X-ray grazing incidence diffraction and Langmuir monolayer studies of the interaction of β-cyclodextrin with model lipid membranes

Flasiński, Michał; Broniatowski, Marcin; Majewski, Jarosław; Dynarowicz-Łątka, Patrycja

doi:10.1016/j.jcis.2010.04.086

Cited by 33 publications

(31 citation statements)

References 57 publications

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“…A similar 2:1 complex is also found for DPPC/ cholesterol and sphingomyelins/cholesterol and has been related to an umbrella effect of the headgroups shielding one cholesterol from the bulk water phase. 25 Interestingly, the Brewster angle micrograph of the Pad-PC-Pad/cholesterol molar fraction of 2:1 does not display phase separation, even at the lowest surface pressures measured ( Figure S1), again indicating that this 2:1 complex represents an optimized interaction between cholesterol and Pad-PC-Pad. Infrared Reflection Absorption Spectroscopy (IRRAS).…”

Section: ■ Results and Discussionmentioning

confidence: 87%

Vesicle Origami and the Influence of Cholesterol on Lipid Packing

et al. 2016

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ABSTRACT:The artificial phospholipid Pad-PC-Pad was analyzed in 2D (monolayers at the air/water interface) and 3D (aqueous lipid dispersions) systems. In the gel phase, the two leaflets of a Pad-PC-Pad bilayer interdigitate completely, and the hydrophobic bilayer region has a thickness comparable to the length of a single phospholipid acyl chain. This leads to a stiff membrane with no spontaneous curvature. Forced into a vesicular structure, Pad-PC-Pad has faceted geometry, and in its extreme form, tetrahedral vesicles were found as predicted a decade ago. Above the main transition temperature, a noninterdigitated L α phase with fluid chains has been observed. The addition of cholesterol leads to a slight decrease of the main transition temperature and a gradual decrease in the transition enthalpy until the transition vanishes at 40 mol % cholesterol in the mixture. Additionally, cholesterol pulls the chains apart, and a noninterdigitated gel phase is observed. In monolayers, cholesterol has an ordering effect on liquid-expanded phases and disorders condensed phases. The wavenumbers of the methylene stretching vibration indicate the formation of a liquid-ordered phase in mixtures with 40 mol % cholesterol. ■ INTRODUCTIONVesicle origami or the guided self-assembly of a soft matter liposome may lead to materials with unprecedented properties. However, imposing a specific form on a liposome remains a formidable challenge. To achieve this goal, more fundamental insight into the forces determining the local curvature in membranes is needed.Here, we analyze the effects of membrane interdigitation and the deinterdigitating effect of cholesterol on monolayers and bilayers. Moreover, the liquid-ordered phase is characterized in unprecedented clarity.Cholesterol is a flat molecule maximizing the hydrophobic forces in model phospholipid membranes. 1 Cholesterol hereby acts as a fluidity buffer, 2 and this leveling effect leads to a liquidordered membrane phase. 3 In a nonideal mixture of low-and high-melting glycerophospholipids, cholesterol associates preferentially with the high-melting, saturated lipids. 4 Cholesterol and the glycerophospholipids interact strongly but transiently 5 via (i) hydrogen bonds between the hydroxy group of cholesterol and the phospholipid phosphodiester, 6 (ii) hydrogen bonds among the hydroxy group of cholesterol, water, and the sn-1 carbonyl moiety of the phospholipid, 7 (iii) van der Waals hydrophobic forces between the planar cholesterol ring system and the sn-1 chain of the phospholipid, 8 and, most importantly, (iv) van der Waals forces between the fatty acyl chains and the cholesterol side chain. 9 The interactions are strongly dependent on the type of phospholipid headgroup and lipid tail saturation 10 and may lead to a positioning of cholesterol in the middle of the bilayer membrane in the presence of polyunsaturated phospholipids. 11 Here, we discuss the effect of cholesterol on monolayers and bilayers formed by artificial 1,3-diamidophospholipid Pad-PCPad (structures in Figure 1). B...

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Section: ■ Results and Discussionmentioning

confidence: 87%

Vesicle Origami and the Influence of Cholesterol on Lipid Packing

et al. 2016

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“…Furthermore, other forces are involved in the formation and stabilization of inclusion complexes, such as van der Waals interactions (dipole-dipole interaction and London dispersion forces), 3-center, 2-electron bonds (between guest molecule and CD hydroxyl groups), hydrophobic interactions, release of deformation energy from the macromolecular ring of CDs, and steric effects (Saenger, 1980;Bekers et al, 1991;Szejtli, 1998;Bibby et al, 2000;Flasinski et al, 2010).…”

Section: Formation Of Inclusion Complexesmentioning

confidence: 99%

Cyclodextrins and ternary complexes: technology to improve solubility of poorly soluble drugs

Miranda

Martins

Veiga

et al. 2011

Braz. J. Pharm. Sci.

147

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Cyclodextrins (CDs) are cyclic oligosaccharides composed of D-glucopyranoside units linked by glycosidic bonds. Their main property is the ability to modify the physicochemical and biological characteristics of low-soluble drugs through the formation of drug:CD inclusion complexes. Inclusion complexation requires that host molecules fit completely or partially within the CD cavity. This adjustment is directly related to the physicochemical properties of the guest and host molecules, easy accommodation of guest molecules within the CD cavity, stoichiometry, therapeutic dose, and toxicity. However, dosage forms may achieve a high volume, depending on the amount of CD required. Thus, it is necessary to increase solubilization efficiency in order to use smaller amounts of CD. This can be achieved by adding small amounts of water-soluble polymers to the system. This review addresses aspects related to drug complexation with CDs using water-soluble polymers to optimize the amount of CD used in the formulation in order to increase drug solubility and reduce dosage form volume. Uniterms:Cyclodextrins. Ternary complexes. Drugs/complexation. Water-soluble polymers/use. Drugs/ solubility. Inclusion complexe.Ciclodextrinas (CDs) são oligossacarídeos cíclicos, compostos por unidades D-glicopiranosídicas ligadas entre si por meio de ligações glicosídicas e sua principal propriedade está na capacidade de alterar as características físico-químicas e biológicas de fármacos com baixa solubilidade por meio da formação de complexos de inclusão fármaco:CD. Para a formação dos complexos de inclusão a molécula hospedeira necessita ajustar-se total ou parcialmente no interior da cavidade da CD, onde este ajuste está diretamente ligado a propriedades físico-químicas da molécula hóspede e hospedeira, facilidade de alojamento da molécula hóspede no interior da cavidade da CD, estequiometria, dose terapêutica e toxicidade. No entanto, as formas farmacêuticas podem atingir um elevado volume, em função da quantidade de CD requerida, sendo necessário aumentar sua eficiência de solubilização para que seja possível utilizar menores quantidades das mesmas. Isso pode ser obtido com a inclusão de pequenas quantidades de polímeros hidrossolúveis ao sistema. Nessa revisão, são abordados aspectos relacionados à complexação de fármacos com ciclodextrinas empregando-se polímeros hidrossolúveis para otimização da quantidade de CD utilizada na formulação, com a finalidade de aumentar a solubilidade do fármaco e reduzir o volume das preparações.Unitermos: SCiclodextrinas. Complexos ternários. Fármacos/complexação. Polímeros hidrossolúveis/ uso. Fármacos/solubilidade. Complexos de inclusão.

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“…Thus, DRMs solubilization after cyclodextrin treatment was indicative of it being part of a raft component. In addition, if a biological process in living cells was disrupted by cyclodextrin treatment, the process was considered to be raft-based3456789. From the chemical point of view, cyclodextrins (CD) are composed of several glucose units, linked together by α -1,4-glucosidic bonds.…”

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confidence: 99%

Computational microscopy of cyclodextrin mediated cholesterol extraction from lipid model membranes

López

Vries

Marrink

2013

Sci Rep

106

118

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Beta-cyclodextrins (β-CDs) can form inclusion complexes with cholesterol, and are commonly used to manipulate cholesterol levels of biomembranes. In this work, we have used multiscale molecular dynamics simulations to provide a detailed view on the interaction between β-CDs and lipid model membranes. We show that cholesterol can be extracted efficiently upon adsorption of β-CD dimers at the membrane/water interface. However, extraction is only observed to occur spontaneously in membranes with high cholesterol levels. Free energy calculations reveal the presence of a kinetic barrier for cholesterol extraction in the case of low cholesterol content. Cholesterol uptake is facilitated in case of (poly)unsaturated lipid membranes, which increases the free energy of the membrane bound state of cholesterol. Comparing lipid/cholesterol compositions typical of liquid-disordered (Ld) and liquid-order (Lo) domains, we furthermore show that cholesterol is preferentially extracted from the disordered regions, in line with recent experimental data.

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X-ray grazing incidence diffraction and Langmuir monolayer studies of the interaction of β-cyclodextrin with model lipid membranes

Cited by 33 publications

References 57 publications

Vesicle Origami and the Influence of Cholesterol on Lipid Packing

Vesicle Origami and the Influence of Cholesterol on Lipid Packing

Cyclodextrins and ternary complexes: technology to improve solubility of poorly soluble drugs

Computational microscopy of cyclodextrin mediated cholesterol extraction from lipid model membranes

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