Synthesis and biological evaluation of bifendate-chalcone hybrids as a new class of potential P-glycoprotein inhibitors

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 8, 2012, Pages 2540-2548

  Gu, Xiaoke ^a   Ren, Zhiguang ^b,c   Tang, Xiaobo ^a   Peng, Hui ^b   Ma, Yuanfang ^c   Lai, Yisheng ^a   Peng, Sixun ^a   Zhang, Yihua ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b INSTITUTE OF BASIC MEDICAL SCIENCES   (China)

^c HENAN UNIVERSITY   (China)

Author keywords

Bifendate; Cancer chemotherapy; Chalcone; Multidrug resistance; P gp inhibitor

Indexed keywords

BIFENDATE CHALCONE HYBRID DERIVATIVE; DOXORUBICIN; GLYCOPROTEIN P INHIBITOR; METHYL 5' (1H IMIDAZOLE 1 CARBONYL) 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' (HYDROXYMETHYL) 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' [2 CYANO 3 (4 METHOXYPHENYL) 3 OXOPROP 1 EN 1 YL] 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' [2 CYANO 3 OXO 3 (3,4,5 TRIMETHOXYPHENYL)PROP 1 EN 1 YL] 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' [3 (2,4 DIMETHOXYPHENYL) 3 OXOPROP 1 EN 1 YL] 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' [3 (2,4 DIMETHYLPHENYL) 3 OXOPROP 1 EN 1 YL] 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' [3 (2,5 DIMETHOXYPHENYL) 3 OXOPROP 1 EN 1 YL] 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' [3 (4 HYDROXYPHENYL) 3 OXOPROP 1 EN 1 YL] 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 5' FORMYL 7,7' DIMETHOXY (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 7,7' DIMETHOXY 5' (3 OXO 3 PHENYLPROP 1 EN 1 YL) (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 7,7' DIMETHOXY 5' [3 (2 METHOXYPHENYL) 3 OXOPROP 1 EN 1 YL] (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 7,7' DIMETHOXY 5' [3 (4 METHOXYPHENYL) 3 OXOPROP 1 EN 1 YL] (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 7,7' DIMETHOXY 5' [3 (4 NITROPHENYL) 3 OXOPROP 1 EN 1 YL] (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; METHYL 7,7' DIMETHOXY 5' [3 OXO 3 (3,4,5 TRIMETHOXYPHENYL)PROP 1 EN 1 YL] (4,4' BIBENZO[D][1,3]DIOXOLE) 5 CARBOXYLATE; RHODAMINE 123; UNCLASSIFIED DRUG; VERAPAMIL;

ALDOL REACTION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACCUMULATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SUBSTRATE; FLOW CYTOMETRY; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; HYBRIDIZATION; IC 50; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SURVIVAL RATE;

ANTINEOPLASTIC AGENTS; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; CELL PROLIFERATION; CHALCONE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; K562 CELLS; P-GLYCOPROTEIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84862796284     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.02.050     Document Type: Article

References (24)

1. S.G. Aller, J. Yu, A. Ward, Y. Weng, S. Chittaboina, R. Zhuo, P.M. Harrell, Y.T. Trinh, Q. Zhang, I.L. Urbatsch, and G. Chang Science 323 2009 1718
2. D. Turk, M.D. Hall, B.F. Chu, J.A. Ludwig, H.M. Fales, M.M. Gottesman, and G. Szakacs Cancer Res. 69 2009 8293
3. C. Martelli, D. Alderighi, M. Coronnello, S. Dei, M. Frosini, B.N.D. Le Bozec, D. Manetti, A. Neri, M.N. Romanelli, M. Salerno, S. Scapecchi, E. Mini, G. Sgaragli, and E. Teodori J. Med. Chem. 52 2009 807
4. J.I. Fletcher, M. Haber, M.J. Henderson, and M.D. Norris Nat. Rev. Cancer 10 2010 147
5. L. Zhang, and S. Ma ChemMedChem 5 2010 811
6. N.A. Colabufo, F. Berardi, M. Cantore, M. Contino, C. Inglese, M. Niso, and R. Perrone J. Med. Chem. 2010 1883 53
7. C.P. Wu, S. Ohnuma, and S.V. Ambudkar Curr. Pharm. Biotechnol. 12 2011 609
8. E. Crowley, C.A. McDevitt, and R. Callaghan Methods Mol. Biol. 596 2010 405
9. J.C. Aponte, M. Verástegui, E. Málaga, M. Zimic, M. Quiliano, A.J. Vaisberg, R.H. Gilman, and G.B. Hammond J. Med. Chem. 51 2008 6230
10. X.L. Liu, H.W. Tee, and M.L. Go Bioorg. Med. Chem. 16 2008 171
11. X. Tang, X. Gu, H. Ai, G. Wang, H. Peng, Y. Lai, and Y. Zhang Bioorg. Med. Chem. Lett. 22 2012 801
12. J. Chang, R. Chen, R. Guo, C. Dong, and K. Zhao Helv. Chim. Acta 86 2003 2239
13. J. Tatsuzaki, K.F. Bastow, K. Nakagawa-Goto, S. Nakamura, H. Itokawa, and K.H. Lee J. Nat. Prod. 69 2006 1445
14. C. Baumert, and A. Hilgeroth Anticancer Agents Med. Chem. 9 2009 415
15. E. Teodori, S. Dei, P. Quidu, R. Budriesi, A. Chiarini, A. Garnier-Suillerot, F. Gualtieri, D. Manetti, M.N. Romanelli, and S. Scapecchi J. Med. Chem. 42 1999 1687
16. X.W. Kong, Y.H. Zhang, T. Wang, Y.S. Lai, and S.X. Peng Chem. Biodivers. 5 2008 1743
17. Y. Ma, and M. Wink Phytomedicine 15 2008 754
18. C.Z. Yang, F.J. Luan, D.S. Xiong, B.R. Liu, Y.F. Xu, and K.S. Gu Zhongguo Yao Li Xue Bao 16 1995 333
19. J. Jin, H. Sun, H. Wei, and G. Liu Invest. New Drugs 25 2007 95
20. J. Qi, S. Wang, G. Liu, H. Peng, J. Wang, Z. Zhu, and C. Yang Biochem. Biophys. Res. Commun. 319 2004 1124
21. C.L. Dai, A.K. Tiwari, C.P. Wu, X.D. Su, S.R. Wang, D.G. Liu, C.R. Ashby Jr., Y. Huang, R.W. Robey, Y.J. Liang, L.M. Chen, C.J. Shi, S.V. Ambudkar, Z.S. Chen, and L.W. Fu Cancer Res. 68 2008 7905
22. C. Martelli, D. Alderighi, M. Coronnello, S. Dei, M. Frosini, B. Le Bozec, D. Manetti, A. Neri, M.N. Romanelli, M. Salerno, S. Scapecchi, E. Mini, G. Sgaragli, and E. Teodori J. Med. Chem. 52 2009 807
23. S. Krawczyk, M. Otto, A. Otto, C. Coburger, M. Krug, M. Seifert, V. Tell, J. Molnar, and A. Hilgeroth Bioorg. Med. Chem. 19 2011 6309
24. Y.M. Wang, L.X. Hu, Z.M. Liu, X.F. You, S.H. Zhang, J.R. Qu, Z.R. Li, Y. Li, W.J. Kong, H.W. He, R.G. Shao, L.R. Zhang, Z.G. Peng, D.W. Boykin, and J.D. Jiang Clin. Cancer Res. 14 2008 6218