Combined 3D-QSAR and docking modelling study on indolocarbazole series compounds as tie-2 inhibitors

International Journal of Molecular Sciences

Volumn 12, Issue 8, 2011, Pages 5080-5097

  Tian, Yuanxin ^a   Xu, Jian ^a   Li, Zhonghuang ^a   Zhu, Zhengguang ^a   Zhang, Jiajie ^a   Wu, Shuguang ^a  

^a SOUTHERN MEDICAL UNIVERSITY   (China)

Author keywords

3D QSAR; CoMFA; CoMSIA; Docking; Tie 2 kinase inhibitor

Indexed keywords

ANGIOPOIETIN RECEPTOR; CARBAZOLE DERIVATIVE; INDOLOCARBAZOLE; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 2; PROTEIN BINDING; PROTEIN KINASE INHIBITOR;

ACCURACY; ARTICLE; BINDING KINETICS; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG BINDING SITE; DRUG STRUCTURE; HYDROGEN BOND; HYDROPHILICITY; HYDROPHOBICITY; LIGAND BINDING; LIPOPHILICITY; MOLECULAR DOCKING; PREDICTION; PROTEIN INTERACTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATIC ELECTRICITY; SUBSTITUTION REACTION; THREE DIMENSIONAL IMAGING; ANTAGONISTS AND INHIBITORS; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; IC50; METABOLISM; MOLECULAR DYNAMICS;

CARBAZOLES; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR DOCKING SIMULATION; MOLECULAR DYNAMICS SIMULATION; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, TIE-2;

EID: 80052171413     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12085080     Document Type: Article

References (22)

1. Carmeliet, P. Angiogenesis in health and disease. Nat. Med. 2003, 9, 653-660.
2. Saharinen, P.; Bry, M.; Alitalo, K. How do angiopoietins Tie in with vascular endothelial growth factors? Curr. Opin. Hematol. 2010, 17, 198-205.
3. Zhang, J.-M.; Yang, P.L.; Gray, N.S. Targeting cancer with small molecule kinase inhibitors. Nat. Rev. Cancer 2009, 9, 28-39.
4. Ferrara, N.; Kerbel, R.S. Angiogenesis as a therapeutic target. Nature 2005, 438, 967-974.
5. Nam, N.-H.; Parang, K. Current targets for anticancer drug discovery. Curr. Drug Targets 2003, 4, 159-179.
6. Becknell, N.C.; Zulli, A.L.; Angeles, T.S.; Yang, S.; Albom, M.S.; Aimone, L.D.; Robinson, C.; Chang, H.; Hudkins, R.L. Novel C-3 N-urea, amide, and carbamate dihydroindazolo[5,4-a] pyrrolo[3,4-c]carbazole analogs as potent TIE-2 and VEGF-R2 dual inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 5368-5372.
7. Dandu, R.; Zulli, A.L.; Bacon, E.R.; Underiner, T.; Robinson, C.; Chang, H.; Miknyoczki, S.; Grobelny, J.; Ruggeri, B.A.; Yang, S.; et al. Design and synthesis of dihydroindazolo[5,4-a]pyrrolo[3,4-c]carbazole oximes as potent dual inhibitors of TIE-2 and VEGF-R2 receptor tyrosine kinases. Bioorg. Med. Chem. Lett. 2008, 18, 1916-1921.
8. Underiner, T.L.; Ruggeri, B.; Aimone, L.; Albom, M.; Angeles, T.; Chang, H.; Hudkins, R.L.; Hunter, K.; Josef, K.; Robinson, C.; et al. TIE-2/VEGF-R2 SAR and in vitro activity of C3-acyl dihydroindazolo[5,4-a] pyrrolo[3,4-c]carbazole analogs. Bioorg. Med. Chem. Lett. 2008, 18, 2368-2372.
9. Hudkins, R.L.; Zulli, A.L.; Underiner, T.L.; Angeles, T.S.; Aimone, L.D.; Meyer, S.L.; Pauletti, D.; Chang, H.; Fedorov, E.V.; Almo, S.C.; et al. 8-THP-DHI analogs as potent Type I dual TIE-2/VEGF-R2 receptor tyrosine kinase inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 3356-3360.
10. Cramer, R.D., III; Patterson, D.E.; Bunce, J.D. Comparative molecular field analysis (CoMFA). Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
11. Cramer, R.D., III; Bunce, J.D.; Patterson, D.E. Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quant. Struct.-Act. Relat. 1988, 7, 18-25.
12. Lan, P.; Chen, W.-N.; Chen, W.-M. Molecular modeling studies on imidazo[4,5-b]pyridine derivatives as Aurora A Kinase inhibitors using 3D-QSAR and docking approaches. Eur. J. Med. Chem. 2011, 46, 77-94.
13. Sun, J.; Cai, S.; Yan, N.; Mei, H. Docking and 3D-QSARstudies of influenza neuraminidase inhibitors using threedimensional holographic vector of atomic interaction field analysis. Eur. J. Med. Chem. 2010, 45, 1008-1014.
14. AbdulHameed, M.D.; Hamza, A.; Liu, J.-J.; Zhan, C.-G. Combined 3D-QSAR modeling and molecular docking study on indolinone derivatives as inhibitors of 3-Phosphoinositide-Dependent protein Kinase-1. J. Chem. Inf. Model. 2008, 48, 1760-1772.
15. Cao, H.-Y.; Zhang, H.-B.; Zheng, X.-F.; Gao, D.-B. 3D QSAR studies on a series of potent and high selective inhibitors for three kinases of RTK family. J. Mol. Graph. Model. 2007, 236-245.
16. Zhang, N.; Zhong, R. Docking and 3D-QSAR studies of 7-hydroxycoumarin derivatives as CK2 inhibitors. Eur. J. Med. Chem. 2010, 45, 292-297.
17. Liao, S.-Y; Qian, L.; Mao, T.-F.; Lu, H.-L.; Zheng, K.-C. CoMFA and docking studies of 2-phenylindole derivatives with anticancer activity. Eur. J. Med. Chem. 2009, 44, 2822-2827.
18. Ai, Y.; Wang, S.-T.; Sun, P.-H.; Song, F.-J. Molecular modeling studies of 4,5-Dihydro-1Hpyrazolo[4,3-h] quinazoline derivatives as potent CDK2/Cyclin a inhibitors using 3D-QSAR and docking. Int. J. Mol. Sci. 2010, 11, 3705-3724.
19. Zhang, B.-D.; Li, Y.; Zhang, H.-X.; Ai, C.-Z. 3D-QSAR and Molecular docking studies on derivatives of MK-0457, GSK1070916 and SNS-314 as inhibitors against Aurora B Kinase. Int. J. Mol. Sci. 2010, 11, 4326-4347.
20. Cao, R.; Mi, N.; Zhang, H.-B. 3D-QSAR study of c-Src kinase inhibitor based on docking. J. Mol. Model. 2010, 16, 361-375.
21. Zeng, H.-H.; Zhang, H.-B. Combined 3D-QSAR modeling and molecular docking study on 1,4-dihydroindenol[1,2-c] pyrazoles as VEGFR2 kinase inhibitors. J. Mol. Graph. Model, 2010, 29, 54-71.
22. Ai, Y.; Wang, S.-T.; Sun, P.-H.; Song, F.-J. Combined 3D-QSAR modeling and molecular docking studies on Pyrrole-Indolin-2-ones as Aurora A Kinase inhibitors. Int. J. Mol. Sci. 2011, 12, 1605-1624.