Riccardin D, a novel macrocyclic bisbibenzyl, induces apoptosis of human leukemia cells by targeting DNA topoisomerase II

Investigational New Drugs

Volumn 30, Issue 1, 2012, Pages 212-222

  Xue, Xia ^a   Qu, Xian Jun ^a   Gao, Zu Hua ^b   Sun, Cui Cui ^a   Liu, Hui Ping ^a   Zhao, Cui Rong ^a   Cheng, Yan Na ^a   Lou, Hong Xiang ^a  

^a SHANDONG UNIVERSITY   (China)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

Apoptosis; DNA relaxation; Human leukemia cells; Macrocyclic bisbibenzyl; Multidrug resistance; Riccardin D.; Topoisomerase II

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 9; CYTOCHROME C; DNA TOPOISOMERASE (ATP HYDROLYSING); ETOPOSIDE; GLYCOPROTEIN P; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; RICCARDIN D; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DNA FRAGMENTATION; DNA SUPERCOILING; DRUG EFFICACY; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVATION; ENZYME REPRESSION; HUMAN; HUMAN CELL; LEUKEMIA CELL; MULTIDRUG RESISTANCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; WESTERN BLOTTING;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CASPASE 3; CASPASE 9; CELL PROLIFERATION; CYTOCHROMES C; DNA FRAGMENTATION; DNA TOPOISOMERASES, TYPE II; DNA, SUPERHELICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; HL-60 CELLS; HUMANS; K562 CELLS; LEUKEMIA; P-GLYCOPROTEIN; PHENYL ETHERS; PHOSPHATIDYLSERINES; POLY(ADP-RIBOSE) POLYMERASES; STILBENES; TIME FACTORS; TOPOISOMERASE II INHIBITORS;

EID: 84856510063     PISSN: 01676997     EISSN: 15730646     Source Type: Journal    
DOI: 10.1007/s10637-010-9554-8     Document Type: Article

References (39)

1. Sakasai R, Teraoka H, Takagi M, Tibbetts RS (2010) Transcriptiondependent activation of ataxia telangiectasia mutated prevents DNA-dependent protein kinase-mediated cell death in response to topoisomerase I poison. J Biol Chem 285:15201-15208. doi:10.1074/ jbc.M110.101808
2. Li TK, Liu LF (2001) Tumor cell death induced by topoisomerase-targeting drugs. Annu Rev Pharmacol Toxicol 41:53-77. doi:10.1146/annurev.pharmtox.41.1.53 (Pubitemid 32385882)
3. Chikamori K, Grozav AG, Kozuki T, Grabowski D, Ganapathi R, GanapathiMK (2010) DNA topoisomerase II enzymes as molecular targets for cancer chemotherapy. Curr Cancer Drug Targets 10:758-771
4. Oppegard LM, Ougolkov AV, Luchini DN, Schoon RA, Goodell JR, Kaur H, Billadeau DD, Ferguson DM, Hiasa H (2009) Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II. Eur J Pharmacol 602:223-229. doi:10.1016/j.ejphar.2008.11.044
5. Sciandrello G, Mauro M, Caradonna F, Catanzaro I, Saverini M, Barbata G (2010) Acrylamide catalytically inhibits topoisomerase II in V79 cells. Toxicol In Vitro 24:830-834. doi:10.1016/j.tiv. 2009.12.010
6. Guo A, Marinaro W, Hu P, Sinko PJ (2002) Delineating the contribution of secretory transporters in the efflux of etoposide using madin-darby canine kidney (MDCK) cells overexpressing p-glycoprotein (P-gp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (CMOAT). Drug Metab Dispos 30:457-463. doi:10.1124/ dmd.30.4.457 (Pubitemid 34263832)
7. Hawtin RE, Stockett DE, Byl JA, McDowell RS, Nguyen T, Arkin MR, Conroy A, YangW, Osheroff N, Fox JA (2010) Voreloxin is an anticancer quinolone derivative that intercalates DNA and poisons topoisomerase II. PLoS One 5:e10186. doi:10.1371/journal.pone. 0010186
8. Lu ZQ, Fan PH, Ji M, Lou HX (2006) Terpenoids and bisbibenzyls from Chinese liverworts Conocephalum conicum and Dumortiera hirsute. J Asian Nat Prod Res 8:187-192. doi:0.1080/1028602042000325537 (Pubitemid 43879883)
9. Cheng A, Sun L, Wu X, Lou H (2009) The inhibitory effect of a macrocyclic bisbibenzyl riccardin D on the biofilms of Candida albicans. Biol Pharm Bull 32:1417-1421. doi:10.1248/ bpb.32.1417
10. Shi YQ, Zhu CJ, Yuan HQ, Li BQ, Gao J, Qu XJ, Sun B, Cheng YN, LiS Li X, Lou HX (2009) Marchantin C, a novel microtubule inhibitor from liverwort with anti-tumor activity both in vivo and in vitro. Cancer Lett 276:160-170. doi:10.1016/j.canlet.2008. 11.004
11. Li X, Sun B, Zhu CJ, Yuan HQ, Shi YQ, Gao J, Li SJ, Lou HX (2009) Reversal of p-glycoprotein-mediated multidrug resistance by macrocyclic bisbibenzyl derivatives in adriamycin-resistant human myelogenous leukemia (K562/A02) cells. Toxicol In Vitro 23:29-36. doi:10.1016/j.tiv.2008.09.015
12. Shi YQ, Qu XJ, Liao YX, Xie CF, Cheng YN, Li S, Lou HX (2008) Reversal effect of a macrocyclic bisbibenzyl plagiochin E on multidrug resistance in adriamycin-resistant K562/A02 cells. Eur J Pharmacol 584:66-71. doi:10.1016/j.ejphar.2008.01.039
13. Xie CY, Zhu H, Lin LP, Miao ZH, Geng MY, Cai YJ, Chen Y, Zhao HJ, Luo HB, Zhang XW, Fan LM, ShenYM DJ (2007) MFTZ-1, an actinomycetes subspecies derived antitumor macrolide, functions as a novel topoisomerase II poison. Mol Cancer Ther 6:3059-3070. doi:10.1158/1535-7163.MCT-07-0014 (Pubitemid 350206784)
14. Yang SY, Jia XZ, Feng LY, Li SY, An GS, Ni JH, Jia HT (2009) Inhibition of topoisomerase II by 8-chloro-adenosine triphosphate induces DNA double-stranded breaks in 8-chloro-adenosineexposed human myelocytic leukemia K562 cells. Biochem Pharmacol 77:433-443. doi:10.1016/j.bcp.2008.10.022
15. Okutucu B, Dincer A, Habib O, Zihnioqlu F (2007) Comparison of five methods for determination of total plasma protein concentration. J Biochem Biophys Methods 70:709-711. doi:10.1016/j. jbbm.2007.05.009 (Pubitemid 47021223)
16. Osheroff N, Shelton ER, Brutlag DL (1983) DNA topoisomerase II from drosophila melanogaster relaxation of supercoiled DNA. J Biol Chem 258:9536-9543
17. Soubeyrand S, Pope L, Haché RJ (2010) Topoisomerase II alphadependent induction of a persistent DNA damage response in response to transient etoposide exposure. Mol Oncol 4:38-51. doi:10.1016/j.molonc.2009.09. 003
18. Kruczynski A, Barret JM, Van Hille B, Chansard N, Astruc J, Menon Y, Duchier C, Créancier L, Hill BT (2004) Decreased nucleotide excision repair activity and alterations of topoisomerase IIalpha are associated with the in vivo resistance of a P388leukemia subline to F11782, a novel catalytic inhibitor of topoisomerases I and II. Clin Cancer Res 10:3156-3168. doi:10.1158/ 1078-0432.CCR-1305-2 (Pubitemid 38619697)
19. Zizak Z, Juranic Z, Opsenica D, Solaja BA (2009) Mixed steroidal tetraoxanes induce apoptotic cell death in tumor cells. Invest New Drugs 27:432-439. doi:10.1007/s10637-008-9197-1
20. Oppegard LM, Ougolkov AV, Luchini DN, Schoon RA, Goodell JR, Kaur H, Billadeau DD, Ferguson DM, Hiasa H (2009) Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II. Eur J Pharmacol 602:223-229. doi:10.1016/j.ejphar.2008.11.044
21. Song K, Sun X, Wang J, Zhou S, Zeng H, Chen F (2008) Role of glycosylphosphatidylinositol-specific phospholipase D in the homing of umbilical cord blood, mobilized peripheral blood and bone marrow-derived hematopoietic stem/progenitor cells. Clin Exp Med 8:151-157. doi:10.1007/s10238-008-0172-0
22. Song T, Wu J, Fang F, Chen F, Huo L, Zhang M, Wu L, Zhai Z, Yang L, Fang J (2007) Correlation analysis between the expression of P21WAF1/CIP1, P16 proteins and human glioma. Leuk Res 31:1701-1707. doi:10.1016/j.leukres.2007.03. 023 (Pubitemid 350051397)
23. Shi LX, Ma R, Lu R, Xu Q, Zhu ZF, Wang L, Zhou CL, Li XL, Zhang HL, Yao Z (2008) Reversal effect of tyroservatide (YSV) tripeptide on multi-drug resistance in resistant human hepatocellular carcinoma cell line BEL-7402/5-FU. Cancer Lett 269:101-10. doi:10.1016/j.canlet.2008.04.033
24. Du Y, Lou H (2008) Catechin and proanthocyanidin B4 from grape seeds prevent doxorubicin-induced toxicity in cardiomyocytes. Eur J Pharmacol 591:96-101. doi:10.1016/j.ejphar.2008.06.068
25. Qin Y, Meng L, Hu C, Duan W, Zuo Z, Lin L, Zhang X, Ding J (2007) Gambogic acid inhibits the catalytic activity of human topoisomerase IIalpha by binding to its ATPase domain. Mol Cancer Ther 6:2429-2440. doi:10.1158/1535- 7163.MCT-07-0147 (Pubitemid 47480408)
26. Hsiao CJ, Li TK, Chan YL, Hsin LW, Liao CH, Lee CH, Lyu PC, Guh JH (2008) WRC-213, an l-methionine-conjugated mitoxantrone derivative, displays anticancer activity with reduced cardiotoxicity and drug resistance: Identification of topoisomerase II inhibition and apoptotic machinery in prostate cancers. Biochem Pharmacol 75:847-856. doi:10.1016/j.bcp.2007.10.012 (Pubitemid 351174110)
27. Chen Z, Liang X, Zhang H, Xie H, Liu J, Xu Y, Zhu W, Wang Y, Wang X, Tan S, Kuang D, Qian X (2010) A new class of naphthalimide-based antitumor agents that inhibit topoisomerase II and induce lysosomal membrane permeabilization and apoptosis. J Med Chem 53:2589-2600. doi:10.1021/jm100025u.
28. López-Lázaro M, Willmore E, Elliott SL, Austin CA (2008) Selenite induces topoisomerase I and II-DNA complexes in K562 leukemia cells. Int J Cancer 123:2217-2221. doi:10.1002/ijc.23783
29. Sadiq AA, Patel MR, Jacobson BA, Escobedo M, Ellis K, Oppegard LM, Hiasa H, Kratzke RA (2010) Anti-proliferative effects of simocyclinone D8 (SD8), a novel catalytic inhibitor of topoisomerase II. Invest New Drugs 28:20-25. doi:10.1007/ s10637-008-9209-1
30. Baldwin EL, Osheroff N (2005) Etoposide, topoisomerase II and cancer. Curr Med Chem Anticancer Agents 5:363-372 (Pubitemid 40974810)
31. Treszezamsky AD, Kachnic LA, Feng Z, Zhang J, Tokadjian C, Powell SN (2007) BRCA1- and BRCA2-deficient cells are sensitive to etoposide-induced DNA double-strand breaks via topoisomerase II. Cancer Res 67:7078-7081. doi:10.1158/0008- 5472.CAN-07-0601 (Pubitemid 47206532)
32. Yao Q, Weigel B, Kersey J (2007) Synergism between etoposide and 17-AAG in leukemia cells: Critical roles for Hsp90, FLT3, topoisomerase II, Chk1, and Rad51. Clin Cancer Res 13:1591-1600. doi:10.1158/1078-0432.CCR-06-1750 (Pubitemid 46450452)
33. Solovyan VT, Bezvenyuk ZA, Salminen A, Austin CA, Courtney MJ (2002) The role of topoisomerase II in the excision of DNA loop domains during apoptosis. J Biol Chem 277:21458-21467. doi:10.1074/jbc.M110621200 (Pubitemid 34952288)
34. Shelton SN, Shawgo ME, Matthews SB, Lu Y, Donnelly AC, Szabla K, Tanol M, Vielhauer GA, Rajewski RA, Matts RL, Blagg BS, Robertson JD (2009) KU135, a novel novobiocinderived C-terminal inhibitor of the 90-kDa heat shock protein, exerts potent antiproliferative effects in human leukemic cells. Mol Pharmacol 76:1314-1322. doi:10.1124/mol.109.058545
35. Chang HY, Yang X (2000) Proteases for cell suicide: Functions and regulation of caspases. Microbiol Mol Biol Rev 64:821-846 (Pubitemid 32475932)
36. Fayad W, Fryknäs M, Brnjic S, Olofsson MH, Larsson R, Linder S (2009) Identification of a novel topoisomerase inhibitor effective in cells overexpressing drug efflux transporters. PLoS One 4:e7238. doi:10.1371/journal. pone.0007238
37. Tang R, Cohen S, Perrot JY, Faussat AM, Zuany-Amorim C, Marjanovic Z, Morjani H, Fava F, Corre E, Legrand O, Marie JP (2009) P-gp activity is a critical resistance factor against AVE9633 and DM4 cytotoxicity in leukaemia cell lines, but not a major mechanism of chemoresistance in cells from acute myeloid leukaemia patients. BMC Cancer 9:199. doi:10.1186/1471-2407- 9-199
38. Mantovani I, Cappellini A, Tazzari PL, Papa V, Cocco L, Martelli AM (2006) Caspase-dependent cleavage of 170-kDa Pglycoprotein during apoptosis of human T-lymphoblastoid CEM cells. J Cell Physiol 207:836-844. doi:10.1002/jcp.20628 (Pubitemid 43668249)
39. Chiarini F, Del Sole M, Mongiorgi S, Gaboardi GC, Cappellini A, Mantovani I, Follo MY, McCubrey JA, Martelli AM (2008) The novel Akt inhibitor, perifosine, induces caspase-dependent apoptosis and downregulates P-glycoprotein expression in multidrug-resistant human T-acute leukemia cells by a JNKdependent mechanism. Leukemia 22:1106-1116. doi:10.1038/leu. 2008.79 (Pubitemid 351833776)