The Characterization of Molecular Organization of Multilamellar Emulsions Containing Pseudoceramide and Type III Synthetic Ceramide

Abstract

To investigate the molecular organization and phase behavior of physiologic lipid mixtures that contain either newly synthesized pseudoceramide or type III synthetic ceramide, various analytical techniques were used. The phase transition temperatures detected in differential scanning calorimetry analysis were 51.19 and 50.52 for the pseudoceramide-containing physiologic lipid mixture and synthetic type III ceramide-containing lipid mixture, respectively. From the small angle XRD patterns, the multilamellar emulsion-pseudoceramide showed 11.5 nm and 7.61 nm lamellar phases, while the multilamellar emulsion-synthetic ceramide showed only a 7.61 nm lamellar phase. The nonceramide containing lipid mixture did not show any distinct repeat pattern. Lateral packing distances of multilamellar emulsion-pseudoceramide and multilamellar emulsion-synthetic ceramide were measured as 0.4119 and 0.4110 nm at 30, respectively, which indicated the presence of hexagonal lattice. On the contrary, non-multilamellar emulsion did not show any definite repeat pattern. Transmission electron microscopy observation showed nearly comparable lamellar structures in all of the tested emulsions compared to the structure of human stratum corneum intercellular lipid. Decrease of water contents resulted in phase transition into liquid phase for all the tested emulsions, whereas phase transition into orthorhombic phase was observed only in multilamellar emulsion-pseudoceramide. From these results, we concluded that the molecular organization of multilamellar emulsion-pseudoceramide was characterized as the lateral hexagonal phase and both the long and short periodicity lamellar phases, which showed structural similarity with the native human stratum corneum intercellular lipid.

Novel synthetic ceramide derivatives increase intracellular calcium levels and promote epidermal keratinocyte differentiation

“…Sphingolipids, especially ceramide, are the major components of the intercellular materials in the stratum corneum, and a decrease in some of these molecules may be the cause of several skin diseases related to abnormal keratinocyte differentiation (24). We have studied synthetic ceramides and the multilamellar emulsion expected to reconstitute the abnormal skin barrier that results from the decrease in ceramide biosynthesis, such as in atopic dermatitis and psoriasis, and the barrier impairment induced by glucocorticoid-epidermal atrophy (15)(16)(17)(18). Here, we studied another possible use of these synthetic ceramides: as a bioactive lipid mediator of keratinocyte differentiation.…”

“…Recently, we developed the synthetic ceramide PC-9S (N-(2,3-dihydroxypropyl)-2-hexyl-3-oxo-decanamide) and reported its effects on skin barrier function (15)(16)(17)(18). During those studies, we postulated that PC-9S also has a biological effect on epidermal differentiation.…”

On the effects of topical synthetic pseudoceramides: Comparison of possible keratinocyte toxicities provoked by the pseudoceramides, PC104 and BIO391, and natural ceramides

“…For example, when present as the dominant species in a 3:1:1 molar ratio, they accelerate barrier recovery after acute abrogation in comparison to vehicletreated sites [4,14]. Two pseudo-Cer, i.e., N-(3-hexadecyloxy-2-hydroxypropyl)-N-2-hydroxyethylhexadecanamide (PC-104) and a similar structural compound, N-(2-hydroxyethyl)-2-pentadecanolylhexadecanamide (Bio391), can form lamellar/multilamellar structures in vitro with cholesterol and free fatty acids [15][16][17]. Accordingly, the cutaneous symptoms of atopic dermatitis appear to improve in patients treated with pseudo-Cer (PC-104 and others)-containing mixtures [4,18,19].…”

Topical application of a novel ceramide derivative, K6PC-9, inhibits dust mite extract-induced atopic dermatitis-like skin lesions in NC/Nga mice

“…In addition to the roles in skin barrier function, ceramide also regulates a variety of cellular processes, including cell growth, differentiation, apoptosis, inflammation and immune responses [10,11]. We previously developed a synthetic ceramide, PC-9S, and showed that it has a protective effect on skin barrier function [12][13][14][15]. Clinical efficacy of PC-9S on atopic or psoriatic patients was also reported [12,14,16].…”