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

Author(s): Michela I. Simone*, Laura J. Mares, Clothilde A. Eveleens, Adam McCluskey, Brighid B. Pappin, Milton J. Kiefel, Todd A. Houston*.

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 18 , Issue 10 , 2018

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Abstract:

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.

Keywords: Cadmium, computational, copper, cyclophellitol, deoxynojirimycin, diabetes, electrophilic, epoxide, fucosidase, galactosidase, glucocerebroside, glucosidase, glycal, homology, hydantocidin, iminosugar, lactam, lactone, mannosidase, metal complex, modeling, molybdenum, natural product, palladium, salacinol, sialidase, silver, transition-state mimic, vanadium, X-ray crystallography, zinc.

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Article Details

VOLUME: 18
ISSUE: 10
Year: 2018
Page: [812 - 827]
Pages: 16
DOI: 10.2174/1389557517666171002161325
Price: $65

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