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Exosomes are small extracellular vesicles (sEVs) involved in distal cell-cell communication and cancer migration by transferring functional cargo molecules. Membrane domains similar to lipid rafts are assumed to occur in exosome membranes and are involved in interactions with target cells. However, the bilayer membrane properties of these small vesicles have not been fully investigated. Therefore, we examined the fluidity, lateral domain separation, and transbilayer asymmetry of exosome membranes using fluorescence spectroscopy. Although there were some differences between the exosomes, TMA-DPH anisotropy showing moderate lipid chain order indicated that ordered phases comprised a significant proportion of exosome membranes. Selective TEMPO quenching of the TMA-DPH fluorescence in the liquid-disordered phase indicated that 40-50% of the exosome membrane area belonged to the ordered phase based on a phase-separated model. Furthermore, NBD-PC in the outer leaflet showed longer fluorescence lifetimes than those in the inner leaflets. Therefore, the exosome membranes maintained transbilayer asymmetry with a topology similar to that of the plasma membranes. In addition, the lateral and transbilayer orders of exosome membranes obtained from different cell lines varied, probably depending on the different membrane lipid components and compositions partially derived from donor cells. As these higher membrane orders and asymmetric topologies are similar to those of cell membranes with lipid rafts, raft-like functional domains are possibly enriched on exosome membranes. These domains likely play key roles in the biological functions and cellular uptake of exosomes by facilitating selective membrane interactions with target organs.

Polymer nanoparticles have attracted attention as antibacterial materials, but the function of the polymer itself has not yet been clarified sufficiently. To estimate the essential surface properties of antibacterial polymer nanoparticles, herein, we synthesized cationic polystyrene (PSt) nanoparticles via soap-free emulsion polymerization using 2,2'-azobis-[2-(1,3-dimethyl-4,5-dihydro-1

Mesoporous silica shells were formed on nonporous spherical silica cores during the sol–gel reaction to elucidate the mechanism for the generation of secondary particles that disturb the efficient growth of mesoporous shells on the cores. Sodium bromide (NaBr) was used as a typical electrolyte for the sol–gel reaction to increase the ionic strength of the reactant solution, which effectively suppressed the generation of secondary particles during the reaction wherein a uniform mesoporous shell was formed on the spherical core. The number of secondary particles (N2nd) generated at an ethanol/water weight ratio of 0.53 was plotted against the Debye–Hückel parameter κ to quantitatively understand the Debye screening effect on secondary particle generation. Parameter κa, where a is the average radius of the secondary particles finally obtained in the silica coating, expresses the trend in N2nd at different concentrations of ammonia and NaBr. N2nd was much lower than that expected theoretically from the variation of secondary particle sizes at a constant Debye–Hückel parameter. A similar correlation with κa was observed at the high and low ethanol/water weight ratios of 0.63 and 0.53, respectively, with different hydrolysis rate constants. The good correlation between N2nd and κa revealed that controlling the ionic strength of the silica coating is an effective approach to suppress the generation of secondary particles for designing mesoporous shells with thicknesses appropriate for their application as high-performance liquid chromatography column packing materials.

The Belousov-Zhabotinsky (BZ) reaction is an oscillating reaction due to periodic oscillations that happen in the concentration of some intermediates. Such systems can be applied together with hydrophobic membranes to create an autonomous behavior in artificial systems. However, because of a complex set of reactions happening in such systems, the interferences caused by hydrophobic membranes are not easily understood. In this study, we tested lipid membranes composed of trimethylammonium-propane (TAP) and phosphate (PA) lipids in an attempt to break down how the polar region of phosphatidylcholine (PC) lipid membranes affect the BZ reaction. According to our findings, the trimethylammonium group and membrane fluidity are crucial to change the frequency of oscillations in the reaction. In addition, the results also indicate a possible complexation of cerium ions with membranes with a phosphate head group.

Coassembly of lipids and polyamidoamine amphiphilic dendrons (AD) is expected to provide desirable characteristics to drug delivery carriers. However, there have been few studies about structure an...

For highly sensitive analysis of anionic lipid membranes, we developed membrane surface enhanced Raman spectroscopy with different sized gold nanoparticles (AuNPs). The employed AuNPs did not distu...

Regenerated cellulose can be prepared by treatment with an ionic liquid (IL) and an anti-solvent such as water, which significantly enhances the enzymatic hydrolysis in comparison to crystalline cellulose. The IL-aqueous two-phase system (IL-ATPS) is consisted of IL-condensed top phase and salt-condensed bottom phase, which could be suitable to produce regenerated cellulose with smaller amount of IL. Using IL-ATPS with different pH, the enzymatic saccharification efficiency of crystalline cellulose was determined. The use of 1-allyl-3-methylimidazolium chloride resulted in relatively higher yield of glucose production as compared to 1-butyl-3-methylimidazolium chloride. The IL-ATPS showing optimal pH for cellulase was prepared with mixed salt (NaH2PO4/Na2HPO4 = 5/1 (wt/wt)), which provide a regenerated cellulose with the pH range of 4.8–4.9 in enzymatic reaction mixture. Using such regenerated cellulose as feed of saccharification, the final yield of glucose was about 70%.

Chiral selective adsorption of L-amino acid, tryptophan (Trp) was achieved using phospholipid membrane-coated porous polymer particles (PPPs). PPPs with numerous pores were prepared by in situ polymerization of divinylbenzene, and then coated with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC, L-phospholipid) via the impregnation method. Elemental mapping of energy dispersive X-ray (EDX) analysis revealed that DPPC molecules were distributed to the surface and the inner part of PPPs, where almost all the DPPC molecules applied for impregnation were deposited on PPPs. The phospholipid membrane properties of DPPC-PPPs were characterized using the fluorescence probe 6-lauroyl-2-dimethylaminonaphthalene (Laurdan). The results show that DPPC-PPPs possessed a lipid membrane-like environment similar to pure DPPC liposomes, especially at temperatures below 35 °C. DPPC-PPPs slightly adsorbed L-Trp and D-Trp at 45 °C, while DPPC-PPPs significantly adsorbed L-Trp but not D-Trp at 30 °C: enantio excess (e.e.) was 75.0%. The time course of Trp adsorption was investigated: for both enantiomers, similar adsorption behaviors were observed for 30 h, thus suggesting surface adsorption onto DPPC-PPPs. L-Trp adsorption continued after 30 h, suggesting that L-Trp could be distributed in the inner part of DPPC-PPPs. Interestingly, the reused DPPC-PPPs featured improved adsorption performance, suggesting that the deposited DPPC membranes on PPPs could act as chiral selectors for L-Trp. The optical resolution of L-/D-Trp was performed using DPPC-PPPs, resulting in the e.e. of D-Trp was 60%. Thus, DPPC-PPPs have the potential of chiral selective adsorption of L-amino acid, which can be used as chiral separation materials.

Numerous research studies have been done for exosomes, particularly focusing on membrane proteins and included nucleic acids, and the volume of the knowledge about the lipids in the exosomal membrane has been increasing. However, the dynamic property of the exosomal membrane is hardly studied. By employing milk exosome as an example, herein the exosomal membrane was characterized focusing on the membrane fluidity and polarity. The lipid composition and phase state of milk exosome (exosome from bovine milk) were estimated. The milk exosome contained enriched Chol (43.6 mol % in total lipid extracts), which made the membrane in the liquid-ordered (lo) phase by interacting with phospholipids. To suggest a model of exosomal vesicle cargo, the liposome compositions that mimic milk exosome were studied: liposomes were made of cholesterol (Chol), milk sphingomyelin (milk SM), and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). By using fluorescent probes 1,6-diphenyl-1,3,5-hexatriene and 6-dodecanoyl-2-dimethylaminonaphthalene, the microenvironments of submicron-sized membranes of exosome and model liposomes were investigated. The membrane fluidity of milk exosome was slightly higher than those of Chol/milk SM/POPC liposomes with a similar content of Chol, suggesting the presence of enriched unsaturated lipids. The most purposeful membrane property was obtained by the liposome composition of Chol/milk SM/POPC = 40/15/45. From the above, it is concluded that Chol is a fundamental component of the milk exosomal membrane to construct the enriched lo phase, which could increase the membrane rigidity and contribute to the function of exosome.

A gold nanoparticle (AuNP) has a localized surface plasmon resonance peak depending on its size, which is often utilized for surface-enhanced Raman scattering (SERS). To obtain information on the cholesterol (Chol)-incorporated lipid membranes by SERS, AuNPs (5, 100 nm) were first functionalized by 1-octanethiol and then modified by lipids (AuNP@lipid). In membrane surface-enhanced Raman spectroscopy (MSERS), both signals from 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and Chol molecules were enhanced, depending on preparation conditions (size of AuNPs and lipid/AuNP ratio). The enhancement factors (EFs) were calculated to estimate the efficiency of AuNPs on Raman enhancement. The size of AuNP100nm@lipid was 152.0 ± 12.8 nm, which showed an surface enhancement Raman spectrum with an EF2850 value of 111 ± 9. The size of AuNP5nm@lipid prepared with a lipid/AuNP ratio of 1.38 × 104 (lipid molecule/particle) was 275.3 ± 20.2 nm, which showed the highest enhancement with an EF2850 value of 131 ± 21. On the basis of fluorescent probe analyses, the membrane fluidity and polarity of AuNP@lipid were almost similar to DOPC/Chol liposome, indicating an intact membrane of DOPC/Chol after modification with AuNPs. Finally, the membrane properties of AuNP@lipid systems were also discussed on the basis of the obtained MSERS signals.

The sterol ergosterol (Erg) is ubiquitous in the membranes of lower eukaryotes such as fungi. To investigate the interactions between Erg and phosphocholine (PC) molecules, we studied ternary lipid mixture systems composed of unsaturated 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), saturated 1,2-dipalmitoyl-sn-glycero-3-phophocholine (DPPC), and Erg. Bilayer membrane fluidity and polarity were systematically analyzed using fluorescent probes. The presence of ≥30 mol % of Erg exhibited a significant ordering effect and stabilized membrane properties when temperatures increased, suggesting that Erg has a similar function to cholesterol (Chol) in comparable lipid systems that form a liquid-ordered phase. Erg was also observed to have a significant condensing effect at the monolayer level in saturated PC-enriched systems. The phase behavior of Erg in bilayer systems was compared with that of Chol, with the data suggesting that Erg behaves in a similar manner to Chol in membranes enriched with saturated lipids.

The hydration properties of the interface between lipid bilayers and bulk water are important for determining membrane characteristics. Here, the emission properties of a solvent-sensitive fluorescence probe, 6-lauroyl-2-dimethylamino naphthalene (Laurdan), were evaluated in lipid bilayer systems composed of the sphingolipids D -erythro-N-palmitoyl-sphingosylphosphorylcholine (PSM) and D -erythro-N-palmitoyl-dihydrosphingomyelin (DHPSM). The glycerophospholipids 1-palmitoyl-2-palmitoyl-sn-glycero-3-phosphocholine and 1-oleoyl-2-oleoyl-sn-glycero-3-phosphocholine were used as controls. The fluorescence properties of Laurdan in sphingolipid bilayers indicated multiple excited states according to the results obtained from the emission spectra, fluorescence anisotropy, and the center-of-mass spectra during the decay time. Deconvolution of the Laurdan emission spectra into four components based on the solvent model enabled us to identify the varieties of hydration and the configurational states derived from intermolecular hydrogen bonding in sphingolipids. Sphingolipids showed specific, interfacial hydration properties stemming from their intra- and intermolecular hydrogen bonds. Particularly, the Laurdan in DHPSM revealed more hydrated properties compared to PSM, even though DHPSM has a higher Tm than PSM. Because DHPSM forms hydrogen bonds with water molecules (in 2NH configurational functional groups), the interfacial region of the DHPSM bilayer was expected to be in a highly polar environment. The careful analysis of Laurdan emission spectra through the four-component deconvolution in this study provides important insights for understanding the multiple polarity in the lipid membrane.

The J-aggregate of chlorophyll a (Chla) functions as a light-harvesting antenna in natural systems. In this study, we employed the phospholipid membranes composed of longer-chain 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and shorter-chain 1,2-dihexanoyl-sn-glycero-3-phosphocholine (DHPC), as a platform to induce Chla aggregates. The DMPC/DHPC assembly at the mixing ratio (q) = 1.5 induced J-aggregates of Chla at 20 °C with a total lipid concentration of 20 mM. While, Chla aggregates were not observed in the membranes at q = ∞ (DMPC vesicles) and q = 0 (DHPC micelles). The surroundings Chla molecules in DMPC/DHPC at q = 1.5 were estimated to comprise a less polar environment, based on the deconvolution analysis of Soret band spectrum (400–440 nm). The photo-reduction activity of Chla J-aggregates was investigated in lower lipid concentration conditions.

Nanostructured lipid carriers (NLCs) are gaining attention as the new generation of lipid vehicles. These carriers consist of saturated lipids with small drops of liquid oil dispersed into the inner lipid matrix and are stabilized by a surfactant. Conventionally, NLC-based drug delivery systems have been widely studied, and many researchers are looking into the composition of NLC properties to improve the performance of NLCs. The membrane fluidity and polarity of self-assembling lipids are also essential properties that must be affected by membrane compositions; however, such fundamental characteristics have not been studied yet. In this study, NLCs were prepared from cetyl palmitate (CP), caprylic triglyceride (CaTG), and Tween 80 (T80). Structural properties, such as particle size and ζ-potential of the CP/CaTG/T80 ternary mixtures, were investigated. Then, the systematic characterization of self-assembly properties using fluorescence-based analysis was applied for the first time to the NLC system. As a final step, the ternary diagram was developed based on the self-assembly properties to summarize the possible structures formed at different compositions. The results showed four states: micelle-like, oil-in-water (O/W) emulsion-like, solid lipid nanoparticle-like, and intermediate (solid-liquid coexistence). For the purpose of making the lipid matrix more liquified, the heterogeneous state and the disordered state of the O/W emulsion-like structure might fulfill the criteria of NLCs. Finally, the ternary diagram provides new information about the assembly state of NLC constituents that could become an important reference for developing high-performance NLCs.

Quercetin (QCT), existing in common dietary sources, is an abundant bioflavonoid with planar structure and exerts multiple pharmacological effects. Herein, four kinds of liposomes were prepared as model biomembranes, and then the partition coefficient, distribution in lipid membrane and influence of the QCT on the membrane properties were evaluated. The partition of QCT to lipid membranes was affected by both membrane phase state and the interference of QCT on membrane properties. The location of QCT in lipid membrane was related to the phase state of lipid membrane. In addition, influence of QCT on the compaction of the hydrocarbon tail in lipid membranes was dependent on the unsaturation degree of lipid molecules. Finally, about its antioxidant activity, from the results of 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay, it can be concluded that the interaction of QCT with lipid membrane greatly influences on QCT reductive activity in lipid membrane. Furthermore, mass spectrometry of DOPC molecule showed no lipid oxidation in the presence of QCT, indicating that in addition to the QCT ability toward radical scavenging, the ordering effect of QCT in unsaturated lipid membrane would be helpful to protect lipid membrane from oxidation by inhibiting radical diffusion (synergy effect). Based on lipid membrane analysis, our study made it clear that the effect of QCT on various lipid membrane and its relation with the antioxidant effect of QCT within lipid membrane. Therefore, our analytical method and findings would be also helpful for understanding the mechanism of other antioxidants effects on biomembrane.

The Belousov-Zhabotinsky (BZ) reaction has been applied to give autonomous dynamic behaviors to artificial systems. This reaction is conducted in an aqueous system, but it produces some hydrophobic intermediates, such as bromine. On the basis of previous works about reactions in the lipid bilayer, we investigated how liposome membranes (water-oil interface) affect the BZ reaction. Herein diacylglycerophosphocholine (PC) molecules with a variety of hydrocarbon tails were selected as components of liposomes, and the BZ reaction in the presence of the liposomes was characterized. As a result, membrane fluidity was the main characteristic leading to changes in the reaction behavior. The decrease of the frequency of oscillations was relevant to membrane fluidity, suggesting the interaction of bromine species in the hydrophobic site of the liposomes. In addition, the heterogeneous membrane (so+ld) of DMPC showed a fast decrease in the amplitude of oscillations. Conclusively, characteristics of the hydrophobic environment play a role in the reaction.

Bicelles are submicrometer-sized disc-shaped molecular self-assemblies that can be obtained in aqueous solution by dispersing mixtures of certain amphiphiles. Although phospholipid bicelle and phospholipid vesicle assemblies adopt similar lipid bilayer structures, the differences in bilayer characteristics, especially physicochemical properties such as bilayer fluidity, are not clearly understood. Herein, we report the lipid ordering properties of bicelle bilayer membranes based on induced circular dichroism (ICD) and fluorescence polarization analyses using 1,6-diphenyl-1,3,5-hexatriene (DPH) as a probe. Bicelles were prepared by using 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and 1,2-dihexanoyl-sn-glycero-3-phosphocholine (DHPC), while pure DMPC vesicles and pure DHPC micelles were used as references. At temperatures below the phase transition temperature of DMPC, the bicelles showed lower membrane fluidities, whereas DHPC micelles showed higher membrane fluidity, suggesting no significant differences in bilayer fluidity between the bicelle and vesicle assemblies. The ICD signals of DPH were induced only when the membrane was in ordered (solid-ordered or ripple-gel) phases. In the bicelle systems, the ICD of DPH was more significant than that of the DMPC vesicle. The induced chirality of DPH was dependent on the chirality of the bilayer lipid. Compared to that of the DMPC/DHPC bicelle, the ICD of the 1,2-dipalmitoyl-sn-glycero-3-phosphocholine/DHPC bicelle was higher, while that of the bovine sphingomyelin/DHPC bicelle was lower. Because the lipids are tightly packed in the ordered phase, the ICD intensity reflects the molecular ordering state of the lipids in the bicelle bilayer.

An l-Proline (l-Pro)-catalyzed aldol reaction of acetone and p-nitrobenzaldehyde (pNBA) occurs in organic solvents such as DMSO, while the presence of excess water inhibits the reaction. Herein, th...

Fluorescence probes are usually employed to analyze pharmacokinetics of drug carriers; however, this method using usual probes is not suitable to monitor drug carriers in detail because fluorescence spectra do not change by the disruption of drug carriers. In this study, pyrene-fatty acid conjugates were investigated as probes to monitor the state of drug carriers in real time. 1-Pyrenemethanol was conjugated with fatty acids, such as lauric acid, stearic acid, and behenic acid, and the conjugates were stirred in ethanol, resulting in the formation of submicron particles; these particles exhibited excimer emission. When J774.1 and Colon 26 cells were treated with these particles, the associated fluorescence spectra shifted from excimer emission to monomer emission. Moreover, the degree of change was controlled by the type of fatty acid. These results support the design of drug carriers that can be used to monitor pharmacokinetics in real time and to control the disruption time.

Vesicles prepared by synthetic surfactant, DDAB (dilauryldimethylammonium bromide), were modified with cholesterol and their membrane surface properties of the vesicle were characterized through the analyses of fluorescent probes, such as Laurdan (6-lauroyl-2-dimethylaminonaphthalene) and DPH (1,6-diphenyl-1,3,5-hexatriene). The self-assembly of DDAB with cholesterol showed stable vesicle structure with a mean diameter of 127 nm through the dynamic light scattering analysis. While the DDAB vesicle showed high polarity and high fluidity, the modification of the DDAB vesicle with cholesterol lead to the formation of "heterogeneous phase" on the vesicle membrane. DDAB:cholesterol = 70:30 vesicle showed unique characteristics that represents polar environment but lower fluidity. A novel platform for the chemical process in aqueous media can be expected by using the artificial surfactant vesicles modified with cholesterol.

Aqueous dispersions of oleic acid (OA) and those modified with 1-oleoylglycerol (monoolein, MO) form various kinds of self-assembled structures: micelles, vesicles, oil-in-water (O/W) emulsions, hexagonal phases, and dispersed cubic phases. Conventionally, these self-assembled structures have been characterized using cryogenic transmission electron microscopy or X-ray diffraction spectroscopy. However, these methodologies require specialized treatment before they can be used, which may lead to the self-assemblies not adopting their true equilibrium state. Herein, we systematically characterized the self-assemblies composed of OA and MO in aqueous solution using Raman spectroscopy and fluorescent probe 6-dodecanoyl-2-dimethylaminonaphthalene (Laurdan). The OA/MO dispersions at pH 5.0 showed increased chain packing in comparison to the OA micelle at pH 11 or OA vesicle at pH 9.0, which were characterized by the intensity ratio of the Raman peaks at 2850 and 2890 cm-1, R = I2890/I2850. In the Laurdan fluorescence measurements, the obtained spectra were deconvoluted to two peak fractions (A1: λem= 490 nm; A2: λem = 440 nm), and the peak area ratio, A1/(A1 + A2), was defined as the membrane hydrophilicity Om. The Om value of the OA/MO dispersion at pH 5.0 was similar to that of the OA O/W emulsion, indicating that the membrane surfaces of these self-assemblies were relatively dehydrated compared to the OA micelle or OA vesicle. To categorize the type of self-assembly dispersion, a Cartesian diagram plot was systematically drawn: R on the x axis and Om on the y axis, with the cross point at x = 1, y = 0.5. By comparing the membrane properties of the OA-based micelles, O/W emulsions, and dispersed cubic phases, we determined that the OA/MO dispersion at pH 5.0 possessed higher chain packing (R > 1) and a dehydrated membrane surface (Om < 0.5), which is similar to that of the ordered membranes in gel phases. This characterization method can be useful in evaluating the ordered membrane properties in dispersed self-assemblies in aqueous media.

Resveratrol (RES) is a type of polyphenolic compound discovered from grapes and has gained prominence as a possible contributor to many disease treatments. Herein, three different types of liposomes were prepared as model cell membranes, and then the influence of the incorporation of RES on their membrane properties was evaluated by utilizing membrane-binding fluorescent probes. The binding of RES lead to the membrane polarities decreasing slightly, regardless of the phase states of the membrane, while the membrane fluidities decreased only in the case of liquid-disordered phase. In each model membrane system, the incorporation of RES dramatically dehydrated the membrane surface, which could prevent the permeation of water-soluble materials. Fluorescence quenching of Laurdan indicated less accessibility of hydroxyl radial into the inner region of the RES-incorporated membrane. The comparison between the mass spectra of oxidized DOPC molecules treated with hydroxyl radical revealed that the RES-incorporation into DOPC membranes can contribute to prevent lipid oxidation. It is concluded that the binding of RES to the lipid membrane can play a key role in affecting membrane properties and functions.

The use of achiral surfactant assemblies as a reaction platform for an alkylation reaction resulted in a high enantiomeric excess. Dilauryldimethylammonium bromide (DDAB) vesicles were modified with cholesterol to promote alkylation of N-(diphenylmethylene)glycine tert-butyl ester (DMGBE) with benzyl bromide, resulting in high conversion (∼90%) and high enantioselectivity (up to 80%). The R-enantiomer was formed on using the DDAB vesicles, whereas the use of phospholipid liposomes prepared from 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) produced an excess of the S-enantiomer. Considering the chemical structures of the reaction substrates and amphiphiles as well as the membrane structures and properties of DDAB vesicles and DOPC liposomes, it is suggested that the enantiomeric excesses result from the location of the quaternary amine of the amphiphiles and the DMGBE at the outer surface of the membrane. We show that the enantioselective reaction at the surface of the self-assembly could be regulated by adjusting the chemical structures and resulting membrane properties of the self-assembly.

Artificial vesicles formed from sodium bis(2-ethylhexyl) sulfosuccinate (AOT) in aqueous solution are used successfully as additives for enzymatic oligomerizations or polymerizations of aniline or the aniline dimer p-aminodiphenylamine (PADPA) under slightly acidic conditions (e.g., pH 4.3 with horseradish peroxidase and hydrogen peroxide as oxidants). In these systems, the reactions occur membrane surface-confined. Therefore, (i) the physicochemical properties of the vesicle membrane and (ii) the interaction of aniline or PADPA with the AOT membrane play crucial roles in the progress and final outcome of the reactions. For this reason, the properties of AOT vesicles with and without added aniline or PADPA were investigated by using two fluorescent membrane probes: 1,6-diphenyl-1,3,5-hexatriene (DPH) and 6-lauroyl-2-dimethylaminonaphthalene (Laurdan). DPH and Laurdan were used as "sensors" of the membrane fluidity, surface polarity, and membrane phase state. Moreover, the effect of hexanol, alone or in combination with aniline or PADPA, as a possible modifier of the AOT membrane, was also studied with the aim of evaluating whether the membrane fluidity and surface polarity is altered significantly by hexanol, which, in turn, may have an influence on the mentioned types of reactions. The data obtained indicate that the AOT vesicle membrane at room temperature and pH 4.3 (0.1 M NaH