Synthesis and immobilization of modified ceramides on functionalized glass surfaces for the investigation of their scaffolding role in the skin lipid barrier Panagiota Velissari and Kateřina Vávrová Charles University, Czech Republic Skin, the biggest organ in the human body, provides protection against excessive water loss and hampers the entrance of undesired substances. 1 Skin’s outermost layer, the stratum corneum (SC), holds the principal skin barrier. Human SC consists of flattened dead cells known as corneocytes, that are embedded in a hydrophobic lipid matrix. Ceramides anchored on the corneocytes surface are forming the so-called “corneocyte lipid envelope” (CLE) 2 . Most research strategies to mimic the SC function, are considering only the lipidic matrix. In our attempt to create an SC alternative model which would incorporate CLE ‘’mimicking’’ entities together with the lipidic matrix, we combine organic synthesis with chemical engineering. The project is divided into two synthetic parts. In the first route, we are focusing on the synthesis of ω-activated ceramide derivatives in high yields ( Scheme 1 ). Thus, the second part consists of the glass surface modification for the selective tethering of the activated ceramides ( Scheme 2 ). This model will be further used for the investigation of the putative scaffolding role for the peculiar CLE structure in skin barrier function. This work was supported by GAUK 262821 and GACR 22-20839K
References 1. Menon K. G.; Cleary W. G.; Lane E. M.; International Journal of Pharmaceutics, 2012, 435 (1): 3-9. 2. Elias M. P.; Gruber R.; Crumrine D.; Menon G.; Williams L. M.; Wakefield S. J.; Holleran M. W.; Uchida Y.; Biochim Biophys Acta. 2014, 1841(3): 314-318.
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