Back to (non-)Basics: An Update on Neutral and Charge-Balanced Glycosidase Inhibitors

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Author(s)
Simone, Michela I
Mares, Laura J
Eveleens, Clothilde A
McCluskey, Adam
Pappin, Brighid B
Kiefel, Milton J
Houston, Todd A
Year published
2018
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Glycosidases have important anti-cancer, anti-viral and anti-diabetic properties. This review covers the literature in the past 15 years since our initial review in this journal on “neutral” glycosidase inhibitors lacking a basic nitrogen found in iminosugars and azasugars or inhibitors that are neutral by virtue of being “charge-balanced” (zwitterionic). These structurally diverse inhibitors include lactones, lactams, epoxides such as cyclophellitol, and sulfonium ion derivatives of the natural product salacinol. Synthetic efforts toward cyclophillitol, salicinol and derivatives are also highlighted. Importantly, certain ...
View more >Glycosidases have important anti-cancer, anti-viral and anti-diabetic properties. This review covers the literature in the past 15 years since our initial review in this journal on “neutral” glycosidase inhibitors lacking a basic nitrogen found in iminosugars and azasugars or inhibitors that are neutral by virtue of being “charge-balanced” (zwitterionic). These structurally diverse inhibitors include lactones, lactams, epoxides such as cyclophellitol, and sulfonium ion derivatives of the natural product salacinol. Synthetic efforts toward cyclophillitol, salicinol and derivatives are also highlighted. Importantly, certain metals can inhibit glycosidases and care must be taken to remove residual catalysts from synthetic material to be tested against these enzymes.
View less >
View more >Glycosidases have important anti-cancer, anti-viral and anti-diabetic properties. This review covers the literature in the past 15 years since our initial review in this journal on “neutral” glycosidase inhibitors lacking a basic nitrogen found in iminosugars and azasugars or inhibitors that are neutral by virtue of being “charge-balanced” (zwitterionic). These structurally diverse inhibitors include lactones, lactams, epoxides such as cyclophellitol, and sulfonium ion derivatives of the natural product salacinol. Synthetic efforts toward cyclophillitol, salicinol and derivatives are also highlighted. Importantly, certain metals can inhibit glycosidases and care must be taken to remove residual catalysts from synthetic material to be tested against these enzymes.
View less >
Journal Title
Mini-Reviews in Medicinal Chemistry
Volume
18
Issue
10
Copyright Statement
© 2018 Bentham Science Publishers. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. The published manuscript is available at EurekaSelect via https://doi.org/10.2174/1389557517666171002161325.
Subject
Medicinal and biomolecular chemistry
Medicinal and biomolecular chemistry not elsewhere classified
Pharmacology and pharmaceutical sciences