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

Kyoko Fukunaga, Masahiro Yoshida, Fumio Nakajima, Rie Uematsu, Mariko Hara, Shintaro Inoue, Hirosato Kondo, Shin Ichiro Nishimura

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

We have established an efficient synthesis of mimics of β-galactosylceramide (β-GalCer) increasing a β-glucocerebrosidase (β-GlcCer'ase) activity that associates with the skin barrier function. Among the synthetic β-GalCer analogues (6a-6e) described herein, compound 6e exhibited a potent effect on the activation of β-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.

Original languageEnglish
Pages (from-to)813-815
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number5
DOIs
Publication statusPublished - Mar 10 2003
Externally publishedYes

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Glucosylceramidase
Galactosylceramides
Keratinocytes
Skin
Cosmetics
Medicine
Water
Chemical activation
In Vitro Techniques

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes. / Fukunaga, Kyoko; Yoshida, Masahiro; Nakajima, Fumio; Uematsu, Rie; Hara, Mariko; Inoue, Shintaro; Kondo, Hirosato; Nishimura, Shin Ichiro.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 13, No. 5, 10.03.2003, p. 813-815.

Research output: Contribution to journalArticle

Fukunaga, Kyoko ; Yoshida, Masahiro ; Nakajima, Fumio ; Uematsu, Rie ; Hara, Mariko ; Inoue, Shintaro ; Kondo, Hirosato ; Nishimura, Shin Ichiro. / Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes. In: Bioorganic and Medicinal Chemistry Letters. 2003 ; Vol. 13, No. 5. pp. 813-815.
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