Induced-fit docking and binding free energy calculation on furostanol saponins from Tupistra chinensis as epidermal growth factor receptor inhibitors

Medicinal Chemistry Research

Volumn 22, Issue 10, 2013, Pages 4970-4979

  Luo, Hua Jun ^a   Wang, Jun Zhi ^a   Deng, Wei Qiao ^b   Zou, Kun ^a  

^a CHINA THREE GORGES UNIVERSITY   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Binding free energy; EGFR; Furostanol saponins; Induced fit docking

Indexed keywords

26 O BETA DEXTRO GLUCOPYRANOSYL FUROST 1 BETA,3BETA,22ALPHA,26TETRAHYDROXY O BETA DEXTRO GLUCOPYRANOSIDE; AMINO ACID; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; ERLOTINIB; FUROSTANOL SAPONIN DERIVATIVE; GEFITINIB; SAPONIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING SITE; CALCULATION; CONTROLLED STUDY; DRUG BINDING; DRUG STRUCTURE; ENERGY; HYDROGEN BOND; LC 50; LILIACEAE; LUNG NON SMALL CELL CANCER; MEDICINAL PLANT; MOLECULAR DOCKING; MOLECULAR MECHANICS; NONHUMAN; SOLVATION; TUPISTRA; TUPISTRA CHINENSIS;

EID: 84883457748     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0509-4     Document Type: Article

References (35)

1. Ahmedm S, Metpally RPR, Sangadala S, Reddy BVB (2010) Virtual screening and selection of drug-like compounds to block noggin interaction with bone morphogenetic proteins. J Mol Graph Model 28:670-682
2. Baselga J, Arteaga CL (2005) Critical update and emerging trends in epidermal growth factor receptor targeting in cancer. J Clin Oncol 23:2445-2459
3. Bishayee S (2000) Role of conformational alteration in the epidermal growth factor receptor (EGFR) function. Biochem Pharmacol 60:1217-1223
4. Cho BC, Im CK, Park MS, Kim SK, Chang J, Park JP, Choi HJ, Kim YJ, Shin SJ, Sohn JH, Kim H, Kim JH (2007) Phase II study of erlotinib in advanced non-small-cell lung cancer after failure of gefitinib. J Clin Oncol 25:2528-2533
5. Choong NW, Ma PC, Salgia R (2005) Therapeutic targeting of receptor tyrosine kinases in lung cancer. Expert Opin Ther Targets 9:533-559
6. De Lano WL (2004) The PyMOL molecular graphics system. DeLano Scientific LLC, San Carlos. http://pymol.sourceforge.net. Accessed 1 June 2004
7. de Oliveira AN, Bocca CC, Carvalho JE, Ruiz ALG, Silva TP, Rittner R, Hoehr NF (2010) New substituted 4-arylaminoquinazolines as potent inhibitors of breast tumor cell lines: in vitro and docking experiments. Eur J Med Chem 45:4339-4342
8. Dutta PR, Maity A (2007) Cellular responses to EGFR inhibitors and their relevance to cancer therapy. Cancer Lett 254:165-177
9. Friesner RA, Banks JL, Murphy RB, Halgren TA, Klicic JJ, Mainz DT, Repasky MP, Knoll EH, Shelley M, Perry JK, Shaw DE, Francis P, Shenkin PS (2004) Glide: a new approach for a rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 47:1739-1749
10. Guo ZY, Zou K, Wang JZ, Liu C, Tang ZC, Yang CY (2009) Structural elucidation and NMR spectral assignment of three new furostanol saponins from the roots of Tupistra chinensis. Magn Reson Chem 47:613-616
11. Herbst RS, Fukuoka M, Baselga J (2004) Gefitinib - a novel targeted approach to treating cancer. Nat Rev Cancer 4:956-965
12. Hynes N, Horsch K, Olayioye M, Badache A (2001) The ErbB receptor tyrosine family as signal integrators. Endocr Relat Cancer 8:151-159
13. Jacobson MP, Pincus DL, Rapp CS, Day TJF, Honig B, Shaw DE, Friesner RA (2004) A hierarchical approach to all-atom protein loop prediction. Proteins 55:351-367
14. Kaminski GA, Friesner RA, Tirado-Rives J, Jorgensen WL (2001) Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides. J Phys Chem B 105:6474-6487
15. Kollman PA, Massova I, Reyes C, Kuhn B, Huo S, Chong L (2011) Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models. Acc Chem Res 33:889-897
16. Kuan C, Wikstrand C, Bigner D (2001) EGF mutant receptor vIII as a molecular target in cancer therapy. Endocr Relat Cancer 8:83-96
17. Li SY, Guo CY, Sun XQ, Li YZ, Zhao HL, Zhan DM, Lan MB, Tang Y (2012a) Synthesis and biological evaluation of quinazoline and quinoline bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential epidermal growth factor receptor(EGFR) tyrosine kinase inhibitors and EPR bio-probe agents. Eur J Med Chem 49:271-278
18. Li SY, Guo CY, Zhao HL, Tang Y, Lan MB (2012b) Synthesis and biological evaluation of 4-[3-chloro-4-(3-fluorobenzyloxy) anilino]-6-(3-substituted- phenoxy)pyrimidines as dual EGFR/ErbB-2 kinase inhibitors. Bioorg Med Chem 20:877-885
19. Liu CX, Guo ZY, Xue YH, Cheng J, Huang NY, Zhou Y, Cheng F, Zou K (2012a) Five new furostanol saponins from the rhizomes of Tupistra chinensis. Fitoterapia 83:323-328
20. Liu CX, Guo ZY, Xue YH, Zhang HY, Zhang HQ, Zou K, Huang NY (2012b) Tupisteroide A-C, three new polyhydroxylated steroidal constituents from the roots of Tupistra chinensis. Magn Reson Chem 50:320-324
21. Lv PC, Li DD, Li QS, Lu X, Xiao ZP, Zhu HL (2011) Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives as EGFR TK inhibitors and potential anticancer agents. Bioorg Med Chem Lett 21:5374-5377
22. Maestro, version 9.3, Schrödinger, LLC, New York (2012). www.schrodinger.com. Accessed 23 Jan 2012
23. Massova I, Kollman PA (2000) Combined molecular mechanical and continuum solvent approach (MM-PBSA/GBSA) to predict ligand binding. Perspect Drug Discov Des 18:113-135
24. Ogiso H, Ishitani R, Nureki O, Fukai S, Yamanaka M, Kim JH, Saito K, Sakamoto A, Inoue M, Shirouzu M, Yokoyama S (2002) Crystal structure of the complex of human epidermal growth factor and receptor extracellular domains. Cell 110:775-787
25. Paul MK, Mukhopadhyay AK (2004) Tyrosine kinase - role and significance in cancer. Int J Med Sci 1:101-115
26. Sawatdichaikul O, Hannongbua S, Sangma C, Wolschann P, Choowongkomon K (2012) In silico screening of epidermal growth factor receptor (EGFR) in the tyrosine kinase domain through a medicinal plant compound database. J Mol Model 18(3):1241-1254
27. Schrödinger, LLC, New York (2010). www.schrodinger.com. Accessed 1 Oct 2010
28. Sherman W, Day T, Jacobson MP, Friesner RA, Farid R (2006) Novel procedure for modeling ligand/receptor induced fit effects. J Med Chem 49:534-553
29. Stamos J, Sliwkowski MX, Eigenbrot C (2002) Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. J Biol Chem 277:46265-46272
30. Wanga H, Aslanian R, Madison VS (2008) Induced-fit docking of mometasone furoate and further evidence for glucocorticoid receptor 17α pocket flexibility. J Mol Graph Model 27:512-521
31. Yun CH, Boggon TJ, Li Y, Woo S, Greulich H, Meyerson M, Eck MJ (2007) Structures of lung cancer-derived EGFR mutants and inhibitor complexes: mechanism of activation and insights into differential inhibitor sensitivity. Cancer Cell 11:217
32. Zhan YH (1994) China Shennongjia resources of medicinal plants. Hubei Scientific and Technological Press, Wuhan
33. Zhong H, Tran LM, Stang JL (2009) Induced-fit docking studies of the active and inactive states of protein tyrosine kinases. J Mol Graph Model 28:336-346
34. Zou K, Wang JZ, Du M, Li Q, Tu GZ (2006) A pair of diastereoisomeric steroidal saponins from cytotoxic extracts of Tupistra chinensis Rhizomes. Chem Pharm Bull 54(10):1440-1442
35. Zou K, Wang JZ, Guo ZY, Du M, Wu J, Zhou Y (2009) Structural elucidation of four new furostanol saponins from Tupistra chinensis by 1D and 2D NMR spectroscopy. Magn Reson Chem 47:87-91