Substituted 2,5′-Bi-1H-benzimidazoles: Topoisoraerase I inhibition and cytotoxicity

Journal of Medicinal Chemistry

Volumn 39, Issue 4, 1996, Pages 992-998

  Kim, Jung Sun ^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

4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL; BENZIMIDAZOLE DERIVATIVE; DNA TOPOISOMERASE; HOE 33342; NSC 32291; PIBENZIMOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DNA CLEAVAGE; DNA STRAND BREAKAGE; DRUG ACTIVITY; DRUG INHIBITION; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; LYMPHOBLAST; STRUCTURE ANALYSIS; TARGET CELL;

ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CELL LINE; CELL SURVIVAL; DNA TOPOISOMERASES, TYPE I; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0001325629     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950412w     Document Type: Article

References (27)

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. Bio/technology, 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, J. S., 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. 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, 1332-1337.
10. Chen, A.; Yu, C.; Gatto, B.; Liu, L. F. DNA minor groove-binding ligands: A different class of mammalian DNA topoisomerase I inhibitors. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8131-8135.
11. Beerman, T. A.; McHugh, M. M.; Sigmund, R.; Lown, J. W.; Rao, K. E.; Bathini, Y. Effects of analogs of the DNA minor groove binder Hoechst 33258 on topoisomerase II and I mediated activities. Biochim. Biophys. Acta 1992, 1131, 53-61.
12. Sun, Q.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. Structure activity of topoisomerase I poisons related to Hoechst 33342. Bioorg. Med. Chem. Lett. 1994, 4, 2871-2876.
13. Sun, Q.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. Synthesis and evaluation of terbenzimidazoles as topoisomerase I inhibitors. J. Med. Chem. 1995, 38, 3638-3644.
14. Gravatt, G. L.; Baguley, B. C.; Wilson, W. R.; Denny, W. A. DNA-directed alkylating agents. 6. Synthesis and antitumor activity of DNA minor groove-targeted aniline mustard analogues of Pibenzimol 〈Hoechst 33258〉. J. Med. Chem. 1994, 37, 4338-4345.
15. Stephens, F. F.; Bower, J. D. The preparation of benzimidazoles and benzoxazoles from Schiff's bases. Part II. J. Chem. Soc. 1950, 1722-1726.
16. Skylyarova, I. V.; Garabadzhiu, A. V.; Ginzburg, O. F. 2′-[2-(4-substituted phenyl)-5 (6)-benzimidazolyl]-5 (6)-benzimidazole-carboxylic acid amides. Zh. Org. Khim. 1991, 27, 395-399; Chem. Abstr. 115:183184y.
17. Skylyarova, I. V.; Garabadzhiu, A. V.; Ginzburg, O. F. 2′-[2-(4-substituted phenyl)-5 (6)-benzimidazolyl]-5 (6)-benzimidazole-carboxylic acid amides. Zh. Org. Khim. 1991, 27, 395-399; Chem. Abstr. 115:183184y.
18. Cacchi, S.; Misiti, D. Amides from nitriles using basic hydrogen peroxide under phase-transfer catalyzed conditions. Synthesis 1980, 243-244.
19. Loewe, Von H.; Urbanietz, J. Basic-substituted 2,6-bisbenzimidazole derivatives, a novel series of substances with chemotherapeutic activity. Arzneim.-Forsch. (Drug Res.) 1974, 24, 1927-1933.
20. International Patent; Chem. Abstr. 1969, 71, 81418h.
21. 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.
22. Hsiang, Y. H.; Hertzberg, R.; Hecht, S.; Liu, L. F. Camptothecin induces protein-linked DNA breaks via Mammalian DNA Topoisomerase I. J. Biol. Chem. 1985, 260, 14873-14878.
23. Maniatis, T.; Fritsch, E. F.; Sambrook, J. Molecular Cloning, a Laboratory Manual; Cold Spring Harbor Laboratory: Cold Spring Harbor, NY, 1982; pp 149-185.
24. 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.
25. Mosmann, T. J. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Immunol. Methods 1983, 65, 55-63.
26. 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.
27. Denizot, F.; Lang, R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 1986, 89, 271-277.