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Design of an amide N-glycoside derivative of ?-glucogallin: a stable, potent, and specific inhibitor of aldose reductase.

ABSTRACT: ?-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.

SUBMITTER: Li L

PROVIDER: S-EPMC3956592 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Design of an amide N-glycoside derivative of β-glucogallin: a stable, potent, and specific inhibitor of aldose reductase.

Li Linfeng L Chang Kun-Che KC Zhou Yaming Y Shieh Biehuoy B Ponder Jessica J Abraham Adedoyin D AD Ali Hadi H Snow Anson A Petrash J Mark JM LaBarbera Daniel V DV

Journal of medicinal chemistry 20131223 1

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 selecti ...[more]

PMID: 24341381

Similar Datasets

The isolation and characterization of ?-glucogallin as a novel aldose reductase inhibitor from Emblica officinalis.

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(-)-Kusunokinin as a Potential Aldose Reductase Inhibitor: Equivalency Observed via AKR1B1 Dynamics Simulation.

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