Structure-activity studies with cytotoxic anthrapyrazoles

Oncology Reports

Volumn 15, Issue 6, 2006, Pages 1575-1580

  Begleiter, Asher ^a   Lin, Denny ^b   Larson, Kimberly K ^c   Lang, Jennifer ^c   Wu, Xing ^b   Cabral, Teresa ^a   Taylor, Hallie ^a   Guziec, Lynn J ^c   Kerr, Paul D ^b   Hasinoff, Brian B ^b   Guziec Jr , Frank S ^c  

^a UNIVERSITY OF MANITOBA   (Canada)

^b UNIVERSITY OF MANITOBA   (Canada)

^c SOUTHWESTERN UNIVERSITY   (United States)

Author keywords

Anthrapyrazoles; Cytotoxic activity; Structure activity; Topoisomerase II inhibition

Indexed keywords

ANTHRACYCLINE; ANTHRAPYRAZOLE; ANTINEOPLASTIC AGENT; DNA TOPOISOMERASE (ATP HYDROLYSING);

ANIMAL; ARTICLE; CELL STRAIN K 562; CHEMISTRY; CHO CELL; CRICETULUS; DRUG ANTAGONISM; DRUG SCREENING; GENETICS; HAMSTER; HUMAN; IC 50; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTHRACYCLINES; ANTINEOPLASTIC AGENTS; CHO CELLS; CRICETINAE; CRICETULUS; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; K562 CELLS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34249280791     PISSN: 1021335X     EISSN: 17912431     Source Type: Journal    
DOI: 10.3892/or.15.6.1575     Document Type: Article

References (25)

1. Gogas H and Mansi JL: The anthrapyrazoles. Cancer Treat Rep 21: 541-552, 1995. (Pubitemid 26126764)
2. Hartley JA, Reszka K, Zuo ET, Wilson WD, Morgan AR and Lown JW: Characteristics of the interaction of anthrapyrazole anticancer agents with deoxyribonucleic acids: structural requirements for DNA binding, intercalation and photosensitization. Mol Pharmacol 33: 265-271, 1988. (Pubitemid 18098589)
3. Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC and Elslager EF: Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. J Med Chem 30: 121-131, 1987. (Pubitemid 17221627)
4. Leteurtre F, Kohlhagen G, Paull KD and Pommier Y: Topoisomerase II inhibition and cytotoxicity of the anthrapyrazoles DuP 937 and DuP 941 (Losoxantrone) in the National Cancer Institute preclinical antitumor drug discovery screen. J Natl Cancer Inst 86: 1239-1244, 1994. (Pubitemid 24253700)
5. Fry DW, Boritzki TJ, Besserer JA and Jackson RC: In vitro DNA strand scission and inhibition of nucleic acid synthesis in L 1210 leukaemia cells by a new class of DNA complexes the anthra[1,9-cd] pyrazol-6(2H)-ones (anthrapyrazoles). Biochem Pharmacol 34: 3499-3508, 1985. (Pubitemid 16252528)
6. Leopold WR, Nelson JM, Plowman J and Jackson RC: Anthrapyrazoles, a new class of intercalating agents with highlevel, broad spectrum activity against murine tumors. Cancer Res 45: 5532-5539, 1985. (Pubitemid 16200815)
7. Klohs WD, Steinkampf RW, Havlick MJ and Jackson RC: Resistance to anthrapyrazoles and anthracyclines in multidrug-resistant P388 murine leukaemia cells. Reversal by calcium blockers and calmodulin antagonists. Cancer Res 46: 4352-4356, 1986. (Pubitemid 16046853)
8. Allan SG, Cummings J, Evans S, Nicolson M, Stewart ME, Cassidy J, Soukop M, Kaye SB and Smyth JF: Phase I study of the anthrapyrazole biantrazole: clinical results and pharmacology. Cancer Chemother Pharmacol 28: 55-58, 1991.
9. Ames M, Loprinzi C, Collins JM, van Heelst-Pisani C, Richardson RL, Rubin J and Moertel CG: Phase I and clinical pharmacological evaluation of pirozantrone hydrochloride (oxantrazole). Cancer Res 50: 3906-3909, 1990.
10. Foster BJ, Newell DR, Graham MA, Gumbrell LA, Jenns KE, Kaye SB and Calvert AH: Phase I trial of the anthrapyrazole CI-941: prospective evaluation of a pharmacokinetically guided dose-escalation. Eur J Cancer 28: 463-469, 1992.
11. Hantel A, Donehower RC, Rowinsky EK, Vance E, Clarke BV, McGuire WP, Ettinger DS, Noe DA and Grochow LB: Phase I study and pharmacodynamics of piroxantrone (NSC 349174), a new anthrapyrazole. Cancer Res 50: 3284-3288, 1990. (Pubitemid 20190132)
12. Belanger K, Jolivet J, Maroun J, Stewart D, Grillo-Lopez A, Whitfield L, Wainman N and Eisenhauer E: Phase I pharmacokinetic study of Dup 937, a new anthrapyrazole. Invest New Drugs 11: 301-308, 1993. (Pubitemid 24043815)
13. Erlichman C, Moore M, Kerr IG, Wong B, Eisenhauer E, Zee B and Whitfield LR: Phase I pharmacokinetic and pharmacodynamic study of a new anthrapyrazole CI-937 (DuP 937). Cancer Res 51: 6317-6322, 1991.
14. Goldhirsh A, Morgan R, Yau J, Stewart J, Skillings J, O'Dwyer P, Dallaire B, Azarnia N, Gyves J and Grillo-Lopez A: A phase II study of DuP 937 in advanced breast cancer. Proc Am Soc Clin Oncol 11: 76, 1992.
15. Ingle JN, Kuross SA, Maillard JA, Loprinzi CL, Jung S, Nelimark RA, KrooK JE and Long HJ: Evaluation of piroxantrone in women with metastatic breast cancer and failure on nonanthracycline chemotherapy. Cancer 74: 1733-1738, 1994. (Pubitemid 24301827)
16. Talbot DC, Smith IE, Mansi JL, Judson I, Calvert AH and Ashley SH: Anthrapyrazole CI 941: a highly active new agent in the treatment of advanced breast cancer. J Clin Oncol 9: 2141-2147, 1991.
17. Huan SD, Natale RB, Stewart DJ, Sartiano GP, Stella PJ, Roberts JD, Symes AL and Finizio M: A multicenter phase II trial of losoxantrone (DuP-941) in hormone-refractory metastatic prostate cancer. Clin Cancer Res 6: 1333-1336, 2000. (Pubitemid 30226216)
18. Malviya VK, Liu PY, Goldberg DA, Hantel A, O'Toole RV, Roach RW, Conrad ME and Alberts DS: A phase II trial of piroxantrone in endometrial cancer: Southwest Oncology Group Study 891. Anti-Cancer Drugs 7: 527-530, 1996. (Pubitemid 26276342)
19. Albain KS, Liu PY, Hantel A, Poplin EA, O'Toole RV, Wade JL III, Maddox AM and Alberts DS: A phase II trial of piroxantrone in advanced ovarian carcinoma after failure of platinum-based chemotherapy: Southwest Oncology Group Study 8904. Gynecol Oncol 57: 407-411, 1995.
20. Showalter HDH, Johnson JL and Hoftiezer JM: Heteroannulated-9,10- anthracenediones. The synthesis of substituted 5- and 7-chloroanthra[1,9-cd] pyrazol-6(2H) -ones, precursors to anticancer anthrapyrazoles. J Heterocyclic Chem 23: 1491-1501, 1986. (Pubitemid 17214477)
21. Johnston JB, Verburg L, Shore T, Williams M, Israels LG and Begleiter A: Combination therapy with nucleoside analogs and alkylating agents. Leukemia 8 (suppl): S140-S143, 1994. (Pubitemid 24126090)
22. Hasinoff BB, Kozlowska H, Creighton AM, Allan WP, Thampatty P and Yalowich JC: Mitindomide is a catalytic inhibitor of DNA topoisomerase II that acts at the bisdioxopiperazine binding site. Mol Pharmacol 52: 839-845, 1997. (Pubitemid 27484177)
23. Wu X and Hasinoff BB: The antitumor anthracyclines doxorubicin and daunorubicin do not inhibit cell growth through the formation of iron-mediated reactive oxygen species. Anticancer Drugs 16: 93-99, 2005.
24. Barnabé N and Hasinoff BB: High-throughput fluorescence flow injection topoisomerase II inhibition assay. J Chromatogr B Biomed Sci Appl 760: 263-269, 2001. (Pubitemid 32727249)
25. 2(levrazoxane), of the topoisomerase II inhibitors dexrazoxane (ICRF-187) and levrazoxane (ICRF-186). J Inorg Biochem 98: 616-624, 2004.