Effects of new 4-aryl-1,4-dihydropyridines and 4-arylpyridines on drug efflux mediated by multidrug resistance-associated protein 1

Journal of Pharmaceutical Sciences

Volumn 94, Issue 10, 2005, Pages 2256-2265

  Zhou, Xiao Fei ^a,b   Coburn, Robert A ^a   Morris, Marilyn E ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b VERTEX PHARMACEUTICALS   (United States)

Author keywords

ATP binding cassette (ABC); Dihydropyridines; Drug efflux; Multidrug resistance (MDR); Multidrug resistance associated protein 1 (MRP1); Pyridines

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; ABC TRANSPORTER; CALCIUM CHANNEL; DAUNORUBICIN; DIMETHYL SULFOXIDE; GLUTATHIONE; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN 1; NIGULDIPINE; PYRIDINE DERIVATIVE; TRITIUM; VERAPAMIL; VERLUKAST; VINBLASTINE;

ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; DRUG TRANSPORT; FLOW CYTOMETRY; HUMAN; HUMAN CELL; LUNG SMALL CELL CANCER; MULTIDRUG RESISTANCE; PANCREAS ADENOCARCINOMA; WESTERN BLOTTING;

EID: 27944510952     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20406     Document Type: Article

References (41)

1. Juliano RL, Ling V. 1976. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim Biophys Acta 455:152-162.
2. Gerlach JH, Kartner N, Bell DR, Ling V. 1986. Multidrug resistance. Cancer Surv 5:25-46.
3. Ambudkar SV, Dey S, Hrycyna CA, Ramachandra M, Pastan I, Gottesman MM. 1999. Biochemical, cellular, and pharmacological aspects of the multidrug transporter. Annu Rev Pharmacol Toxicol 39:361-398.
4. Baas F, Jongsma AP, Broxterman HJ, Arceci RJ, Housman D, Scheffer GL, Riethorst A, van Groenigen M, Nieuwint AW, Joenje H. 1990. Non-P-glycoprotein mediated mechanism for multidrug resistance precedes P-glycoprotein expression during in vitro selection for doxorubicin resistance in a human lung cancer cell line. Cancer Res 50:5392-5398.
5. Mirski SE, Gerlach JH, Cole SP. 1987. Multidrug resistance in a human small cell lung cancer cell line selected in adriamycin. Cancer Res 47:2594-2598.
6. Cole SP, Bhardwaj G, Gerlach JH, Mackie JE, Grant CE, Almquist KC, Stewart AJ, Kurz EU, Duncan AM, Deeley RG. 1992. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 258:1650-1654.
7. Hipfner DR, Deeley RG, Cole SP. 1999. Structural, mechanistic and clinical aspects of MRP1. Biochim Biophys Acta 1461:359-376.
8. Leslie EM, Deeley RG, Cole SP. 2001. Toxicological relevance of the multidrug resistance protein 1, MRP1 (ABCC1) and related transporters. Toxicology 167:3-23.
9. Loe DW, Deeley RG, Cole SP. 2000. Verapamil stimulates glutathione transport by the 190-kDa multidrug resistance protein 1 (MRP1). J Pharmacol Exp Ther 293:530-538.
10. Teodori E, Dei S, Quidu P, Budriesi R, Chiarini A, Garnier-Suillerot A, Gualtieri F, Manetti D, Romanelli MN, Scapecchi S. 1999. Design, synthesis, and in vitro activity of catamphiphilic reverters of multidrug resistance: Discovery of a selective, highly efficacious chemosensitizer with potency in the nanomolar range. J Med Chem 42:1687-1697.
11. Teodori E, Dei S, Scapecchi S, Gualtieri F. 2002. The medicinal chemistry of multidrug resistance (MDR) reversing drugs. Farmaco 57:385-415.
12. Wigler PW, Patterson FK. 1993. Inhibition of the multidrug resistance efflux pump. Biochim Biophys Acta 1154:173-181.
13. Shudo N, Mizoguchi T, Kiyosue T, Arita M, Yoshimura A, Seto K, Sakoda R, Akiyama S. 1990. Two pyridine analogues with more effective ability to reverse multidrug resistance and with lower calcium channel blocking activity than their dihydropyridine counterparts. Cancer Res 50:3055-3061.
14. Sumizawa T, Chen ZS, Chuman Y, Seto K, Furukawa T, Haraguchi M, Tani A, Shudo N, Akiyama SI. 1997. Reversal of multidrug resistance-associated protein-mediated drug resistance by the pyridine analog PAK-104P. Mol Pharmacol 51:399-405.
15. Zhou XF, Zhang L, Tseng E, Scott-Ramsay EA, Schentag JJ, Coburn RA, Morris ME. 2005. New 4-Aryl-1, 4-Dihydropyridines and 4-Arylpyridines as P-glycoprotein inhibitors. Drug Metab Dispos 33:321-328.
16. Zhou XF, Yang X, Morris ME. 2004. Newly synthesized dihydropyridine and pyridines as multidrug resistance modulators in cancer chemotherapy. AAPS Pharm Sci 6: Abstract T2350.
17. Nguyen H, Zhang S, Morris ME. 2003. Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J Pharm Sci 92:250-257.
18. Aszalos A, Weaver JL. 1998. Estimation of drug resistance by flow cytometry. In: Jaroszeski MJ, Heller R, editors. Flow cytometry protocols, 1st edn. Totowa, NJ: Humana Press, pp 117-122.
19. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. 1990. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107-1112.
20. Tietze F. 1969. Enzymic method for quantitative determination of nanogram amounts of total and oxidized glutathione: Applications to mammalian blood and other tissues. Anal Biochem 27:502-522.
21. Miller DW, Fontain M, Kolar C, Lawson T. 1996. The expression of multidrug resistance-associated protein (MRP) in pancreatic adenocarcinoma cell lines. Cancer Lett 107:301-306.
22. Cole SP, Downes HF, Mirski SE, Clements DJ. 1990. Alterations in glutathione and glutathione-related enzymes in a multidrug-resistant small cell lung cancer cell line. Mol Pharmacol 37:192-197.
23. Flens MJ, Zaman GJ, van der Valk P, Izquierdo MA, Schroeijers AB, Scheffer GL, van der Groep P, de Haas M, Meijer CJ, Scheper RJ. 1996. Tissue distribution of the multidrug resistance protein. Am J Pathol 148:1237-1247.
24. Kruh GD, Gaughan KT, Godwin A, Chan A. 1995. Expression pattern of MRP in human tissues and adult solid tumor cell lines. J Natl Cancer Inst 87:1256-1258.
25. Aszalos A, Ross DD. 1998. Biochemical and clinical aspects of efflux pump related resistance to anticancer drugs. Anticancer Res 18:2937-2944.
26. Abe T, Koike K, Ohga T, Kubo T, Wada M, Kohno K, Mori T, Hidaka K, Kuwano M. 1995. Chemosensitisation of spontaneous multidrug resistance by a 1,4-dihydropyridine analogue and verapamil in human glioma cell lines overexpressing MRP or MDR1. Br J Cancer 72:418-423.
27. Versantvoort CH, Broxterman HJ, Lankelma J, Feller N, Pinedo HM. 1994. Competitive inhibition by genistein and ATP dependence of daunorubicin transport in intact MRP overexpressing human small cell lung cancer cells. Biochem Pharmacol 48:1129-1136.
28. Hu K, Morris ME. 2004. Effects of benzyl-, phenethyl-, and alpha-naphthyl isothiocyanates on P-glycoprotein- and MRP1-mediated transport. J Pharm Sci 93:1901-1911.
29. Potschka H, Baltes S, Loscher W. 2004. Inhibition of multidrug transporters by verapamil or probenecid does not alter blood-brain barrier penetration of levetiracetam in rats. Epilepsy Res 58:85-91.
30. Chauvier D, Kegelaer G, Morjani H, Manfait M. 2002. Reversal of multidrug resistance-associated protein-mediated daunorubicin resistance by camptothecin. J Pharm Sci 91:1765-1775.
31. Tang R, Faussat AM, Majdak P, Perrot JY, Chaoui D, Legrand O, Marie JP. 2004. Valproic acid inhibits proliferation and induces apoptosis in acute myeloid leukemia cells expressing P-gp and MRP1. Leukemia 18:1246-1251.
32. Gekeler V, Ise W, Sanders KH, Ulrich WR, Beck J. 1995. The leukotriene LTD4 receptor antagonist MK571 specifically modulates MRP associated multidrug resistance. Biochem Biophys Res Commun 208:345-352.
33. Trompier D, Chang XB, Barattin R, du Moulinet D'Hardemare A, Di Pietro A, Baubichon-Cortay H. 2004. Verapamil and its derivative trigger apoptosis through glutathione extrusion by multidrug resistance protein MRP1. Cancer Res 64:4950-4956.
34. Cole SP, Downes HF, Slovak ML. 1989. Effect of calcium antagonists on the chemosensitivity of two multidrug-resistant human tumour cell lines which do not overexpress P-glycoprotein. Br J Cancer 59:42-46.
35. Meijer C, Mulder NH, Timmer-Bosscha H, Peters WH, de Vries EG. 1991. Combinedm vitro modulation of adriamycin resistance. Int J Cancer 49:582-586.
36. Slovak ML, Hoeltge GA, Dalton WS, Trent JM. 1988. Pharmacological and biological evidence for differing mechanisms of doxorubicin resistance in two human tumor cell lines. Cancer Res 48:2793-2797.
37. Barrand MA, Rhodes T, Center MS, Twentyman PR. 1993. Chemosensitisation and drug accumulation effects of cyclosporin A, PSC-833 and verapamil in human MDR large cell lung cancer cells expressing a 190k membrane protein distinct from P-glycoprotein. Eur J Cancer 29A:408-415.
38. Suzukake K, Petro BJ, Vistica DT. 1982. Reduction in glutathione content of L-PAM resistant L1210 Cells confers drug sensitivity. Biochem Pharmacol 31:121-124.
39. Ahmad S, Okine L, Le B, Najarian P, Vistica DT. 1987. Elevation of glutathione in phenylalanine mustard-resistant murine L1210 leukemia cells. J Biol Chem 262:15048-15053.
40. Benderra Z, Trussardi A, Morjani H, Villa AM, Doglia SM, Manfait M. 2000. Regulation of cellular glutathione modulates nuclear accumulation of daunorubicin in human MCF7 cells overexpressing multidrug resistance associated protein. Eur J Cancer 36:428-434.
41. Salerno M, Loechariyakul P, Saengkhae C, Gamier-Suillerot A. 2004. Relation between the ability of some compounds to modulate the MRP1-mediated efflux of glutathione and to inhibit the MRP1-mediated efflux of daunorubicin. Biochem Pharmacol 68:2159-2165.