Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives - Eleutherin, α lapachone, and β lapachone

Biochemical Pharmacology

Volumn 60, Issue 9, 2000, Pages 1367-1379

  Krishnan, Preethi ^a   Bastow, Kenneth F ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

Catalytic inhibitors; Naphthoquinones; Topoisomerase II

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALPHA LAPACHONE; ANTINEOPLASTIC AGENT; BETA LAPACHONE; DNA TOPOISOMERASE (ATP HYDROLYSING); ELEUTHERIN; ETOPOSIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; DNA STRAND BREAKAGE; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; PRIORITY JOURNAL;

ADENOSINE TRIPHOSPHATE; BACTERIA; BINDING SITES; CATALYSIS; DNA; DNA TOPOISOMERASES, TYPE II; ENZYME INHIBITORS; FUNGI; MERCAPTOETHANOL; NAPHTHOQUINONES;

EID: 0034333371     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(00)00437-8     Document Type: Article

References (30)

1. Berger J.M., Gamblin S.J., Harrison S.C., Wang J.C. Structure and mechanism of DNA topoisomerase II. Nature. 379:1996;225-232.
2. Wang J.C. DNA topoisomerases. Annu Rev Biochem. 65:1996;635-692.
3. Liu L.F. DNA topoisomerase poisons as antitumor drugs. Annu Rev Biochem. 58:1989;351-375.
4. Andoh T., Ishida R. Catalytic inhibitors of DNA topoisomerase II. Biochim Biophys Acta. 1400:1998;155-171.
5. Hara H, Maruyama N, Yamashita S, Hayashi Y, Lee KH, Bastow KF, Chairul, Marumoto R and Imakura Y, Elecanacin, a novel new naphthoquinone from the bulb of Eleutherine americana. Chem Pharm Bull (Tokyo) 45: 1714-1716, 1997.
6. Goijman S.G., Stoppani A.O.M. Effects of β-lapachone, a peroxide-generating quinone, on macromolecule synthesis and degradation in Trypanosoma cruzi. Arch Biochem Biophys. 240:1985;273-280.
7. Li C.J., Averboukh L., Pardee A.B. β-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J Biol Chem. 268:1993;22463-22468.
8. Frydman B., Marton L.J., Sun J.S., Neder K., Witiak D.T., Liu A.A., Wang H., Mao Y., Wu H., Sanders M.M., Liu L.F. Induction of DNA topoisomerase II-mediated cleavage by β-lapachone and related naphthoquinones. Cancer Res. 57:1997;620-627.
9. Moore H.W. Bioactivation as a model for drug design bioreductive alkylation. Science. 197:1977;527-532.
10. Portela M.P.M., Stoppani A.O.M. Redox cycling of β-lapachone and related o-naphthoquinones in the presence of dihydrolipoamide and oxygen. Biochem Pharmacol. 51:1996;275-283.
11. Li J.C., Wang C., Pardee A.B. Induction of apoptosis by β-lapachone in human prostate cancer cells. Cancer Res. 55:1995;3712-3715.
12. Planchon S.M., Wuerzberger S., Frydman B., Witiak D.T., Hutson P., Church D.R., Wilding G., Boothman D.A. β-Lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells A p53-independent response . Cancer Res. 55:1995;3706-3711.
13. Neder K., Marton L.J., Liu L.F., Frydman B. Reaction of β-lapachone and related naphthoquinones with 2-mercaptoethanol A biomimetic model of topoisomerase II poisoning by quinones . Cell Mol Biol. 44:1998;465-474.
14. Hooker S.C. The constitution of "Lapachic Acid" (lapachol) and its derivatives. J Chem Soc. 61:1892;611-650.
15. Osheroff N. Eukaryotic topoisomerase II Characterization of enzyme turnover . J Biol Chem. 261:1986;9944-9950.
16. Vance J.R., Bastow K.F. Inhibition of DNA topoisomerase II catalytic activity by antiviral agents 7-chloro-1,3-dihydroxyacridone and 1,3,7-trihydroxyacridone. Biochem Pharmacol. 58:1999;703-708.
17. Liu L.F., Rowe T.C., Yang L., Tewey K.M., Chen G.L. Cleavage of DNA by mammalian DNA topoisomerase II. J Biol Chem. 258:1983;15365-15370.
18. Robinson M.J., Osheroff N. Effects of antineoplastic drugs on post-strand passage DNA cleavage/religation equilibrium of topoisomerase II. Biochemistry. 30:1991;1807-1813.
19. Osheroff N. Biochemical basis for the interactions of type I and type II topoisomerase with DNA. Pharmacol Ther. 41:1989;223-241.
20. Sorensen B.S., Sinding J., Anderson A.H., Alsner J., Jensen P.B., Westergaard O. Mode of action of topoisomerase II-targeting agents at a specific DNA sequence Uncoupling the DNA binding, cleavage and religation events . J Mol Biol. 228:1992;778-786.
21. Fortune J.M., Osheroff N. Merbarone inhibits the catalytic activity of human topoisomerase IIα by blocking DNA cleavage. J Biol Chem. 273:1998;17643-17650.
22. Lassota P., Singh G., Kramer R. Mechanism of topoisomerase II inhibition by staurosporine and other protein kinase inhibitors. J Biol Chem. 271:1996;26418-26423.
23. Hoffman G.A., Mirabelli C.K., Drake F.H. Quantitative adaptation of the bacteriophage P4 unknotting assay for use in the biochemical and pharmacological characterization of topoisomerase II. Anticancer Drug Des. 5:1990;273-282.
24. Roca J., Ishida R., Berger J.M., Andoh T., Wang J.C. Antitumor bisdioxopiperazines inhibit yeast DNA topoisomerase II by trapping the enzyme in the form of a closed protein clamp. Proc Natl Acad Sci USA. 91:1994;1781-1785.
25. Tsai-Pflugfelder M., Liu L.F., Liu A.A., Tewey K.M., Whang-Peng J., Knutsen T., Huebner K., Croce C.M., Wang J.C. 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. 85:1988;7177-7181.
26. Lindsley J.E. Intradimerically tethered DNA topoisomerase II is catalytically active in DNA transport. Proc Natl Acad Sci USA. 93:1996;2975-2980.
27. Takano H., Kohno K., Ono M., Ichida Y., Kuwano M. Increased phosphorylation of DNA topoisomerase II in etoposide-resistant mutants of human cancer KB cells. Cancer Res. 51:1991;3951-3957.
28. Ferguson P.J., Fisher M.H., Stephenson J., Li D.-H., Zhou B.-S., Cheng Y.-C. Combined modalities of resistance in etoposide-resistant human KB cell lines. Cancer Res. 48:1988;5956-5964.
29. Davies S.L., Harris A.L., Hickson I.D. Response of ICRF-159 in cell lines resistant to cleavable complex-forming inhibitors. Br J Cancer. 75:1997;816-821.
30. Fattman C.I., Allan W.P., Hashinoff B.B., Yalowich J.C. Collateral sensitivity to the bisdioxopiperazine dexrazoxane (ICRF-187) in etoposide (VP-16)-resistant human leukemia K562 cells. Biochem Pharmacol. 52:1996;635-642.