Induction of apoptosis in cholangiocarcinoma by an andrographolide analogue is mediated through topoisomerase II alpha inhibition

European Journal of Pharmacology

Volumn 723, Issue 1, 2014, Pages 148-155

  Nateewattana, Jintapat ^a   Dutta, Suman ^a   Reabroi, Somrudee ^a   Saeeng, Rungnapha ^b   Kasemsook, Sakkasem ^b   Chairoungdua, Arthit ^a   Weerachayaphorn, Jittima ^a   Wongkham, Sopit ^c   Piyachaturawat, Pawinee ^a  

^a Mahidol University   (Thailand)

^b BURAPHA UNIVERSITY   (Thailand)

^c KHON KAEN UNIVERSITY   (Thailand)

Author keywords

Andrographolide analogue; Apoptosis; Cholangiocarcinoma; KKU M213 cell line; Topoisomerase II

Indexed keywords

19 TERT BUTYLDIPHENYLSILYL 8,17 EPOXY ANDROGRAPHOLIDE; ANTINEOPLASTIC AGENT; CASPASE 3; CYCLIN D1; CYCLIN DEPENDENT KINASE 6; CYCLOOXYGENASE 2; DNA TOPOISOMERASE (ATP HYDROLYSING); ETOPOSIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE 1; PROTEIN BAX; PROTEIN P53; TOPOISOMERASE II ALPHA; UNCLASSIFIED DRUG; VINBLASTINE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BILE DUCT CARCINOMA; CANCER CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; LONG TERM EXPOSURE; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANDROGRAPHOLIDE ANALOGUE; APOPTOSIS; CHOLANGIOCARCINOMA; KKU-M213 CELL LINE; TOPOISOMERASE II Α;

ANTIGENS, NEOPLASM; ANTINEOPLASTIC AGENTS; APOPTOSIS; BCL-2-ASSOCIATED X PROTEIN; BILE DUCT NEOPLASMS; CASPASE 3; CELL CYCLE; CELL LINE, TUMOR; CELL SURVIVAL; CHOLANGIOCARCINOMA; CYCLOOXYGENASE 2; DITERPENES; DNA; DNA TOPOISOMERASES, TYPE II; DNA-BINDING PROTEINS; HUMANS; ORGANOSILICON COMPOUNDS; POLY(ADP-RIBOSE) POLYMERASES; TUMOR SUPPRESSOR PROTEIN P53;

EID: 84891545203     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2013.12.002     Document Type: Article

References (31)

1. K. Aravindaram, and N.S. Yang Anti-inflammatory plant natural products for cancer therapy Planta Med. 76 2010 1103 1117
2. A.G. Asting, H. Carén, M. Andersson, C. Lönnroth, K. Lagerstedt, and K. Lundholm COX-2 gene expression in colon cancer tissue related to regulating factors and promoter methylation status BMC Cancer 13 2010 211 238
3. A.L. Bodley, and L.F. Liu Topoisomerases as novel targets for cancer chemotherapy Nat. Biotechnol. 6 1998 1315 1319
4. K. Chikamori, A.G. Grozav, T. Kozuki, D. Grabowski, R. Ganapathi, and M.K. Ganapathi DNA topoisomerase II enzymes as molecular targets for cancer chemotherapy Curr. Cancer Drug Targets 10 2010 758 771
5. P.C. De Groen, G.J. Gores, N.F. La Russo, L.L. Gunderso, and D.M. Nagorney Biliary tract cancers N. Engl. J. Med. 3411 1999 1368 1378
6. A. Diandra Effective treatment strategies for cholangiocarcinoma: the challenge remains Gastrointest. Cancer Res. 2 2008 251 252
7. M. Geethangili, Y.K. Rao, S.H. Fang, and Y.M. Tzeng Cytotoxic constituents from Andrographis paniculata induce cell cycle arrest in Jurkat cells Phytother. Res. 22 2008 1336 1341
8. P. Hainaut The tumor suppressor protein p53: a receptor to genotoxic stress that controls cell growth and survival Curr. Opin. Oncol. 7 1995 76 82
9. D.M. Huang, YC. Shen, C. Wu, Y.T. Huang, F.L. Kung, C.M. Teng, and J.H. Guh Investigation of extrinsic and intrinsic apoptosis pathways of new clerodane diterpenoids in human prostate cancer PC-3 cells Eur. J. Pharmacol. 503 2004 17 24
10. S.R. Jada, C. Matthews, M.S. Saad, A.S. Hamzah, N.H. Lajis, M.F. Stevens, and J. Stanslas Benzylidene derivatives of andrographolide inhibit growth of breast and colon cancer cells in vitro by inducing G (1) arrest and apoptosis Br. J. Pharmacol. 155 2008 641 654
11. S.R. Jada, A.S. Hamzah, N.H. Lajis, M.S. Saad, M.F. Stevens, and J. Stanslas Semisynthesis and cytotoxic activities of andrographolide analogues J. Enzyme Inhib. Med. Chem. 21 2006 145 155
12. M.J. Judith, J.M. Aldo, M. Mang, W. Winnie, B. Michael, Sawyer, and G.B. Vincent Cholangiocarcinoma: has there been any progress? J. Gastroenterol. 24 2010 52 57
13. J.F. Kerr, A.H. Wyllie, and A.R. Currie Apoptosis: a basic biological phenomenon with wide-ranging implications in tissue kinetics Br. J. Cancer 26 1972 239 257
14. Q.A. Khan, G. Kohlhagen, R. Marshall, C.A. Austin, G.P. Kalena, H. Kroth, J.M. Sayer, D.M. Jerina, and Y. Pommier Position-specific trapping of topoisomerase II by benzo[a]pyrene diol epoxide adducts: implications for interactions with intercalating anticancer agents Proc. Nat. Acad. Sci. 100 2003 12498 12503
15. J. Li, H.Y. Cheung, Z. Zhang, G.K. Chan, and W.F. Fong Andrographolide induces cell cycle arrest at G2/M phase and cell death in HepG2 cells via alteration of reactive oxygen species Eur. J. Pharm. 568 2007 31 44
16. A.H. Lori Detection of DNA damage induced by topoisomerase II inhibitors, gamma radiation and cross linking agents using the comet assay Methods Mol. Biol. 523 2009 169 176
17. S. Nanduri, V.K. Nyavanandi, S.S. Thunuguntla, S. Kasu, M.K. Pallerla, P.S. Ram, S. Rajagopal, R.A. Kumar, R. Ramanujam, J.M. Babu, K. Vyas, A.S. Devi, G.O. Reddy, and V. Akella Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents Bioorg. Med. Chem. Lett. 14 2004 4711 4717
18. J. Nateewattana, R. Saeeng, S. Kasemsook, K. Suksen, S. Dutta, S. Jariyawat, A. Chairoungdua, A. Suksamrarn, and P. Piyachaturawat Inhibition of topoisomerase II α activity and induction of apoptosis in mammalian cells by semi-synthetic andrographolide analogues Invest. New Drugs 3 2013 320 332
19. P. Rattanasinganchan, K. Leelawat, S. Treepongkaruna, C. Tocharoentanaphol, S. Subwongcharoen, T. Suthiphongchai, and R. Tohtong Establishment and characterization of a CCA cell line (RMCCA-1) from a Thai patient World J. Gastroenterol. 12 2006 6500 6506
20. C. Satyanarayana, D.S. Deevi, R. Rajagopalan, N. Srinivas, and S. Rajagopal DRF 3188 a novel semi-synthetic analog of andrographolide: cellular response to MCF 7 breast cancer cells BMC Cancer 4 26 2004 1 8
21. E. Schneider, Y.H. Hsiang, and L.F. Liu DNA topoisomerases as anticancer drug targets Adv. Pharmacol. 21 1990 149 183
22. U. Sirion, S. Sakkasem, K. Suksen, P. Piyachaturawat, A. Suksamrarn, and R. Saeeng New substituted C-19-andrographolide analogues with potent cytotoxic activities Bioorg. Med. Chem. Lett. 22 2011 49 52
23. N. Songserm, S. Promthet, and P. Sithithaworn MTHFR polymorphisms and Opisthorchis viverrini infection: a relationship with increased susceptibility to cholangiocarcinoma in Thailand Asian Pac. J. Cancer Prev. 12 2011 1341 1345
24. S. Soubeyrand, L. Popea, and R. Hache Topoisomerase IIalpha-dependent induction of a persistent DNA damage response in response to transient etoposide exposure Mol. Oncol. 4 2010 38 51
25. S. Sperandio, I. de Belle, and D.E. Bredesen An alternative, non apoptotic form of programmed cell death Proc. Nat. Acad. Sci. 97 2000 14376 14381
26. B. Sripa, and C. Pairojkul Cholangiocarcinoma: lessons from Thailand Curr. Opin. Gastroenterol. 24 2008 349 356
27. P. Srivatanakul, H. Ohshima, M. Khlat, M. Parkin, S. Sukaryodhin, I. Brouet, and H. Bartsch Opisthorchis viverrini infestation and endogenous nitrosamines as risk factors for cholangiocarcinoma in Thailand Int. J. Cancer 48 1991 821 825
28. P. Thisoda, N. Rangkadilok, N. Pholphana, L. Worasuttayangkurn, S. Ruchirawat, and J. Satayavivad Inhibitory effect of Andrographis paniculata extract and its active diterpenoids on platelet aggregation Eur. J. Pharmacol. 553 2006 39 45
29. N.I. Valkov, and D.M. Sullivan Tumor p53 status and response to topoisomerase II inhibitors Drug Resist. Updates 6 2003 27 39
30. P. Wanitchakool, S. Jariyawat, K. Suksen, D. Soorukram, P. Tuchinda, and P. Piyachaturawat Cleistanthoside A tetraacetate-induced DNA damage leading to cell cycle arrest and apoptosis with the involvement of p53 in lung cancer cells Eur. J. Pharmacol. 696 2012 35 42
31. J. Yuan, and B.A. Yankner Apoptosis in the nervous system Nature 407 2000 802 809