N-Alkyl-1,5-dideoxy-1,5-imino-L-fucitols as fucosidase inhibitors: synthesis, molecular modelling and activity against cancer cell lines
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...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2019
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| In: |
Bioorganic chemistry
Year: 2018, Volume: 84, Pages: 418-433 |
| ISSN: | 1090-2120 |
| DOI: | 10.1016/j.bioorg.2018.12.003 |
| Online Access: | Verlag, Volltext: https://doi.org/10.1016/j.bioorg.2018.12.003 Verlag, Volltext: http://www.sciencedirect.com/science/article/pii/S0045206818311519 
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| Author Notes: | Jian Zhou, Arvind Negi, Styliana I. Mirallai, Rolf Warta, Christel Herold-Mende, Michael P. Carty, Xin-Shan Ye, Paul V. Murphy |
| Summary: | 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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| Item Description: | Available online 04 December 2018 Gesehen am 18.09.2019 |
| Physical Description: | Online Resource |
| ISSN: | 1090-2120 |
| DOI: | 10.1016/j.bioorg.2018.12.003 |