Carboxylated aurone derivatives as potent inhibitors of xanthine oxidase
[Display omitted] •Carboxylated aurone derivatives are able to inhibit xanthine oxidase in vitro.•The inhibition efficiency of the aurone derivatives is higher than that of sulfuretin.•Modes of inhibitor binding to the enzyme active site are proposed. Xanthine oxidase is a potential target for treat...
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Published in | Bioorganic & medicinal chemistry Vol. 25; no. 14; pp. 3606 - 3613 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
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Elsevier Ltd
15.07.2017
Elsevier |
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Abstract | [Display omitted]
•Carboxylated aurone derivatives are able to inhibit xanthine oxidase in vitro.•The inhibition efficiency of the aurone derivatives is higher than that of sulfuretin.•Modes of inhibitor binding to the enzyme active site are proposed.
Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4′-position of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 50 fold higher than of A-ring modified aurones with carboxymethoxy group at the 6-position. The binding modes of the carboxylated aurones in the active site of xanthine oxidase were explained using molecular docking calculations. |
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AbstractList | Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4'-position of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 50 fold higher than of A-ring modified aurones with carboxymethoxy group at the 6-position. The binding modes of the carboxylated aurones in the active site of xanthine oxidase were explained using molecular docking calculations. Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4'-position of B-ring were found to be potent inhibitors of the enzyme with IC values in the low micromolar range. The effects of these compounds were about 50 fold higher than of A-ring modified aurones with carboxymethoxy group at the 6-position. The binding modes of the carboxylated aurones in the active site of xanthine oxidase were explained using molecular docking calculations. Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4'-position of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 50 fold higher than of A-ring modified aurones with carboxymethoxy group at the 6-position. The binding modes of the carboxylated aurones in the active site of xanthine oxidase were explained using molecular docking calculations. (C) 2017 Elsevier Ltd. All rights reserved. [Display omitted] •Carboxylated aurone derivatives are able to inhibit xanthine oxidase in vitro.•The inhibition efficiency of the aurone derivatives is higher than that of sulfuretin.•Modes of inhibitor binding to the enzyme active site are proposed. Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4′-position of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 50 fold higher than of A-ring modified aurones with carboxymethoxy group at the 6-position. The binding modes of the carboxylated aurones in the active site of xanthine oxidase were explained using molecular docking calculations. |
Author | Kobzar, Oleksandr L. Vovk, Andriy I. Muzychka, Oksana V. Popova, Antonina V. Frasinyuk, Mykhaylo S. |
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Keywords | Enzyme inhibition Aurone derivatives Xanthine oxidase Structure-activity relationship Molecular docking DESIGN MECHANISM MOLYBDENUM OXIDOREDUCTASE FLAVONOIDS SCAVENGERS DISCOVERY ENZYMES AGENTS SCAFFOLD |
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•Carboxylated aurone derivatives are able to inhibit xanthine oxidase in vitro.•The inhibition efficiency of the aurone derivatives is higher... Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were... |
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SubjectTerms | Aurone derivatives Benzofurans - chemical synthesis Benzofurans - chemistry Benzofurans - metabolism Binding Sites Biochemistry & Molecular Biology Carboxylic Acids - chemistry Catalytic Domain Chemistry Chemistry, Medicinal Chemistry, Organic Enzyme inhibition Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - metabolism Inhibitory Concentration 50 Kinetics Life Sciences & Biomedicine Molecular docking Molecular Docking Simulation Pharmacology & Pharmacy Physical Sciences Science & Technology Structure-Activity Relationship Xanthine oxidase Xanthine Oxidase - antagonists & inhibitors Xanthine Oxidase - metabolism |
Title | Carboxylated aurone derivatives as potent inhibitors of xanthine oxidase |
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