title: Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates.
abstract: 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.
authors.affiliation: Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea. hwanhee@konkuk.ac.kr.
authors.forename: Hwanhee
authors.initials: H
authors.lastname: Kim
authors.affiliation: Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea. lannyhu0806@hotmail.com.
authors.forename: Yiluo
authors.initials: Y
authors.lastname: Hu
authors.affiliation: Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea. amir@konkuk.ac.kr.
authors.forename: Daham
authors.initials: D
authors.lastname: Jeong
authors.affiliation: Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea. bjun@konkuk.ac.kr.
authors.forename: Bong-Hyun
authors.initials: BH
authors.lastname: Jun
authors.affiliation: 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. echo@konkuk.ac.kr.
authors.forename: Eunae
authors.initials: E
authors.lastname: Cho
authors.affiliation: Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea. shjung@konkuk.ac.kr.|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. shjung@konkuk.ac.kr.
authors.forename: Seunho
authors.initials: S
authors.lastname: Jung
mesh_terms: D000577:Amides / Q000737:chemistry*; D004339:Drug Compounding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D014801:Vitamin A / Q000737:chemistry*; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000577:Amides; D047392:beta-Cyclodextrins; D014867:Water; D014801:Vitamin A
keywords: all-trans-retinol; amphiphilic cyclodextrin; self-assembly; stabilization