The interaction of 4-thiazolidinone derivatives containing indolin-2-one moiety with P-glycoprotein studied using K562 cell lines

European Journal of Medicinal Chemistry

Volumn 101, Issue , 2015, Pages 126-132

  Wang, Feng ^a   Liu, Zijian ^b   Wang, Jian ^b   Tao, Jun ^c   Gong, Ping ^b   Bao, Xue ^a   Zhao, Yanfang ^b   Wang, Yulin ^a  

^a DALIAN MEDICAL UNIVERSITY   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^c HUBEI CANCER HOSPITAL   (China)

Author keywords

4 Thiazolidinone derivatives; Cytotoxicity assay; Molecular docking; P glycoprotein

Indexed keywords

4 THIAZOLIDINONE DERIVATIVE; ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; GLYCOPROTEIN P INHIBITOR; INDOLE DERIVATIVE; INDOLIN 2 ONE DERIVATIVE; MULTIDRUG RESISTANCE PROTEIN; RHODAMINE 123; SERINE; UNCLASSIFIED DRUG; VERAPAMIL; INDOLIN-2-ONE; THIAZOLIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL INTERACTION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC50; K562 CELL LINE; MOLECULAR DOCKING; MOLECULAR DYNAMICS; PROTEIN DOMAIN; PROTEIN INTERACTION; PROTEIN TRANSPORT; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; K562 CELLS; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; P-GLYCOPROTEIN; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINES;

EID: 84933051249     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.06.002     Document Type: Article

References (25)

1. S. B. Kaye, The multidrug resistance phenotype, Br. J. Cancer 58 (1988) 691-694.
2. R. L. Juliano, V. Ling, A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants, Biochim. Biophys. Acta 455 (1976) 152-162.
3. S. G. Aller, J. Yu, A. Ward, Y. Weng, S. Chittaboina, R. Zhuo, P. M. Harrell, Y. T. Trinh, Q. Zhang, I. L. Urbatsch, G. Chang, Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding, Science 323 (2009) 1718-1722.
4. F. J. Sharom, ABC multidrug transporters: structure, function and role in chemoresistance, Pharmacogenomics 9 (2008) 105-127.
5. J. M. Ford, Experimental reversal of P-glycoprotein-mediated multidrug resistance by pharmacological chemosensitisers, Eur. J. Cancer 32A (1996) 991-1001.
6. T. Tomasic, L. P. Masic, Rhodanine as a privileged scaffold in drug discovery, Curr. Med. Chem. 16 (2009) 1596-1629.
7. A. Verma, S. K. Saraf, 4-thiazolidinoneea biologically active scaffold, Eur. J. Med. Chem. 43 (2008) 897-905.
8. M. E. Welsch, S. A. Snyder, B. R. Stockwell, Privileged scaffolds for library design and drug discovery, Curr. Opin. Chem. Biol. 14 (2010) 347-361.
9. I. Kucukguzel, G. Satilmis, K. R. Gurukumar, A. Basu, E. Tatar, D. B. Nichols, T. T. Talele, N. Kaushik-Basu, 2-Heteroarylimino-5-arylidene-4-thiazolidinones as a new class of non-nucleoside inhibitors of HCV NS5B polymerase, Eur. J. Med. Chem. 69 (2013) 931-941.
10. M. O. Taha, M. A. Al-Sha'er, M. A. Khanfar, A. H. Al-Nadaf, Discovery of nanomolar phosphoinositide 3-kinase gamma (PI3Kgamma) inhibitors using ligand-based modeling and virtual screening followed by in vitro analysis, Eur. J. Med. Chem. 84 (2014) 454-465.
11. F. Teraishi, S. Wu, J. Sasaki, L. Zhang, J. J. Davis, W. Guo, F. Dong, B. Fang, JNK1-dependent antimitotic activity of thiazolidin compounds in human nonsmall-cell lung and colon cancer cells, Cell. Mol. Life Sci. 62 (2005) 2382-2389.
12. F. Teraishi, S. Wu, J. Sasaki, L. Zhang, H. B. Zhu, J. J. Davis, B. Fang, P-glycoprotein-independent apoptosis induction by a novel synthetic compound, MMPT [5-[(4-methylphenyl) methylene]-2-(phenylamino)-4 (5H)-thiazolone], J. Pharmacol. Exp. Ther. 314 (2005) 355-362.
13. S. Wu, W. Guo, F. Teraishi, J. Pang, K. Kaluarachchi, L. Zhang, J. Davis, F. Dong, B. Yan, B. Fang, Anticancer activity of 5-benzylidene-2-phenylimino-1, 3-thiazolidin-4-one (BPT) analogs, Med. Chem. 2 (2006) 597-605.
14. S. Wang, Y. Zhao, G. Zhang, Y. Lv, N. Zhang, P. Gong, Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent, Eur. J. Med. Chem. 46 (2011) 3509-3518.
15. C. Loetchutinat, C. Saengkhae, C. Marbeuf-Gueye, A. Garnier-Suillerot, New insights into the P-glycoprotein-mediated effluxes of rhodamines, Eur. J. Biochem. 270 (2003) 476-485.
16. Y. Wang, D. Hao, W. D. Stein, L. Yang, A kinetic study of Rhodamine123 pumping by P-glycoprotein, Biochim. Biophys. Acta 1758 (2006) 1671-1676.
17. Y. Cheng, W. H. Prusoff, Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction, Biochem. Pharmacol. 22 (1973) 3099-3108.
18. G. E. Jara, D. M. Vera, A. B. Pierini, Binding of modulators to mouse and human multidrug resistance P-glycoprotein. A computational study, J. Mol. Graph Model 46 (2013) 10-21.
19. I. K. Pajeva, C. Globisch, M. Wiese, Comparison of the inward- and outwardopen homology models and ligand binding of human P-glycoprotein, FEBS J. 276 (2009) 7016-7026.
20. T. W. Loo, D. M. Clarke, Defining the drug-binding site in the human multidrug resistance P-glycoprotein using a methanethiosulfonate analog of verapamil, MTS-verapamil, J. Biol. Chem. 276 (2001) 14972-14979.
21. A. Beauchard, H. Laborie, H. Rouillard, O. Lozach, Y. Ferandin, R. Le Guevel, C. Guguen-Guillouzo, L. Meijer, T. Besson, V. Thiery, Synthesis and kinase inhibitory activity of novel substituted indigoids, Bioorg. Med. Chem. 17 (2009) 6257-6263.
22. L. Mologni, R. Rostagno, S. Brussolo, P. P. Knowles, S. Kjaer, J. Murray-Rust, E. Rosso, A. Zambon, L. Scapozza, N. Q. McDonald, V. Lucchini, C. Gambacorti-Passerini, Synthesis, structure-activity relationship and crystallographic studies of 3-substituted indolin-2-one RET inhibitors, Bioorg. Med. Chem. 18 (2010) 1482-1496.
23. L. Chen, Y. Li, H. Yu, L. Zhang, T. Hou, Computational models for predicting substrates or inhibitors of P-glycoprotein, Drug Discov. Today 17 (2012) 343-351.
24. G. Housman, S. Byler, S. Heerboth, K. Lapinska, M. Longacre, N. Snyder, S. Sarkar, Drug resistance in cancer: an overview, Cancers (Basel) 6 (2014) 1769-1792.
25. V. Vichai, K. Kirtikara, Sulforhodamine B colorimetric assay for cytotoxicity screening, Nat. Protoc. 1 (2006) 1112-1116.