Synthesis and biochemical characterization of new phenothiazines and related drugs as MDR reversal agents

Archiv der Pharmazie

Volumn 341, Issue 10, 2008, Pages 624-638

  Schmidt, Matthias ^a   Teitge, Marlen ^a   Castillo, Marianela E ^a   Brandt, Tobias ^a   Dobner, Bodo ^a   Langner, Andreas ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Chemotherapy; Crystalviolet assay; LLC PK1 MDR1 cells; P glycoprotein; Structure acitivity relationships

Indexed keywords

10 [4 (2,2 DIPHENYLPROPYLAMINO)BUTYL]PHENOTHIAZINE HYDROGEN MALEATE; 10 [4 (3,3 DIPHENYLPROPYLAMINO)BUTYL]PHENOTHIAZINE HYDROGEN MALEATE; 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 10 [4 [4 (2,2 DIPHENYLETHYL)PIPERAZINO]BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 10 [4 [4 (3,3 DIPHENYLETHYL)PIPERAZINO]BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 10 [4 [4 (4,4 DIPHENYLBUTYL)PIPERAZINO]BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 10 [4 [4 (5,5 DIPHENYLPENTYL)PIPERAZINO]BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 10 [4 [4 DIPHENYLMETHYL)PIPERAZINO]BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 2 ACETYL 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 2 BENZOYL 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 2 BUTYRYL 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 2 METHOXY 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 2 METHYLTHIO 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 2 PROPIONYL 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 3 [4 [4 (5,5 DIPHENYLPENTYL)PIPERAZINYL]BUTYL] 5,5 DIPHENYLIMIDAZOLIDINE 2,4 DION BIS (HYDROGEN MALEATE); 3 BUTOXY 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 3 BUTYL 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 3 PHENYL 10 [4 (4 METHYLPIPERAZINO)BUTYL]PHENOTHIAZINE BIS(HYDROGEN MALEATE); 5 [4 [4 (5,5 DIPHENYLPENTYL)PIPERAZINYL]BUTYL] 10,11 DIHYDRO 5H DIBENZ[B,F]AZEPINE BIS(HYDROGENE OXALATE); 5 [4 [4 (5,5 DIPHENYLPENTYL)PIPERAZINYL]BUTYL] 5H DIBENZ[B,F]AZEPINE BIS(HYDROGEN OXALATE); 6 [4 [4 (4,4 DIPHENYLPENTYL)PIPERAZINYL]BUTYL] 1,2,3,9 TETRAMETHOXY 6,7 DIHYDRO 5H DIBENZ[C,E]AZEPINE BIS(HYDROGEN MALEATE); 6 [4 [4 (5,5 DIPHENYLPENTYL)PIPERAZINYL]BUTYL] 6,7 DIHYDRO 5H DIBENZ[C,E]AZEPINE BIS (HYDROGEN OXALATE); 9 [4 (4 [5,5 DIPHENYLPENTYL]PIPERAZINYL)BUTYL] 9H CARBAZOLE BIS(HYDROGEN OXALATE); FLUPENTIXOL; FLUPHENAZINE; PHENOTHIAZINE DERIVATIVE; PROPAFENONE; TRIFLUOPERAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VERAPAMIL;

ANIMAL CELL; ARTICLE; CELL STRAIN; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; REVERSAL REACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CELL SURVIVAL; DRUG DESIGN; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; LLC-PK1 CELLS; PHENOTHIAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

EID: 53549133107     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.200800115     Document Type: Article

References (41)

1. C. Avendano, J. Menéndez, Curr. Med. Chem. 2002, 9, 159-193.
2. R. Krishna, L. D. Mayer, Eur. J. Pharm. Sci. 2000, 11, 265-283.
3. J. Robert, C. Jarry, J. Med. Chem. 2003, 23, 4805-4817.
4. J. M. Ford, E. P. Briggeman, I. Pastan, M. Gottesman, W. N. Hait, Cancer Res. 1990, 50, 1748-1756.
5. I. Pajeva, M. Wiese, J. Med. Chem. 1998, 41, 1815-1826.
6. J. M. Ford, W. C. Prozialeck, W. N. Hait, Mol. Pharmacol. 1989, 35, 105-115.
7. J. M. Zamora, H. L. Pearce, W. T. Beck, Mol. Pharmacol. 1988, 33, 454465.
8. M. Wiese, I. K. Pajeva, Current Med. Chem. 2001, 8, 685-713.
9. H. Pearce, A. Safa, N. Bach, M. Winter, et al., Proc. Natl. Acad. Sci. U. S. A 1989, 5128-5132.
10. W. Hait, D. Aftab, Biochem. Pharmacol. 1992, 43, 103-107.
11. T. Suzuki, N. Fukazawa, K. San-nohe, W. Sato, et al., J. Med. Chem. 1997, 2047-2052.
12. A. Seelig, Eur. J. Biochem. 1997, 252-261.
13. A. Seelig, E. Landwojtowicz, Eur. J. Pharm. Sci. 2000, 31-40.
14. T. W. Loo, D. M. Clarke, J. Membrane Biol. 2005, 173-185.
15. S. Ekins, R. B. Kim, B. F. Leake, A. H. Dantzig, et al., Mol. Pharmacol. 2002, 974-981.
16. I. K. Pajeva, M. Wiese, J. Med. Chem. 2002, 45, 5671-5686.
17. S. Döppenschmitt, H. Spahn-Langguth, C. Regårdh, P. Langguth, Pharm. Res. 1998, 1001-1006.
18. I. K. Pajeva, C. Globisch, M. Wiese, J. Med. Chem. 2004, 47, 2523-2533.
19. C. Globisch, I. Pajewa, M. Wiese, Chem.Med.Chem. 2008, 3, 280-295.
20. T. Tsuruo, H. Iida, S. Tsukagoshi, Y. Sakurai, Cancer Res. 1982, 42, 4730-4733.
21. R. Ganapathi, D. Grabowski, R. Turinic, R. Valenzuela, Eur. J. Cancer Clin. Oncol. 1984, 20, 799-806.
22. M. Schmidt, J. Ungvári, J. Glöde, B. Dobner, A. Langner, Bioorg. Med. Chem. 2007, 15, 2283-2297.
23. R. L. Miller, R. M. Bukowski, G. T Budd, J. Clin. Oncol. 1988, 6, 880-888.
24. A. Ramu, N. Ramu, Cancer Chemother. Pharmacol. 1992, 30, 165-173.
25. I. Pajeva, M. Wiese, Quant. Struct.-Act. Relat. 1997, 16, 1-10.
26. G. Klopman, L. M. Shi, A. Ramu, Mol. Pharmacol. 1997, 52, 323-334.
27. J. Guan, D. E. Kyle, L. Gerena, Q. Zhang, et al., J. Med. Chem. 2002, 45, 2741-2748.
28. S. Darvesh, R. S. McDonald, A. Penwell, S. Conrad, et al., Bioorg. Med. Chem. 2005, 13, 211-222.
29. A. Bernthsen, Ber. Dtsch. Chem. Ges. 1883, 16, 2896-2904.
30. Rhône-Poulenc, Belg. P. 556475, C. 1960, 16863.
31. H. L. Yale, JACS, 1955, 77, 2270-2272.
32. W. J. Evans, S. Smiles, J. Chem. Soc. 1935, 181, 1263-1265.
33. M. Golinski, P. J. DelaLuz, R. Floresca, T. J. Delcamp, et al., Bioconjugate Chem. 1995, 6, 549-557.
34. S. P. Massie, I. Cooke, W. A. Hills, J. Org. Chem. 1956, 21, 1006-1008.
35. J. M. Hawkins, G. C. Fu, J. Org. Chem. 1986, 51, 2820-2822.
36. L. Adams, C. Gray, R. Williams, Tetrahedron Letters 2004, 45, 4489-4493.
37. O. Kimura, T. Osawa, K. Mochida, Jpn. Kokai Tokkyo Koho, 1989, 7-11.
38. D. A. Flick, G. E. Gifford, J. Immunol. Methods 1984, 167-175.
39. Y. Tanigawara, N. Okamura, M. Hirai, M. Yasuhara, et al., J. Pharmacol. Exp. Ther. 1992, 263, 840-845.
40. A. H. Schinkel, E. Wagenaar, L. van Deemter, C. A. Mol, P. Borst, J. Clin. Invest. 1995, 1698-1705.
41. P. Scafato, G. Cunsolo, S. Labano, C. Rosini, Tetrahedron 2004, 40, 8801-8806.