N-Alkyl-1,5-dideoxy-1,5-imino-l-fucitols as fucosidase inhibitors: Synthesis, molecular modelling and activity against cancer cell lines
Zhou, Jian Negi, Arvind Mirallai, Styliana I. Warta, Rolf Herold-Mende, Christel Carty, Michael P. Ye, Xin-Shan Murphy, Paul V.
Zhou, Jian
Negi, Arvind
Mirallai, Styliana I.
Warta, Rolf
Herold-Mende, Christel
Carty, Michael P.
Ye, Xin-Shan
Murphy, Paul V.
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Publication Date
2018-12-04
Type
Article
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Citation
Zhou, Jian, Negi, Arvind, Mirallai, Styliana I., Warta, Rolf, Herold-Mende, Christel, Carty, Michael P., Ye, Xin-Shan, Murphy, Paul V. (2019). N-Alkyl-1,5-dideoxy-1,5-imino-l-fucitols as fucosidase inhibitors: Synthesis, molecular modelling and activity against cancer cell lines. Bioorganic Chemistry, 84, 418-433. doi:https://doi.org/10.1016/j.bioorg.2018.12.003
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 ¿-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.
Publisher
Elsevier
Publisher DOI
10.1016/j.bioorg.2018.12.003
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Attribution-NonCommercial-NoDerivs 3.0 Ireland