Dibenzocyclooctadiene lignans overcome drug resistance in lung cancer cells - Study of structure-activity relationship

Toxicology in Vitro

Volumn 23, Issue 6, 2009, Pages 1047-1054

  Slaninova I ^a   Brezinova L ^a   Koubikova L ^a   Slanina, J ^a  

^a MASARYK UNIVERSITY   (Czech Republic)

Author keywords

COR L23 R; Cytotoxicity; Dibenzocyclooctadiene lignans; Doxorubicin; MRP proteins; Multidrug; Resistance

Indexed keywords

ANGELOYLGOMISIN H; DEOXYSCHIZANDRIN; DIBENZO[A,C]CYCLOOCTADIENE LIGNAN; DOXORUBICIN; GAMMA SCHIZANDRIN; GOMISIN; GOMISIN A; HYDROXYL GROUP; LIGNAN; MULTIDRUG RESISTANCE PROTEIN 1; SCHIZANDRIN; TIGLOYLGOMISIN P; UNCLASSIFIED DRUG; WUWEIZISU C;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL PROLIFERATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACCUMULATION; DRUG POTENTIATION; DRUG STRUCTURE; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; INHIBITION KINETICS; LUNG CARCINOMA; MULTIDRUG RESISTANCE; PLANT SEED; SCHISANDRACEAE; STRUCTURE ACTIVITY RELATION;

ANTIBIOTICS, ANTINEOPLASTIC; CARCINOMA, LARGE CELL; CELL DIVISION; CELL LINE, TUMOR; CYCLOOCTANES; DOSE-RESPONSE RELATIONSHIP, DRUG; DOXORUBICIN; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; G2 PHASE; HUMANS; LIGNANS; LUNG NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 68049086622     PISSN: 08872333     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tiv.2009.06.008     Document Type: Article

References (38)

1. Barrand M.A., Rhodes T., Center M.S., and Twentyman P.R. Chemosensitisation and drug accumulation effects of cyclosporine-A, Psc-833 and verapamil in human Mdr large cell lung-cancer cells expressing A 190 K membrane-protein distinct from P-glycoprotein. European Journal of Cancer 29A (1993) 408-415
2. Batrakova E.V., Li S., Alakhov V.Y., Elmquist W.F., Miller D.W., and Kabanov A.V. Sensitization of cells overexpressing multidrug-resistant proteins by pluronic P85. Pharmaceutical Research 20 (2003) 1581-1590
3. Boumendjel A., Baubichon-Cortay H., Trompier D., Perrotton T., and Di Pietro A. Anticancer multidrug resistance mediated by MRP1: recent advances in the discovery of reversal agents. Medicinal Research Reviews 25 (2005) 453-472
4. Chiu P.Y., Tang M.H., Mak D.H.F., Poon M.K.T., and Ko K.M. Hepatoprotective mechanism of schisandrin B: role of mitochondrial glutathione antioxidant status and heat shock proteins. Free Radical Biology and Medicine 35 (2003) 368-380
5. Chiu P.Y., Leung H.Y., Poon M.K.T., Lee S.S.T., and Ko K.M. Schisandrin B induced antioxidant response is partly mediated by cytochrome P-4502E1 catalyzed reaction in mouse liver. Molecular and Cellular Biochemistry 293 (2006) 87-92
6. Coley H.M., Workman P., and Twentyman P.R. Retention of activity by selected anthracyclines in A multidrug resistant human large cell lung-carcinoma line without P-glycoprotein hyperexpression. British Journal of Cancer 63 (1991) 351-357
7. Filipits M. Mechanisms of cancer: multidrug resistance. Drug Discovery Today: Disease Mechanisms I 229 (2004) 234
8. Hancke J.L., Burgos R.A., and Ahumada F. Schisandra chinensis (Turcz.) Baill. Fitoterapia 70 (1999) 451-471
9. Hollo Z., Homolya L., Hegedus T., and Sarkadi B. Transport properties of the multidrug resistance-associated protein (MRP) in human tumour cells. FEBS Letters 383 (1996) 99-104
10. Huang M., Jin J., Sun H., and Liu G.T. Reversal of P-glykoprotein-mediated multidrug resistance of cancer cells by five schizandrins isolated from the Chinese herb Fructus Schisandrae. Cancer Chemotherapy and Pharmacology 62 (2008) 1015-1026
11. Huang X., Song F., Liu Z., and Liu S. Structural characterization and identification of dibenzocyclooctadiene lignans in Fructus Schisandrae using electrospray ionization ion trap multiple-stage tandem mass spectrometry and electrospray ionization Fourier transform ion cyclotron resonance multiple-stage tandem mass spectrometry. Analytica Chimica Acta 615 (2008) 124-135
12. Ikeya Y., Taguchi H., and Yosioka I. The constituents of Schizandra chinensis Baill. X. The structures of γ-schizandrin and 4 new lignans, (-)-gomisins L1 and L2, (±)-gomisin M1 and (+)-gomisin M2. Chemical and Pharmaceutical Bulletin 30 (1982) 132-139
13. Ip S.P., and Ko K.M. The crucial antioxidant action of schisandrin B in protecting against carbon tetrachloride hepatotoxicity in mice. A comparative study with butylated hydroxytoluene. Biochemical Pharmacology 52 (1996) 1687-1693
14. Li X.J., Zhao B.L., Liu G.T., and Xin W.J. Scavenging effects on active oxygen radicals by schizandrins with different structures and configurations. Free Radical Biology and Medicine 9 (1990) 99-104
15. Li L., Lu Q.H., Shen Y.W., and Hu X. Schisandrin B enhances doxorubicin-induced apoptosis of cancer cells but not normal cells. Biochemical Pharmacology 71 (2006) 584-595
16. Li L., Pan Q., Han W., Liu Z., Li L., and Hu X. Schisandrin B prevents doxorubicin-induced cardiotoxicity via enhancing glutathione redox cycling. Clinical Cancer Research 13 (2007) 6753-6760
17. Li L., Pan Q.R., Sun M., Lu Q.H., and Hu X. Dibenzocyclooctadiene lignans - a class of novel inhibitors of multidrug resistance-associated protein 1. Life Sciences 80 (2007) 741-748
18. Lin S.G., Fujii M., and Hou D.X. Molecular mechanism of apoptosis induced by schizandrae-derived lignans in human leukemia HL-60 cells. Food and Chemical Toxicology 46 (2008) 590-597
19. Liu X.N., Zhang C.Y., Jin X.D., Li Y.Z., Zheng X.Z., and Li L. Inhibitory effect of schisandrin B on gastric cancer cells in vitro. World Journal of Gastroenterology 13 (2007) 6506-6511
20. Loe D.W., Deeley R.G., and Cole S.P.C. Biology of the multidrug resistance-associated protein, MRP. European Journal of Cancer 32A (1996) 945-957
21. Manzano R.G., Versanvoort C., Wright K., and Twentyman P.R. Rapid recovery of a functional MDR phenotype caused by MRP after a transient exposure to MDR drugs in a revertant human lung cancer cell line. European Journal of Cancer 32A (1996) 2136-2141
22. Marek J., and Slanina J. Gomisin N. Acta Crystallographica C 54 (1998) 1548-1550
23. Min H.Y., Park E.J., Hong J.Y., Kang Y.J., Kim S.J., Chung H.J., Woo E.R., Hung T.M., Youn U.J., Kim Y.S., Kang S.S., Bae K., and Lee S.K. Antiproliferative effects of dibenzocyclooctadiene lignans isolated from Schisandra chinensis in human cancer cells. Bioorganic and Medicinal Chemistry Letters 18 (2008) 523-526
24. Nomura M., Ohtaki Y., Hida T., Aizawa T., Wakita H., and Miyamoto K.I. Inhibition of early 3-methyl-4-dimethylaminoazobenzene-induced hepatocarcinogenesis by gomisin-A in rats. Anticancer Research 14 (1994) 1967-1971
25. Ohtaki Y., Hida T., Hiramatsu K., Kanitani M., Ohshima T., Nomura M., Wakita H., Aburada M., and Miyamoto K. Deoxycholic acid as an endogenous risk factor for hepatocarcinogenesis and effects of gomisin A, a lignan component of schizandra fruits. Anticancer Research 16 (1996) 751-755
26. Opletal L., Sovova H., and Bartlova M. Dibenzo[a, c]cyclooctadiene lignans of the genus schisandra: importance, isolation and determination. Journal of Chromatography B - Analytical Technologies in the Biomedical and Life Sciences 812 (2004) 357-371
27. Pan Q.R., Tao W., Lu Q.H., and Hu X. Schisandrin B - a novel inhibitor of P-glycoprotein. Biochemical and Biophysical Research Communications 335 (2005) 406-411
28. Pan Q.R., Lu Q.H., Zhang K., and Hu X. Dibenzocyclooctadiene lingnans: a class of novel inhibitors of P-glycoprotein. Cancer Chemotherapy and Pharmacology 58 (2006) 99-106
29. Sun M., Xu X.L., Lu Q.H., Pan Q.R., and Hu X. Schisandrin B: a dual inhibitor of P-glycoprotein and multidrug resistance-associated protein 1. Cancer Letters 246 (2007) 300-307
30. Teodori E., Dei S., Scapecchi S., and Gualtieri F. The medicinal chemistry of multidrug resistance (MDR) reversing drugs. Farmaco 57 (2002) 385-415
31. Thomas G.A., Barrand M.A., Stewart S., Rabbitts P.H., Williams E.D., and Twentyman P.R. Expression of the multidrug resistance-associated protein (Mrp) gene in human lung-tumors and normal tissue as determined by in situ hybridization. European Journal of Cancer 30A (1994) 1705-1709
32. Tsuruo T., Iida H., Tsukagoshi S., and Sakurai Y. Overcoming of vincristine resistance in P388 leukemia invivo and invitro through enhanced cyto-toxicity of vincristine and vinblastine by verapamil. Cancer Research 41 (1981) 1967-1972
33. Twentyman P.R. Lung cancer cell lines as model systéme for studying drug resistance. Lung Cancer 9 (1993) 327-342
34. Wan C.K., Zhu G.Y., Shen X.L., Chattopadhyay A., Dey S., and Fong W.F. Gomisin A alters substrate interaction and reverses P-glycoprotein-mediated multidrug resistance in HepG2-DR cells. Biochemical Pharmacology 72 (2006) 824-837
35. Wang J.P., Raung S.L., Hsu M.F., and Chen C.C. Inhibition by gomisin-C (a lignan from Schizandra chinensis) of the respiratory burst of rat neutrophils. British Journal of Pharmacology 113 (1994) 945-953
36. Yasukawa K., Ikeya Y., Mitsuhashi H., Iwasaki M., Aburada M., Nakagawa S., Takeuchi M., and Takido M. Gomisin-A inhibits tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in 2-stage carcinogenesis in mouse skin. Oncology 49 (1992) 68-71
37. Yu X.Q., Xue C.C., Wang G., and Zhou S.F. Multidrug resistance associated proteins as determining factors of pharmacokinetics and pharmacodynamics of drugs. Current Drug Metabolism 8 (2007) 787-802
38. Zhao B.L., Li X.J., Liu G.T., Jia W.Y., and Xin W.J. Scavenging effect of schizandrins on active oxygen radicals. Cell Biology International Reports 14 (1990) 99-109