Synthesis and Evaluation of Terbenzimidazoles as Topoisomerase I Inhibitors

Journal of Medicinal Chemistry

Volumn 38, Issue 18, 1995, Pages 3638-3644

  Sun, Qun ^a   Gatto, Barbara ^b   Yu, Chiang ^b   Liu, Angela ^b   Liu, Leroy F ^b   LaVoie, Edmond J ^a  

^a RUTGERS UNIVERSITY   (United States)

^b RUTGERS ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; CAMPTOTHECIN; DNA; DNA TOPOISOMERASE; DNA TOPOISOMERASE INHIBITOR; GYRASE INHIBITOR; HOE 33342; TERBENZIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DNA CLEAVAGE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL;

ANIMAL; ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CATTLE; CELL LINE; DNA TOPOISOMERASES, TYPE I; DRUG EVALUATION; HUMAN; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, NON-P.H.S.; SUPPORT, U.S. GOV'T, P.H.S.; TUMOR CELLS, CULTURED;

EID: 0029134061     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00018a024     Document Type: Article

References (35)

1. Wang, J. C. DNA topoisomerases. Annu. Rev. Biochem. 1985, 54, 665-697.
2. Liu, L. DNA topoisomerase poisons as antitumor drugs. Annu. Rev. Biochem. 1989, 58, 351-375.
3. D’Arpa, P.; Liu, L. Topoisomerase-targeting antitumor drugs. Biochim. Biophys. Acta 1989, 989, 163-177.
4. Bodley, A. L.; Liu, L. F. Topoisomerases as novel targets for cancer chemotherapy. Biotechnology 1988, 6, 1315-1318.
5. Schneider, E.; Hsiang, Y.-H.; Liu, L. F. DNA topoisomerase as anticancer drug targets. Adv. Pharmacol. 1990, 21, 149-183.
6. Chen, A. Y.; Liu, L. F. DNA topoisomerases: Essential enzymes and lethal targets. Annu. Rev. Pharmacol. Toxicol. 1994, 34, 191-218.
7. Gallo, R. C.; Whang-Peng, J.; Adamson, R. A. H. Studies on the antitumor activity, mechanism of action, and cell cycle effects of camptothecin. J. Natl. Cancer Inst. 1971, 46, 789-795.
8. Giovanella, B. C.; Hinz, H. R.; Kozielski, A. J.; Stehlin, A. J., Jr.; Silber, R.; Potmesil, M. Complete growth inhibition of human cancer xenografts in nude mice by treatment with 20-(S)- camptothecin. Cancer Res. 1991, 51, 3052-3055.
9. Larsen, A. K.; Grondard, L.; Couprie, J.; Desoize, B.; Comoe, L.; Jardillier, J.-C.; Riou, J.-F. The antileukemic alkaloid fagaronine is an inhibitor of DNA topoisomerase I and II. Biochem. Pharmacol. 1993, 46, 1403-1412.
10. Fang, S.-D.; Wang, L.-K.; Hecht, S. M. Inhibitors of DNA topoisomerase I isolated from the roots of Zanthoxylum nitidum. J. Org. Chem. 1993, 58, 5025-5027.
11. Makhey, D.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVole, E., Protoberberine alkaloids and related compounds as dual inhibitors of mammalian topoisomerase I and II. Med. Chem. Res. 1994, 5, 1-12.
12. Fujii, N.; Yamashita, Y.; Saitoh, Y.; Nakano, H. Induction of mammalian DNA topoisomerase I-mediated DNA cleavage and DNA unwinding by Bulgarein. J. Biol. Chem. 1993, 268, 13160-13165.
13. Yamashita, Y.; Kawada, S.-Z.; Fujii, N.; Nakano, H. Induction of mammalian topoisomerase I and II mediated DNA cleavage by Saintopin, a new antitumor agent from fungus. Biochemistry 1991, 30, 5838-5845.
14. Yamashita, Y.; Fujii, N.; Murakaya, C.; Ashizawa, T.; Okabe, M.; Nakano, H. Induction of mammalian DNA topoisomerase mediated DNA cleavage by antitumor indolocarbazole derivatives. Biochemistry 1992, 31, 12069-12075.
15. Chen, A. Y.; Yu, C.; Bodley, A. L.; Peng, L. F.; Liu, L. F. A new mammalian DNA topoisomerase I poison Hoechst 33342: Cytotoxicity and drug resistance in human cell cultures. Cancer Res. 1993, 53, 1332-1335.
16. Chen, A.; Yu; C.; Gatto, B.; Liu, L. F. DNA minor groove-binding ligands: A different class of mammalian DNA toposiomerase I inhibitors. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 8131-8135.
17. Sun, Q.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVole, E. J. Structure activity of topoisomerase I poisons related to Hoechst 33342. Bioorg. Med. Chem. Lett. 1994, 4, 2871-2876.
18. Singh, M. P.; Joseph, T.; Kumar, S.; Bathini, Y.; Lown, J. W. Synthesis and sequence -specific DNA binding of a topoisomerase inhibitory analog of Hoechst 33258 designed for altered base and sequence recognotion. Chem. Res. Toxicol. 1992, 5, 597-607.
19. Bathini, Y.; Lown, J. W. Convenient routes to substituted benzimidazoleas and imadazolo[4, 5-b]pyridines using nitrobenzene as oxidant. Syn. Commun. 1990, 20, 955-963.
20. Fox, G. J.; Hallas, G.; Hepworth, J. D.; Paskins, K. N. para- Bromination of aromatic amines: 4-Bromo-N, N, -dimethyl-3-(trifluoromethyl) aniline. Org. Syn. 1973, 55, 20-23.
21. Heppolette, R. L.; Miller, J. The SN mechanism in aromatic compounds. V. Halogen substituents. J. Am. Chem. Soc. 1953, 75, 4265-4268.
22. Peters, D.; Homfeldt, A.-B.; Gronowitz, S. Synthesis of various 5-substituted uracils. J. Heterocycl. Chem. 1990, 27, 2165-2173.
23. Iwao, M.; Takehara, H.; Furukawa, S.; Wantanabe, M. A regiospecific synthesis of carbazoles via consecutive palladium- catalyzed cross-coupling and aryne-mediated cyclization. Heterocycles 1993, 36, 1483-1492.
24. Cherif, A.; Farquhar, D. N-(5, 5-Diacetoxypent-1-yl) doxorubicin: A new intensely potent doxorubicin analogue. J. Med. Chem. 1992, 35, 3208-3114.
25. Pipier, J. R.; McCaleb, G. S.; Montogomery, J. A.; Kisliuk, R. L.; Glaumont, Y.; Thorndike, J.; Sirotnak, F. M. Synthesis and antifolate activity of 5-methyl-5, 10-dideaza analogues of ami- nopterin and folic acid and an alternative synthesis of 5, 10- dideazatetrahydrofolic acid, a potent inhibitor of glycinamide ribonucleotide formyltransferase. J. Med. Chem. 1988, 31, 2164-2169.
26. Andoh, T.; Okada, K. Drug resistance mechanisms of topoisomerase I drugs. Adv. Pharmacol. 1994, 29B, 93-103.
27. Aliyama, S.; Fojo, A.; Hanover, J. A.; Pastan; I.; Gottesman, M. M. Isolation and genetic characterization of human KB cell lines resistant to multiple drugs. Somatic Cell Mol. Genet. 1985, 11, 117-126.
28. Shen, D.-W.; Fojo, A.; Chin, J. E.; Roninson, I. B.; Richert; N.; Paston, I.; Gottesman, M. M. Human multi-drug resistant cell lines; increased mdrl expression can precede gene amplification. Science 1986, 232, 643-645.
29. Chen, A. Y.; Liu, L. F. Design of topoisomerase inhibitors to overcome MDRl-mediated drug resistance. Adv. Pharmacol. 1994, 29B, 245-256.
30. Halligan, B. D.; Edwards, K. A.; Liu, L. F. Purification and characterization of a type II DNA topoisomerase from bovine calf thymus. J. Biol. Chem. 1985, 260, 2475-2482.
31. Maniatis, T.; Fritsch, E. F.; Sambrook, J. Molecular Cloning, a Laboratory Manual, Cold Spring Harbor Laboratory: Cold Spring Harbor, New York, 1982; pp 149-185.
32. Liu, L. F.; Rowe, T. C.; Yang, L.; Tewey, K. M.; Chen, G. L. Cleavage of DNA by mammalian topoisomerase II in cultured human cells. J. Biol. Chem. 1983, 258, 15365-15370.
33. Mosmann, T. J. Rapid colorimetric assay for cellular growth and survivcal: application to proliferation and cytotoxicity assays. Immunol. Methods 1983, 65, 55-63.
34. Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Mitchell, J. B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 1987, 47, 936-942.
35. Denizot, F.; Lang, R. Rapid colorimetric assay for cell growth and survival. Modifications to the tétrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 1986, 89, 271-277.