Phosphatidylcholine structure determines cholesterol solubility and lipid polymorphism

Epand, Richard M.; Hughes, Donald W.; Sayer, Brian G.; Borochov, Nina; Bach, D.; Wachtel, Ellen

doi:10.1016/j.chemphyslip.2005.01.008

Cited by 21 publications

(16 citation statements)

References 39 publications

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“…Our previous in vitro serum stability study investigated higher cholesterol contents and demonstrated that DOTAP:Chol (mol/mol 1:4)/DNA lipoplex (DOTAP + /DNA − = 4) is much more stable in serum than DOTAP:Chol (mol/mol 1:1)/DNA lipoplexes when assessed for both biological and biophysical characteristics. 31 Recent studies in our laboratory (L. Xu, unpublished work) have demonstrated that DOTAP:Chol formulations are similar to that described for phosphatidylcholine:Chol liposomes in which 80 mol% cholesterol can be achieved 32–34. It should be noted that cholesterol can form highly symmetrical domains at high mole fraction, and this may contribute to the enhanced serum stability of such formulations 32–34.…”

Section: Introductionmentioning

confidence: 62%

“…31 Recent studies in our laboratory (L. Xu, unpublished work) have demonstrated that DOTAP:Chol formulations are similar to that described for phosphatidylcholine:Chol liposomes in which 80 mol% cholesterol can be achieved 32–34. It should be noted that cholesterol can form highly symmetrical domains at high mole fraction, and this may contribute to the enhanced serum stability of such formulations 32–34. Therefore, we proposed that DOTAP:Chol (mol/mol 1:4)/DNA lipoplexes would have extended circulation life and broader biodistribution as compared to DOTAP:Chol (mol/mol 1:1).…”

Section: Introductionmentioning

confidence: 70%

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In Vivo comparative study of lipid/DNA complexes with different In Vitro serum stability: Effects on biodistribution and tumor accumulation

Zhang

Bradshaw‐Pierce

DeLille

et al. 2008

Journal of Pharmaceutical Sciences

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Section: Introductionmentioning

confidence: 62%

Section: Introductionmentioning

confidence: 70%

In Vivo comparative study of lipid/DNA complexes with different In Vitro serum stability: Effects on biodistribution and tumor accumulation

Zhang

Bradshaw‐Pierce

DeLille

et al. 2008

Journal of Pharmaceutical Sciences

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“…Cholesterol and diunsaturated forms of phospholipids have been shown to favor hexagonal H II phase formation in model membranes (Chen and Rand, 1997;Epand et al, 2003Epand et al, , 2005. The presence of H II promoting lipids results in curvature stress, a biophysical parameter of membranes that has been reported to regulate the folding and/or activity of integral proteins (for reviews, see Lee, 2003;van den Brinkvan der Laan et al, 2004).…”

Section: Hexagonal Phase Propensity Of Phosphatidylethanolamine Is Rementioning

confidence: 99%

A Lipid-mediated Quality Control Process in the Golgi Apparatus in Yeast

Pineau

Bonifait

Berjeaud

et al. 2008

MBoC

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When heme biosynthesis is disrupted, the yeast Saccharomyces cerevisiae becomes unable to synthesize its major sterol, ergosterol, and desaturate fatty acids. We took advantage of this physiological peculiarity to evaluate the consequences of ergosterol and/or unsaturated fatty acid (UFA) depletions on the biogenesis of a model polytopic plasma membrane protein, the uracil permease Fur4p. We show that under UFA shortage, which results in low amounts of diunsaturated phospholipid species, and under ergosterol depletion, Fur4p is prematurely routed from the Golgi apparatus to the vacuolar lumen in a process that requires the ubiquitin ligase Rsp5p. Interestingly, this diversion is not correlated to Fur4p exclusion from detergent-resistant membranes. In an independent set of experiments, we show that Fur4p targeting to the plasma membrane depends on phosphatidylethanolamine amounts and more specifically on the propensity of this phospholipid to form a hexagonal phase. In light of recent literature, we propose a model in which ergosterol and diunsaturated phospholipid species maintain optimal membrane curvature for Fur4p to evade the Golgi quality control process and to be properly delivered to its normal destination.

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“…For instance, N-substituted amides of lithocholic acid and derivatives of 3a-hydroxy-24-amino-5b-cholane have shown in vitro activity against Gram positive strains and mycetes [14]. Bile acids and steroids exhibit variable crystal structures, solvates, and co-crystals [15][16][17][18][19][20][21][22]. Although structural studies of systems involving bile acid derivatives have long been a challenge due to their complex and supramolecular nature, papers dealing with single crystal X-ray diffraction characterization of crystalline host-guest assemblies of steroidal and related molecules have been published.…”

Section: Introductionmentioning

confidence: 98%

Structural studies on lithocholyl-N-(2-aminoethyl)amide in the solid state

et al. 2009

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The synthetic procedure of lithocholyl-N-(2-aminoethyl)amide yielded a mixture of several forms detected by solid state 13 C CP/MAS NMR although the solution state NMR unambiguously ascertained that the compound was pure. By recrystallization from various solvents one pure polymorph alongside with four solvates were isolated. The structures of the pure polymorph and the solvates were characterized by 13 C and 15 N CP/MAS NMR and powder X-ray diffraction (PXRD) methods. Variable contact time and dipolar dephasing experiments were employed to obtain optimized CP parameters and to distinguish various CH n (n = 0-3) resonances. CSA analyses of spinning side bands at different spinning rates showed small variations in the shielding tensor values of the carbonyl group between the pure polymorph (recrystallized from acetonitrile, tetrahydrofuran and 1,4-dioxane) and p-xylene solvate.

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Phosphatidylcholine structure determines cholesterol solubility and lipid polymorphism

Cited by 21 publications

References 39 publications

In Vivo comparative study of lipid/DNA complexes with different In Vitro serum stability: Effects on biodistribution and tumor accumulation

In Vivo comparative study of lipid/DNA complexes with different In Vitro serum stability: Effects on biodistribution and tumor accumulation

A Lipid-mediated Quality Control Process in the Golgi Apparatus in Yeast

Structural studies on lithocholyl-N-(2-aminoethyl)amide in the solid state

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