1-Naphthol as a Sensitive Fluorescent Molecular Probe for Monitoring the Interaction of Submicellar Concentration of Bile Salt with a Bilayer Membrane of DPPC, a Lung Surfactant
01 Nov 2010-Journal of Physical Chemistry B (American Chemical Society)-Vol. 114, Iss: 46, pp 14934-14940
TL;DR: Steady-state and time-resolved fluorescence of the two excited state prototropic forms of 1-naphthol indicate that the incorporation of monomeric bile salt molecules in the lipid bilayer membrane induces appreciable wetting of the bilayer up to the hydrocarbon core region, even at very low (≤1 mM) concentrations of the bile salts.
Abstract: In this study, 1-naphthol has been used as a sensitive ESPT fluorescent molecular probe to investigate the interaction of submicellar concentrations of two physiologically important bile salts, sodium deoxycholate and sodium cholate, with dipalmitoylphosphatidylcholine small unilamellar vesicles in solid gel and liquid crystalline phases. Steady-state and time-resolved fluorescence of the two excited state prototropic forms of 1-naphthol indicate that the incorporation of monomeric bile salt molecules in the lipid bilayer membrane induces appreciable wetting of the bilayer up to the hydrocarbon core region, even at very low (≤1 mM) concentrations of the bile salts.
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TL;DR: Steady-state and time-resolved fluorescence of the two excited-state prototropic forms of 1-naphthol indicate that submicellar bile salt concentration induces hydration of the lipid bilayer membrane into the core region.
Abstract: The interaction of submicellar concentrations of various physiologically important unconjugated [sodium deoxycholate (NaDC), sodium cholate (NaC)] and conjugated [sodium glycodeoxycholate (NaGDC), sodium glycocholate (NaGC), sodium taurodeoxycholate (NaTDC), sodium taurocholate (NaTC)] bile salts with dipalmitoylphosphatidylcholine (DPPC) and dimyristoylphosphatidylcholine (DMPC) small unilamellar vesicles in solid gel (SG) and liquid crystalline (LC) phases was investigated using the excited-state prototropism of 1-naphthol. Steady-state and time-resolved fluorescence of the two excited-state prototropic forms of 1-naphthol indicate that submicellar bile salt concentration induces hydration of the lipid bilayer membrane into the core region. This hydration effect is a general phenomenon of the bile salts studied. The bilayer hydration efficiency of the bile salt follows the order NaDC > NaC > NaGDC > NaTDC > NaGC > NaTC for both DPPC and DMPC vesicles in their SG and LC phases.
57 citations
TL;DR: The present study explores effects of three different kinds of widely used ILs, such as 1‐methyl‐3‐octylimidazolium chloride, 1‐buytl‐ 3‐methyl imadazolity tetrafluoroborate and 1‐benzyl‐3-methyl imidazlium tetrafLUoborate, on liposome properties of 1,2‐dipalmitoyl‐sn‐glycero‐3'phosphoch
Abstract: Recent increase and wider use of ionic liquids (ILs) for various applications has drawn attention to their toxicological consequence on human health. The present study explores effects of three different kinds of widely used ILs, such as 1-methyl-3-octylimidazolium chloride, 1-buytl-3-methyl imadazolium tetrafluoroborate and 1-benzyl-3-methyl imidazolium tetrafluoroborate, on liposome properties of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) by applying curcumin as molecular probe. Fluorescence intensity of curcumin is reported as a novel rotor which is sensitive to viscosity and thus the fluidity of the solvent. It follows a linear relationship of log fluorescence vs viscosity as proposed by Forster-Hoffmann equation. Curcumin binds strongly to liposome. At low concentration, the lipophilic drug curcumin does not appreciably influence the phase transition temperature of DPPC but as concentration reaches high levels significantly depresses the phase transition temperature. ILs diminish membrane fluidity. 1-methyl-3-octylimidazolium chloride disorders membrane properties by lowering the phase transition as is observed for higher concentration of curcumin, but 1-buytl-3-methyl imidazolium tetrafluoroborate and 1-benzyl-3-methyl imidazolium tetrafluoroborate do not modify phase transition temperature perceptibly; rather they broaden the phase transition at low molar concentration ratio. The three different kinds of ILs under study behave similarly at a high IL:DPPC ratio (1:2), while they behave differently at lower ratios (1:10-1:5).
54 citations
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TL;DR: This review will give an insight into the selection of drugs in different applications as their properties get modified by interaction with bile salts, thus influencing their solution behavior which, in turn, modifies the phase-forming behavior, microemulsion, and clouding phenomenon, besides solubilization.
Abstract: In this review, bile salt, bile salt–surfactant, and bile salt–drug interactions and their solubilization studies are mainly focused. Usefulness of bile salts in digestion, absorption, and excretion of various compounds and their rare properties in ordering the shape and size of the micelles owing to the presence of hydrophobic and hydrophilic faces are taken into consideration while compiling this review. Bile salts as potential bio-surfactants to solubilize drugs of interest are also highlighted. This review will give an insight into the selection of drugs in different applications as their properties get modified by interaction with bile salts, thus influencing their solution behavior which, in turn, modifies the phase-forming behavior, microemulsion, and clouding phenomenon, besides solubilization. Finally, their future perspectives are taken into consideration to assess their possible uses as bio-surfactants without side effects to human beings.
52 citations
TL;DR: It was found that only the lipid interface and tail regions change, and only when the rearrangement of the lipid hydrocarbon chain packing reaches a certain extent can the interfacial C═O groups be induced to undergo vibrational environment changes.
Abstract: We have a long-standing interest to explore the answer of the question: Which part of the amphiphilic molecule triggers the phase transition of the self-assembled aggregates consisting of these amphiphiles? This is an important issue regarding the phase transition kinetics of amphiphiles. To this end, we studied the phase transition behaviors of dipalmitoylphosphatidylcholine (DPPC) by differential scanning calorimetry, synchrotron X-ray scattering, Fourier transform infrared spectroscopy, and image analysis. We found that different parts (head, interface, and tail) of DPPC molecules all exhibit nonsynchronous changes during the sub-, pre-, and main transitions. Particular efforts have been devoted to studying the isothermal subgel (L(c')) formation process. It was found that only the lipid interface and tail regions change, and only when the rearrangement of the lipid hydrocarbon chain packing reaches a certain extent can the interfacial C═O groups be induced to undergo vibrational environment changes. The result means that the hydrocarbon tail is the part that triggers the gel (L(β')) to L(c') phase transition. The present work deepens our understanding on the phase transition mechanisms of DPPC and may shed light on those of other phospholipids and other types of amphiphiles.
38 citations
TL;DR: Alteration of membrane fluidity by bile salts is found to have an opposing effect in the liquid crystalline phase compared to in the solid gel phase, and is sensitive to the nature of bile salt.
37 citations
References
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843 citations
TL;DR: The lipid composition of mammalian surfactant and the techniques that have been utilized to study the involvement of these lipids in reducing the surface tension at an air-liquid interface, the main function of pulmonary surfactants are described.
688 citations
TL;DR: Analysis of existing data suggests that within experimental error both these distinctively different approaches are valid, indicating that the critical effective ratio at which solubilization occurs is approximately equal to the product of the critical micelle concentration and the distribution coefficient K.
403 citations
TL;DR: In this paper, a molecular dynamics simulation of a hydrated phosphatidylcholine bilayer membrane in the liquid crystalline phase was studied using H-bonding between water and DMPC molecules, and it was shown that water bridges are involved in reducing head group mobility and in stabilizing the membrane structure.
Abstract: Hydrogen (H-) bonding between water and phosphatidylcholine was studied using a molecular dynamics simulation of a hydrated phosphatidylcholine bilayer membrane in the liquid crystalline phase. A membrane in the liquid-crystalline phase composed of 72 L-R-dimyristoylphosphatidylcholine (DMPC) and 1622 water molecules was generated, starting from the crystal structure of DMPC. At the beginning of the equilibration process, the temperature of the system was raised to 550 K for 20 ps, which was effective in breaking the initial crystalline structure. The thermodynamic and structural parameters became stable after the equilibration period of 1100 ps, and the trajectory of the system obtained during the following 500 ps agreed well with most of the published experimental data. Each DMPC molecule forms 5.3 H-bonds with water, while only 4.5 water molecules are H-bonded to DMPC. The primary targets of water for the formation of H-bonds are the non-ester phosphate oxygens (4.0 H-bonds) and the carbonyl oxygens (1.0 H-bonds). Of DMPC’s H-bonds, 1.7 are formed with water molecules that are simultaneously H-bonded to two different DMPC oxygens (bridging water). In effect, approximately 70% of the DMPC molecules are linked by water molecules and form clusters of two to seven DMPC molecules. Approximately 70% of the intermolecular water bridges are formed between non-ester phosphate oxygens. The rest are formed between non-ester phosphate and carbonyl oxygens. About half of the intermolecular water bridges are involved in formation of multiple bridges, where two DMPC molecules are linked by more than one parallel bridge. These results suggest a possibility that water bridges are involved in reducing head group mobility and in stabilizing the membrane structure. Non-ester phosphate oxygen of DMPC makes one, two, or three H-bonds with water, but two H-bonds are formed most often (60%). In the case where two H-bonds are formed on non-ester phosphate or carbonyl oxygens, the average geometry of H-bonding is planar trigonal (in the case of water oxygen with two H-bonds, geometry is steric tetragonal). When oxygen atoms form three H-bonds, the geometry of H-bonding is steric tetragonal both for non-ester phosphate and water oxygens. On average, H-bonds make nearly right angles with each other when two or three water molecules are bound to the same DMPC oxygen, but the distribution of the angle is broad.
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