Phosphatidic acid affects structural organization of phosphatidylcholine liposomes. A study of 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammonium-phenyl)-6-phenyl,1,3,5-hexatriene (TMA-DPH) fluorescence decay using distributional analysis

Zolese, Giovanna; Gratton, Enrico; Curatola, G

doi:10.1016/0009-3084(90)90146-i

Cited by 24 publications

(12 citation statements)

References 37 publications

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“…Fluorescence emission spectrometry and DPH, as a nonpolar probe, were used to determine the polarization of liposomes prepared by using DPPC, POPC, and Lipoid and two sterols (cholesterol and β‐sitosterol). The polarization of DPH fluorophore indicates changes in lipid bilayer fluidity in the liposome membrane interior . As explained by Kushnareva and Dell polarization is reciprocally correlated to the membrane fluidity.…”

Section: Resultssupporting

confidence: 93%

Comparative Effects of Cholesterol and β‐Sitosterol on the Liposome Membrane Characteristics

Jovanović

Balanč

Ota

et al. 2018

Euro J Lipid Sci & Tech

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The influence of different phospholipid types (pure phospholipids 1‐palmitoyl‐2‐oleoyl‐sn‐glycero‐3‐phosphocholine, POPC, 1,2‐dipalmitoyl‐sn‐glycero‐3‐phosphocholine, DPPC, and one commercial phospholipid mixture, Lipoid H100), sterol types (cholesterol vs. β‐sitosterol), and various sterol concentrations (5–50 mol%) on liposomal membrane fluidity, thermotropic properties, liposome size, zeta potential, and lipid oxidation kinetics using fluorescent lipid probe BODIPY 581/591 C11 (4,4‐difluoro‐5‐[4‐phenyl‐1,3‐butadienyl]‐4‐bora‐3a,4a‐diaza‐s‐indacene‐3‐undecanoic acid) are investigated. DPPC bilayer is more rigid than POPC and phospholipids mixture membranes. Pure DPPC gives the smallest liposomes, while liposomes of Lipoid H100 have the largest diameter. Both sterols reduce membrane fluidity of all liposomes, increase absolute zeta potential, cause significant changes in particle size, and decrease phase transition temperature (Tm) and enthalpy of DPPC. POPC/β‐sitosterol liposomes exhibit the most significant lipid oxidation of the lipophilic probe. Along with beneficial effects of phytosterols on human health, better membrane fluidity, more favorable and stabilizing interactions with phospholipids, smaller vesicle size, and enhanced physical stability in comparison to cholesterol are some of the encouraging results for the use of β‐sitosterol in liposome formulations for potential application in foods, pharmaceutics, and cosmetics. Practical Applications: Adjusting the composition of liposomal membrane (lipid type, sterol type, and concentration) can be used as a tool to control membrane fluidity, permeability, and thermotropic properties, and thus predict release properties, physical, thermal, and oxidative stability. A commercial phospholipid mixture of different natural phospholipids with impurities creates less uniform liposomal membrane that is characterized by higher fluidity in comparison to DPPC. The type of phospholipid has huge influence on MLVs size. β‐sitosterol, which is a phytosterol with beneficial effects on human health can be used as a replacement for cholesterol in liposomal formulations, but with the following in mind: β‐sitosterol reduces fluidity of the phospholipid bilayer to a lesser extent than cholesterol, β‐sitosterol gives smaller MLVs than cholesterol, DPPC/β‐sitosterol SUVs are bigger than 100 nm in diameter (relevant for intravenous administration), MLVs with ≥30 mol% of β‐sitosterol can be considered as physically stable (unlike those with cholesterol), irrespective to the phospholipid type. The influence of different phospholipid types, sterol types, and various sterol concentrations on liposomal membrane fluidity, thermo tropic properties, liposomesize, zeta potential, and lipid oxidation kinetics are investigated.

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Section: Resultssupporting

confidence: 93%

Comparative Effects of Cholesterol and β‐Sitosterol on the Liposome Membrane Characteristics

Jovanović

Balanč

Ota

et al. 2018

Euro J Lipid Sci & Tech

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“…DPH and its derivatives are often the probes of choice for studies of the structure and dynamic properties of membranes (11,12), and have been most often used to estimate membrane fluidity and/or order (13)(14)(15)(16)(17)(18)(19). These probes were chosen for a number of reasons.…”

mentioning

confidence: 99%

“…These probes were chosen for a number of reasons. Derivatives of DPH are often chosen to probe different regions of the bilayer (15)(16)(17)(18)(21)(22)(23)(24), but their exact locations within the bilayer have not been determined (see Discussion), and it has been a constant ambiguity whether changes in DPH behavior due to its attachment to an anchoring group reflect changes in probe location or motional properties. DPH and its derivatives are often the probes of choice for studies of the structure and dynamic properties of membranes (11,12), and have been most often used to estimate membrane fluidity and/or order (13)(14)(15)(16)(17)(18)(19).…”

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confidence: 99%

Location of Diphenylhexatriene (DPH) and Its Derivatives within Membranes: Comparison of Different Fluorescence Quenching Analyses of Membrane Depth

1998

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The average membrane location of a series of diphenylhexatriene (DPH)-derived membrane probes was analyzed by measuring the quenching of DPH fluorescence with a series of nitroxide-labeled lipids in which the depth of the nitroxide group is varied. All DPH derivatives were located deeply within the bilayer. Some derivatives were anchored at a shallower depth than free DPH by attachment to cationic or anionic groups. However, the absolute change in DPH depth upon attachment to such groups was relatively modest (<4 A). In fact, protonated DPH fatty acid and a DPH fatty acyl group attached to a phosphatidylcholine were found to locate slightly more deeply than free DPH. The location of DPH derivatives can be explained by the length of the DPH group and its tendency to orient predominantly parallel to the fatty acyl chains of the bilayer. These factors allow a charged group attached to one end of a DPH molecule to be accommodated at the polar surface while maintaining a deep DPH location. Basically, it appears that most DPH derivatives probe the same region in the bilayer. We conclude previously reported differences in fluorescence polarization of free and anchored forms of DPH may reflect a direct effect of anchoring on motion rather than an effect on average DPH location. Other experiments showed the localization of DPH probes was found to be similar in the presence and absence of cholesterol. This implies that previously observed cholesterol-induced effects on DPH fluorescence polarization also largely reflect differences in DPH motion, not DPH location. From the quenching results it was also possible to define rules governing the location of a variety of chemical groups in membranes by comparison of the results obtained with DPH derivatives to those of similar derivatives of other fluorescent groups. Finally, an important goal of this study was to compare different methods of analysis of quenching data: parallax analysis, distribution (Gaussian) analysis (using a single Gaussian), and a second-order polynomial analysis. To evaluate the accuracy of these methods, the apparent depths of a series of fluorescence probes previously analyzed by parallax analysis was reanalyzed with all three methods. There was good agreement unless the fluorescent molecule was very shallow or very deep. In such cases, only parallax analysis gave physically reasonable results. This is likely to be due to the lack of a sufficient number of quenchers spanning a wide enough range for other analyses to compensate for deviations from ideal curves. Parallax analysis was also compared to distribution (Gaussian) analysis using a double Gaussian fit to account for quenching from the trans leaflet (Ladokhin, A. (1997) Methods Enzymol. 278, 462-473). Again more physically reasonable results were obtained from parallax analysis, likely due to non-Gaussian behavior of the depth dependence of quenching. Notwithstanding these observations, the significant number of cases where Gaussian curve fitting methods for quenching analysis are most powerful are...

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“…DPH and DPH derivative lifetime values are sensitive to the lipid phase, decreasing during the transition from the gel to the liquid-crystalline phases, in agreement with an increased water penetration in the bilayer [23,25,26].…”

Section: Resultsmentioning

confidence: 57%

Study of plasma membrane heterogeneity using a phosphatidylcholine derivative of 1,6-diphenyl-1,3,5-hexatriene [2-(3-(diphenylhexatriene)propanoyl)-3-palmitoyl-l-α-phosphatidylcholine]

et al. 1994

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The fluorescent probe 1,6-diphenyl-1,3,5-hexatriene (DPH) and DPH derivatives have been used to characterize structural and physicochemical properties of specific membrane domains. Steady-state and fluorescence decay measurements of three probes, DPH (1,6-diphenyl-1,3,5-hexatriene), TMA-DPH [1-(4-trimethyl-ammonium-phenyl)-6-phenyl-1,3,5-hexatriene], and a phosphatidylcholine derivative of DPH, DPH-pPC [2-(3-(diphenylhexatriene)propanoyl)-3-pamitoyl-L-α-phosphatidyl choline], have been performed in erythrocyte membranes and in lymphocyte plasma membranes. The steady-state fluorescence polarization of the three probes showed a similar trend in both membranes. In fact either in erythrocyte or in lymphocyte plasma membranes the fluorescence polarization values of DPH-pPC and TMA-DPH were similar, but significantly higher with respect to DPH. A better characterization of erythrocyte and lymphocyte plasma membranes was possible by using fluorescence decay measurements. The data suggest the possible use of different DPH derivatives to characterize specific domains in biological membranes.

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Phosphatidic acid affects structural organization of phosphatidylcholine liposomes. A study of 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammonium-phenyl)-6-phenyl,1,3,5-hexatriene (TMA-DPH) fluorescence decay using distributional analysis

Cited by 24 publications

References 37 publications

Comparative Effects of Cholesterol and β‐Sitosterol on the Liposome Membrane Characteristics

Comparative Effects of Cholesterol and β‐Sitosterol on the Liposome Membrane Characteristics

Location of Diphenylhexatriene (DPH) and Its Derivatives within Membranes: Comparison of Different Fluorescence Quenching Analyses of Membrane Depth

Study of plasma membrane heterogeneity using a phosphatidylcholine derivative of 1,6-diphenyl-1,3,5-hexatriene [2-(3-(diphenylhexatriene)propanoyl)-3-palmitoyl-l-α-phosphatidylcholine]

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