Gene/Protein Disease Symptom Drug Enzyme Compound
Pivot Concepts:   Target Concepts:
Query: EC:3.2.1.20 (alpha-glucosidase)
 4,237 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Chromatographic separation of the pod extract of Angylocalyx pynaertii resulted in the isolation of 13 sugar-mimic alkaloids (1-13). The structures of the new alkaloids were elucidated by spectroscopic methods as the 6-O-beta-D-glucoside (10) and N-hydroxyethyl derivative (11) of 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) (1), 1,6-dideoxynojirimycin (12), and 1,3,4-trideoxynojirimycin (13). 2,5-Imino-1,2,5-trideoxy-L-glucitol (7), 2,5-dideoxy-2,5-imino-D-fucitol (8), and beta-homofuconojirimycin (9), isolated from the pods as well as the bark, were very specific inhibitors of alpha-L-fucosidase with no significant inhibitory activity toward other glycosidases. In this work, 1,4-dideoxy-1,4-imino-D-ribitol (6) was found to be a better inhibitor of lysosomal beta-mannosidase than 2,5-imino-1,2,5-trideoxy-D-mannitol (2). N-Hydroxyethyl-1-deoxynojirimycin (miglitol), which is commercially available for the treatment of diabetes, retained its inhibitory potential toward rat intestinal maltase and sucrase, whereas 11 and the synthetic N-hydroxyethyl derivative of 2,5-dideoxy-2,5-imino-D-mannitol markedly lowered or abolished their inhibition toward all enzymes tested.
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PMID:New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii. 1185 56

Discovery of a very potent alpha-fucosidase inhibitor 5a-carba-alpha-L-fucopyranosylamine led to preparation of its beta-anomer and the respective unsaturated derivatives, fucose-type alpha- and beta-valienamines, in order to elucidate the structure-activity relationship of carba-aminosugar inhibitors of this kind. Compound was demonstrated to be a potent inhibitor (K(i)=2.0 x 10(-7) M, bovine kidney), possessing ca. one-tenth of the activity of the parent. Interestingly, and were found to be rather weak inhibitors, contrary to the expectations based on the activity relationships between the alpha-glucosidase inhibitors, alpha-glucose-type validamine and valienamine.
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PMID:Synthesis of an alpha-fucosidase inhibitor, 5a-carba-beta-L-fucopyranosylamine, and fucose-type alpha- and beta-DL-valienamine unsaturated derivatives. 1185 94

In order to investigate the hypothesis that the glycosidase inhibitor isofagomine was bound to alpha- or beta-glucosidase in a 1,4B conformation, a number of bicyclic aziridines that adopt the 1,4B or B1,4 conformations were synthesised and investigated. (1R)-2-endo,3-exo-2,3-Dihydroxy-4-endo-4-hydroxymethyl-6- azabicyclo[3.1.0]hexane (5) and its N-methyl and N-benzyl analogues and (1S)-2-exo-3-endo-2,3-dihydroxy-4- endo-4-hydroxymethyl-6-azabicyclo-[3.1.0]hexane (6) were synthesised. The aziridines 5 and 6 were found to be weak or not inhibitors of alpha-glucosidase, beta-glucosidase and alpha-fucosidase.
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PMID:Aziridines as a structural motif to conformational restriction of azasugars. 1292 48

Coproantigen ELISA based tests for diagnosis of canine echinococcosis provide high specificity and sensitivity. However, the antigenic molecules present in faeces from infected dogs have not yet been characterised. While initial attempts to determine the molecular weights of Echinococcus granulosus coproantigens by SDS-PAGE and Western blotting with coproantigen reactive capture antibodies were equivocal, they suggested presence of a significant carbohydrate component. Periodate treatment of coproantigen positive faecal supernatants resulted in a significant reduction (53%) in ELISA activity, suggesting that carbohydrates are involved in the antigenic structure of E. granulosus coproantigens. Protease treatment of antigenic molecules resulted in an 11% reduction in absorbance in ELISA, indicating that protein components were also present which affected by enzyme activity. Lectin-binding ELISA assays indicated strong affinity of E. granulosus coproantigens to concanavalin agglutinin and Lens culinaris agglutinin, and moderate binding to wheat-germ agglutinin and peanut agglutinin. No binding was detectable to Ulex europaensis agglutinin-I, Bandeiraea simplicifolia or Dolichos biflorus agglutinin. These data indicate that E. granulosus coproantigens from infected dog faeces possibly contained alpha-D-mannose and/or alpha-D-glucose, beta-galactose and N-acetyl-beta-glucosamine residues. To verify the role of carbohydrate moieties in coproantigens, faecal samples were treated with exoglycosidase and tested in the coproantigen ELISA. Treatment with beta-galactosidase or N-acetyl-beta-glucosamine reduced ELISA activity by 44 and 30%, respectively. Incubation with a panel of other specific exoglycosidases including alpha-galactosidase as well as alpha-L-fucosidase, alpha-mannosidase, beta-mannosidase, alpha-glucosidase, beta-glucosidase, beta- fructosidase, or neuraminidase, did not alter coproantigen detection in ELISA. The results indicate that coproantigens present in faeces from E. granulosus naturally infected dogs were highly glycosylated and contain beta- galactose and N-acetyl-beta-glucosamine. The putative relationship of antigenic molecules with the tapeworm glycocalyx is discussed.
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PMID:Partial characterisation of carbohydrate-rich Echinococcus granulosus coproantigens. 1457 18

A few alpha-L-fucosidase inhibitors and alpha-D-glucosidase inhibitors have shown in vitro anti-HIV activities, that have been attributed to their ability to inhibit HIV entry. The mechanism of action of inhibitors such as 1-deoxynojirimycin (1) is not clearly established. One possible hypothesis is that the glycosidase inhibition affects the final conformation of the glycoproteins involved in the virus/cell recognition and fusion phenomena. This hypothesis is presented critically and the mechanisms of some glycoprotein biosynthesis are out-lined. Up to now, very few glycosidase inhibitors have been assayed for their potential as HIV entry inhibitors. Further assaying should be done and larger collections of glycosidase inhibitors should be prepared. To help investigations in that perspective, the inhibitory activities of alpha-glucosidase and alpha-L-fucosidase inhibitors have been summarized.
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PMID:Glycosidase inhibitors as potential HIV entry inhibitors? 1532 Jul 5

A series of 16 new chiral nonracemic polyhydroxylated piperidines was synthesized utilizing several chiral beta-amino-alcohols. They act as a nitrogen source, chirality inducer and iminium stabilizer, in the desymmetrization of meso-trihydroxylated glutaraldehyde. The biological activity of these compounds towards several glycosidases (alpha-D-glucosidase, alpha-D-mannosidase, alpha-L-fucosidase) has been evaluated.
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PMID:Synthesis of polyhydroxylated piperidines and evaluation as glycosidase inhibitors. 1535 92

Activities of seven acid glycosidases: beta-N-acetylhexosaminidase (beta-HEX), alpha- and beta-galactosidase (alpha- and beta-GAL), alpha- and beta-mannosidase (alpha- and beta-MAN), alpha-glucosidase and alpha-fucosidase in magnum region of hen (Gallus gallus domesticus) oviduct, and four acid glycosidases: beta-HEX, beta-GAL, alpha- and beta-MAN in egg albumen, were investigated. beta-HEX from magnum and egg albumen hydrolysed 4-methylumbelliferyl-beta-N-acetylhexosamine-6-sulphate (4-MeUmbGlcNAc-6-SO(4)) like mammalian beta-HEX form A. Multiple forms of magnum and egg albumen beta-HEX, beta-GAL, alpha- and beta-MAN were separated by strong anion exchange chromatography and chromatofocusing method. Chromatofocusing of the magnum resulted in the appearance of multiple forms for beta-HEX with pI of 6.18, 5.43, 5.55, 5.34, 5.27 and 5.16, for beta-GAL with pI of 4.98, 4.84, 4.77, 4.64 and 4.68-4.63, for alpha-MAN with pI of >or=7.4, 6.75, 6.62 and 6.26, and for beta-MAN two forms with pI of 6.37 and 5.77. Chromatofocusing of egg albumen yields multiple forms for beta-HEX with pI of 6.24, 6.08, 5.55 and 5.35, for beta-GAL two forms with pI of 5.10 and 4.86-4.80 for alpha-MAN multiple forms with pI of >or=7.4, 6.80, 6.60 and 6.30, and for beta-MAN forms with pI of 6.30 and 5.77. In conclusion, this study was the first to show beta-HEX activity against 4-MeUmbGlcNAc-6-SO(4) in the magnum and albumen of bird eggs, corresponding to beta-HEX A activity in mammals. Main multiple forms of beta-HEX, beta-GAL, alpha- and beta-MAN occurring in the magnum were revealed in the egg albumen. Comparison with a cock of the same breed showed that hen egg magnum and albumen has the same multiple forms of the enzymes that are found in the epididymides and seminal plasma of the cock.
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PMID:Acid glycosidases from hen oviduct and egg albumen. 1623 36

Specific activities of seven acid glycosidases: beta-hexosaminidase, alpha- and beta-galactosidase, alpha- and beta-mannosidase, alpha-glucosidase and alpha-fucosidase were determined in various parts of the domestic hen oviduct (infundibulum, isthmus, shell gland and vagina). The activity of most enzymes was the highest in the isthmus. Multiple forms of all acid glycosidases from the isthmus were separated by strong anion exchange chromatography at pH 6.0. The isoelectric points of the isthmus forms of beta-hexosaminidase, beta-galactosidase and alpha- and beta-mannosidase were determined by chromatofocusing. For the first time the high beta-galactosidase activity was found in hen egg shell membranes.
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PMID:Acid glycosidases in the isthmus of the hen oviduct and egg shell membranes. 1722 Sep 42

5a-Carba-alpha-D-glucopyranosylamine, validamine, and analogous compounds valienamine and valiolamine, have proved to be important lead compounds for development of clinically useful medicines, including the very strong alpha-glucosidase inhibitor, voglibose, N-(1,3-dihydroxyprop-2-yl)valiolamine, now used widely as a clinically important antidiabetic agent. In this review, we describe recent advances in development of glycosidase inhibitors on the basis of the ground-state mimics of the postulated glycopyranosyl cation, considered to be formed during hydrolysis of glycopyranosides, and introduce a new type of highly potent alpha-fucosidase inhibitor, 5a-carba-alpha-L-fucopyranosylamine, alpha-fuco validamine. Interestingly, the corresponding beta-anomer, and in particular its D-enantiomer, has been shown to possess very strong cross-inhibitory activity toward beta-galactosidase and beta-glucosidase. Structure and inhibitory activity relationships concerning these alpha,beta-fuco derivatives, as well as parent alpha,beta-galacto validamines are discussed here with reference to our results.
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PMID:Design and synthesis of 5a-carbaglycopyranosylamime glycosidase inhibitors. 1919 96

Iminosugars are monosaccharide analogues that have been demonstrated to be specific inhibitors for glycosidases and are currently used therapeutically in several human disorders. N-alkylated derivatives of D-fagomine and (2R,3S,4R,5S)-2-(hydroxymethyl)-5-methylpyrrolidine-3,4-diol with aliphatic chains were tested in eight human cancer cell lines to analyze their cytotoxicity and the inhibitory effect in the activities of specific glycosidases. Results indicate that these compounds were more cytotoxic as the length of the alkyl chain increases. N-dodecyl-D-fagomine inhibited specifically the alpha-D-glucosidase activity in cell lysates, whereas no effect was detected in other glycosidases. The N-dodecyl derivative of (2R,3S,4R,5S)-2-(Hydroxymethyl)-5-methylpyrrolidine-3,4-diol induced specific inhibition against alpha-L-fucosidase in cell lysates. Our results indicated that the length of the alkyl chain linked to the iminosugars determine their cytotoxicity as well as the inhibitory effect on the enzymatic activities of specific glycosidases, in human cancer cell lines.
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PMID:Cytotoxicity and enzymatic activity inhibition in cell lines treated with novel iminosugar derivatives. 2004 Dec 92


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