Abstract
β-Glucogallin (BGG), a major component of the Emblica officinalis medicinal plant, is a potent and selective inhibitor of aldose reductase (AKR1B1). New linkages (ether/triazole/amide) were introduced via high yielding, efficient syntheses to replace the labile ester, and an original two-step (90%) preparation of BGG was developed. Inhibition of AKR1B1was assessed in vitro and using transgenic lens organ cultures, which identified the amide linked glucoside (BGA) as a stable, potent, and selective therapeutic lead toward the treatment of diabetic eye disease.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Aldehyde Reductase / antagonists & inhibitors*
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Amides / chemical synthesis*
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Amides / chemistry
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Amides / pharmacology
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Drug Design
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Drug Stability
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Glycosides / chemical synthesis*
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Glycosides / chemistry
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Glycosides / pharmacology
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Humans
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Hydrolyzable Tannins / chemical synthesis
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Hydrolyzable Tannins / chemistry*
Substances
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Amides
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Enzyme Inhibitors
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Glycosides
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Hydrolyzable Tannins
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glucogallin
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AKR1B1 protein, human
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Aldehyde Reductase