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dc.contributor.authorZhou, Jian
dc.contributor.authorNegi, Arvind
dc.contributor.authorMirallai, Styliana I.
dc.contributor.authorWarta, Rolf
dc.contributor.authorHerold-Mende, Christel
dc.contributor.authorCarty, Michael P.
dc.contributor.authorYe, Xin-Shan
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2021-01-08T09:30:05Z
dc.date.available2021-01-08T09:30:05Z
dc.date.issued2018-12-04
dc.identifier.citationZhou, 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.2018.12.003en_IE
dc.identifier.issn1090-2120
dc.identifier.urihttp://hdl.handle.net/10379/16431
dc.description.abstract1,5-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.en_IE
dc.description.sponsorshipResearch presented herein was supported by Science Foundation Ireland (07/IN.1/B966), the Irish Research Council (GOI PhD Scholarships to JZ, AN) and the European Commission through COST Action CM1106. The authors thank Guan-Nan Wang for recording NMR spectra and to Nadine Martinet for organization of the COST Action CM1106 screening library that led to identification of the activity for 16. The authors thank Dr. Stephen Rea and Dr. Helen Dodson for gifts of tumour cells.en_IE
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherElsevieren_IE
dc.relation.ispartofBioorganic Chemistryen
dc.subject1-Deoxyfuconojirimycinen_IE
dc.subjectFucosidaseen_IE
dc.subjectHomology modellingen_IE
dc.subjectAnti-cancer activityen_IE
dc.subjectN-alkylationen_IE
dc.subjectIminosugaren_IE
dc.titleN-Alkyl-1,5-dideoxy-1,5-imino-l-fucitols as fucosidase inhibitors: Synthesis, molecular modelling and activity against cancer cell linesen_IE
dc.typeArticleen_IE
dc.date.updated2021-01-06T19:50:45Z
dc.identifier.doi10.1016/j.bioorg.2018.12.003
dc.local.publishedsourcehttps://doi.org/10.1016/j.bioorg.2018.12.003en_IE
dc.description.peer-reviewedpeer-reviewed
dc.contributor.funderScience Foundation Irelanden_IE
dc.contributor.funderIrish Research Councilen_IE
dc.internal.rssid18272924
dc.local.contactPaul Murphy, School Of Chemistry, Room 108, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie
dc.local.copyrightcheckedYes
dc.local.versionACCEPTED
dcterms.projectinfo:eu-repo/grantAgreement/SFI/SFI Principal Investigator Programme (PI)/07/IN.1/B966/IE/Towards Novel Therapeutics for Angiogenesis Dependant Disease Based on Macrolides and Related Compounds/en_IE
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