Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain

Nicolas Ardes-Guisot; Dominic S. Alonzi; Gabriele Reinkensmeier; Terry D. Butters; Caroline Norez; Frédéric Becq; Yousuke Shimada; Shinpei Nakagawa; Atsushi Kato; Yves Blériot; Matthieu Sollogoub; Boris Vauzeilles

doi:10.1039/c1ob05119a

Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain

Nicolas Ardes-Guisot, Dominic S. Alonzi, Gabriele Reinkensmeier, Terry D. Butters, Caroline Norez, Frédéric Becq, Yousuke Shimada, Shinpei Nakagawa, Atsushi Kato, Yves Blériot^*, Matthieu Sollogoub, Boris Vauzeilles

^*この論文の責任著者

薬剤部

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

44 被引用数 (Scopus)

抄録

A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-α-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.

本文言語	英語
ページ（範囲）	5373-5388
ページ数	16
ジャーナル	Organic and Biomolecular Chemistry
巻	9
号	15
DOI	https://doi.org/10.1039/c1ob05119a
出版ステータス	出版済み - 2011/08/07

ASJC Scopus 主題領域

生化学
物理化学および理論化学
有機化学

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Ardes-Guisot, N., Alonzi, D. S., Reinkensmeier, G., Butters, T. D., Norez, C., Becq, F., Shimada, Y., Nakagawa, S., Kato, A., Blériot, Y., Sollogoub, M., & Vauzeilles, B. (2011). Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain. Organic and Biomolecular Chemistry, 9(15), 5373-5388. https://doi.org/10.1039/c1ob05119a

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title = "Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain",

abstract = "A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-α-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.",

author = "Nicolas Ardes-Guisot and Alonzi, {Dominic S.} and Gabriele Reinkensmeier and Butters, {Terry D.} and Caroline Norez and Fr{\'e}d{\'e}ric Becq and Yousuke Shimada and Shinpei Nakagawa and Atsushi Kato and Yves Bl{\'e}riot and Matthieu Sollogoub and Boris Vauzeilles",

year = "2011",

month = aug,

day = "7",

doi = "10.1039/c1ob05119a",

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Ardes-Guisot, N, Alonzi, DS, Reinkensmeier, G, Butters, TD, Norez, C, Becq, F, Shimada, Y, Nakagawa, S, Kato, A, Blériot, Y, Sollogoub, M & Vauzeilles, B 2011, 'Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain', Organic and Biomolecular Chemistry, vol. 9, no. 15, pp. 5373-5388. https://doi.org/10.1039/c1ob05119a

TY - JOUR

T1 - Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain

AU - Ardes-Guisot, Nicolas

AU - Alonzi, Dominic S.

AU - Reinkensmeier, Gabriele

AU - Butters, Terry D.

AU - Norez, Caroline

AU - Becq, Frédéric

AU - Shimada, Yousuke

AU - Nakagawa, Shinpei

AU - Kato, Atsushi

AU - Blériot, Yves

AU - Sollogoub, Matthieu

AU - Vauzeilles, Boris

PY - 2011/8/7

Y1 - 2011/8/7

N2 - A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-α-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.

AB - A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-α-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.

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U2 - 10.1039/c1ob05119a

DO - 10.1039/c1ob05119a

M3 - 学術論文

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AN - SCOPUS:79960343811

SN - 1477-0520

VL - 9

SP - 5373

EP - 5388

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 15

ER -

Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain

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