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Molecules 2016, 21(7), 963;

Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea
Center for Biotechnology Research in UBITA (CBRU), Institute for Ubiquitous Information Technology and Applications (UBITA), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea
Authors to whom correspondence should be addressed.
Academic Editor: Bernard Martel
Received: 15 June 2016 / Revised: 19 July 2016 / Accepted: 20 July 2016 / Published: 22 July 2016
(This article belongs to the Special Issue Cyclodextrin Chemistry)
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Amphiphilic cyclodextrin (CD) has been the object of growing scientific attention because of its two recognition sites, the cavity and the apolar heart, formed by self-assembly. In the present study, mono[6-deoxy-6-(octadecanamido)]-β-CD and mono[6-deoxy-6-(octadecenamido)]-β-CD were successfully synthesized by reacting mono-6-amino-6-deoxy-β-CD with N-hydroxysuccinimide esters of corresponding fatty acids in DMF. The structures were analyzed using nuclear magnetic resonance spectroscopy and mass spectrometry. The amphiphilic β-CDs were able to form self-assembled nano-vesicles in water, and the supramolecular architectures were characterized using fluorescence spectroscopy, dynamic light scattering, and transmission electron microscopy. Using the cavity-type nano-vesicles, all-trans-retinol was efficiently encapsulated; it was then stabilized against the photo-degradation. Therefore, the present fatty amide-β-CD conjugate will be a potential molecule for carrier systems in cosmetic and pharmaceutical applications. View Full-Text
Keywords: amphiphilic cyclodextrin; self-assembly; all-trans-retinol; stabilization amphiphilic cyclodextrin; self-assembly; all-trans-retinol; stabilization

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kim, H.; Hu, Y.; Jeong, D.; Jun, B.-H.; Cho, E.; Jung, S. Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates. Molecules 2016, 21, 963.

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