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Chemical Compound Review:

AC1L3RPB 2-[[(2R)-2,3- dioctadecanoyloxypropoxy]...

Synonyms: DI-STEAROYL-3-SN-PHOSPHATIDYLCHOLINE

Li, W.M. et al., Warschawski, D.E. et al., Folgering, J.H. et al., Przybylo, M. et al., Burns, A.R. et al., et al.

Burns, Frankel, Buranda, Warschawski, Devaux,

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Disease relevance of DI-STEAROYL-3-SN-PHOSPHATIDYLCHOLINE

For these experiments, the mechanosensitive channel of large conductance (MscL) protein from Lactococcus lactis and Escherichia coli was reconstituted in lipid bilayers composed of 80 mol % 1,2-dioleoyl-sn-glycero-3-phosphocholine and 20 mol % di-(5-[[4-(4-butylphenyl)azo]phenoxy]pentyl)phosphate (4-Azo-5P) [1].
Concomitant neutron and X-ray studies were undertaken in order to locate accurately the anti-influenza and Parkinson's disease drug amantadine in multilayers of 1,2-dioleoyl-sn-glycero-3-phosphocholine [2].

High impact information on DI-STEAROYL-3-SN-PHOSPHATIDYLCHOLINE

A model membrane system composed of egg sphingomyelin (SM), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), and cholesterol was studied with static and magic angle spinning (31)P NMR spectroscopy [3].
Fluorescence correlation spectroscopy (FCS) is used to examine mobility of labeled probes at specific sites in supported bilayers consisting of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) lipid domains in 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) [4].
These peptides were incorporated into bilayers of 1,2-dioleoyl-sn-glycero-3-phosphocholine at either low pH (N-terminus protonated) or high pH (N-terminus unprotonated) [5].
In this work, we investigate the effect of azithromycin on lipid model membranes made of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) or 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) [6].
A high-performance liquid chromatography (HPLC) method for the determination of cholesterol and 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) in liposome-based drug formulations has been developed [7].

Anatomical context of DI-STEAROYL-3-SN-PHOSPHATIDYLCHOLINE

For the first time, the performed measurements on 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) bilayers maintain exactly the same experimental conditions for both systems, which allows for a quantitative comparison of lipid diffusion in these two commonly used model membranes [8].

Associations of DI-STEAROYL-3-SN-PHOSPHATIDYLCHOLINE with other chemical compounds

Cholesterol, stigmastanol, and stigmastanyl-phosphorylcholine (ST-PC) were incorporated into model membranes composed of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) or 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) [9].

Gene context of DI-STEAROYL-3-SN-PHOSPHATIDYLCHOLINE

In addition, they show stronger interaction with 1,2-dioleoyl-sn-glycero-3-phosphocholine and 1,2-dioleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)] monolayers than native stefin A or nonaggregated stefin B [10].
Taking advantage of the very good (13)C chemical shift dispersion, one can easily follow the segmental order along the acyl chains and, particularly, around the double bonds where we have been able to determine the previously misassigned order parameters of each acyl chain of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) [11].
The influence of temperature and acyl chain composition on the transfer of PEG-diacyl PEs from donor liposomes to acceptor liposomes, consisting of 1,2-dioleoyl-sn-glycero-3-phosphocholine, cholesterol and N-((6-biotinoyl)amino)hexanoyl)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine (54.9:45:0.1 mole ratio), was measured [12].

Analytical, diagnostic and therapeutic context of DI-STEAROYL-3-SN-PHOSPHATIDYLCHOLINE

The membrane states of the alpha-series ganglioside GM1alpha in 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC)/1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) mixed monolayers and hybrid bilayers were investigated using atomic force microscopy (AFM) [13].

References

Lipid-mediated light activation of a mechanosensitive channel of large conductance. Folgering, J.H., Kuiper, J.M., de Vries, A.H., Engberts, J.B., Poolman, B. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
The location of amantadine hydrochloride and free base within phospholipid multilayers: a neutron and X-ray diffraction study. Duff, K.C., Cudmore, A.J., Bradshaw, J.P. Biochim. Biophys. Acta (1993) [Pubmed]
Distinguishing individual lipid headgroup mobility and phase transitions in raft-forming lipid mixtures with 31P MAS NMR. Holland, G.P., McIntyre, S.K., Alam, T.M. Biophys. J. (2006) [Pubmed]
Local mobility in lipid domains of supported bilayers characterized by atomic force microscopy and fluorescence correlation spectroscopy. Burns, A.R., Frankel, D.J., Buranda, T. Biophys. J. (2005) [Pubmed]
A combined X-ray and neutron diffraction study of selectively deuterated melittin in phospholipid bilayers: effect of pH. Bradshaw, J.P., Dempsey, C.E., Watts, A. Mol. Membr. Biol. (1994) [Pubmed]
Effect of the antibiotic azithromycin on thermotropic behavior of DOPC or DPPC bilayers. Fa, N., Ronkart, S., Schanck, A., Deleu, M., Gaigneaux, A., Goormaghtigh, E., Mingeot-Leclercq, M.P. Chem. Phys. Lipids (2006) [Pubmed]
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., Ajagbe, M., Bhamidipati, S., Ahmad, Z., Ahmad, I. Journal of chromatography. A. (2005) [Pubmed]
Lipid Diffusion in Giant Unilamellar Vesicles Is More than 2 Times Faster than in Supported Phospholipid Bilayers under Identical Conditions. Przybylo, M., S??kora, J., Humpol??ckova, J., Benda, A., Zan, A., Hof, M. Langmuir : the ACS journal of surfaces and colloids. (2006) [Pubmed]
Influence of stigmastanol and stigmastanyl-phosphorylcholine, two plasma cholesterol lowering substances, on synthetic phospholipid membranes. A 2H- and 31P-NMR study. Habiger, R.G., Cassal, J.M., Kempen, H.J., Seelig, J. Biochim. Biophys. Acta (1992) [Pubmed]
Interaction of human stefin B in the prefibrillar oligomeric form with membranes. Correlation with cellular toxicity. Anderluh, G., Gutierrez-Aguirre, I., Rabzelj, S., Ceru, S., Kopitar-Jerala, N., Macek, P., Turk, V., Zerovnik, E. FEBS J. (2005) [Pubmed]
Order parameters of unsaturated phospholipids in membranes and the effect of cholesterol: a 1H-13C solid-state NMR study at natural abundance. Warschawski, D.E., Devaux, P.F. Eur. Biophys. J. (2005) [Pubmed]
Intermembrane transfer of polyethylene glycol-modified phosphatidylethanolamine as a means to reveal surface-associated binding ligands on liposomes. Li, W.M., Xue, L., Mayer, L.D., Bally, M.B. Biochim. Biophys. Acta (2001) [Pubmed]
Atomic force microscopy studies of ganglioside GM1alpha in dioleoylphosphatidylcholine/dipalmitoylphosphatidylcholine mixed monolayers and hybrid bilayers. Takeda, Y., Horito, S. Colloids and surfaces. B, Biointerfaces. (2005) [Pubmed]

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