Zebularine partially reverses GST methylation in prostate cancer cells and restores sensitivity to the DNA minor groove binder brostallicin

References

• Crea F, Sun L, Mai A, Chiang YT, Farrar WL, Danesi R, et al. The emerging role of histone lysine demethylases in prostate cancer. Mol Cancer 2012; 11:52; http://dx.doi.org/10.1186/1476-4598-11-52; PMID: 22867098
   PubMed Web of Science ®Google Scholar
• Mahapatra S, Klee EW, Young CYF, Sun Z, Jimenez RE, Klee GG, et al. Global methylation profiling for risk prediction of prostate cancer. Clin Cancer Res 2012; 18:2882 - 95; http://dx.doi.org/10.1158/1078-0432.CCR-11-2090; PMID: 22589488
   PubMed Web of Science ®Google Scholar
• Esteller M, Corn PG, Urena JM, Gabrielson E, Baylin SB, Herman JG. Inactivation of glutathione S-transferase P1 gene by promoter hypermethylation in human neoplasia. Cancer Res 1998; 58:4515 - 8; PMID: 9788592
   PubMed Web of Science ®Google Scholar
• Santourlidis S, Florl A, Ackermann R, Wirtz HC, Schulz WA. High frequency of alterations in DNA methylation in adenocarcinoma of the prostate. Prostate 1999; 39:166 - 74; http://dx.doi.org/10.1002/(SICI)1097-0045(19990515)39:3<166::AID-PROS4>3.0.CO;2-J; PMID: 10334105
   PubMed Web of Science ®Google Scholar
• Yoon H-Y, Kim Y-W, Kang H-W, Kim WT, Yun S-J, Lee S-C, et al. DNA methylation of GSTP1 in human prostate tissues: pyrosequencing analysis. Korean J Urol 2012; 53:200 - 5; http://dx.doi.org/10.4111/kju.2012.53.3.200; PMID: 22468217
   PubMedGoogle Scholar
• Ban N, Takahashi Y, Takayama T, Kura T, Katahira T, Sakamaki S, et al. Transfection of glutathione S-transferase (GST)-pi antisense complementary DNA increases the sensitivity of a colon cancer cell line to adriamycin, cisplatin, melphalan, and etoposide. Cancer Res 1996; 56:3577 - 82; PMID: 8758929
   PubMed Web of Science ®Google Scholar
• Hall AG, Matheson E, Hickson ID, Foster SA, Hogarth L. Purification of an alpha class glutathione S-transferase from melphalan-resistant Chinese hamster ovary cells and demonstration of its ability to catalyze melphalan-glutathione adduct formation. Cancer Res 1994; 54:3369 - 72; PMID: 8012951
   PubMed Web of Science ®Google Scholar
• Hao X-Y, Bergh J, Brodin O, Hellman U, Mannervik B. Acquired resistance to cisplatin and doxorubicin in a small cell lung cancer cell line is correlated to elevated expression of glutathione-linked detoxification enzymes. Carcinogenesis 1994; 15:1167 - 73; http://dx.doi.org/10.1093/carcin/15.6.1167; PMID: 8020151
   PubMed Web of Science ®Google Scholar
• Sánchez-Gómez FJ, Díez-Dacal B, Pajares MA, Llorca O, Pérez-Sala D. Cyclopentenone prostaglandins with dienone structure promote cross-linking of the chemoresistance-inducing enzyme glutathione transferase P1-1. Mol Pharmacol 2010; 78:723 - 33; http://dx.doi.org/10.1124/mol.110.065391; PMID: 20631055
   PubMed Web of Science ®Google Scholar
• Beria I, Baraldi PG, Cozzi P, Caldarelli M, Geroni C, Marchini S, et al. Cytotoxic alpha-halogenoacrylic derivatives of distamycin A and congeners. J Med Chem 2004; 47:2611 - 23; http://dx.doi.org/10.1021/jm031051k; PMID: 15115402
   PubMed Web of Science ®Google Scholar
• Broggini M, Marchini S, Fontana E, Moneta D, Fowst C, Geroni C. Brostallicin: a new concept in minor groove DNA binder development. Anticancer Drugs 2004; 15:1 - 6; http://dx.doi.org/10.1097/00001813-200401000-00001; PMID: 15090736
   PubMed Web of Science ®Google Scholar
• Cozzi P. The discovery of a new potential anticancer drug: a case history. Farmaco 2003; 58:213 - 20; http://dx.doi.org/10.1016/S0014-827X(03)00014-4; PMID: 12620417
   PubMedGoogle Scholar
• Cozzi P, Beria I, Caldarelli M, Geroni C, Mongelli N, Pennella G. Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety. Bioorg Med Chem Lett 2000; 10:1273 - 6; http://dx.doi.org/10.1016/S0960-894X(00)00205-5; PMID: 10866398
   PubMed Web of Science ®Google Scholar
• Lorusso D, Mainenti S, Pietragalla A, Ferrandina G, Foco G, Masciullo V, et al. Brostallicin (PNU-166196), a new minor groove DNA binder: preclinical and clinical activity. Expert Opin Investig Drugs 2009; 18:1939 - 46; http://dx.doi.org/10.1517/13543780903401284; PMID: 19938904
   PubMed Web of Science ®Google Scholar
• Geroni C, Marchini S, Cozzi P, Galliera E, Ragg E, Colombo T, et al. Brostallicin, a novel anticancer agent whose activity is enhanced upon binding to glutathione. Cancer Res 2002; 62:2332 - 6; PMID: 11956092
   PubMed Web of Science ®Google Scholar
• Pezzola S, Antonini G, Geroni C, Beria I, Colombo M, Broggini M, et al. Role of glutathione transferases in the mechanism of brostallicin activation. Biochemistry 2010; 49:226 - 35; http://dx.doi.org/10.1021/bi901689s; PMID: 19950984
   PubMed Web of Science ®Google Scholar
• Sabatino MA, Colombo T, Geroni C, Marchini S, Broggini M. Enhancement of in vivo antitumor activity of classical anticancer agents by combination with the new, glutathione-interacting DNA minor groove-binder, brostallicin. Clin Cancer Res 2003; 9:5402 - 8; PMID: 14614026
   PubMed Web of Science ®Google Scholar
• Appleton K, Mackay HJ, Judson I, Plumb JA, McCormick C, Strathdee G, et al. Phase I and pharmacodynamic trial of the DNA methyltransferase inhibitor decitabine and carboplatin in solid tumors. J Clin Oncol 2007; 25:4603 - 9; http://dx.doi.org/10.1200/JCO.2007.10.8688; PMID: 17925555
   PubMed Web of Science ®Google Scholar
• Plumb JA, Strathdee G, Sludden J, Kaye SB, Brown R. Reversal of drug resistance in human tumor xenografts by 2′-deoxy-5-azacytidine-induced demethylation of the hMLH1 gene promoter. Cancer Res 2000; 60:6039 - 44; PMID: 11085525
   PubMed Web of Science ®Google Scholar
• Watanabe YOH, Ueda H, Etoh T, Koike E, Fujinami N, Mitsuhashi A, et al. A change in promoter methylation of hMLH1 is a cause of acquired resistance to platinum-based chemotherapy in epithelial ovarian cancer. Anticancer Res 2007; 27:3B 1449 - 52; PMID: 17595760
   PubMed Web of Science ®Google Scholar
• Strathdee G, MacKean MJ, Illand M, Brown R. A role for methylation of the hMLH1 promoter in loss of hMLH1 expression and drug resistance in ovarian cancer. Oncogene 1999; 18:2335 - 41; http://dx.doi.org/10.1038/sj.onc.1202540; PMID: 10327053
   PubMed Web of Science ®Google Scholar
• Zhou L, Cheng X, Connolly BA, Dickman MJ, Hurd PJ, Hornby DP. Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases. J Mol Biol 2002; 321:591 - 9; http://dx.doi.org/10.1016/S0022-2836(02)00676-9; PMID: 12206775
   PubMed Web of Science ®Google Scholar
• Cheng JC, Matsen CB, Gonzales FA, Ye W, Greer S, Marquez VE, et al. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. J Natl Cancer Inst 2003; 95:399 - 409; http://dx.doi.org/10.1093/jnci/95.5.399; PMID: 12618505
   PubMed Web of Science ®Google Scholar
• Bradbury J. Zebularine: a candidate for epigenetic cancer therapy. Drug Discov Today 2004; 9:906 - 7; http://dx.doi.org/10.1016/S1359-6446(04)03266-0; PMID: 15501719
   PubMed Web of Science ®Google Scholar
• Cheng JC, Weisenberger DJ, Gonzales FA, Liang G, Xu GL, Hu YG, et al. Continuous zebularine treatment effectively sustains demethylation in human bladder cancer cells. Mol Cell Biol 2004; 24:1270 - 8; http://dx.doi.org/10.1128/MCB.24.3.1270-1278.2004; PMID: 14729971
   PubMed Web of Science ®Google Scholar
• Cheng JC, Yoo CB, Weisenberger DJ, Chuang J, Wozniak C, Liang G, et al. Preferential response of cancer cells to zebularine. Cancer Cell 2004; 6:151 - 8; http://dx.doi.org/10.1016/j.ccr.2004.06.023; PMID: 15324698
   PubMed Web of Science ®Google Scholar
• Yoo CB, Cheng JC, Jones PA. Zebularine: a new drug for epigenetic therapy. Biochem Soc Trans 2004; 32:910 - 2; http://dx.doi.org/10.1042/BST0320910; PMID: 15506921
   PubMed Web of Science ®Google Scholar
• Lemaire M, Momparler LF, Bernstein ML, Marquez VE, Momparler RL. Enhancement of antineoplastic action of 5-aza-2′-deoxycytidine by zebularine on L1210 leukemia. Anticancer Drugs 2005; 16:301 - 8; http://dx.doi.org/10.1097/00001813-200503000-00009; PMID: 15711182
   PubMed Web of Science ®Google Scholar
• Andersen JB, Factor VM, Marquardt JU, Raggi C, Lee YH, Seo D, et al. An integrated genomic and epigenomic approach predicts therapeutic response to zebularine in human liver cancer. Sci Transl Med 2010; 2:54ra77; http://dx.doi.org/10.1126/scitranslmed.3001338; PMID: 20962331
   PubMed Web of Science ®Google Scholar
• Billam M, Sobolewski MD, Davidson NE. Effects of a novel DNA methyltransferase inhibitor zebularine on human breast cancer cells. Breast Cancer Res Treat 2010; 120:581 - 92; http://dx.doi.org/10.1007/s10549-009-0420-3; PMID: 19459041
   PubMed Web of Science ®Google Scholar
• Dote H, Cerna D, Burgan WE, Carter DJ, Cerra MA, Hollingshead MG, et al. Enhancement of in vitro and in vivo tumor cell radiosensitivity by the DNA methylation inhibitor zebularine. Clin Cancer Res 2005; 11:4571 - 9; http://dx.doi.org/10.1158/1078-0432.CCR-05-0050; PMID: 15958643
   PubMed Web of Science ®Google Scholar
• Meador JA, Su Y, Ravanat JL, Balajee AS. DNA-dependent protein kinase (DNA-PK)-deficient human glioblastoma cells are preferentially sensitized by Zebularine. Carcinogenesis 2010; 31:184 - 91; http://dx.doi.org/10.1093/carcin/bgp284; PMID: 19933707
   PubMed Web of Science ®Google Scholar
• Suzuki M, Shinohara F, Nishimura K, Echigo S, Rikiishi H. Epigenetic regulation of chemosensitivity to 5-fluorouracil and cisplatin by zebularine in oral squamous cell carcinoma. Int J Oncol 2007; 31:1449 - 56; PMID: 17982671
   PubMed Web of Science ®Google Scholar
• Champion C, Guianvarc’h D, Sénamaud-Beaufort C, Jurkowska RZ, Jeltsch A, Ponger L, et al. Mechanistic insights on the inhibition of c5 DNA methyltransferases by zebularine. PLoS One 2010; 5:e12388; http://dx.doi.org/10.1371/journal.pone.0012388; PMID: 20808780
   PubMed Web of Science ®Google Scholar