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'Click chemistry' synthesis of 1-(?-D-mannopyranosyl)-1,2,3-triazoles for inhibition of ?-mannosidases.

ABSTRACT: Three new triazole conjugates derived from d-mannose were synthesized and assayed in in vitro assays to investigate their ability to inhibit ?-mannosidase enzymes from the glycoside hydrolase (GH) families 38 and 47. The triazole conjugates were more selective for a GH47 ?-mannosidase (Aspergillus saitoi ?1,2-mannosidase), showing inhibition at the micromolar level (IC50 values of 50-250 ?M), and less potent towards GH38 mannosidases (IC50 values in the range of 0.5-6 mM towards jack bean ?-mannosidase or Drosophila melanogaster lysosomal and Golgi ?-mannosidases). The highest selectivity ratio [IC50(GH38)/IC50(GH47)] of 100 was exhibited by the phenyltriazole conjugate. To understand structure-activity properties of synthesized compounds, 3-D complexes of inhibitors with ?-mannosidases were built using molecular docking calculations.

SUBMITTER: Polakova M 

PROVIDER: S-EPMC4382718 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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'Click chemistry' synthesis of 1-(α-D-mannopyranosyl)-1,2,3-triazoles for inhibition of α-mannosidases.

Poláková Monika M   Stanton Rhiannon R   Wilson Iain B H IB   Holková Ivana I   Šesták Sergej S   Machová Eva E   Jandová Zuzana Z   Kóňa Juraj J  

Carbohydrate research 20150119

Three new triazole conjugates derived from d-mannose were synthesized and assayed in in vitro assays to investigate their ability to inhibit α-mannosidase enzymes from the glycoside hydrolase (GH) families 38 and 47. The triazole conjugates were more selective for a GH47 α-mannosidase (Aspergillus saitoi α1,2-mannosidase), showing inhibition at the micromolar level (IC50 values of 50-250 μM), and less potent towards GH38 mannosidases (IC50 values in the range of 0.5-6 mM towards jack bean α-mann  ...[more]

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