Penetration behaviour of alkylbetainate chlorides into lipid monolayers

Zakanda, F. Nsimba; Nott, Kathérine; Paquot, Michel; Lelo, Georges Mvumbi; Deleu, Magali

doi:10.1016/j.colsurfb.2011.03.039

Cited by 9 publications

(9 citation statements)

References 39 publications

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“…The molecular area ( A c ) and the surface pressure (Π c ) at the collapse are 19.4 ± 0.4 Å 2 /molecule and 46.2 ± 0.5 mN/m, respectively. A c is higher and Π c lower with the PBS subphase than with the pure water subphase used in our previous study (17.3 ± 0.3 Å 2 /molecule and 52.3 ± 0.6 mN/m) . This is the result of the interaction between the positive head groups of C 16 BC molecules and the subphase hydrophilic anions (H 2 PO 4 ¯, HPO 4 2 ¯, and Cl¯) which expands and slightly destabilizes the C 16 BC monolayer …”

Section: Resultsmentioning

confidence: 60%

“…In PBS buffer, all of the lipids tested exert thus a positive effect on C 16 BC adsorption. In a pure water medium, it was the case for CHOL but not for POPC …”

Section: Resultsmentioning

confidence: 96%

“…Hexadecylbetainate chloride (C 16 BC; Figure ) was synthesized in our laboratory . Briefly, betainyl chloride was formed by adding thionyl chloride dropwise to a stirred solution of glycine betaine which was then mixed for ∼2 h. C 16 BC was obtained by the acylation of 1-hexadecanol by betainyl chloride.…”

Section: Methodsmentioning

confidence: 99%

“…Glycine betaine ( N , N , N -trimethylglycine) also called betaine is present in various plants, animals, and microorganisms. Recently, a review of the synthesis methods and potential applications of glycine betaine derivatives has been published . Betaine can be used to form the hydrophilic part of green surfactants, and several surfactants including esters (alkylbetainates chlorides, C n BC) are based on this molecule. − These compounds are generally referred to as “mild to the skin” and are used to improve the dermatological properties of other surfactants (e.g., alkylbetaines decrease the skin irritation of anionic compounds).…”

Section: Introductionmentioning

confidence: 99%

“…9 Considerable research is currently carried out on surfactant−lipid combinations which can be used as drug delivery systems for poorly soluble therapeutic agents. 10 Since C n BC are a novel class of green surface-active agents potentially useful for the formulation of a wide range of products, 1 in particular for the cosmetic and pharmaceutical fields, a basic physicochemical study of their interaction with mammalian plasma membrane is required. Due to the complexity of biological membranes, interactions with major lipid components have been examined individually as a first approach.…”

Section: Introductionmentioning

confidence: 99%

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Interaction of Hexadecylbetainate Chloride with Biological Relevant Lipids

et al. 2012

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The present work investigates the interaction of hexadecylbetainate chloride (C(16)BC), a glycine betaine-based ester with palmitoyl-oleoyl-phosphatidylcholine (POPC), sphingomyelin (SM), and cholesterol (CHOL), three biological relevant lipids present in the outer leaflet of the mammalian plasma membrane. The binding affinity and the mixing behavior between the lipids and C(16)BC are discussed based on experimental (isothermal titration calorimetry (ITC) and Langmuir film balance) and molecular modeling studies. The results show that the interaction between C(16)BC and each lipid is thermodynamically favorable and does not affect the integrity of the lipid vesicles. The primary adsorption of C(16)BC into the lipid film is mainly governed by a hydrophobic effect. Once C(16)BC is inserted in the lipid film, the polar component of the interaction energy between C(16)BC and the lipid becomes predominant. Presence of CHOL increases the affinity of C(16)BC for membrane. This result can be explained by the optimal matching between C(16)BC and CHOL within the film rather by a change of membrane fluidity due to the presence of CHOL. The interaction between C(16)BC and SM is also favorable and gives rise to highly stable monolayers probably due to hydrogen bonds between their hydrophilic groups. The interaction of C(16)BC with POPC is less favorable but does not destabilize the mixed monolayer from a thermodynamic point of view. Interestingly, for all the monolayers investigated, the exclusion surface pressures are above the presumed lateral pressure of the plasma membranes suggesting that C(16)BC would be able to penetrate into mammalian plasma membranes in vivo. These results may serve as a useful basis in understanding the interaction of C(16)BC with real membranes.

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Section: Resultsmentioning

confidence: 60%

“…In PBS buffer, all of the lipids tested exert thus a positive effect on C 16 BC adsorption. In a pure water medium, it was the case for CHOL but not for POPC …”

Section: Resultsmentioning

confidence: 96%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Interaction of Hexadecylbetainate Chloride with Biological Relevant Lipids

et al. 2012

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Correlation of Insulin‐Enhancing Properties of Vanadium‐Dipicolinate Complexes in Model Membrane Systems: Phospholipid Langmuir Monolayers and AOT Reverse Micelles

Sostarecz

Gaidamauskas

Distin

et al. 2014

Chemistry A European J

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We explore the interactions of V(III) -, V(IV) -, and V(V) -2,6-pyridinedicarboxylic acid (dipic) complexes with model membrane systems and whether these interactions correlate with the blood-glucose-lowering effects of these compounds on STZ-induced diabetic rats. Two model systems, dipalmitoylphosphatidylcholine (DPPC) Langmuir monolayers and AOT (sodium bis(2-ethylhexyl)sulfosuccinate) reverse micelles present controlled environments for the systematic study of these vanadium complexes interacting with self-assembled lipids. Results from the Langmuir monolayer studies show that vanadium complexes in all three oxidation states interact with the DPPC monolayer; the V(III) -phospholipid interactions result in a slight decrease in DPPC molecular area, whereas V(IV) and V(V) -phospholipid interactions appear to increase the DPPC molecular area, an observation consistent with penetration into the interface of this complex. Investigations also examined the interactions of V(III) - and V(IV) -dipic complexes with polar interfaces in AOT reverse micelles. Electron paramagnetic resonance spectroscopic studies of V(IV) complexes in reverse micelles indicate that the neutral and smaller 1:1 V(IV) -dipic complex penetrates the interface, whereas the larger 1:2 V(IV) complex does not. UV/Vis spectroscopy studies of the anionic V(III) -dipic complex show only minor interactions. These results are in contrast to behavior of the V(V) -dipic complex, [VO2 (dipic)](-) , which penetrates the AOT/isooctane reverse micellar interface. These model membrane studies indicate that V(III) -, V(IV) -, and V(V) -dipic complexes interact with and penetrate the lipid interfaces differently, an effect that agrees with the compounds' efficacy at lowering elevated blood glucose levels in diabetic rats.

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Binding of a Ruthenium Complex to a Thioether Ligand Embedded in a Negatively Charged Lipid Bilayer: A Two‐Step Mechanism

Bahreman

Rabe

Kros

et al. 2014

Chemistry A European J

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The interaction between the ruthenium polypyridyl complex [Ru(terpy)(dcbpy)(H2O)](2+) (terpy = 2,2';6',2"-terpyridine, dcbpy = 6,6'-dichloro-2,2'-bipyridine) and phospholipid membranes containing either thioether ligands or cholesterol were investigated using UV-visible spectroscopy, Langmuir-Blodgett monolayer surface pressure measurements, and isothermal titration calorimety (ITC). When embedded in a membrane, the thioether ligand coordinated to the dicationic metal complex only when the phospholipids of the membrane were negatively charged, that is, in the presence of attractive electrostatic interaction. In such a case coordination is much faster than in homogeneous conditions. A two-step model for the coordination of the metal complex to the membrane-embedded sulfur ligand is proposed, in which adsorption of the complex to the negative surface of the monolayers or bilayers occurs within minutes, whereas formation of the coordination bond between the surface-bound metal complex and ligand takes hours. Finally, adsorption of the aqua complex to the membrane is driven by entropy. It does not involve insertion of the metal complex into the hydrophobic lipid layer, but rather simple electrostatic adsorption at the water-bilayer interface.

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Penetration behaviour of alkylbetainate chlorides into lipid monolayers

Cited by 9 publications

References 39 publications

Interaction of Hexadecylbetainate Chloride with Biological Relevant Lipids

Interaction of Hexadecylbetainate Chloride with Biological Relevant Lipids

Correlation of Insulin‐Enhancing Properties of Vanadium‐Dipicolinate Complexes in Model Membrane Systems: Phospholipid Langmuir Monolayers and AOT Reverse Micelles

Binding of a Ruthenium Complex to a Thioether Ligand Embedded in a Negatively Charged Lipid Bilayer: A Two‐Step Mechanism

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