Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes

被引:16
|
作者
Fukunaga, K
Yoshida, M
Nakajima, F
Uematsu, R
Hara, M
Inoue, S
Kondo, H
Nishimura, SI
机构
[1] Kanebo Ltd, Basic Res Lab, Odawara, Kanagawa 2500002, Japan
[2] Hokkaido Univ, Japan Bioind Assoc, Sapporo Lab Glycocluster Project, Sapporo, Hokkaido 0600810, Japan
[3] Nippon Organon Ltd, Dept Chem, Miyakojima Ku, Osaka, Japan
[4] Hokkaido Univ, Grad Sch Sci, Div Biol Sci, Lab Biomacromol Chem, Sapporo, Hokkaido 0600810, Japan
关键词
D O I
10.1016/S0960-894X(03)00006-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We have established an efficient synthesis of mimics of beta-galactosylceramide (beta-GalCer) increasing a beta-glucocerebrosidase (beta-GlcCer'ase) activity that associates with the skin barrier function. Among the synthetic beta-GalCer analogues (6a-6e) described herein, compound 6e exhibited a potent effect on the activation of beta-GlcCer'ase function in vitro and reduced the transepidermal water loss (TEWL) level in a UVB-induced barrier disrupted mice model. These findings indicated that compound 6e could be useful for cosmetics and medicines to improve skin barrier function. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:813 / 815
页数:3
相关论文
共 50 条
  • [41] Phenylalanyl tRNA synthetase (PheRS) substrate mimics: design, synthesis, molecular dynamics and antimicrobial evaluation
    Noureldin, Nada A.
    Richards, Jennifer
    Kothayer, Hend
    Baraka, Mohammed M.
    Eladl, Sobhy M.
    Wootton, Mandy
    Simons, Claire
    RSC ADVANCES, 2022, 12 (04) : 2511 - 2524
  • [42] SYNTHESIS OF A FLUORESCENT DERIVATIVE OF GLUCOSYL CERAMIDE FOR THE SENSITIVE DETERMINATION OF GLUCOCEREBROSIDASE ACTIVITY
    DINUR, T
    GRABOWSKI, GA
    DESNICK, RJ
    GATT, S
    ANALYTICAL BIOCHEMISTRY, 1984, 136 (01) : 223 - 234
  • [43] Design and synthesis of phosphatidylcholine mimics and their mixing behavior with phosphatidylglycerol mimics in the fluid bilayer state
    Uragami, M
    Miyake, Y
    Tokutake, N
    Zhang, LH
    Regen, SL
    LANGMUIR, 2000, 16 (21) : 8010 - 8015
  • [44] Design, synthesis, and antitumor activity evaluation of steroidal oximes
    Gomes, Ana R.
    Pires, Ana S.
    Abrantes, Ana M.
    Goncalves, Ana C.
    Costa, Saul C.
    Varela, Carla L.
    Silva, Elisiario T.
    Botelho, Maria F.
    Roleira, Fernanda M. F.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 46
  • [45] Design, synthesis, and evaluation of benzodioxolane compounds for antitumor activity
    Wang, Xiu-Jun
    Qiao, Yue
    Jiang, Zi-Rui
    He, Jing-Liang
    Wang, Bing-Yan
    Wan, Jia-Rui
    Ji, Jing
    Liu, Bin
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2024, 111
  • [46] Design, synthesis and antifungal activity evaluation of isocryptolepine derivatives
    Li, Jun-cai
    Wang, Ren-xuan
    Sun, Yu
    Zhu, Jia-kai
    Hu, Guan-fang
    Wang, Yu-ling
    Zhou, Rui
    Zhao, Zhong-min
    Liu, Ying-qian
    Peng, Jing-wen
    Yan, Yin-fang
    Shang, Xiao-fei
    BIOORGANIC CHEMISTRY, 2019, 92
  • [47] Design, synthesis, and anticancer activity evaluation of curcumol derivatives
    Meng, Xiang-Wei
    Wei, Ying-Ying
    Nong, Bin-Lu
    Zhao, Hua-Jun
    Zhang, Xing-Xian
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2022, 24 (06) : 556 - 568
  • [48] Novel amidrazone derivatives: Design, synthesis and activity evaluation
    Zhou, Hua
    Wang, Zhi Sen
    Liu, Xin Hua
    Chen, Fei Hu
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (12) : 3158 - 3165
  • [49] Design, synthesis and evaluation of antitubercular activity of Triclosan analogues
    Cinu, Thomas A.
    Sidhartha, S. Kar
    Indira, Bairy
    Varadaraj, Bhat G.
    Vishnu, P. Shenoy
    Shenoy, G. Gautham
    ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (08) : 3316 - 3323
  • [50] Design, Synthesis and Evaluation of Antifungal Activity of Pyrazoleacetamide Derivatives
    Kachi, Onkar G.
    Pawar, Hari R.
    Chabukswar, Anuruddha R.
    Jagdale, Swati
    Swamy, Vishwanath
    Vinayak, Kadam
    Hingane, Dattatray
    Shinde, Mahadev
    Pawar, Nagesh
    MEDICINAL CHEMISTRY, 2024, 20 (10) : 957 - 968