Hydrophobic Mismatch Concept to Amphiphilic Membranolytic Peptides.
Grau-Campistany A1,2, Strandberg E1, Wadhwani P1, Rabanal F2, Ulrich AS1,3. J Phys Chem Lett. 2016 Apr 7;7(7):1116-20. doi: 10.1021/acs.jpclett.6b00136. Epub 2016 Mar 10.
A series of nine amphiphilic, pore-forming α-helical KIA peptides (KIAGKIA repeats) with lengths between 14 and 28 residues were studied by solid-state (15)N NMR to determine their alignment in oriented lipid bilayers. In a 2:1 mixture of 1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine (DMPC) with its corresponding 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (lyso-MPC), which has a highly positive spontaneous curvature, the helix tilt angle was found to vary steadily with peptide length. The shortest peptide was aligned transmembrane and upright, while the longer ones successively became tilted away from the membrane normal. This behavior is in agreement with the hydrophobic matching concept, conceived so far only for hydrophobic helices. In 1,2-dioleoyl-sn-glycero-3-phosphatidylcholine, with a negative spontaneous curvature, all KIA peptides remained flat on the bilayer surface, while the cylindrical DMPC lipids permitted a slight tilt.
3.Molecular Packing in Langmuir Monolayers Composed of a Phosphatidylcholine and a Pyrene Lipid.
Gradella Villalva D1, Diociaiuti M2, Giansanti L3, Petaccia M3, Bešker N4, Mancini G5. J Phys Chem B. 2016 Feb 18;120(6):1126-33. doi: 10.1021/acs.jpcb.5b11836. Epub 2016 Feb 9.
Pyrene lipids are useful tools to investigate membrane organization and intracellular lipid trafficking. The molecular interactions controlling the organization of lipid monolayers composed of a cationic amphiphile tagged with a pyrene residue and a saturated or unsaturated phospholipid, namely, 1,2-dimyristoyl-sn-glycero-3-phosphocholine and 1,2-dioleoyl-sn-glycero-3-phosphocholine, were investigated by Langmuir trough isotherms to understand how the molecular structure of the components and their relative amount affect the physicochemical properties of lipid monolayers. The obtained results show that the cationic headgroups and unsaturation of hydrophobic chains strongly affect the organization of the lipid monolayer as a function of the amount of components. On the other hand, the presence of the pyrene moiety does not seem to have a marked influence on the interaction within lipid assembly.
4.The use of zeta potential as a tool to study phase transitions in binary phosphatidylcholines mixtures.
Sierra MB1, Pedroni VI1, Buffo FE2, Disalvo EA3, Morini MA4. Colloids Surf B Biointerfaces. 2016 Jun 1;142:199-206. doi: 10.1016/j.colsurfb.2016.02.061. Epub 2016 Mar 3.
Temperature dependence of the zeta potential (ZP) is proposed as a tool to analyze the thermotropic behavior of unilamellar liposomes prepared from binary mixtures of phosphatidylcholines in the absence or presence of ions in aqueous suspensions. Since the lipid phase transition influences the surface potential of the liposome reflecting a sharp change in the ZP during the transition, it is proposed as a screening method for transition temperatures in complex systems, given its high sensitivity and small amount of sample required, that is, 70% less than that required in the use of conventional calorimeters. The sensitivity is also reflected in the pre-transition detection in the presence of ions. Plots of phase boundaries for these mixed-lipid vesicles were constructed by plotting the delimiting temperatures of both main phase transition and pre-transition vs. the lipid composition of the vesicle. Differential scanning calorimetry (DSC) studies, although subject to uncertainties in interpretation due to broad bands in lipid mixtures, allowed the validation of the temperature dependence of the ZP method for determining the phase transition and pre-transition temperatures.
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