Synthesis of Novel Pseudo-ceramide and Its Properties

Ceramides, a constituent of stratum corneum lipids, play a crucial role in the formation and maintenance of the epidermal permeability barrier. As in many other skin disorders, atopic dermatitis and psoriasis show decrease and transformation of the ceramides. The application of ceramide has been demonstrated to be efficient in the repair of these skin disorders. Nevertheless, natural ceramides are still too expensive and small in quantity to be used as a cosmetic ingredient. Although a lot of pseudo-ceramides have been developed and on the market until now, those pseudo-ceramides did not fully meet the consumer's needs, therefore, there is still a demand for a novel pseudo-ceramides. We synthesized a novel pseudo-ceramide BPC-16 from 2-(2-amino-ethylamino)-ethanol(AEEA), which was characterized by structures having both amide bonds and hydroxyl groups as hydrophilic units, as well as two long alkyl chains. We formulated emulsion with BPC-16, cholesterol, stearic acid, and other components to make an emulsion. These emulsion showed a typical optical anisotropy on cross-polarized microscopy. This 'Maltese cross' appearance is a characteristic figure observed in concentric lamellar emulsion under cross-polarized microscopy. In cytotoxicity assay using MTT in monolayer and three dimension(3D) cell culture, a BPC-16 showed only negligible cytotoxicity up to the effective concentration for barrier repair and moisturization(less than 10 mM). In the measurement of TEWL, this BPC-16 showed significant recovery of water-retaining properties when it was topically applied to either SDS-induced dry skin or normal skin compared to that of base cream. This novel pseudo-ceramide BPC-16 showed as effective in skin barrier repair and moisturization as natural ceramides.

신규 유사세라마이드의 합성과 그 특성

세라마이드는 콜레스테롤, 지방산과 함께 각질층을 구성하는 주요성분으로 각질층의 피부장벽 기능에 중요한 역할을 하며, 아토피 피부염, 건선, 건성습진, 주부습진 등과 같은 염증성 피부질환 방지에 도움이 되는 것으로 알려져 있다. 본 연구에서 2-(2-amino-ethylamino)-ethanol(AEEA)을 출발물질로 하여 신규 유사세라마이드 BPC-16을 합성하고, 그 물리화학적 성질과 화장품의 신규 소재로 활용하기 위하여 세포독성, 보습, 각질제거효능 등을 평가하였다. 합성된 BPC-16을 이용하여 콜레스테롤, 스테아린산을 포함하는 에멀젼을 제조했고, 편광현미경에서 'Maltese Cross'를 확인함으로써 BPC-1이 라멜라 에멀젼을 형성함을 확인하였다. 단층배양세포와 삼차원배양세포에서의 세포독성 실험에서 BPC-16은 보습과 피부손상회복 효과를 보이는 10 mM 이하의 농도에서 독성이 없음을 확인하였다. BPC-16의 보습효능을 확인하기 위하여 Vapormeter와 Corneometer를 이용하여 임상실험을 실시하였으며, 우수한 효과를 확인할 수 있었다. 또한, 피부손상에 대한 회복효과와 Visioscan을 이용한 각질량의 변화 실험에서도 우수한 효과를 확인하였다.