Novel easily accessible glucosidase inhibitors: 4-hydroxy-5-alkoxy-1,2-cyclohexanedicarboxylic acids

Brazdova, Barbora; Tan, Nikmala S.; Samoshina, Nataliya M.; Samoshin, Vyacheslav V.

doi:10.1016/j.carres.2008.11.009

Cited by 26 publications

(31 citation statements)

References 52 publications

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“…Its inhibitors are be used to treat diabetics, HIV and cancers [3,4]. Clinical trials showed that the α-glucosidase inhibitors improved long-term glycemic control as measured by decreased hemoglobin A1c (HbA1c) in patients with type II diabetes and delayed the development of type II diabetes in patients with impaired glucose tolerance [5]. Recently, there had been widespread interest in α-glucosidase inhibitors, partly because of their potential as therapeutic targets, especially the inhibition of these enzymes had been found to help control postprandial blood glucose levels in diabetic patients [6,7], and can have profound effects on maturation, transport, and secretion of glycoproteins and can alter cell-cell recognition processes [8][9][10].…”

Section: Introdcutionmentioning

confidence: 99%

Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

Rahim

Ullah

Javid

et al. 2015

Bioorganic Chemistry

119

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Section: Introdcutionmentioning

confidence: 99%

Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

Rahim

Ullah

Javid

et al. 2015

Bioorganic Chemistry

119

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“…The preliminary tests against fungal glycosidases revealed only a weak to moderate inhibition of β-D-glucosidase by compounds 125 (R = H) and 127+128 (R = CH 3 , n-C 6 H 13 ), and a weak inhibition of α-L-fucosidase by compounds 125+126, and 127+128 (R = CH 3 , n-C 6 H 13 ). 111,155,156 However, very promising results were obtained for cyclohexanedicarboxylic acids of types 129-131. 111,[155][156][157][158] The synthesis of compounds 129-131…”

Section: 155-158mentioning

confidence: 99%

“…111,155,156 However, very promising results were obtained for cyclohexanedicarboxylic acids of types 129-131. 111,[155][156][157][158] The synthesis of compounds 129-131…”

Section: 155-158mentioning

confidence: 99%

“…These diacids were assayed for inhibitory activity against several glycosidases in multienzyme complexes isolated from fungi Penicillium canescens and Aspergillus oryzae. 111,[155][156][157][158] The inhibition was found to be specific with regard to the configuration of inhibitor, the type of enzyme, and even the particular source of enzyme. Most noticeably, these compounds inhibited α-and β-D-glucosidases.…”

Section: 155-158mentioning

confidence: 99%

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Syntheses of small cluster oligosaccharide mimetics

Franz¹,

Gross²,

Samoshin³

2009

Arkivoc

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We designed multiple Small Cluster Oligosaccharide Mimetics (SCOMs) -potential glycosidase inhibitors -to be metabolically stable and small enough to enter cells or bacteria. Therefore, minimal scaffolds (urea, amide, ammonia) or simply non-glycosidic linkages of carbohydrate structures were central to our synthetic strategy, including: (a) coupling of several natural carbohydrate precursors; (b) total syntheses of aminomethyl tetrahydropyrans and their chiral amides with quinic acid; (c) glycopyranosyl cyanide reduction to prepare crowded clusters on a urea scaffold; (d) total syntheses via cycloadditions leading to amide-linked C-glycosides; (e) reduction of nitromethyl C-glycosides; and (f) a synthesis of hydroxylated 1,2-cyclohexanedicarboxylic acids.

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“…-Glucosidase ( -D-glucoside glucohydrolase, EC 3.2.1.20) catalyses the release of D-glucose residues from the non-reducing end of a variety of substrates, including disaccharides, oligosaccharides and aryl-and alkyl--glucopyranosides (Zdzieb and Synowiecki, 2002;Brazdova et al, 2009). Thermostable -glucosidases isolated from a variety of microorganisms are suitable for the improvement of industrial starch processing into glucose syrup.…”

Section: Introductionmentioning

confidence: 99%

Essential groups and stability of α-glucosidase ofPenicillium notatum

2009

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--Glucosidase ( -D-glucoside glucohydrolase, EC 3.2.1.20) was isolated from Penicillium notatum. The enzyme was induced by gibberellic acid (GA 3 ). The GA 3 -mediated increase in the enzyme activity was repressed in presence of abscisic acid, cycloheximide and the antibiotics chloramphenicol, cordycepin, and rifampicin which are inhibitors of protein synthesis. -Glucosidase was purified 440-fold with of 27.8-fold of purification. The enzyme was immobilized using chitosan gel. The optimal pH values were 6.5 and 7.5 for free and the immobilized enzymes, respectively. The optimal temperatures were 50 and 65 °C for free and immobilized enzymes, respectively. The enzyme hydrolyzed maltose, sucrose, isomaltose, maltotriose but not starch, amylopectin and amylose. Trehalose and glycerol protected the free and immobilized enzymes against inactivation at 70 °C, however trehalose was the better protector. Phytate protected the free enzyme against heat inactivation at both 65 and 70 °C. 2,4,6 Trinitrobenzenesulfonic acid, butanedione and diethylpyrocarbonate inactivated the enzyme and suggest that, lysyl, arginyl and histidyl groups are taking part in enzyme catalysis. The inactivation by the three compounds was protected by the substrate para-nitrophenyl--D-glucopyranoside. Treatment of the enzyme with 1-ethyl-3(3-dimethyl aminopropyl)-carbodiimide, p-chloromercuribenzoate, N-bromosuccinimide, N-acetlyimidazole revealing the involving of carboxyl, sulfhydryl, trptophenyl and tyrosyl groups, respectively in the catalysis of -glucosidase. EDTA, o-phenanthroline, dipyridyl and 8-quinolinol inhibited the enzyme activity and the inhibition was higher in case of free enzyme compared with immobilized enzyme.

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Novel easily accessible glucosidase inhibitors: 4-hydroxy-5-alkoxy-1,2-cyclohexanedicarboxylic acids

Cited by 26 publications

References 52 publications

Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

Syntheses of small cluster oligosaccharide mimetics

Essential groups and stability of α-glucosidase ofPenicillium notatum

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