Identification of potential glycogen kinase-3 inhibitors by structure based virtual screening

Biophysical Chemistry

Volumn 128, Issue 2-3, 2007, Pages 165-175

  Dessalew, Nigus ^a   Bharatam, Prasad V ^b  

^a ADDIS ABABA UNIVERSITY   (Ethiopia)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Docking; FlexX; GSK3; Pharmacophore mapping; Virtual screening

Indexed keywords

GLYCOGEN SYNTHASE KINASE 3; GLYCOGEN SYNTHASE KINASE 3 INHIBITOR;

ARTICLE; BINDING SITE; CRYSTALLOGRAPHY; DRUG ACTIVITY; ENZYME BINDING; HYDROGEN BOND; PHARMACOPHORE; PRIORITY JOURNAL; SCORING SYSTEM; VIRTUAL REALITY;

COMPUTER SIMULATION; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; GLYCOGEN SYNTHASE KINASE 3; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

RUMEX;

EID: 34249861511     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2007.04.001     Document Type: Article

References (53)

1. Renfrey S., and Featherstone J. Structural proteomics. Nat. Rev. Drug Discov. 1 (2002) 175-176
2. Cohen P. Protein kinases - the major drug targets for the twenty-first century?. Nat. Rev. Drug Discov. 1 (2002) 309-315
3. Noble M.E., Endicott J.A., and Johnson L.N. Protein kinase inhibitors: insight into drug design from structures. Science 303 (2004) 1800-1805
4. Adams J.L., and Lee D. Recent progress towards the identification of selective inhibitors of serine/threonine protein kinases. Curr. Opin. Drug Discov. Dev. 2 (1999) 96-109
5. Garcia-Echeverria C., Traxler P., and Evans D.B. ATP site directed competitive and irreversible inhibitors of protein kinases. Med. Res. Rev. 20 (2000) 28-57
6. Sridhar R., Hanson-Painton O., and Cooper D.R. Protein kinases as therapeutic targets. Pharm. Res. 17 (2000) 1345-1353
7. Dumas J. Protein kinase inhibitors: emerging pharmacophores 1997-2000. Expert Opin. Ther. Pat. 11 (2001) 405-429
8. Frame S., and Cohen P. GSK3 takes center stages more than 20 years after its discovery. Biochem. J. 359 (2001) 1-16
9. Doble B.W., and Woodget J.R. GSK3: tricks of the trade for a multi-staking kinase. J. Cell Sci. 116 (2003) 1175-1186
10. Jope R.S., and Johnson G.V.W. The glamour and gloom of GSK3. Trends Biochem. Sci. 29 (2004) 95-102
11. Welsh G.I., and Proud C.G. Glycogen synthase kinase-3 is rapidly inactivated in response to insulin and phosphorylates eukaryotic initiation factor Eif-2B. Biochem. J. 294 (1993) 625-629
12. Woodget J.R. Molecular cloning and expression of glycogen synthasekinase-3/factor A. EMBO J. 9 (1990) 2431-2438
13. Grimes C.A., and Jope R.S. The multifaceted role of glycogen synthase kinase-3β in cellular signaling. Prog. Neurobiol. 65 (2001) 391-426
14. Eldar-Finkelman H. Glycogen synthase kinase-3β: an emerging therapeutic target. Trends Mol. Med. 8 (2002) 126-132
15. Kaidanovich O., and Eldar-Finkelman H. The role of glycogen synthase kinase-3 in insulin resistance and type II diabetes. Expert Opin. Ther. Targets 6 (2002) 555-561
16. Castro A., and Martinez A. Inhibition of tau hyperphosphorylation: a new therapeutic strategy for the treatment of Alzheimer's disease and other neurodegenerative disorders. Expert Opin. Ther. Pat. 10 (2000) 1519-1527
17. Phiel C.J., and Klein P.S. Molecular targets of insulin action. Annu. Rev. Pharmacol. Toxicol. 41 (2001) 789-813
18. Hoeflich K.P., Luo J., Rubie E.A., Tsao M.S., Jin O., and Woodget J.R. Requirement of glycogen synthase kinase-3β in cell survival and NF-Kb activation. Nature 46 (2000) 86-90
19. Maryse L., Schultz C., Andreas L., Yong-Zhong W., Gretchem L.S., and Zaharevitz D.W. Paullones are potent inhibitors of glycogen synthase kinase-3β and cyclin dependant kinase 5/p25. Eur. J. Biochem. 267 (2000) 5983-5994
20. Meijer L., Skaltsounis A., Magiatis P., and Knockaert M. GSK-3 selective inhibitors derived from tyrian purple indirubins. Chem. Biol. 10 (2003) 1255-1266
21. Thomas A.E., Sushant M., Timothy P.B., James R.H., David M., Warren J.P., and Kelly F. The development of potent and selective bisarylmaleimide GSK3 inhibitors. Bioorg. Med. Chem. Lett. 15 (2005) 899-903
22. David G.S., Marianne B., Ashley E.F., David H., Robert J.I., Martin S., Brian P.S., Rachel S., and Robert W.W. 3-Anilino-4-arylmaleimides: potent and selective inhibitors of glycogen synthase kinase-3. Bioorg. Med. Chem. Lett. 11 (2001) 635-639
23. Hang-Cheng Z., Kimberly B.W., Hong Y., David F.M., Claudia K.D., Michael F.A., Patricia A.G., Annette J.E., Bruce R.C., Lori W., Jun Z.X., Richard A.L., Keith T.D., Stuart E., and Bruce E.M. Macrocyclic bisindolylymaleimides as inhibitors of protein kinase C and glycogen kinase-3. Bioorg. Med. Chem. Lett. 13 (2003) 3049-3053
24. Gee-Hong K., Catherine P., Alan D., Lan S., David J.O., Chandra S., and Peter J.C. Synthesis and discovery of macrocyclic and polyoxygenated Bis-7-azaindolylmaleimides as a novel series of potent and highly selective glycogen synthase kinase-3β inhibitors. J. Med. Chem. 46 (2003) 4021-4031
25. Dajani R., Fraser E., Roe S.M., Young N., Good V., Dale T.C., and Pearl L.H. Crystal structure of glycogen synthase kinase 3β: structural basis for phosphate-primed substrate specificity and autoinhibition. Cell 105 (2001) 721-732
26. Gund P. Pharmacophoric pattern searching and receptor mapping. Annu. Rep. Med. Chem. 4 (1977) 299-308
27. van Drie J.H. Pharmacophore discovery - lessons learned. Curr. Pharm. Des. 9 (2003) 1649-1664
28. Kozikowski A.P., Salah M.K.E., Johnson K.M., and Bergman J.S. Chemistry and biology of the 2 beta-alkyl-3-beta-phenyl analogues of cocaine: subnanomolar affinity ligands that suggest a new pharmacophore model at the C-2 position. J. Med. Chem. 38 (1995) 3086-3093
29. Wang S., Sakamuri S., Enyedy I.J., Kozikowski A.P., Deschaux O., Bandyopadhyay B.C., Tella S.R., Zaman W.A., and Johnson K.M. Discovery of a novel dopamine transporter inhibitor, 4-hydroxy-1-methyl-4-(4-methylphenyl)-3-piperidyl 4-methylphenyl ketone, as a potential cocaine antagonist through 3D-database pharmacophore searching. Molecular modeling, structure-activity relationships, and behavioral pharmacological studies. J. Med. Chem. 43 (2000) 351-360
30. Barnum D., Greene J., Smelllie A., and Sprague P. Identification of common functional configurations among molecules. J. Chem. Inf. Comput. Sci. 36 (1996) 563-576
31. Sprague P.W. In: Müller K. (Ed). Perspectives in drug discovery and design. Automated Chemical Hypothesis Generation and Database Searching with Catalyst vol. 3 (1995), ESCOM Science 1-20
32. Martin Y.C., Bures M.G., Danaher E.A., Delazzer J., Lico I., and Pavlik P.A. A fast new approach to pharmacophore mapping and its application to dopaminergic and benzodiazepine agonists. J. Comput.-Aided Mol. Des. 7 (1993) 83-102
33. Beusen D. Alignment of angiotensin two receptors antagonists using GASP. Tripos Technical Notes vol. 1(4) (1996) November
34. Dessalew N., and Bharatam P.V. Investigation of potential glycogen synthase kinase 3 inhibitors using pharmacophore mapping and virtual screening. Chem. Biol. Drug Des. 68 (2006) 154-165
35. Catalyst program, version 4.10 Accelrys Inc., San Diego, CA, USA.
36. Bertrand J.A., Thieffine S., Vulpetti A., Cristiani C., Valsasina B., Knapp S., Kalisz H.M., and Flocco M. Structural characterization of GSK3β active site using selective and non-selective ATP-mimetic inhibitors. J. Mol. Biol. 333 (2003) 393-407
37. SYBYL6.9; Tripos Inc., 1699 South Hanley Rd., St. Louis, MO 63144 USA.
38. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and developmental settings. Adv. Drug Deliv. Rev. 46 (2001) 3-26
39. Walters W.P., and Murcko M.A. Prediction of 'drug-likeness. Adv. Drug Deliv. Rev. 54 (2002) 255-271
40. Rarey M., Kramer B., Lengauer T., and Klebe G. A fast flexible docking method using an incemental construction algorithm. J. Mol. Biol. 261 (1996) 470-489
41. Jones G., Willett P., Glen R.C., Leach A.R., and Taylor R. Development and validation of genetic algorithms for flexible docking. J. Mol. Biol. 267 (1997) 727-748
42. Muegge I., and Martin Y.C. A general and fast scoring function for protein ligand interactions: a simplified potential approach. J. Med. Chem. 42 (1999) 791-804
43. Kuntz I.D., Blaney J.M., Oatley S.J., Langridge R., and Ferrin T.E. A geometric approach to macromolecule ligand interactions. J. Mol. Biol. 161 (1982) 269-288
44. Eldridge M.D., Murray C.W., Auston T.R., Paolini G.V., and Mee R.P. Empirical scoring functions: the development of a fast scoring function to estimate the binding affinity of ligands in receptor complexes. J. Comput.-Aided Mol. Des. 11 (1997) 425-445
45. Kunick C., Lauenroth K., Wieking K., Xie X., Schultz C., Gussio R., Zaharevitz D., Leost M., Meijer L., Weber A., Jorgensen F.S., and Lemcke T. Evaluation and Comparison of 3D-QSAR CoMSIA Models for CDK1, CDK5, and GSK3 Inhibition by Paullones. J. Med. Chem. 47 (2004) 22-36
46. Dessalew N., Patel D., and Bharatam P.V. 3D-QSAR and molecular docking studies on pyrazolopyrimidine derivatives as glycogen synthase kinase-3β inhibitors. J. Mol. Graph. Model. 25 (2007) 885-895
47. Van Drie J.H. Strategies for the determination of pharmacophoric 3D database queries. J. Comput.-Aided Mol. Des. 11 (1997) 39-52
48. Meijer L., Thunnissen A.M., and Whit A.W. Inhibition of cyclin dependent kinases, GSK3β and CK1 by hymenialdisine, a marine sponge constituent. Chem. Biol. 7 (2000) 51-63
49. Witherington J., Bordas V., Haigh D., Hickey D.M., Ife R.J., Rawlings A.D., Slingsby B.P., Smith D.G., and Ward R.W. 5-Aryl-pyrazolo[3,4-b] pyridazines: potent inhibitors of glycogen synthase kinase-3. Bioorg. Med. Chem. Lett. 13 (2003) 1581-1584
50. Cross D.A.E., Cubert A.A., Chalmers K.A., Facci L., Skaper S.D., and Reith A.D. Glycogen synthase kinase 3 (GSK-3) inhibitors as new promising drugs for diabetes, neurodegeneration, cancer, and inflammation. J. Neurochem. 77 (2001) 94-102
51. Wagman A.S., Johnson K.W., and Bussiere D.E. Discovery and development of GSK3 inhibitors for the treatment of Type 2 diabetes. Curr. Pharm. Des. 10 (2004) 1105-1137
52. Witherington J., Bordas V., Garland S.L., Hickey D.M.B., Ife R.J., and Liddle J. 5-Aryl-pyrazolo[3, 4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK3). Bioorg. Med. Chem. Lett. 13 (2003) 1577-1580
53. Hers I., Tavare J.M., and Denton R.M. The protein kinase C inhibitors bisindolylmaleimide I (GF 109203X) and IX (Ro 31-8220) are potent inhibitors of glycogen kinase-3 activity. FEBS Lett. 460 (1999) 433-436