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Soluble 3',6-substituted indirubins with enhanced selectivity toward glycogen synthase kinase -3 alter circadian period.

Abstract：

:Glycogen synthase kinase -3 (GSK-3) is a key enzyme involved in numerous physiological events and in major diseases, such as Alzheimer's disease, diabetes, and cardiac hypertrophy. Indirubins are bis-indoles that can be generated from various natural sources or chemically synthesized. While rather potent and selective as GSK-3 inhibitors, most indirubins exhibit low water solubility. To address the issue of solubility, we have designed novel analogues of 6-bromo-indirubin-3'-oxime with increased hydrophilicity based on the GSK-3/indirubins cocrystal structures. The new derivatives with an extended amino side chain attached at position 3' showed potent GSK-3 inhibitory activity, enhanced selectivity, and dramatically increased water solubility. Furthermore, some of them displayed little or no cytotoxicity. The new indirubins inhibit GSK-3 in a cellular reporter model. They alter the circadian period measured in rhythmically expressing cell cultures, suggesting that they might constitute tools to investigate circadian rhythm regulation.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Vougogiannopoulou K,Ferandin Y,Bettayeb K,Myrianthopoulos V,Lozach O,Fan Y,Johnson CH,Magiatis P,Skaltsounis AL,Mikros E,Meijer L

doi

10.1021/jm800648y

subject

Has Abstract

pub_date

2008-10-23 00:00:00

pages

6421-31

issue

20

eissn

0022-2623

issn

1520-4804

journal_volume

51

pub_type

杂志文章

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