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Open AccessArticle

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

1
Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea
2
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
Molecules 2016, 21(7), 963; https://doi.org/10.3390/molecules21070963
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)
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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MDPI and ACS Style

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. https://doi.org/10.3390/molecules21070963

AMA Style

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(7):963. https://doi.org/10.3390/molecules21070963

Chicago/Turabian Style

Kim, Hwanhee; Hu, Yiluo; Jeong, Daham; Jun, Bong-Hyun; Cho, Eunae; Jung, Seunho. 2016. "Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates" Molecules 21, no. 7: 963. https://doi.org/10.3390/molecules21070963

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Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

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