3D-QSAR and Molecular Docking Studies on 3-Anilino-4-Arylmaleimide Derivatives as Glycogen Synthase Kinase-3β Inhibitors

Chemical Biology and Drug Design

Volumn 79, Issue 4, 2012, Pages 560-571

  Akhtar, Mymoona ^a   Bharatam, Prasad V ^b  

^a HAMDARD UNIVERSITY   (India)

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

Author keywords

Comparative molecular field analysis; CoMSIA; Diabetes mellitus; Glycogen synthase kinase 3; Maleimide; Molecular docking; Three dimensional quantitative structure activity relationship

Indexed keywords

3,5 DIBROMO INDIRUBIN; 5 ARYLPYRAZOLO[3,4 B]PYRIDINE; ALSTERPAULLONE; BISINDOYLMALEIMIDE; GLYCOGEN SYNTHASE KINASE 3 INHIBITOR; GLYCOGEN SYNTHASE KINASE 3BETA; HYMENIALDISINE; MALEIMIDE DERIVATIVE; PYRIDAZINE DERIVATIVE; THIADIAZINE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CELL ACTIVITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; CORRELATION COEFFICIENT; DRUG CONFORMATION; DRUG DESIGN; ENZYME INHIBITION; HYDROPHOBICITY; IC 50; IN VITRO STUDY; MOLECULAR DOCKING; MOLECULAR MODEL; MOLECULE; PREDICTIVE VALUE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATIC ELECTRICITY; THREE DIMENSIONAL IMAGING;

ANILINE COMPOUNDS; DRUG DESIGN; ENZYME INHIBITORS; GLYCOGEN SYNTHASE KINASE 3; HUMANS; LEAST-SQUARES ANALYSIS; MALEIMIDES; MODELS, MOLECULAR; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84858794991     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01291.x     Document Type: Article

References (41)

1. Embi N., Rylatt D.B., Cohen P. (1980) Glycogen synthase kinase-3 from rabbit skeletal muscle. Separation from cyclic-AMP-dependent protein kinase and phosphorylase kinase. Eur J Biochem;107:519-527.
2. Welsh G.I., Proud C.G. (1993) Glycogen synthase kinase-3 is rapidly inactivated in response to insulin and phosphorylates eukaryotic initiation factor eIF-2B. Biochem J;15:625-629.
3. Yoganathan T.N., Costello P., Chen X., Jabali M., Yan J., Leung D., Zhang Z., Yee A., Dedhar S., Sanghera J. (2000) Integrin-linked kinase (ILK): a "hot" therapeutic target. Biochem Pharmacol;60:1115-1119.
4. Li M., Wang X., Meintzer M.K., Laessig T., Birnbaum M.J., Heidenreich K.A. (2000) Cyclic AMP promotes neuronal survival by phosphorylation of glycogen synthase kinase 3beta. Mol Cell Biol;20:9356-9363.
5. Xavier I.J., Mercier P.A., McLoughlin C.M., Ali A., Woodgett J.R., Ovsenek N. (2000) Glycogen synthase kinase 3β negatively regulates both DNA-binding and transcriptional activities of heat shock factor 1. J Biol Chem;275:29147-29152.
6. Davies G., Jiang W.G., Mason M.D. (2001) The interaction between beta-catenin, GSK3beta and APC after motogen induced cell-cell dissociation, and their involvement in signal transduction pathways in prostate cancer. Int J Oncol;18:843-847.
7. Ali A., Hoeflich K.P., Woodgett J.R. (2001) Glycogen synthase kinase-3: properties, functions, and regulation. Chem Rev;101:2527-2540.
8. Mandelkow E.M., Mandelkow E. (1998) Tau in Alzheimer's disease. Trends Cell Biol;8:425-427.
9. Lillioja S., Mott D.M., Zawadzki J.K., Young A.A., Abbott W.G., Bogardus C. (1986) Glucose storage is a major determinant of in vivo "insulin resistance" in subjects with normal glucose tolerance. J Clin Endocrinol Metab;62:922-927.
10. Van Wauwe J., Haefner B. (2003) Glycogen synthase kinase-3 as drug target: from wallflower to center of attention. Drug News Perspect;16:557-565.
11. Martinez A., Alonso M., Castro A., Pérez C., Moreno F.J. (2002) First non-ATP competitive glycogen synthase kinase 3 beta (GSK-3beta) inhibitors: thiadiazolidinones (TDZD) as potential drugs for the treatment of Alzheimer's disease. J Med Chem;45:1292-1299.
12. Meijer L., Thunnissen A.M., White A.W., Garnier M., Nikolic M., Tsai L.H., Walter J., Cleverley K.E., Salinas P.C., Wu Y.Z., Biernat J., Mandelkow E.M., Kim S.H., Pettit G.R. (2000) Inhibition of cyclin-dependent kinases, GSK-3beta and CK1 by hymenialdisine, a marine sponge constituent. Chem Biol;7:51-63.
13. Leost M., Schultz C., Link A., Wu Y.Z., Biernat J., Mandelkow E.M., Bibb J.A., Snyder G.L., Greengard P., Zaharevitz D.W., Gussio R., Senderowicz A.M., Sausville E.A., Kunick C., Meijer L. (2000) Paullones are potent inhibitors of glycogen synthase kinase-3beta and cyclin-dependent kinase 5/p25. Eur J Biochem;267:5983-5994.
14. Kunick C., Lauenroth C., Leost M., Meijer L., Lemcke T. (2004) 1-Azakenpaullone is a selective inhibitor of glycogen synthase kinase-3β. Bioorg Med Chem Lett;14:413-416.
15. Meijer L., Skaltsounis A.L., Magiatis P., Polychronopoulos P., Knockaert M., Leost M., Ryan X.P. et al. (2003) GSK-3-selective inhibitors derived from Tyrian purple indirubins. Chem Biol;10:1255-1266.
16. Witherington J., Bordas V., Garland S.L., Deirdre D.J.M.B. (2003) 6-Heteroaryl-pyrazolo[3, 4-b]pyridines: potent and selective inhibitors of glycogen synthase kinase-3 (GSK-3). Bioorg Med Chem Lett;13:3059-3062.
17. Zhang H.C., Ye H., Conway B.R., Derian C.K., Addo M.F., Kuo G.H., Hecker L.R. et al. (2004) 3-(7-Azaindolyl)-4-arylmaleimides as potent, selective inhibitors of glycogen synthase kinase-3. Bioorg Med Chem Lett;14:3245-3250.
18. Olesen P.H., Sørensen A.R., Ursø B., Kurtzhals P., Bowler A.N., Ehrbar U., Hansen B.F. (2003) Synthesis and in vitro characterization of 1-(4-aminofurazan-3-yl)-5-dialkylaminomethyl-1H-[1, 2, 3]triazole-4-carboxylic acid derivatives. A new class of selective GSK-3 inhibitors. J Med Chem;46:3333-3341.
19. Smith D.G., Buffet M., Fenwick A.E., Haigh D., Ife R.J., Saunders M., Slingsby B.P., Stacey R., Ward R.W. (2001) 3-Anilino-4-arylmaleimides: potent and selective inhibitors of glycogen synthase kinase-3 (GSK-3). Bioorg Med Chem Lett;11:635-639.
20. Cramer R.D., Patterson D.E., Bunce J.D. (1988) Comparative molecular field analysis (CoMFA). I. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc;110:5959-5967.
21. Desiraju G.R., Gopalakrishnan B., Jetti R.K., Nagaraju A., Raveendra J.D., Sharma A., Sobhia M.E., Thilagavathi R. (2002) Computer-aided design of selective COX-2 inhibitors: comparative molecular field analysis, comparative molecular similarity indices analysis, and docking studies of some 1, 2-diarylimidazole derivatives. J Med Chem;45:4847-4857.
22. Lescot E., Bureau R., Santos S.O.J., Rochais C., Lisowski V., Lancelot J.C., Rault S. (2005) 3D-QSAR and docking studies of selective GSK-3β inhibitors. Comparison with a Thieno [2, 3-b] pyrrolizinone derivative, a new potential lead for GSK-3β ligands. J Chem Inf Model;45:708-712.
23. Yang G.F., Lu H.T., Xiong Y., Zhan C.G. (2006) Understanding the structure-activity and structure-selectivity correlation of cyclic guanine derivatives as phosphodiesterase-5 inhibitors by molecular docking, CoMFA and CoMSIA analyses. Bioorg Med Chem Lett;14:1462-1473.
24. 4 agonists using CoMFA and receptor based alignment. Eur J Med Chem;41:16-26.
25. Oliveira A.M., Custódio F.B., Donnici C.L., Montanar C.A. (2003) QSAR and molecular modelling studies on B-DNA recognition of minor groove binders. Eur J Med Chem;38:141-155.
26. Patel D.S., Bharatam P.V. (2006) New leads for selective GSK-3 inhibition: pharmacophore mapping and virtual screening studies. J Comput Aided Mol Des;20:55-66.
27. Dessalew N., Patel D.S., Bharatam P.V. (2007) 3D-QSAR and molecular docking studies on pyrazolopyrimidine derivatives as glycogen synthase kinase-3β inhibitors. J Mol Grap Mod;25:885-895.
28. Vulpetti A., Crivori P., Cameron A., Bertrand J.A., Brasca M.G., Alessio R.D., Paverello P. (2005) Structure-based approaches to improve selectivity: CDK2-GSK3β binding site analysis. J Chem Inf Model;45:1282-1290.
29. Martinez A., Alonso M., Castro A., Dorronsoro I., Gelpi J.L., Luque F.J., Perez C., Moreno F.J. (2005) SAR and 3D-QSAR studies on thiadiazolidinone derivatives: exploration of structural requirements for glycogen synthase kinase 3 inhibitors. J Med Chem;48:7103-7112.
30. Kunick C., Lauenroth K., Wieking K., Xie X., Schultz C., Gussio R., Zaharevitz D., Maryse L., Meijer L., Weber A., Jørgensen F.S., Lemcke T. (2004) Evaluation and comparison of 3D-QSAR CoMSIA models for CDK1, CDK5, and GSK-3 inhibition by paullones. J Med Chem;47:22-36.
31. Zeng M., Jiang Y., Zhang B., Zheng K., Zhang N., Yu Q. (2005) 3D QSAR studies on GSK-3 inhibition by aloisines. Bioorg Med Chem Lett;15:395-399.
32. Klebe G., Abraham U., Mietzner T. (1994) Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem;37:4130-4146.
33. Wold S., Johansson A., Cochi M. (1993) D QSAR in drug design: theory, methods and applications. In: Kubinyi H., editor. PLS - Partial Least Squares Projection to Latent Structures. Lieden: ESCOM; p. 523-550.
34. Clark M., Cramer R.D. III, Van Opdenbosch N. (1989) Validation of the general purpose tripos 5.2 force field. J Comput Chem;10:982-1012.
35. Bertrand J.A., Thieffine S., Vulpetti A., Cristiani C., Valsasina B., Knapp S., Kalisz H.M., Flocco M. (2003) Structural characterization of the GSK-3beta active site using selective and non-selective ATP-mimetic inhibitors. J Mol Biol;333:393-407.
36. Cramer R.D., Bunce J.D., Paterson D.E. (1988) Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quant Struct Act Relat;7:18-25.
37. Rarey M., Kramer B., Lengauer T., Klebe G. (1996) A fast flexible docking method using an incremental construction algorithm. J Mol Biol;261:470-489.
38. Jones G., Willett P., Glen R.C., Leach A.R., Taylor R. (1997) Development and validation of a genetic algorithm for flexible docking. J Mol Biol;267:727-748.
39. Muegge I., Martin Y.C. (1999) A general and fast scoring function for protein-ligand interactions: a simplified potential approach. J Med Chem;42:791-804.
40. Kuntz I.D., Blaney J.M., Oatley S.J., Langridge R., Ferrin T.E. (1982) A geometric approach to macromolecule-ligand interactions. J Mol Biol;161:269-288.
41. Eldridge M.D., Murray C.W., Auton T.R., Paolini G.V., Mee R.P. (1997) Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J Comput Aided Mol Des;11:425-445.