Characterization of a novel anti-cancer compound for astrocytomas

PLoS ONE

Volumn 9, Issue 9, 2014, Pages

  Lee, Sang Y ^a   Slagle Webb, Becky ^a   Rizk, Elias ^a   Patel, Akshal ^a   Miller, Patti A ^a   Sung, Shen Shu ^a   Connor, James R ^a  

^a PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHEMOTYPE COMPOUND I; DNA TOPOISOMERASE (ATP HYDROLYSING); ETOPOSIDE; MERBARONE; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; TEMOZOLOMIDE; TOPOISOMERASE IIALPHA; TUMOR NECROSIS FACTOR; UNCLASSIFIED DRUG; DACARBAZINE; DNA BINDING PROTEIN; DNA LIGASE; DNA METHYLTRANSFERASE; DNA TOPOISOMERASE II ALPHA; MGMT PROTEIN, HUMAN; TUMOR ANTIGEN; TUMOR SUPPRESSOR PROTEIN;

ACUTE TOXICITY; ADJUVANT THERAPY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; ASTROCYTOMA; ASTROCYTOMA CELL LINE; CANCER INHIBITION; CANCER SURVIVAL; COMPARATIVE EFFECTIVENESS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA SEQUENCE; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG EFFECT; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION; FEMALE; G2 PHASE CELL CYCLE CHECKPOINT; GENE EXPRESSION PROFILING; GLIOBLASTOMA CELL LINE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR MODEL; MOUSE; NONHUMAN; NUCLEOTIDE SEQUENCE; S PHASE CELL CYCLE CHECKPOINT; SURVIVAL TIME; TEMOZOLOMIDE RESISTANT ASTROCYTOMA CELL LINE; TUMOR XENOGRAFT; ANALOGS AND DERIVATIVES; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL CYCLE; CHEMISTRY; DISEASE MODEL; DNA METHYLATION; DRUG EFFECTS; DRUG RESISTANCE; GENETICS; PROMOTER REGION; TOXICITY TESTING; TUMOR CELL LINE;

ANIMALS; ANTIGENS, NEOPLASM; ANTINEOPLASTIC AGENTS; APOPTOSIS; ASTROCYTOMA; CELL CYCLE; CELL LINE, TUMOR; DACARBAZINE; DISEASE MODELS, ANIMAL; DNA METHYLATION; DNA MODIFICATION METHYLASES; DNA REPAIR ENZYMES; DNA TOPOISOMERASES, TYPE II; DNA-BINDING PROTEINS; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; GENE EXPRESSION PROFILING; HUMANS; MICE; PROMOTER REGIONS, GENETIC; TOXICITY TESTS, ACUTE; TUMOR SUPPRESSOR PROTEINS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84907457183     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0108166     Document Type: Article

References (52)

1. Ostrom QT, Gittleman H, Farah P., Ondracek A, Chen Y, et al. (2013) CBTRUS Statistical Report: Primary brain and central nervous system tumors diagnosed in the United States in 2006-2010. Neuro Oncol 15 Suppl 2:ii1-56. doi:10.1093/neuonc/not151.
2. American Cancer Society (2012) Cancer Facts & Figures 2012. Atlanta: American Cancer Society. Available: http://www.cancer.org/research/cancerfactsstatistics/cancerfactsfigures2012/.
3. Stupp R, Mason WP, van den Bent MJ, Weller M, Fisher B, et al. (2005) Radiotherapy plus concomitant and adjuvant temozolomide for glioblastoma. N Engl J Med 352: 987-996.
4. Theeler BJ, Groves MD (2011) High-Grade Gliomas. Curr Treat Options Neurol 13: 386-399.
5. Nishikawa R (2010) Standard therapy for glioblastoma - a review of wehere we are. Neurol Med Chir (Tokyo) 50: 713-719.
6. Friedman HS, Kerby T, Calvert H (2000) TMZ and treatment of malignant glioma. Clin Cancer Res 6: 2585-2597.
7. Atallah E, Flaherty L (2005) Treatment of metastatic malignant melanoma. Curr Treat Options Oncol 6: 185-193.
8. van Brussel JP, Busstra MB, Lang M.S., Catsburg T., Schröder FH, et al. (2000) A phase II study of TMZ in hormone-refractory prostate cancer. Cancer Chemother Pharmacol 45: 509-512.
9. Moore MJ, Feld R, Hedley D., Oza A, Siu LL (1998) A phase II study of TMZ in advanced untreated pancreatic cancer. Invest New drugs 16: 77-79.
10. Jakob J, Wenz F, Dinter D.J., Ströbel P, Hohenberger P (2009) Preoperative intensity-modulated radiotherapy combined with TMZ for locally advanced soft-tissue sarcoma. Int J Radiat Oncol Biol Phys 75: 810-816.
11. Park DK, Ryan CW, Dolan M.E., Vogelzang NJ, Stadler WM (2007) A phase II trial of oral TMZ in patients with metastatic renal cell cancer. Cancer Chemother Pharmacol 50: 160-162.
12. Marchesi F (2007) Triazene compounds: mechanism of action and related DNA repair systems. Pharmacol Res 56: 275-287.
13. Friedman HS, McLendon RE, Kerby T, Dugan M., Bigner SH, et al. (1998) DNA mismatch repair and O6-alkylguanine-DNA alkyltransferase analysis and response to Temodal in newly diagnosed malignant glioma. J Clin Oncol 16: 3851-3857.
14. Hegi ME, Liu L, Herman J.G., Stupp R., Wick W, et al. (2008) Correlation of O6-methylguanine methyltransferase (MGMT) promoter methylation with clinical outcomes in glioblastoma and clinical strategies to modulate MGMT activity. J Clin Oncol 26: 4189-4199.
15. Cahill DP, Levine KK, Betensky R.A., Codd PJ, Romany CA, et al. (2007) Loss of the mismatch repair protein MSH6 in human glioblastomas is associated with tumor progression during temozolomide treatment. Clin Cancer Res 13: 2038-2045.
16. Yip S, Miao J, Cahill D.P., Lafrate AJ, Aldape K, et al. (2009) MSH6 mutations arise in glioblastomas during temozolomide therapy and mediate temozolomide resistance. Clin Cancer Res 15: 4622-4629.
17. McClendon AK, Osheroff N (2007) DNA topoisomerase II, genotoxicity, and cancer. Mutat Res 623: 83-97.
18. Champoux JJ (2001) DNA topoisomerases: structure, function, and mechanism. Annu Rev Biochem 70: 369-413.
19. Beck WT (1996) DNA topoisomerases and tumor cell resistance to their inhibitors. In: Schilsky R, Milano G, Ratain M, editors. Principles of Antineoplastic Drug Development and Pharmacology (Basic and Clinical Oncology). CRC Press. 487-502.
20. Falaschi A, Abdurashidova G, Sandoval O., Radulescu S, Biamonti G, et al. (2007) Molecular and structural transactions at human DNA replication origins. Cell Cycle 6: 1705-1712.
21. Bruce JN, Fine RL, Canoll P, Yun J., Kennedy BC, et al. (2011) Regression of recurrent malignant gliomas with convection-enhanced delivery of topotecan. Neurosurgery 69: 1272-1279.
22. Minturn JE, Janss AJ, Fisher P.G., Allen JC, Patti R, et al. (2011) A phase II study of metronomic oral topotecan for recurrent childhood brain tumors. Pediatr Blood Cancer 56: 39-44.
23. Matsumoto Y, Tamiya T, Nagao S (2005) Resistance to topoisomerase II inhibitors in human glioma cell lines overexpressing multidrug resistant associated protein (MRP) 2. J Med Invest 52: 41-48.
24. Chen Y, Su YH, Wang C.H., Wu JM, Chen JC, et al. (2005) Induction of apoptosis and cell cycle arrest in glioma cells by GL331 (a topoisomerase II inhibitor). Anticancer Res 25: 4203-4208.
25. Schmidt F, Knobbe CB, Frank B, Wolburg H., Weller M (2008) The topoisomerase II inhibitor, genistein, induces G2/M arrest and apoptosis in human malignant glioma cell lines. Oncol Rep 19: 1061-1066.
26. Lee SY, Liu S, Mitchell R.M., Slagle-Webb B, Hong Y-S, et al. (2011) HFE polymorphisms influence the response to chemotherapeutic agents via induction of p16INK4A. Int J Cancer 129: 2104-2114.
27. de Almeida SF, Picarote G, Fleming J.V., Carmo-Fonseca M, Azevedo JE, et al. (2007) Chemical chaperones reduce endoplasmic reticulum stress and prevent mutant HFE aggregate formation. J Biol Chem 282: 27905-27912.
28. Liu Y, Lee SY, Neely E, Nandar W., Moyo M, et al. (2011) Mutant HFE H63D protein is associated with prolonged endoplasmic reticulum stress and increased neuronal vulnerability. J Biol Chem 286: 13161-13170.
29. Lee SY, Patton SM, Henderson R.J., Connor JR (2007) Consequences of expressing mutants of the hemochromatosis gene (HFE) into a human neuronal cell line lacking endogenous HFE. FASEB J 21: 564-576.
30. Gong Y, Firestone GL, Bjeldanes LF (2006) 3,39-diindolylmethane is a novel topoisomerase IIalpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells. Mol Pharmacol 69: 1320-1327.
31. Wendorff TJ, Schmidt BH, Heslop P, Austin C.A., Berqer JM (2012) The structure of DNA-bound human topoisomerase II alpha: conformational mechanisms for coordinating inter-subunit interactions with DNA cleavage. J Mol Biol 424: 109-124.
32. Friesner RA, Banks JL, Murphy R.B., Halgren TA, Klicic JJ, et al. (2004) Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 47: 1739-1749.
33. Halgren TA, Murphy RB, Friesner R.A., Beard HS, Frye LL, et al. (2004) Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J Med Chem 47: 1750-1759.
34. Mellai M, Monzeglio O, Piazzi A., Caldera V, Annovazzi L, et al. (2012) MGMT promoter hypermethylation and its associations with genetic alterations in a series of 350 brain tumors. J Neurooncol 107: 617-631.
35. Kanzawa T, Germano IM, Kondo Y, Ito H., Kyo S, et al. (2003) Inhibition of telomerase activity in malignant glioma cells correlates with their sensitivity to TMZ. Br J Cancer 89: 922-929.
36. Uzzaman M, Keller G, Germano IM (2007) Enhanced proapoptotic effects of tumor necrosis factor-related apoptosis-inducing ligand on TMZ-resistant glioma cells. J Neurosurg 106: 646-651.
37. Cebo B, Krupinska J, Mazur J., Piotrowicz J (1980) Antiinflammatory activity of the new aminomethyl derivatives of 1-cyclohexyl-5-alkyl and 1-cyclohexyl-5,5-dialklbarbituric acids. Farmaco Sci 35: 248-252.
38. Brewer AD, Minatelli JA, Plowman J, Paull K.D., Narayanan VL (1985) 5-(N-phenylcarboxamido)-2-thiobarbituric acid (NSC 336628), a novel potential antitumor agent. Biochem Pharmacol 34: 2047-2050.
39. Singh P, Kaur M, Verma P (2009) Design, synthesis and anticancer activities of hybrids of indole and barbituric acids-identification of highly promising leads. Bioorg Med Chem Lett 19: 3054-3058.
40. Balas VI, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N., Light ME, et al. (2008) Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-butyltin(IV) with 2-thiobarbituric acid. Bioinorg Chem Appl 654137. doi:10.1155/2008/654137.
41. Balas VI, Verginadis II, Geromichalos G.D., Kourkoumelis N., Male L, et al. (2011) Synthesis, structural characterization and biological studies of the triphenyltin(IV) complex with 2-thiobarbituric acid. Eur J Med Chem 46: 2835-2844.
42. Rajamaki S, Innitzer A, Falciani C., Tintori C, Christ F, et al. (2009) Exploration of novel thiobarbituric acid-, rhodanine- and thiohydrantoin-based HIV-1 integrase inhibitors. Bioorg Med Chem Lett 19: 3615-3618.
43. Lee JH, Lee S, Park M.Y., Myung H (2011) Characterization of thiobarbituric acid derivatives as inhibitors of hepatitis C virus NS5B polymerase. Virol J 8: 18. doi:10.1186/1743-422X-8-18.
44. Warrell RP Jr, Muindi J, Stevens Y.W., Isaacs M., Young CW (1989) Induction of profound hypouricemia by a non-sedating thiobarbiturate. Metabolism 38: 550-554.
45. Glover A, Chun HG, Kleinman L.M., Cooney DA, Plowman J, et al. (1987) Merbarone: an antitumor agent entering clinical trials. Invest New Drugs 5: 137-143.
46. Drake FH, Hofmann GA, Mong S.M., Bartus JO, Hertzberg RP, et al. (1989) In vitro and intracellular inhibition of topoisomerase II by the antitumor agent merbarone. Cancer Res 49: 2578-2583.
47. Wang H, Ao M, Wu J., Yu L (2013) TNFa and Fas/FasL pathways are involved in 9-Methoxycamptothecin-induced apoptosis in cancer cells with oxidative stress and G2/M cell cycle arrest. Food Chem Toxicol 55: 396-410.
48. Kolb RH, Greer PM, Cao P.T., Cowan KH, Yan Y (2012) ERK1/2 signaling plays an important role in topoisomerase II poison-induced G2/M checkpoint activation. PLoS One 7: e50281. doi:10.1371/journal.pone.0050281.
49. Bhonde MR, Hanski ML, Notter M, Gillissen B.F., Daniel PT, et al. (2006) Equivalent effect of DNA damage-induced apoptotic cell death or long-term cell cycle arrest on colon carcinoma cell proliferation and tumour growth. Oncogene 25: 165-175.
50. Melguizo C, Prados J, González B, Ortiz R., Concha A, et al. (2012) MGMT promoter methylation status and MGMT and CD133 immunohistochemical expression as prognostic markers in glioblastoma patients treated with temozolomide plus radiotherapy. J Transl Med 10: 250. doi:10.1186/1479-5876-10-250.
51. Vlachostergios PJ, Hatzidaki E, Befani C.D., Liakos P., Papandreou CN (2013) Bortezomib overcomes MGMT-related resistance of glioblastoma cell lines to temozolomide in a schedule-dependent manner. Invest New Drugs 31: 1169-1181.
52. Peigñan L, Garrido W, Segura R., Melo R, Rojas D, et al. (2011) Combined use of anticancer drugs and an inhibitor of multiple drug resistance-associated protein-1 increases sensitivity and decreases survival of glioblastoma multiforme cells in vitro. Neurochem Res 36: 1397-1406.