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

doi:10.1016/S0960-894X(03)00006-4

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 journal › Article › peer-review

19 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 language	English
Pages (from-to)	813-815
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	13
Issue number	5
DOIs	https://doi.org/10.1016/S0960-894X(03)00006-4
Publication status	Published - Mar 10 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

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

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10.1016/S0960-894X(03)00006-4

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

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.",

author = "Kyoko Fukunaga and Masahiro Yoshida and Fumio Nakajima and Rie Uematsu and Mariko Hara and Shintaro Inoue and Hirosato Kondo and Nishimura, {Shin Ichiro}",

note = "Funding Information: The present work was supported by a grant for {\textquoteleft}Research and Development on Glycocluster Controlling Biomolecules{\textquoteright} from the New Energy and Industrial Technology Development Organization (NEDO).",

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doi = "10.1016/S0960-894X(03)00006-4",

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T1 - Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes

AU - Fukunaga, Kyoko

AU - Yoshida, Masahiro

AU - Nakajima, Fumio

AU - Uematsu, Rie

AU - Hara, Mariko

AU - Inoue, Shintaro

AU - Kondo, Hirosato

AU - Nishimura, Shin Ichiro

N1 - Funding Information: The present work was supported by a grant for ‘Research and Development on Glycocluster Controlling Biomolecules’ from the New Energy and Industrial Technology Development Organization (NEDO).

PY - 2003/3/10

Y1 - 2003/3/10

N2 - 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.

AB - 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.

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DO - 10.1016/S0960-894X(03)00006-4

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SN - 0960-894X

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 5

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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