Evodiamine, a dual catalytic inhibitor of type i and II topoisomerases, exhibits enhanced inhibition against camptothecin resistant cells

Phytomedicine

Volumn 19, Issue 7, 2012, Pages 618-624

  Pan, Xiaobei ^a   Hartley, Janet M ^b   Hartley, John A ^b   White, Kenneth N ^a   Wang, Zhengtao ^a,c   Bligh, S W Annie ^a  

^a LONDON METROPOLITAN UNIVERSITY   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

Catalytic inhibitor; CPT resistant; Evodia rutaecarpa; Evodiamine; Quinazolinocarboline; Quinolone; Topoisomerase

Indexed keywords

AMSACRINE; CAMPTOTHECIN; CELL DNA; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); ETOPOSIDE; EVODIAMINE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CELL STRAIN K 562; CONTROLLED STUDY; DNA DAMAGE; DRUG EFFICACY; DRUG ISOLATION; DRUG MECHANISM; DRUG TARGETING; FRUIT; G2 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; NONHUMAN; PRIORITY JOURNAL; TETRADIUM RUTICARPUM;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; CELL LINE, TUMOR; CELL PROLIFERATION; DNA DAMAGE; DNA TOPOISOMERASES; DNA TOPOISOMERASES, TYPE I; DNA TOPOISOMERASES, TYPE II; DRUG RESISTANCE, NEOPLASM; DRUGS, CHINESE HERBAL; EVODIA; FRUIT; HUMANS; INHIBITORY CONCENTRATION 50; LEUKEMIA; PHYTOTHERAPY; QUINAZOLINES; TOPOISOMERASE I INHIBITORS; TOPOISOMERASE II INHIBITORS; TOPOISOMERASE INHIBITORS;

EVODIA RUTAECARPA;

EID: 84862790283     PISSN: 09447113     EISSN: 1618095X     Source Type: Journal    
DOI: 10.1016/j.phymed.2012.02.003     Document Type: Article

References (37)

1. M. Adams, A. Mahringer, O. Kunert, G. Fricker, T. Efferth, and R. Bauer Cytotoxicity and p-glycoprotein modulating effects of quinolones and indoloquinazolines from the Chinese herb Evodia rutaecarpa Planta Med. 73 2007 1554 1557
2. J. Bergman, and S. Bergman Studies of rutaecarpine and related quinazolinocarboline alkaloids J. Org. Chem. 50 1985 1246 1255 (Pubitemid 15097107)
3. J.J. Champoux DNA topoisomerases: structure, function, and mechanism Annu. Rev. Biochem. 70 2001 369 413 (Pubitemid 32662215)
4. A.L.F. Chan, W.S. Chang, L.M. Chen, C.M. Lee, C.E. Chen, C.M. Lin, and J.L. Hwang Evodiamine stabilizes topoisomerase I-DNA cleavable complex to inhibit topoisomerase I activity Molecules 14 2009 1342 1352
5. A.Y. Chen, and L.F. Liu DNA topoisomerases - essential enzymes and lethal targets Annu. Rev. Pharmacol. Toxicol. 34 1994 191 218
6. M.C. Chen, C.H. Yu, S.W. Wang, H.F. Pu, S.F. Kan, L.C. Lin, C.W. Chi, L.L.T. Ho, C.H. Lee, and P.S. Wang Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO J. Cell. Biochem. 110 2010 1495 1503
7. N. Hajji, S. Mateos, N. Pastor, I. Domínguez, and F. Cortés Induction of genotoxic and cytotoxic damage by aclarubicin, a dual topoisomerase inhibitor Mutat. Res. 583 2005 26 35 (Pubitemid 40615200)
8. D.M. Huang, J.H. Guh, Y.T. Huang, S.C. Chueh, P.C. Chiang, and C.M. Teng Induction of mitotic arrest and apoptosis in human prostate cancer PC-3 cells by evodiamine J. Urol. 173 2005 256 261
9. Y.C. Huang, J.H. Guh, and C.M. Teng Induction of mitotic arrest and apoptosis by evodiamine in human leukemic T-lymphocytes Life Sci. 75 2004 35 49
10. F. Kanzawa, Y. Sugimoto, K. Minato, K. Kasahara, M. Bungo, K. Nakagawa, Y. Fujiwara, L.F. Liu, and N. Saijo Establishment of a camptothecin analog (Cpt-11)-resistant cell-line of human non-small cell lung-cancer - characterization and mechanism of resistance Cancer Res. 50 1990 5919 5924 (Pubitemid 20331400)
11. R. Kapoor, D.L. Slade, A. Fujimori, Y. Pommier, and W.G. Harker Altered topoisomerase I expression in two subclones of human CEM leukemia selected for resistance to camptothecin Oncol. Res. 7 1995 83 95
12. A.K. Larsen, A.E. Eseargueil, and A. Skladanowski Catalytic topoisomerase II inhibitors in cancer therapy Pharmacol. Ther. 99 2003 167 181 (Pubitemid 36897748)
13. L.F. Liu DNA topoisomerase poisons as antitumor drugs Annu. Rev. Biochem. 58 1989 351 375 (Pubitemid 19172974)
14. R.M. Liu, X. Chu, A.L. Sun, and L.Y. Kong Preparative isolation and purification of alkaloids from the Chinese medicinal herb Evodia rutaecarpa (Juss.) Benth by high-speed counter-current chromatography J. Chromatogr. A 1074 2005 139 144 (Pubitemid 40615051)
15. B.H. Long, and B.N. Balasubramanian Non-camptothecin topoisomerase I active compounds as potential anticancer agents Expert. Opin. Ther. Pat. 10 2000 635 666 (Pubitemid 30251757)
16. Y.B. Lu, W.Y. Ma, R.L. Hu, A. Berthod, and Y.J. Pan Rapid and preparative separation of traditional Chinese medicine Evodia rutaecarpa employing elution-extrusion and back-extrusion counter-current chromatography: comparative study J. Chromatogr. A 1216 2009 4140 4146
17. F.R. Mauro, R. Foa, G. Meloni, M. Gentile, E. Giammartini, D. Giannarelli, M.S. De Propris, M.C. Rapanotti, P. de Fabritiis, and F. Mandelli Fludarabine, ara-C, novantrone and dexamethasone (FAND) in previously treated chronic lymphocytic leukemia patients Haematologica 87 2002 926 933
18. T. Mosmann Rapid colorimetric assay for cellular growth and survival - application to proliferation and cyto-toxicity assays J. Immunol. Methods 65 1983 55 63 (Pubitemid 14203433)
19. M. Ogasawara, T. Matsunaga, S. Takahashi, I. Saiki, and H. Suzuki Anti-invasive and metastatic activities of evodiamine Biol. Pharm. Bull. 25 2002 1491 1493 (Pubitemid 39663174)
20. P. Peixoto, C. Bailly, and M.-H. David-Cordonnier Topoisomerase I-mediated DNA relaxation as a tool to study intercalation of small molecules into supercoiled DNA K.R. Fox, Drug-DNA Interaction Protocols 2nd ed. 2010 Human Press
21. Y. Pommier, and M. Cushman The indenoisoquinoline noncamptothecin topoisomerase I inhibitors: update and perspectives Mol. Cancer Ther. 8 2009 1008 1014
22. Y. Pommier, J.K. Minford, R.E. Schwartz, L.A. Zwelling, and K.W. Kohn Effects of the DNA intercalators 4′-(9-acridinylamino)methanesulfon-m- anisidide and 2-methyl-9-hydroxyellipticinium on topoisomerase II mediated DNA strand cleavage and strand passage Biochemistry 24 1985 6410 6416 (Pubitemid 16207110)
23. Y. Pommier, P. Pourquier, Y. Fan, and D. Strumberg Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme Biochim. Biophys. Acta: Gene Struct. Expression 1400 1998 83 106 (Pubitemid 28475097)
24. Y. Pommier, R.E. Schwartz, L.A. Zwelling, and K.W. Kohn Effects of DNA intercalating agents on topoisomerase II induced DNA strand cleavage in isolated mammalian cell nuclei Biochemistry 24 1985 6406 6410 (Pubitemid 16207109)
25. R. Riemsma, J.P. Simons, Z. Bashir, C.L. Gooch, and J. Kleijnen Systematic review of topotecan (Hycamtin) in relapsed small cell lung cancer BMC Cancer 10 2010 436 449
26. J.F. Riou, P. Fosse, C.H. Nguyen, A.K. Larsen, M.C. Bissery, L. Grondard, J.M. Saucier, E. Bisagni, and F. Lavelle Intoplicine (RP 60475) and its derivatives, a new class of antitumor agents inhibiting both topoisomerase I and II activities Cancer Res. 53 1993 5987 5993 (Pubitemid 24006171)
27. V.J. Spanswick, J.M. Hartley, and J.A. Hartley Measurement of DNA interstrand crosslinking in individual cells using the single cell gel electrophoresis (comet) assay Drug-DNA Interaction Protocols 2nd ed. 2010 pp. 267-282
28. Y. Sugimoto, S. Tsukahara, T. Ohhara, T. Isoe, and T. Tsuruo Decreased expression of DNA topoisomerase-I in camptothecin-resistant tumor-cell lines as determined by a monoclonal-antibody Cancer Res. 50 1990 6925 6930 (Pubitemid 20361092)
29. B.A. Teicher Next generation topoisomerase I inhibitors: rationale and biomarker strategies Biochem. Pharmacol. 75 2008 1262 1271 (Pubitemid 351305209)
30. J.C. Wang DNA topoisomerases as targets of therapeutics: an overview Adv. Pharmacol. 29A 1994 1 19
31. J.C. Wang DNA topoisomerases Annu. Rev. Biochem. 65 1996 635 692 (Pubitemid 26250622)
32. J.C. Wang Cellular roles of DNA topoisomerases: a molecular perspective Nat. Rev. Mol. Cell Biol. 3 2002 430 440 (Pubitemid 34685700)
33. E. Willmore, S.L. Elliott, C. Crawford, E. Mulligan, G. Summerfield, P. Newton, J. Wallis, T. Mainou-Fowler, P. Evans, C. Bedwell, and B.W. Durkacz Mitoxantrone in combination with an inhibitor of DNA-dependent protein kinase: a potential therapy for high risk B-cell chronic lymphocytic leukaemia Br. J. Haematol. 152 2011 61 71
34. L.R. Wiseman, and A. Markham Irinotecan. A review of its pharmacological properties and clinical efficacy in the management of advanced colorectal cancer Drugs 52 1996 606 623 (Pubitemid 26340542)
35. J.M. Woynarowski, M. McHugh, R.D. Sigmund, and T.A. Beerman Modulation of topoisomerase II catalytic activity by DNA minor groove binding agents distamycin. Hoechst 33258, and 4′,6-diamidine-2-phenylindole Mol. Pharmacol. 35 1989 177 182 (Pubitemid 19069592)
36. Y. Zhang, L.J. Wu, S. Tashiro, S. Onodera, and T. Ikejima Intracellular regulation of evodiamine-induced A375-S2 cell death Biol. Pharm. Bull. 26 2003 1543 1547 (Pubitemid 41699632)
37. Y. Zhang, Q.H. Zhang, L.J. Wu, S. Tashiro, S. Onodera, and T. Ikejima Atypical apoptosis in L929 cells induced by evodiamine isolated from Evodia rutaecarpa J. Asian Nat. Prod. Res. 6 2004 19 27 (Pubitemid 38190218)