Identification of novel FAK and S6K1 dual inhibitors from natural compounds via ADMET screening and molecular docking

Biomedicine and Pharmacotherapy

Volumn 80, Issue , 2016, Pages 52-62

  Thiyagarajan, Varadharajan ^a   Lin, Shin Hung ^a   Chang, Yu Chuan ^a   Weng, Ching Feng ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

ADMET; FAK; Molecular docking; S6K1; Virtual screening

Indexed keywords

ACTINODAPHNINE; ANTINEOPLASTIC AGENT; ANTROQUINONOL D; BERBERINE; CATECHIN; CISPLATIN; CURCUMIN; FOCAL ADHESION KINASE INHIBITOR; KAEMPFEROL; NATURAL PRODUCT; NEFERINE A; NEFERINE B; PROTEIN SERINE THREONINE KINASE INHIBITOR; QUERCETIN; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; FOCAL ADHESION KINASE; PROTEIN KINASE INHIBITOR; S6 KINASE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTRODIA CAMPHORATA; ARTICLE; BLOOD BRAIN BARRIER; CARCINOGENICITY; CELL PROLIFERATION; CELL SURVIVAL; CELL VIABILITY; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG SCREENING; DRUG STRUCTURE; GLIOMA CELL LINE; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; IC50; MOLECULAR DOCKING; MOLECULAR LIBRARY; MTT ASSAY; MUTAGENICITY; NONHUMAN; PREDICTION; PRIORITY JOURNAL; RAT; WESTERN BLOTTING; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; COMPUTER INTERFACE; DRUG EFFECTS; HIGH THROUGHPUT SCREENING; METABOLISM; TUMOR CELL LINE;

ANIMALS; BIOLOGICAL PRODUCTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; FOCAL ADHESION PROTEIN-TYROSINE KINASES; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; HYDROGEN BONDING; MOLECULAR DOCKING SIMULATION; PROTEIN KINASE INHIBITORS; RATS; RIBOSOMAL PROTEIN S6 KINASES; USER-COMPUTER INTERFACE;

EID: 84960338532     PISSN: 07533322     EISSN: 19506007     Source Type: Journal    
DOI: 10.1016/j.biopha.2016.02.020     Document Type: Article

References (42)

1. Fingar D.C., Blenis J. Target of rapamycin (TOR): an integrator of nutrient and growth factor signals and coordinator of cell growth and cell cycle progression. Oncogene 2004, 23:3151-3171.
2. Thiyagarajan V., Tsai M.J., Weng C.F. Antroquinonol targets FAK-signaling pathway suppressed cell migration, invasion, and tumor growth of C6 Glioma. PLoS One 2015, 10:e0141285.
3. Eide B.L., Turck C.W., Escobedo J.A. Identification of Tyr-397 as the primary site of tyrosine phosphorylation and pp60src association in the focal adhesion kinase, pp125FAK. Mol. Cell. Biol. 1995, 15:2819-2827.
4. Xing Z., Chen H.C., Nowlen J.K., Taylor S.J., Shalloway D., Guan J.L. Direct interaction of v-Src with the focal adhesion kinase mediated by the Src SH2 domain. Mol. Biol. Cell 1994, 5:413-421.
5. Cohen L.A., Guan J.L. Residues within the first subdomain of the FERM-like domain in focal adhesion kinase are important in its regulation. J. Biol. Chem. 2005, 280:8197-8207.
6. Toutant M., Costa A., Studler J.M., Kadare G., Carnaud M., Girault J.A. Alternative splicing controls the mechanisms of FAK autophosphorylation. Mol. Cell. Biol. 2002, 22:7731-7743.
7. Cooper L.A., Shen T.L., Guan J.L. Regulation of focal adhesion kinase by its amino-terminal domain through an autoinhibitory interaction. Mol. Cell. Biol. 2003, 23:8030-8041.
8. Sood A.K., Coffin J.E., Schneider G.B., Fletcher M.S., DeYoung B.R., Gruman L.M., Gershenson D.M., Schaller M.D., Hendrix M.J. Biological significance of focal adhesion kinase in ovarian cancer: role in migration and invasion. Am. J. Pathol. 2004, 165:1087-1095.
9. Cance W.G., Harris J.E., Iacocca M.V., Roche E., Yang X., Chang J., Simkins S., Xu L. Immunohistochemical analyses of focal adhesion kinase expression in benign and malignant human breast and colon tissues: correlation with preinvasive and invasive phenotypes. Clin. Cancer Res. 2000, 6:2417-2423.
10. Thiyagarajan V., Lin S.H., Chia Y.C., Weng C.F. A novel inhibitor 16-hydroxy-cleroda-3,13-dien-16,15-olide, blocks the autophosphorylation site of focal adhesion kinase (Y397) by molecular docking. Biochim. Biophys. Acta 2013, 1830:4091-4101.
11. Jones G., Machado J., Tolnay M., Merlo A. PTEN-independent induction of caspase-mediated cell death and reduced invasion by the focal adhesion targeting domain (FAT) in human astrocytic brain tumors which highly express focal adhesion kinase (FAK). Cancer Res. 2001, 61:5688-5691.
12. Golubovskaya V.M., Cance W.G. Focal adhesion kinase and p53 signaling in cancer cells. Int. Rev. Cytol. 2007, 263:103-153.
13. Zoncu R., Efeyan A., Sabatini D.M. mTOR: from growth signal integration to cancer, diabetes and ageing. Nat. Rev. Mol. Cell Biol. 2011, 12:21-35.
14. Woo M.S., Ohta Y., Rabinovitz I., Stossel T.P., Blenis J. Ribosomal S6 kinase (RSK) regulates phosphorylation of filamin A on an important regulatory site. Mol. Cell. Biol. 2004, 24:3025-3035.
15. Alessi D.R., Kozlowski M.T., Weng Q.P., Morrice N., Avruch J. 3-Phosphoinositide-dependent protein kinase 1 (PDK1) phosphorylates and activates the p70 S6 kinase in vivo and in vitro. Curr. Biol. 1998, 8:69-81.
16. Isotani S., Hara K., Tokunaga C., Inoue H., Avruch J., Yonezawa K. Immunopurified mammalian target of rapamycin phosphorylates and activates p70 S6 kinase alpha in vitro. J. Biol. Chem. 1999, 274:34493-34498.
17. Holz M.K. The role of S6K1 in ER-positive breast cancer. Cell Cycle 2012, 11:3159-3165.
18. Magnuson B., Ekim B., Fingar D.C. Regulation and function of ribosomal protein S6 kinase (S6K) within mTOR signalling networks. Biochem. J. 2012, 441:1-21.
19. Perez-Tenorio G., Karlsson E., Waltersson M.A., Olsson B., Holmlund B., Nordenskjold B., Fornander T., Skoog L., Stal O. Clinical potential of the mTOR targets S6K1 and S6K2 in breast cancer. Breast Cancer Res. Treat. 2011, 128:713-723.
20. Yamnik R.L., Digilova A., Davis D.C., Brodt Z.N., Murphy C.J., Holz M.K. S6 kinase 1 regulates estrogen receptor alpha in control of breast cancer cell proliferation. J. Biol. Chem. 2009, 284:6361-6369.
21. Ismail H.M. Overexpression of s6 kinase 1 in brain tumours is associated with induction of hypoxia-responsive genes and predicts patients' survival. J. Oncol. 2012, 2012:416927.
22. Meng X.Y., Zhang H.X., Mezei M., Cui M. Molecular docking: a powerful approach for structure-based drug discovery. Curr. Comput. Aided Drug Des. 2011, 7:146-157.
23. Girija C.R., Karunakar P., Poojari C.S., Begum N.S., Syed A.A. Molecular docking studies of curcumin derivatives with multiple protein targets for procarcinogen activating enzyme inhibition. J. Proteomics Bioinform. 2010, 3:200-203.
24. Moroy G., Martiny V.Y., Vayer P., Villoutreix B.O., Miteva M.A. Toward in silico structure-based ADMET prediction in drug discovery. Drug Discov. Today 2012, 17:44-55.
25. Daidone F., Montioli R., Paiardini A., Cellini B., Macchiarulo A., Giardina G., Bossa F., Borri Voltattorni C. Identification by virtual screening and in vitro testing of human DOPA decarboxylase inhibitors. PLoS One 2012, 7:e31610.
26. Sulake R.S., Jiang Y.F., Lin H.H., Chen C. Total synthesis of (+/-)-antroquinonol d. J. Org. Chem. 2014, 79:10820-10828.
27. Sunami T., Byrne N., Diehl R.E., Funabashi K., Hall D.L., Ikuta M., Patel S.B., Shipman J.M., Smith R.F., Takahashi I., Zugay-Murphy J., Iwasawa Y., Lumb K.J., Munshi S.K., Sharma S. Structural basis of human p70 ribosomal S6 kinase-1 regulation by activation loop phosphorylation. J. Biol. Chem. 2010, 285:4587-4594.
28. Ceccarelli D.F., Song H.K., Poy F., Schaller M.D., Eck M.J. Crystal structure of the FERM domain of focal adhesion kinase. J. Biol. Chem. 2006, 281:252-259.
29. Venkatachalam C.M., Jiang X., Oldfield T., Waldman M. LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites. J. Mol. Graph. Model. 2003, 21:289-307.
30. Balani S.K., Miwa G.T., Gan L.S., Wu J.T., Lee F.W. Strategy of utilizing in vitro and in vivo ADME tools for lead optimization and drug candidate selection. Curr. Top. Med. Chem. 2005, 5:1033-1038.
31. Thiyagarajan V., Lin S.X., Lee C.H., Weng C.F. A focal adhesion kinase inhibitor 16-hydroxy-cleroda-3,13-dien-16,15-olide incorporated into enteric-coated nanoparticles for controlled anti-glioma drug delivery. Colloids Surf. B Biointerfaces 2016, 141:120-131.
32. Wu F., Xu T., He G., Ouyang L., Han B., Peng C., Song X., Xiang M. Discovery of novel focal adhesion kinase inhibitors using a hybrid protocol of virtual screening approach based on multicomplex-based pharmacophore and molecular docking. Int. J. Mol. Sci. 2012, 13:15668-15678.
33. Wang S.C., Lee T.H., Hsu C.H., Chang Y.J., Chang M.S., Wang Y.C., Ho Y.S., Wen W.C., Lin R.K. Antroquinonol D isolated from Antrodia camphorata, with DNA demethylation and anticancer potential. J. Agric. Food Chem. 2014, 62:5625-5635.
34. Yu J., Hu W.S. Effects of neferine on platelet aggregation in rabbits. Yao Xue Xue Bao 1997, 32:1-4.
35. Qian J.Q. Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives. Acta Pharmacol. Sin. 2002, 23:1086-1092.
36. Law B.Y., Chan W.K., Xu S.W., Wang J.R., Bai L.P., Liu L., Wong V.K. Natural small-molecule enhancers of autophagy induce autophagic cell death in apoptosis-defective cells. Sci. Rep. 2014, 4:5510.
37. Zhang X., Liu Z., Xu B., Sun Z., Gong Y., Shao C. Neferine an alkaloid ingredient in lotus seed embryo, inhibits proliferation of human osteosarcoma cells by promoting p38 MAPK-mediated p21 stabilization. Eur. J. Pharmacol. 2012, 677:47-54.
38. Cheng Y., Qiu F., Tashiro S., Onodera S., Ikejima T. ERK and JNK mediate TNFalpha-induced p53 activation in apoptotic and autophagic L929 cell death. Biochem. Biophys. Res. Commun. 2008, 376:483-488.
39. Cao J.G., Tang X.Q., Shi S.H. Multidrug resistance reversal in human gastric carcinoma cells by neferine. World J. Gastroenterol. 2004, 10:3062-3064.
40. Poornima P., Weng C.F., Padma V.V. Neferine from Nelumbo nucifera induces autophagy through the inhibition of PI3K/Akt/mTOR pathway and ROS hyper generation in A549 cells. Food Chem. 2013, 141:3598-3605.
41. Poornima P., Weng C.F., Padma V.V. Neferine an alkaloid from lotus seed embryo, inhibits human lung cancer cell growth by MAPK activation and cell cycle arrest. Biofactors 2014, 40:121-131.
42. Poornima P., Kumar V.B., Weng C.F., Padma V.V. Doxorubicin induced apoptosis was potentiated by neferine in human lung adenocarcima, A549 cells. Food Chem. Toxicol. 2014, 68:87-98.