Structures of Langmuir-Gibbs Films Consisting of Long-Chain Fatty Acid and Water-Soluble Surfactants

Oka, Kenichiro; Shibata, Hirobumi; Watanabe, Satoshi; Sakai, Kenichi; Abe, Masahiko; Matsumoto, Mutsuyoshi

doi:10.5650/jos.62.681

Cited by 4 publications

(7 citation statements)

References 44 publications

(44 reference statements)

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“…This indicates that the accommodation of the C 11 -IMe·HI component is hampered by DPPC, which imposes a great degree of lateral repulsion among the interfacial molecules, resulting in a more fluidized state. This effect fits nicely with the monolayer behavior of an LG film at higher concentrations of the water-soluble surfactant component, as described by Oka et al., where all of the long-chain surfactant molecules are dissolved in the aqueous solution but leave the monolayer enriched in short-chain water-soluble surfactants.…”

Section: Resultssupporting

confidence: 87%

“…Instead, in the presence of C 11 -IMe·HI, a hysteresis response can be observed (Figure B), indicating that C 11 -IMe·HI’s are partially extruded out of the monolayer when the compression approaches the collapse point of the film and are not able to efficiently readsorb to the interface upon expansion. This corresponds to the behavior of a Langmuir–Gibbs (LG) monolayer rather than a typical Langmuir film at the air–water interface. , Oka et al have previously reported the formation of an LG film for similar water-soluble surfactants carrying a medium hydrophobic chain of 12 carbon atoms, such as SDS and C12E8 (octaethylene glycol monododecyl ether) Figure C also shows the hysteresis response for the mixed monolayer containing C 7 -IMe·HI.…”

Section: Resultsmentioning

confidence: 90%

“…This corresponds to the behavior of a Langmuir−Gibbs (LG) monolayer rather than a typical Langmuir film at the air−water interface. 60,61 Oka et al have previously reported the formation of an LG film for similar water-soluble surfactants carrying a medium hydrophobic chain of 12 carbon atoms, such as SDS and C12E8 (octaethylene glycol monododecyl ether). 60 Figure 3C also shows the hysteresis response for the mixed monolayer containing C 7 -IMe•HI.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Imidazolium-Based Lipid Analogues and Their Interaction with Phosphatidylcholine Membranes

et al. 2016

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4,5-Dialkylated imidazolium lipid salts are a new class of lipid analogues showing distinct biological activities. The potential effects of the imidazolium lipids on artificial lipid membranes and the corresponding membrane interactions was analyzed. Therefore, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) was employed to create an established lipid monolayer model and a bilayer membrane. Mixed monolayers of DPPC and 4,5-dialkylimidazolium lipids differing by their alkyl chain length (C, C, and C) were characterized by surface pressure-area (π-A) isotherms using a Wilhelmy film balance in combination with epifluorescence microscopy. Monolayer hysteresis for binary mixtures was examined by recording triplicate consecutive compression-expansion cycles. The lipid miscibility and membrane stability of DPPC/imidazolium lipids were subsequently evaluated by the excess mean molecular area (ΔA) and the excess Gibbs free energy (ΔG) of mixing. Furthermore, the thermotropic behavior of mixed liposomes of DPPC/imidazolium lipids was investigated by differential scanning calorimetry (DSC). The C-imidazolium lipid (C-IMe·HI) forms a thermodynamically favored and kinetically reversible Langmuir monolayer with DPPC and exhibits a rigidification effect on both DPPC monolayer and bilayer structures at low molar fractions (X ≤ 0.3). However, the incorporation of the C-imidazolium lipid (C-IMe·HI) causes the formation of an unstable and irreversible Langmuir-Gibbs monolayer with DPPC and disordered DPPC liposomes. The C-imidazolium lipid (C-IMe·HI) displays negligible membrane activity. To better understand these results on a molecular level, all-atom molecular dynamics (MD) simulations were performed. The simulations yield two opposing molecular mechanisms governing the different behavior of the three imidazolium lipids: a lateral ordering effect and a free volume/stretching effect. Overall, our study provides the first evidence that the membrane interaction of the C and C derivatives modulates the structural organization of lipid membranes. On the contrary, for the C derivative its membrane activity is too low to contribute to its earlier reported potent cytotoxicity.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 90%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Imidazolium-Based Lipid Analogues and Their Interaction with Phosphatidylcholine Membranes

et al. 2016

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“…Water soluble and dispersible polymers have been widely used as detergents and surfactants, in which fatty acid esters of carbohydrates are an important member of surfactants . Thus, incorporation of sugars or polyols as components of aliphatic polyesters could probably be a promising method for constructing novel amphiphilic structures.…”

Section: Regioselective Enzymatic Polymerizationmentioning

confidence: 99%

Enantio‐, Regio‐, and Chemoselective Lipase‐Catalyzed Polymer Synthesis

Yang

Liu

Liang

et al. 2018

Macromolecular Bioscience

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In contrast to chemical routes, enzymatic polymerization possesses favorable characteristics of mild reaction conditions, few by-products, and high activity toward cyclic lactones which make it a promising technique for constructing polymeric materials. Meanwhile, it can avoid the trace residue of metallic catalysts and potential toxicity, and thus exhibits great potential in the biomedical fields. More importantly, lipase-catalyzed polymer synthesis usually shows favorable enantio-, regio-, and chemoselectivity. Here, the history and recent developments in lipase-catalyzed selective polymerization for constructing polymers with unique structures and properties are highlighted. In particular, the synthesis of polymeric materials which are difficult to prepare in a chemical route and the construction of polymers through the combination of selective enzymatic and chemical methods are focused. In addition, the future direction is proposed especially based on the rapid developments in computational chemistry and protein engineering techniques.

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“…Therefore, the phase diagrams at the interfaces were expected to differ from those in the homogeneous bulk phases. The adsorption of amphiphilic molecules with long alkyl chains at air/water interfaces − is common in Gibbs films, and adsorption at air/oil interfaces has also been reported …”

Section: Introductionmentioning

confidence: 99%

Quasi-Phase Diagrams at Air/Oil Interfaces and Bulk Oil Phases for Crystallization of Small-Molecular Semiconductors by Adjusting Gibbs Adsorption

et al. 2017

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The temperature and concentration dependencies of the crystallization of two small-molecular semiconductors were clarified by constructing quasi-phase diagrams at air/oil interfaces and in bulk oil phases. A quinoidal quaterthiophene derivative with four alkyl chains (QQT(CN)4) in 1,1,2,2-tetrachroloethane (TCE) and a thienoacene derivative with two alkyl chains (C8-BTBT) in o-dichlorobenzene were used. The apparent crystal nucleation temperature (T) and dissolution temperature (T) of the molecules were determined based on optical microscopy examination in closed glass capillaries and open dishes during slow cooling and heating processes, respectively. T and T were considered estimates of the critical temperatures for nuclear formation and crystal growth, respectively. The T values of QQT(CN)4 and C8-BTBT at the air/oil interfaces were higher than those in the bulk oil phases, whereas the T values at the air/oil interfaces were almost the same as those in the bulk oil phases. These Gibbs adsorption phenomena were attributed to the solvophobic effect of the alkyl chain moieties. The temperature range between T and T corresponds to suitable supercooling conditions for ideal crystal growth based on the suppression of nucleation. The T values at the water/oil and oil/glass interfaces did not shift compared with those of the bulk phases, indicating that adsorption did not occur at the hydrophilic interfaces. Promotion and inhibition of nuclear formation for crystal growth of the semiconductors were achieved at the air/oil and hydrophilic interfaces, respectively.

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Structures of Langmuir-Gibbs Films Consisting of Long-Chain Fatty Acid and Water-Soluble Surfactants

Cited by 4 publications

References 44 publications

Imidazolium-Based Lipid Analogues and Their Interaction with Phosphatidylcholine Membranes

Imidazolium-Based Lipid Analogues and Their Interaction with Phosphatidylcholine Membranes

Enantio‐, Regio‐, and Chemoselective Lipase‐Catalyzed Polymer Synthesis

Quasi-Phase Diagrams at Air/Oil Interfaces and Bulk Oil Phases for Crystallization of Small-Molecular Semiconductors by Adjusting Gibbs Adsorption

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