Dual topoisomerase I/II inhibitors

Journal of Oncology Pharmacy Practice

Volumn 6, Issue 3, 2000, Pages 92-108

  Van Gijn, R ^a   Lendfers, R R H ^b   Schellens, J H M ^b,c   Bult, A ^b   Beijnen, J H ^a,b  

^a NETHERLANDS CANCER INSTITUTE   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c ANTONI VAN LEEUWENHOEK HOSPITAL   (Netherlands)

Author keywords

dual inhibitors; intoplicine; multidrug resistance; PZA; TAS 103; Topoisomerase I II

Indexed keywords

EID: 77955887390     PISSN: 10781552     EISSN: None     Source Type: Journal    
DOI: 10.1177/107815520000600303     Document Type: Article

References (95)

1. Samuels DS, Shimuzu N. DNA topoisomerase I phosphorylation in murine fibroblasts treated with 12-O-tetradecanoylphorbol-13-acetate and in vitro by protein kinase. J Biol Chem. 1992; 267: 11156-11162.
2. Cardenass ME, Gasser SM. Regulation of topoisomerase II by phosphorylation: a role for casein kinase II. J Cell Sci. 1993; 104: 219-225.
3. Corbett AH, Fernald AW, Osheroff N. Protein kinase C modulates the catalytic activity of topoisomerase II by enhancing the rate of ATP hydrolysis: evidence for a common mechanism of regulation by phosphorylation. Biochemistry. 1993; 32: 2090-2097.
4. Jongstra Bilen J, Ittel ME, Niedergang C, Vosberg HP, Mandel P. DNA topoisomerase I from calf thymus is inhibited in vitro by poly(ADP) ribosylation. Eur J Biochem. 1983; 136: 391-396.
5. Darby MK, Schmitt B, Jongstra Bilen J, Vosberg HP. Inhibition of calf thymus type II DNA topoisomerase by poly(ADP) ribosylation. EMBO J. 1985; 4: 2129-2134.
6. Wang JC. Type I topoisomerases. In: Boyer P, ed. The Enzymes. New York: Academic; 1981: 331-344.
7. Liu LF. DNA topoisomerases: enzymes that catalyze the breaking and rejoining of DNA. Crit Rev Biochem. 1983; 15: 1-24.
8. Rose KM. DNA topoisomerases as targets for chemotherapy. FASEB J. 1988; 2: 2474-2478.
9. Drlica K, Franco RJ. Inhibitors of topoisomerases. Biochemistry. 1998; 27: 2253-2258.
10. Beck WT, Danks MK. Mechanisms of resistance to drugs that inhibit DNA topoisomerases. Semin Cancer Biol. 1991; 2: 235-244.
11. D’Arpa P, Beardmore C, Liu LF. Involvement of nucleic acid synthesis in cell killing mechanisms of topoisomerase poisons. Cancer Res. 1990; 50: 6919-6924.
12. Kaufmann SH. Antagonism between camptothecin and topoisomerase II-directed chemotherapeutic agents in a human leukemia cell line. Cancer Res. 1991; 51: 1129-1136.
13. Bertrand R, O’Connor PM, Kerrigan D, Pommier Y. Sequential administration of camptothecin and etoposide circumvents the antagonistic cytotoxicity of simultaneous drug administration in slowly growing human colon carcinoma HT-29 cells. Eur J Cancer. 1991; 28A: 743-748.
14. Kim R, Hirabayashi N, Nishiyama H, Jinushi K, Toge T, Okada K. Experimental studies on biochemical modulation targeting topoisomerase I and II in human tumor xenografts in nude mice. Int J Cancer. 1992; 50: 760-766.
15. Vasey PA, Kaye SB. Combined inhibition of topoisomerase I and II—is this a worldwhile/feasible strategy? Br J Cancer. 1997; 76: 1395-1397.
16. Riou JF, Fosse P, Nguyen CH, et al. Intoplicine (RP 60475) and its derivatives, a new class of antitumor agents inhibiting both topoisomerase I and II activities. Cancer Res. 1993; 53: 5987-5993.
17. Eckhardt JR, Burris III HA, Rodriguez GA. A phase I study of the topoisomerase I and II inhibitors topotecan and etoposide. Proc Am Soc Clin Oncol. 1993; 12: 136.
18. Poddevin B, Riou JF, Lavelle F, Pommier Y. Dual topoisomerase I and II inhibition by intoplicine (RP-60475), a new antitumor agent in early clinical trials. Mol Pharmacol. 1993; 44: 767-774.
19. Chen AY, Liu LF. DNA topoisomerase: essential enzymes and lethal targets. Annu Rev Pharmacol Toxicol. 1994; 34: 191-218.
20. Bonner JA, Kozelsky TF. The significance of sequence of administration of topotecan and etoposide. Cancer Chemother Pharmacol. 1996; 39: 109-112.
21. Champoux JJ, Conaughy BL. Purification and characterization of the DNA untwisting enzyme from rat liver. Biochemistry. 1976; 15: 4638-4642.
22. Miller KG, Miller KG, Liu LF, Englund PT. A homogenous type II DNA topoisomerase from HeLa cell nuclei. J Biol Chem. 1981; 256: 9334-9339.
23. Kunze N, Yang GC, Jiang ZY, et al. Localization of the active type I DNA topoisomerase gen on human chromosome 20q11.2-13.1. and two pseudogenes on chromosomes 1q23-24 and 22q11.2-13.1. Hum Genet. 1989; 84: 6-6 okt.
24. Juan C-C, Hwang J, Liu AA, et al. Human DNA topoisomerase I is encoded by a single-copy gene that maps to chromosome region 20q12-13.2. Proc Natl Acad Sci USA. 1988; 85: 8910-8913.
25. D’Arpa P, Machlin PS, Ratrie H III, Rothfield NF, Cleveland DW, Earnshaw WC. cDNA cloning of human DNA topoisomerase I: catalytic activity of a 67.7-kDa carboxyl-terminal fragment. Proc Natl Acad Sci USA. 1988; 85: 2543-2547.
26. Ralph RK, Judd W, Pommier Y, Kohn KW. DNA Topoisomerases. Topics in Molecular and Structural Biology: Molecular Aspects of Anticancer Drug-DNA Interactions. 1994.
27. Wang JC. DNA topoisomerases. Annu Rev Biochem. 1996; 65: 635-692.
28. Osheroff N. Biochemical basis for the interactions of type I and type II topoisomerases with DNA. Pharmacol Ther. 1989; 41: 223-241.
29. Dean FB, Cozzarelli NR. Mechanism of strand passage by Escherichia coli topoisomerase I. J Biol Chem. 1985; 260: 4984-4994.
30. Merino A, Madden KR, Lane WS, Champoux JJ, Reinberg D. DNA topoisomerase is involved in both repression and activation of transcription. Nature. 1993; 365: 227-232.
31. Osheroff N, Shelton ER, Brutlage DL. DNA topoisomerase II from Drosophila melanogaster. Relaxation of supercoiled DNA. J Biol Chem. 1983; 258: 9536-9543.
32. Drake FH, Zimmerman JP, McCabe FL, et al. Purification of topoisomerase II from amsacrine-resistant P388 leukemia cells. J Biol Chem. 1987; 262: 16739-16747.
33. Drake FH, Hofmann GA, Bartus HF, Mattern MR, Crooke ST, Mirabelli CK. Biochemical and pharmacological properties of P170 and P180 forms os topoisomerase II. Biochemistry. 1989; 28: 8154-8160.
34. Tsai-Pflugfelder M, Liu LF, Liu AA, et al. Cloning and sequencing of cDNA encoding human DNA topoisomerase II and localization of the gene to chromosome region 17q21-22. Proc Natl Acad Sci USA. 1988; 85: 7177-7181.
35. Tan KB, Dorman TE, Falls KM, et al. Topoisomerase II alpha and topoisomerase II beta genes: characterization and mapping to human chromosomes 17 and 3, respectively. Cancer Res. 1992; 52: 231-234.
36. Osheroff N, Corbett AH, Elsea SH, Westergaard M. Defining functional drug interaction domains on topoisomerase II by exploiting mechanistic differences between drug classes. Cancer Chemother Pharmacol. 1994; 34: S19-S25.
37. Maxwell G, Gellert M. Mechanistic aspects of DNA topoisomerases. Adv Protein Chem. 1994; 38: 69-107.
38. Wood ER, Earnshaw WC. Mitotic chromatin condensation in vitro using somatic cell extracts and nuclei with variable levels of endogenous topoisomerase II. J Cell Biol. 1990; 111: 2839-2850.
39. Negri C, Chiesa R, Cerino A, et al. Monoclonal antibodies to human DNA topoisomerase I and the two isoforms of DNA topoisomerase II: 170- and 180-kDa isozymes. Exp Cell Res. 1992; 200: 452-459.
40. Ura K, Hirose S. Possible role of DNA topoisomerase II on transcription of the homebox gene Hox-2.1 in F9 embryonal carcinoma cells. Nucleic Acids Res. 1991; 19: 6087-6092.
41. Herzberg RP, Busby RW, Caranfa MJ, et al. Irreversible trapping of the DNA-topoisomerase I covalent complex affinity labeling of the camptothecin-binding site. J Biol Chem. 1990; 265: 19287-19295.
42. Liu LF, ed. Adv Pharmacol. San Diego, CA, USA: Academic Press; 1994:29B:297.
43. Tanisawa A, Kohn KW, Kohlhagen G, Leteurtre F, Pommier Y. Differential stabilization of eukaryotic DNA topoisomerase I cleavable complexes by camptothecin derivatives. Biochemistry. 1995; 34: 7200-7206.
44. Redinbo MR, Stewart L, Kuhn P, Champoux JJ, Hol WGJ. Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA. Science. 1988; 279: 1504-1513.
45. Howard MT, Neece SH, Matson SW, Kreuzer KN. Disruption of a topoisomerase-DNA cleavage complex by a DNA helicase. Proc Natl Acad Sci USA. 1994; 91: 12031-12035.
46. Avemann K, Knippers R, Koller T, Sogo JM. Camptothecin, a specific inhibitor of type I DNA topoisomerase, induces DNA breakage at replication forks. Mol Cell Biol. 1998; 8: 3026-3034.
47. Liu LF. DNA topoisomerase poisons as antitumor drugs. Annu Rev Biochem. 1989; 58: 351-375.
48. Roca J, Ishida R, Berger JM, Andoh T, Wang JC. Antitumor bisdioxopiperazines inhibit yeast DNA topoisomerase II by trapping the enzyme in the form of a closed protein clamp. Proc Natl Acad Sci USA. 1994; 91: 1781-1785.
49. Chen AY, Liu LF. DNA topoisomerases: essential enzymes and lethal targets. Annu Rev Pharmacol Toxicol. 1994; 34: 191-218.
50. Sorensen BS. Antagonistic affect of alarubicin on camptothecin-induced cytotoxicity: role of topoisomerase I. Biochem Pharmacol. 1994; 47: 2105-2110.
51. Jensen PB, Sorensen BS, Demant EJ, et al. Antagonistic effect of aclarubicin on the cytotoxicity of etoposide and 4′-(9-acridinylamino) methanesulfon-m-aniside in human small cell lung cancer cell lines and on topoisomerase II-mediated DNA cleavage. Cancer Res. 1990; 50: 3311-3316.
52. Nitiss JL, Pourquier P, Pommier Y. Aclacinomycin A stabilizes topoisomerase I covalent complexes. Cancer Res. 1997; 57: 4564-4569.
53. Cummings J, Macpherson JS, Meikl I, Smyth JF. Development of anthracenyl-amino acid conjugates as topoisomerase I and II inhibitors that circumvent drug resistance. Biochem Pharmacol. 1996; 52: 979-990.
54. Crow RT, Crothers DM. Inhibition of topoisomerase I by anthracycline antibiotics: evidence for general inhibition of topoisomerase I by DNA-binding agents. J Med Chem. 1994; 37: 3191-3194.
55. Finlay GJ, Marshall ES, Matthews JHL, Paull KD, Baguley BC. In vitro assessment of N-[2-(dimethylamino)ethyl]-acridine-4-carboxamide, a DNA-intercalating antitumour drug with reduced sensitivity to multidrug resistance. Cancer Chemother Pharmacol. 1993; 31: 401-406.
56. Finlay GJ, Riou JF, Baguley BC. From amsacrine to DACA (N-[2-(dimethylamino) ethyl] acridine-4-carboxamide): selectivity for topoisomerases I and II among acridine derivatives. Eur J Cancer. 1995; 32A: 708-714.
57. Spicer JA, Finlay GJ, Baguley BC, Velea L, Graves DE, Denny WA. 5,7-Disubstituted analogues of the mixed topoisomerase I/II poison N-[2-dimethylamino) ethyl] acridine-4-carboxamide (DACA): DNA binding and patterns of cytotoxicity. Anticancer Drug Resist. 1999; 14: 37-45.
58. Adjei AA, Charron M, Rowinski EK, et al. Effect of pyrazoloacridine (NSC 366140) on topoisomerases I and II. Clin Cancer Res. 1998; 4: 683-691.
59. Rowinsky EK, Noe D, Grochow L, et al. Phase I and pharmacologic studies of pyrazoloacridine, a novel intercalating agent, on single, and multiple dosing schedules. J Clin Oncol. 1995; 13: 1975-1984.
60. Berg SL, Blaney SM, Adamson PC, et al. Phase I trial and pharmacologic study of pyrazoloacridine in children and young adults with refractory cancers. J Clin Oncol. 1988; 16: 181-186.
61. Zalupski MM, Philip PA, LoRusso P, Shields AF. Phase II study of pyrazoloacridine in patients with advanced colorectal carcinoma. Cancer Chem Pharm. 1997; 40: 225-227.
62. Adjei AA. Current status of pyrazoloacridine as an anticancer agent. Invest New Drugs. 1999; 17: 43-48.
63. Niederberger E, Marko D, Genzlinger A, Zankl H, Tang WC, Eisenbrand G. Inhibition of topoisomerase I + II by flavones from the Chinese plant Scutellaria baicalensis. In: The Eighth Conference on DNA Topoisomerases in Therapy. 1997: 27.
64. Fujii N, Yamashita Y, Saitoh Y, Nakano H. Induction of mammalian DNA topoisomerase I-mediated DNA cleavage and DNA winding by bulgarein. J Biol Chem. 1993; 268: 13160-13165.
65. Markovits J, Larsen AK, Segal Bendirdjian E, et al. Inhibition of DNA topoisomerase I and II and induction of apoptosis by erbstatin and tyrphostin derivatives. Biochem Pharmacol. 1994; 48: 549-560.
66. Wang LK, Johnson RK, Hecht SM. Inhibition of topoisomerase I function by nitidine and fagaronine. Chem Res Toxicol. 1993; 6: 813-818.
67. Larsen AK, Grondard L, Couprie J, et al. The antileukemic alkaloid fagaronine is an inhibitor of DNA topoisomerases I and II. Biochem Pharmacol. 1993; 46: 1403-1412.
68. Janin YL, Croisy A, Riou JF, Bisagni E. Synthesis and evaluation of new 6-amino-substituted benzo [c] phenanthridine derivatives. J Med Chem. 1993; 36: 3686-3692.
69. Riou JF, Grondard L, Naudin A, Bailly C. Effects of two distamycin-ellipticine hybrid molecules on topoisomerase I- and II-mediated DNA cleavage: relation to cytotoxicity. Biochem Pharmacol. 1995; 50: 424-428.
70. Ray S, Sadhukhan PK, Mandal NB, Mahato SB, Majumder HK. Dual inhibition of DNA topoisomerases of Leishmania donovani by novel indolyl quinolines. Biochem Biophys Res Commun. 1997; 230B: 171-175.
71. Aoyagi Y, Kobunai T, Utsugi T, Oh-hara T, Yamada Y. In vitro antitumor activity of TAS-103, a novel quinoline derivative that targets topoisomerases I and II. Jpn J Cancer Res. 1999; 90: 578-587.
72. Rowinsky EK, Rothenberg M, Von Hoff D. Topoisomerase I-targeting agents (T1Tas) In: The Eighth Conference on DNA Topoisomerases in Therapy. 1997: 78.
73. Byl Ja, Fortune JM, Burden DA, et al. DNA topoisomerases as targets for the anticancer drug TAS-103: primary cellular target and DNA cleavage enhancement. Biochemistry. 1999; 38: 15573-15579.
74. Fortune JM, Velea L, Graves DE, Utsugi T, Yamada Y, Osheroff N. DNA topoisomerases as targets for the anticancer drug TAS-103: DNA interactions and topoisomerase catalytic interactions. Biochemistry. 1999; 38: 15580-15586.
75. Aoyagi Y, Utsugi T, Kobunai T, Yamada Y. In vitro antitumor activity of the novel quinoline derivative, TAS-103, inhibiting topoisomerase I and II. Proc Am Assoc Cancer Res. 1998; 39: 82.
76. Ohyama T, Utsugi T, Yamada Y, Sato T. Investigation of mechanisms of apoptosis induced by a dual inhibitor of DNA I and II (TAS103). Proc Am Assoc Cancer Res. 1998; 39: 529.
77. Sunami T, Nishio K, Kanwanza F, Fukuoka K, Yoshikawa J, Saijo N. Combination effects of TAS-103, a novel dual topoisomerase I and II inhibitor, with other anticancer agents on human small cell lung cancer cells. Proc Am Assoc Cancer Res. 1998; 39: 596.
78. Parajuli P, Yano S, Nishioka Y, et al. Therapeutic efficacy of a new topoisomerase I and II inhibitor TAS-103, against both P-glycoprotein-expressing and -nonexpressing drug-resistant human small cell lung cancer. Oncol Res. 1999; 11: 219-224.
79. Sunami T, Nishio K, Kanzawa F, et al. Combination effects of TAS-103, a novel dual topoisomerase I and II inhibitor, with other anticancer agents on human small cell lung cancer cells. Cancer Chemother Pharmacol. 1999; 43: 394-401.
80. Donehower R, Elza-Brown K, O’Reilly S, Israel B, Grochow L. A phase I dose escalation, safety, tolerability, and pharmacokinetic study of TAS-103 in patients with refractory solid tumors. Proc Am Soc Clin Oncol. 1998; 17: 209a.
81. Morjani H, Riou JF, Nabiev I, Lavelle F, Manfait M. Molecular and cellular interactions between intoplicine, DNA, and topoisomerase II studied by surface-enhanced Raman scattering spectroscopy. Cancer Res. 1993; 53: 4784-4790.
82. Nabiev I, Chourpa I, Riou JF, Nguyen CH, Lavelle F, Manfait M. Molecular interactions of DNA-topoisomerase I and II inhibitor with DNA and topoisomerases in ternary complexes: binding modes and biological effects for intoplicine derivatives. Biochemistry. 1994; 33: 9013-9023.
83. Bissery MC, Nguyen CH, Bisagni E, Vignaud P, Lavelle F. Antitumor activity of intoplicine (RP 60475, NSC 645008), a new benzopyrido-indole: evaluation against solid tumors and leukemias in mice. Invest New Drugs. 1993; 11: 263-277.
84. Eckhardt JR, Burris HA III, Kuhn JG, et al. Activity of intoplicine (RP60475), a new DNA topoisomerase I and II inhibitor, against human tumor colony-forming units in vitro. J Natl Cancer Inst. 1994; 86: 30-33.
85. Abigerges D, Armand JP, Chabot CG, et al. Phase I and pharmacologic study of intoplicine, a novel topoisomerase I and II inhibitor, in cancer patients. Anticancer Drugs. 1996; 7: 166-174.
86. van Gijn R, ten Bokkel Huinink WW, Rodenhuis S, et al. Phase I and pharmacologic study with the novel topoisomerase I/II inhibitor intoplicine administered as a 24-hour infusion. Ann Oncol. 1998; 9: 66.
87. Newman RA, Kim J, Newman BM, et al. Phase I trial of intoplicine (RP60475) administered as a 72-h infusion every 3 weeks in patients with solid tumors. Anticancer Drugs. 1999; 10: 889-894.
88. Yamashita Y, Kawada S, Fujii N, Nakano H. Induction of mammalian DNA topoisomerase I- and II-mediated DNA cleavage by saintopin, a new antitumour agent from fungus. Biochemistry. 1991; 30: 5838-5845.
89. Leteurtre F, Fujimori A, Tanizawa A, et al. Saintopin, a dual inhibitor of DNA topoisomerases I and II as a probe for drug-enzyme interactions. J Biol Chem. 1994; 269: 28702-28707.
90. Taniguchi K, Kohno K, Kawanami K, Wada M, Kanematsu T, Kuwano M. Drug-induced down-regulation of topoisomerase I in human epidermoid cancer cells resistant to saintopin and camptothecins. Cancer Res. 1996; 56: 2348-2354.
91. Fujii N, Yamashita Y, Mizukami T, Nakano H. Correlation between the formation of cleavable complex with topoisomerase I and growth-inhibitory activity for saintopin-type antibiotics. Mol Pharmacol. 1997; 51: 269-276.
92. Takada M, Fukuoka M, Kudoh S, et al. Synergistic effects of CPT-11 and cisplatin or etoposide on human lung cancer cells and xenografts in nude mice. Proc Am Assoc Cancer Res. 1992; 33: 226.
93. Kano Y, Suzuki K, Akutsu M, et al. Effects of CPT-11 in combination with other anticancer agents in culture. Int J Cancer. 1992; 50: 604-610.
94. Herben VMM, ten Bokkel Huinink WW, Dubbelman AC, et al. Phase I and pharmacological study of sequential intravenous topotecan and oral etoposide. Br J Cancer. 1997; 76: 1500-1508.
95. Ferguson LR, Baguley BC. Mutagenicity of anticancer drugs that inhibit topoisomerase enzymes. Mutat Res. 1996; 355: 91-101.