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Structural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases
Open accessAbstract
Pharmacological inhibitors of glycogen synthase kinase-3 (GSK-3) and cyclin-dependent kinases have a promising potential for applications against several neurodegenerative diseases such as Alzheimer's disease. Indirubins, a family of bis-indoles isolated from various natural sources, are potent inhibitors of several kinases, including GSK-3. Using the cocrystal structures of various indirubins with GSK-3beta, CDK2 and CDK5/p25, we have modeled the binding of indirubins within the ATP-binding pocket of these kinases. This modeling approach provided some insight into the molecular basis of indirubins' action and selectivity and allowed us to forecast some improvements of this family of bis-indoles as kinase inhibitors. Predicted molecules, including 6-substituted and 5,6-disubstituted indirubins, were synthesized and evaluated as CDK and GSK-3 inhibitors. Control, kinase-inactive indirubins were obtained by introduction of a methyl substitution on N1.
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Cites
Indirubin and Indigo Are Potent Aryl Hydrocarbon Receptor Ligands Present in Human Urine
Adachi, J., Mori, Y., Matsui, S., Takigami, H., Fujino, J., Kitagawa, H., Miller, C. A., Kato, T., Saeki, K., & Matsuda, T. (2001) · Journal of Biological Chemistry · doi:10.1074/jbc.c100238200 · Cited by 407
Oxidation of Indole by Cytochrome P450 Enzymes
Gillam, E. M. J., Notley, L. M., Cai, H., De Voss, J. J., & Guengerich, F. P. (2000) · Biochemistry · doi:10.1021/bi001229u · Cited by 313
Cited by
Impact of Natural Products on Developing New Anti-Cancer Agents
Cragg, G. M., Grothaus, P. G., & Newman, D. J. (2009) · Chemical Reviews · doi:10.1021/cr900019j · Cited by 1,302
Pharmacological inhibitors of glycogen synthase kinase 3
MEIJER, L., FLAJOLET, M., & GREENGARD, P. (2004) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2004.07.006 · Cited by 584
Self-citationSturgeon, C. M., Ditadi, A., Awong, G., Kennedy, M., & Keller, G. (2014) · Nature Biotechnology · doi:10.1038/nbt.2915 · Cited by 467
Untangling tau hyperphosphorylation in drug design for neurodegenerative diseases
Mazanetz, M. P., & Fischer, P. M. (2007) · Nature Reviews Drug Discovery · doi:10.1038/nrd2111 · Cited by 459
GSK-3 Inhibitors: Preclinical and Clinical Focus on CNS
Eldar-Finkelman, H., & Martinez, A. (2011) · Frontiers in Molecular Neuroscience · doi:10.3389/fnmol.2011.00032 · Cited by 354
Metadata
- Authors
- Polychronopoulos, P., Magiatis, P., Skaltsounis, A.-L., Myrianthopoulos, V., Mikros, E., Tarricone, A., Musacchio, A., Roe, S. M., Pearl, L., Leost, M., Greengard, P., & Meijer, L.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-01-08
- Volume
- 47
- Issue
- 4
- Pages
- 935-946
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1970197612
- Cited by
- 380
- References
- 2
- FWCI
- 21.09
- Type
- journal article
- Language
- en
- Open access
- green
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- Polychronopoulos, P., Magiatis, P., Skaltsounis, A.-L., Myrianthopoulos, V., Mikros, E., Tarricone, A., Musacchio, A., Roe, S. M., Pearl, L., Leost, M., Greengard, P., & Meijer, L. (2004). Structural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm031016d
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