N-Alkyl-1,5-dideoxy-1,5-imino-l-fucitols as fucosidase inhibitors: Synthesis, molecular modelling and activity against cancer cell lines

Jian Zhou,Arvind Negi,Styliana I Mirallai,Rolf Warta,Christel Herold-Mende,Michael P Carty,Xin-Shan Ye,Paul V Murphy

doi:10.1016/j.bioorg.2018.12.003

N-Alkyl-1,5-dideoxy-1,5-imino-l-fucitols as fucosidase inhibitors: Synthesis, molecular modelling and activity against cancer cell lines

Jian Zhou, Arvind Negi + Show 6 more

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https://doi.org/10.1016/j.bioorg.2018.12.003

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Journal: Bioorganic chemistry	Publication Date: Dec 4, 2018
Citations: 16	License type: cc-by-nc-nd

Affiliation: University College Dublin, National University of Ireland, Heidelberg University, Peking University

#Bacterial Fucosidase #Fucosidase Inhibitors + Show 8 more

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Abstract

1,5-Dideoxy-1,5-imino-l-fucitol (1-deoxyfuconojirimycin, DFJ) is an iminosugar that inhibits fucosidases. Herein, N-alkyl DFJs have been synthesised and tested against the α-fucosidases of T. maritima (bacterial origin) and B. taurus (bovine origin). The N-alkyl derivatives were inactive against the bacterial fucosidase, while inhibiting the bovine enzyme. Docking of inhibitors to homology models, generated for the bovine and human fucosidases, was carried out. N-Decyl-DFJ was toxic to cancer cell lines and was more potent than the other N-alkyl DFJs studied.

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