How does the N-acylation and esterification of amphotericin B molecule affect its interactions with cellular membrane components—the Langmuir monolayer study
“…The weaker interaction between AmB and cholesterol compared with that between AmB and ergosterol leads to the different behavior of this antibiotic in monolayers containing these sterols (Saint-Pierre-Chazalet et al 1988 ; Seoane et al 1998 , 1999a , b ; Miñones et al 2005 ; Chang et al 2010 ). These differences are also observed for modified AmB molecules (Hac-Wydro et al 2005a , b , c ; Baginski et al 2006 ). Fig.…”
In the past decade substantial progress has been made in understanding the organization and biological activity of amphotericin B (AmB) in the presence of sterols in lipid environments. This review concentrates mainly on interactions of AmB with lipids and sterols, AmB channel formation in membranes, AmB aggregation, AmB modifications important for understanding its biological activity, and AmB models explaining its mechanism of action. Most of the reviewed studies concern monolayers at the water–gas interface, monolayers deposited on a solid substrate by use of the Langmuir–Blodgett technique, micelles, vesicles, and multi-bilayers. Liposomal AmB formulations and drug delivery are intentionally omitted, because several reviews dedicated to this subject are already available.
“…The weaker interaction between AmB and cholesterol compared with that between AmB and ergosterol leads to the different behavior of this antibiotic in monolayers containing these sterols (Saint-Pierre-Chazalet et al 1988 ; Seoane et al 1998 , 1999a , b ; Miñones et al 2005 ; Chang et al 2010 ). These differences are also observed for modified AmB molecules (Hac-Wydro et al 2005a , b , c ; Baginski et al 2006 ). Fig.…”
In the past decade substantial progress has been made in understanding the organization and biological activity of amphotericin B (AmB) in the presence of sterols in lipid environments. This review concentrates mainly on interactions of AmB with lipids and sterols, AmB channel formation in membranes, AmB aggregation, AmB modifications important for understanding its biological activity, and AmB models explaining its mechanism of action. Most of the reviewed studies concern monolayers at the water–gas interface, monolayers deposited on a solid substrate by use of the Langmuir–Blodgett technique, micelles, vesicles, and multi-bilayers. Liposomal AmB formulations and drug delivery are intentionally omitted, because several reviews dedicated to this subject are already available.
“…The simple and fast method of preparing the semipermanent phospholipid coating, and its versatility, make CE a promising technique for studies on phospholipid-analyte interactions. Liposomes [6], or phospholipid vesicles, have been used as models of the bilayer core of cellular membranes and also as models for interaction studies with lipophilic substances such as doxorubicin [7] and amphotericin B [8,9]. Cellular membranes, such as human red blood cell (RBC) membranes, consist mainly of phospholipids, the most common being zwitterionic phosphatidylcholine (PC) and cholesterol (chol) [10].…”
The purpose was to develop a stable biological membrane coating for CE useful for membrane interaction studies. The effect of cholesterol (chol) on the stability of dipalmitoylphosphatidylcholine (DPPC) and sphingomyelin (SM) coatings was studied. In addition, a fused-silica capillary for CE was coated with human red blood cell (RBC) ghost lipids. Liposomes prepared of DPPC/SM with and without chol or RBC ghost lipids were flushed through the capillary and the stability of the coating was measured electrophoretically. Similar mixtures of DPPC/SM with and without chol were further studied by differential scanning calorimetry. The presence of phosphatidylcholine as a basic component in the coating solution of DPPC/SM/chol was found to be essential to achieve a good and stable coating. The results also confirmed the stability of coatings obtained with solutions of DPPC with 0-30 mol% of chol and SM in different ratios, which more closely resemble natural membranes. Finally, the electrophoretic measurements revealed that a stable coating is formed when capillaries are coated with liposomes of RBC ghost lipids.
It is known that sterols are key components of cellular membranes, which can modulate membrane properties and induce influence on the organization of membrane phospholipids. Howerer, the influence of these sterols on membrane properties sees to be unclear. It is worth studying. The interactions between β-sitosterol and stigmasterol and dipalmitoyl phosphatidycholine (DPPC) in mixed monolayers were studied by langmuir technique and atomic force microscopy (AFM). The influence of β-sitosterol and stigmasterol effects on properties of DPPC membrane on phase transition from the liquid expanded (LE) to liquid condensed (LC) state were investigated and the condensing and ordering potency of binary monolayers containing β-sitosterol and stigmasterol were thoroughly analyzed. Based on the analysis of mixing values as well as AFM images it was evidenced that the effect of the plant sterol depends on the composition of model membrane. The results show that the addition of the plant sterols into model membrane modifies the condensation, ordering and interactions in the system. Moreover, at their higher concentration X sterols ＝0.8, the values of the excess molecular area and excess Gibbs enerqy displayed negative values, which indicate that between molecules in the mixed monolayer exist stronger attraction than in the respective one-component films and suggest β-sitosterol and stigmasterol in the mixed system have the similar effects on its properties. Examination of the excess free energy of mixing reveals an enhanced stability of binary monolayers. At lower content, X sterols ＝0.2, 0.4, the values of the excess molecular area and excess Gibbs energy suggested stronger attractive interaction between stigmasterol and DPPC, while an intermolecular stronger repulsion interaction between β-sitosterol and DPPC. It shows that stigmasterol was found to modify the properties of model membrane more strongly than β-sitosterol. It reflects that side-chain can reduce packing effectiveness, increased tilt of the molecules with respect to the monolayer plane, and the presence of the double bond reduces the hydrophobicity of the branched hydrocarbon tail of stigmasterol, which could cause strols to have long axis parallel to the interface. The result of AFM supported the theoretic analysis.
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