Effect of N-alkyl-N,N,N-trimethylammonium ions on phosphatidylcholine model membrane structure as studied by 31P-NMR

Balgavý, P; Gawrisch, Klaus; Frischleder, H.

doi:10.1016/0005-2736(84)90517-0

Cited by 21 publications

(5 citation statements)

References 15 publications

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“…micelle) forms in the membrane at a minimum energy of elastic deformation (Charvolin & Mely 1978; Derzhanski & Bivas 1979). In our previous study we observed the formation of non-bilayer structures in model lipid membranes in the presence of N-alkyltrimethylammonium iodides with chain lengths of n = 6 and 9, but not with shorter or longer alkyl chains (Balgavy et al 1984). Since the mode of membrane interaction with different types of long chain substances is similar as shown by the A(AG )CH2 values, we would also predict formation of non-bilayer structures in E. coli lipids for DMAOs with maximum of efficiency at n z 10-12 as observed for membrane structure Perturbation detected by the CAT-16 spin probe.…”

Section: Resultsmentioning

confidence: 93%

Cut-off Effect in Antimicrobial Activity and in Membrane Perturbation Efficiency of the Homologous Series of N,N-Dimethylalkylamine Oxides

Devı́nsky

Kopecka-Leitmanová

Šeršeň

et al. 1990

Journal of Pharmacy and Pharmacology

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The antimicrobial activity of the homologous series of N,N-dimethylalkylamine oxides (DMAO) was found to be quasi parabolically dependent on alkyl chain length with a maximum at n approximately 15 and n approximately 12 for Staphylococcus aureus and Escherichia coli, respectively. The physiochemical properties of DMAOs as characterized by critical micelle concentrations, retention times of 1-alkenes generated from DMAOs by gas-liquid chromatography, Rm values in reversed phase chromatography, and bacterial lipid/aqueous phase partition coefficients were found to correlate with the alkyl chain length. The effect of DMAOs on the structure of the model membrane prepared from isolated lipids from Escherichia coli as detected by a spin probe method was maximal for the alkyl chain length n approximately 10-12 coinciding with the maximum in the antimicrobial activity observed with Escherichia coli. It is suggested that the cut-off in the DMAO antimicrobial activity is caused by the cut-off in the DMAO perturbing effect on the membrane structure.

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Section: Resultsmentioning

confidence: 93%

Cut-off Effect in Antimicrobial Activity and in Membrane Perturbation Efficiency of the Homologous Series of N,N-Dimethylalkylamine Oxides

Devı́nsky

Kopecka-Leitmanová

Šeršeň

et al. 1990

Journal of Pharmacy and Pharmacology

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“…After the intercalation of cationic amphiphiles into the bilayer between zwitterionic phospholipid molecules, the bilayer surface becomes positively charged (Haydon and Myers, 1973;Requena and Haydon, 1985) and the bilayer structure is disturbed depending on the amphiphile concentration, alkyl chain length and counter-ion (Balgavý et al, 1984;Balgavý and Devínsky, 1996;Sarapuk et al, 1998). The smallest bilayer structural perturbation occurs when the cationic amphiphile and the lipid have approximately equal lengths of hydrocarbon chains (Balgavý and Devínsky, 1996;Gallová et al, 1990).…”

Section: Resultsmentioning

confidence: 99%

The structural diversity of DNA–neutral phospholipids–divalent metal cations aggregates: a small-angle synchrotron X-ray diffraction study

Uhrı́ková

Lengyel

Hanulová³

et al. 2006

Eur Biophys J

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“…3B) rhodopsin protons and lipid phosphorus. It was previously reported that the methylene protons of g3, and of the ␣-methylene group of headgroups are the primary contributors to intramolecular dipolar interaction with the 31 P nucleus (34,35). During the long saturation time of 500 ms, magnetization is partially exchanged by spin-diffusion within the intramolecular proton network of lipids (36).…”

Section: P St-mas Nmr On Ros-mentioning

confidence: 98%

Evidence for Specificity in Lipid-Rhodopsin Interactions

Soubias

Teague

Gawrisch

2006

Journal of Biological Chemistry

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The interaction of bovine rhodopsin with poly-and monounsaturated lipids was studied by 1 H MAS NMR with magnetization transfer from rhodopsin to lipid. Experiments were conducted on bovine rod outer segment (ROS) disks and on recombinant membranes containing lipids with polyunsaturated, docosahexaenoyl (DHA) chains. Poly-and monounsaturated lipids interact specifically with different sites on the rhodopsin surface. Rates of magnetization transfer from protein to DHA are lipid headgroup-dependent and increased in the sequence PC < PS < PE. Boundary lipids are in fast exchange with the lipid matrix on a time scale of milliseconds or shorter. All rhodopsin photointermediates transferred magnetization preferentially to DHA-containing lipids, but highest rates were observed for Meta-III rhodopsin. The experiments show clearly that the surface of rhodopsin has sites for specific interaction with lipids. Current theories of lipid-protein interaction do not account for such surface heterogeneity.Rhodopsin is the light receptor responsible for dim light vision in the rod photoreceptor cells of vertebrates. A large body of research demonstrated that efficiency of the rhodopsindependent steps of the visual process is exquisitely sensitive to membrane lipid composition, in particular to the content of -3 polyunsaturates (1-3). Retinal membranes of mammals, similar to synaptosomal membranes in brain, contain up to 50 mol % of docosahexaenoic acid (DHA, 2 22:6n3), a polyunsaturated fatty acid with 22 carbon atoms and six double bonds that are evenly distributed over the length of the chain (4).In earlier reconstitution experiments with bovine rhodopsin it was established that the equilibrium concentration of Meta-II rhodopsin increased with the concentration of DHA hydrocarbon chains in the lipid matrix (5-7). Also the headgroups of phospholipids had a significant effect on Meta-II formation (5, 7) and activation of G t (8, 9). It was observed that phosphatidylethanolamines (PE) and the negatively charged phosphatidylserines (PS) increased the amount of Meta-II.The influence of PS on the equilibrium was assigned to changes of the membrane electric surface potential (7). In contrast, the sensitivity of membranes to PE content correlated with an alteration of membrane curvature elasticity (10) as proposed for other membrane proteins by Navarro et al. (11), Jensen and Schutzbach (12), Gruner (13), Lindblom and coworkers (14), and Cantor (15). Litman and co-workers (6, 16) found a correlation between mobility and orientation of the fluorescence probe DPH in lipid bilayers, summarized as a membrane free volume parameter, and Meta-II formation. Furthermore, they observed a preference of rhodopsin to locate in domains rich in di-22:6n3-PC that formed in di-16:0-PC/ di-22:6-PC/cholesterol mixtures. Mouritsen proposed a link between hydrophobic thickness of lipid bilayers and activity of membrane proteins (18). Brown and co-workers (10) suggested that Meta-II has a greater hydrophobic thickness than Meta-I, and that the lipid bilayer...

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Effect of N-alkyl-N,N,N-trimethylammonium ions on phosphatidylcholine model membrane structure as studied by 31P-NMR

Cited by 21 publications

References 15 publications

Cut-off Effect in Antimicrobial Activity and in Membrane Perturbation Efficiency of the Homologous Series of N,N-Dimethylalkylamine Oxides

Cut-off Effect in Antimicrobial Activity and in Membrane Perturbation Efficiency of the Homologous Series of N,N-Dimethylalkylamine Oxides

The structural diversity of DNA–neutral phospholipids–divalent metal cations aggregates: a small-angle synchrotron X-ray diffraction study

Evidence for Specificity in Lipid-Rhodopsin Interactions

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