Effects of Sterol-Like Additives on Phase Transition Behavior of Ion-Pair Amphiphile Bilayers

Chang, Wei Han; Chuang, Yun Ting; Cheng, Yu; Chang, Chien Hsiang; Yang, Yu Min

doi:10.5650/jos.ess17086

Cited by 6 publications

(8 citation statements)

References 39 publications

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“…for the HTMA-DS/DXDAB vesicular bilayers. This may imply that the bilayer structure was changed to a liquid ordered state, which is generally happened in lipid and IPA bilayers with high cholesterol contents 31,39 . The disordering effect of cholesterol on bilayers of the catanionic vesicles has been ascribed to the fact that the added cholesterol in the rigid bilayers would increase the space between the molecular headgroups and create a void near the bilayer centers, decreasing the conformational order in the front and end segments of the hydrocarbon chains 25 .…”

Section: Molecular Packingmentioning

confidence: 99%

Enhanced Physical Stability of Mixed Ion Pair Amphiphile/Double-chained Cationic Surfactant Vesicles in the Presence of Cholesterol

Kuo

Yang

et al. 2018

J. Oleo Sci.

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In this study, a pseudodouble-chained ion pair amphiphile (IPA), hexadecyltrimethylammoniumdodecylsulfate (HTMA-DS), and dialkyldimethylammonium bromide (DXDAB) with different chain lengths were used as the main materials to fabricate positively charged catanionic vesicles with various mole fractions of cholesterol. The effects of cholesterol and DXDAB alkyl chain length on physical stability of the catanionic vesicles were then investigated by size, zeta potential, and Fourier transform infrared analyses. With the presence of cholesterol in the mixed HTMA-DS/DXDAB vesicles or with increasing the DXDAB content in the presence of a proper amount of cholesterol, the physical stability of the catanionic vesicles could be enhanced. The spacing effect of cholesterol would reduce the counterion binding tendency at the charged vesicle surfaces, resulting in a more pronounced charge character of the catanionic vesicles. Furthermore, cholesterol-induced disordered structure contributed to the flexibility of the vesicular bilayers. Thus the physical stability of the vesicles was improved by adding cholesterol. With increasing the hydrocarbon chain length of DXDAB, cholesterol located toward the middle of the bilayers, enhancing the effects of cholesterol on charge and molecular packing characteristics of the vesicles. This led to a more pronounced stability enhancement effect on the vesicles with a longer alkyl chain length of DXDAB. The results suggested that the presence of cholesterol in the HTMA-DS/DXDAB catanionic vesicles could enhance vesicle stability through adjusting intra-vesicle and/or inter-vesicle interactions. In addition, the stability enhancement effect was more pronounced in the systems with a long DXDAB alkyl chain. The findings will be useful for developing new formulas of catanionic vesicles as drug delivery carriers.

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Section: Molecular Packingmentioning

confidence: 99%

Enhanced Physical Stability of Mixed Ion Pair Amphiphile/Double-chained Cationic Surfactant Vesicles in the Presence of Cholesterol

Kuo

Yang

et al. 2018

J. Oleo Sci.

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“…Also, the cholesterol additives give rise to similar effects on the IPA bilayer’s phase behavior and mechanical properties as the phospholipid bilayers [19]. Recent studies showed that high cholesterol content can stabilize the IPA vesicles, possibly due to the vanishing of the local phase separation [20]. These results demonstrate a close structural correlation and similar response to cholesterol between the biomimetic IPA and the lipid bilayer system.…”

Section: Introductionmentioning

confidence: 83%

Effects of Cholesterol on Water Permittivity of Biomimetic Ion Pair Amphiphile Bilayers: Interplay between Membrane Bending and Molecular Packing

Tien

Chen

Huang

et al. 2019

IJMS

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Ion pair amphiphile (IPA), a molecular complex composed of a pair of cationic and anionic amphiphiles, is an inexpensive phospholipid substitute to fabricate vesicles with various pharmaceutical applications. Modulating the physicochemical and permeation properties of IPA vesicles are important for carrier designs. Here, we applied molecular dynamics simulations to examine the cholesterol effects on the structures, mechanics, and water permittivity of hexadecyltrimethylammonium-dodecylsulfate (HTMA-DS) and dodecyltrimethylammonium- hexadecylsulfate (DTMA-HS) IPA bilayers. Structural and mechanical analyses indicate that both IPA systems are in gel phase at 298 K. Adding cholesterol induces alkyl chain ordering around the rigid sterol ring and increases the cavity density within the hydrophilic region of both IPA bilayers. Furthermore, the enhanced alkyl chain ordering and the membrane deformation energy induced by cholesterol increase the permeation free energy penalty. In contrast, cholesterol has minor effects on the water local diffusivities within IPA membranes. Overall, the cholesterol reduces the water permittivity of rigid IPA membranes due to the synergistic effects of increased alkyl chain ordering and enhanced membrane mechanical modulus. The results provide molecular insights into the effects of molecular packing and mechanical deformations on the water permittivity of biomimetic IPA membranes, which is critical for designing IPA vesicular carriers.

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“…The interesting opposite effects of CHOL, therefore, lead to the formation of a single liquidordered phase, L o 46, 47 , and resulted in gradual disappearance of lipid bilayer phase transition with increasing CHOL concentration as observed in DSC experiments. Actually, possible mechanism of sterol-like additive effects on phase transition of IPA bilayers in excess water was proposed by Chang et al 7 in line with that of lipid bilayers.…”

Section: Ethanol Effect On the Thermotropic Phase Transition Of Ipa Bmentioning

confidence: 91%

Effects of Ethanol and Cholesterol on Thermotropic Phase Behavior of Ion-Pair Amphiphile Bilayers

et al. 2017

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Effects of Sterol-Like Additives on Phase Transition Behavior of Ion-Pair Amphiphile Bilayers

Cited by 6 publications

References 39 publications

Enhanced Physical Stability of Mixed Ion Pair Amphiphile/Double-chained Cationic Surfactant Vesicles in the Presence of Cholesterol

Enhanced Physical Stability of Mixed Ion Pair Amphiphile/Double-chained Cationic Surfactant Vesicles in the Presence of Cholesterol

Effects of Cholesterol on Water Permittivity of Biomimetic Ion Pair Amphiphile Bilayers: Interplay between Membrane Bending and Molecular Packing

Effects of Ethanol and Cholesterol on Thermotropic Phase Behavior of Ion-Pair Amphiphile Bilayers

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