Design of new topoisomerase II inhibitors based upon a quinobenzoxazine self-assembly model

Journal of Medicinal Chemistry

Volumn 41, Issue 22, 1998, Pages 4273-4278

  Zeng, Qingping ^a   Kwok, Yan ^a   Kerwin, Sean M ^b   Mangold, Gina ^b   Hurley, Laurence H ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b CTRC Institute for Drug Development   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 AMINO 1 PYRROLIDINYL) 2 FLUORO 4 OXO 4H QUINO[8,1A,1 B,C][1,4]BENZOXAZINE 5 CARBOXYLIC ACID; 3 AMINO 1 (3 AMINO 1 PYRROLIDINYL) 2 FLUORO 4 OXO 4H QUINO[8,1A,1 B,C][1,4]BENZOXAZINE 5 CARBOXYLIC ACID; ANTINEOPLASTIC AGENT; BENZOXAZINE DERIVATIVE; DNA TOPOISOMERASE INHIBITOR; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CANCER CHEMOTHERAPY; CYTOTOXICITY; DRUG DNA BINDING; HUMAN; HUMAN CELL;

ANTINEOPLASTIC AGENTS; DNA TOPOISOMERASES, TYPE II; DNA, SUPERHELICAL; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; OXAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0032561380     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980265c     Document Type: Article

References (15)

1. Chu, D. T. W.; Maleczka, R. E., Jr. Synthesis of 4-Oxo-4H-quino[2,3,4-i,j][1, 4]benoxazine-5-carboxylic Acid Derivatives. J. Heterocycl. Chem. 1987, 24, 453-456.
2. Chu, D. T. W.; Hallas, R.; Clement, J. J.; Alder, J.; McDonald, E.; Plattner, J. J. Synthesis and Antitumour Activities of Quinolone Antineoplastic Agents. Drugs Exp. Clin. Res. 1992, 18, 275-282
3. Chu, D. T. W.; Hallas, R.; Tanaka, S. K.; Alder, J.; Balli, D.; Plattner, J. J. Synthesis and Antitumour Activities of Tetracyclic Quinolone Antineoplastic Agents. Drugs Exp. Clin. Res. 1994, 20, 177-183.
4. Clement, J. J.; Burres, N.; Jarvis, K.; Chu, D. T. W.; Swiniarski, J.; Alder, J. Biological Characterization of a Novel Antitumor Quinolone. Cancer Res. 1995, 5, 830-835.
5. Shen, L. L.; Baranowski, J.; Pernet, A. G. Mechanism of Inhibition of DNA Gyrase by Quinolone Antibacterials. Specificity and Cooperativity of Drug Binding to DNA. Biochemistry 1989, 28, 3879-3885.
6. Shen, L. L.; Kohlbrenner, W. E.; Weigl, D.; Baranowski, J. Mechanism of Quinolone Inhibition of DNA Gyrase. Appearance of Unique Norfloxacin Binding Sites in Enzyme-DNA Complexes. J. Biol. Chem. 1989, 264, 2973-2978.
7. Shen, L. L.; Mitscher, L. A.; Sharma, P. N.; O'Donnell, T. J.; Chu, D. W. T.; Cooper, C. S.; Rosen, T.; Pernet, A. G. Mechanism of Inhibition of DNA Gyrase by Quinolone Antibacterials: A Cooperative Drug-DNA Binding Model. Biochemistry 1989, 28, 3886-3894.
8. Willmott, C. J.; Maxwell, A. A Single Point Mutation in the DNA Gyrase A Protein Greatly Reduces Binding of Fluoroquinolones to the Gyrase-DNA Complex. Antimicrob. Agents Chemother. 1993, 37, 126-127.
9. Permana, P. A.; Snapka, R. M.; Shen, L. L.; Chu, D. T. W.; Clement, J. J.; Plattner, J. J. Quinobenoxazines: A Class of Novel Antitumor Quinolones and Potent Mammalian DNA Topoisomerase II Catalytic Inhibitors. Biochemistry 1994, 33, 11333-11339.
10. 2++ Self-Assembly Complex in the Presence of Topoisomerase II. J. Biol. Chem. 1998, submitted.
11. 2+ Complex on DNA: A New Paradigm for the Structure of a Drug-DNA Complex and Implications for the Structure of the Quinolone Bacterial Gyrase-DNA Complex. J. Med. Chem. 1995, 38, 408-424.
12. 2+ Dimers in Solution and for the Formation of Dimeric Drug Complexes on DNA from the DNA-Accelerated Photochemical Recation of Antineoplastic Quinobenzoxazines. J. Am. Chem. Soc. 1996, 118, 7040-7048.
13. Marini, J. C.; Miller, K. G.; Englund, P. T. Decatenation of Kinetoplast DNA by Topoisomerases, J. Biol. Chem. 1980, 255, 4976-4979.
14. Liu, L. F. DNA Topoisomerase Poisons as Antitumor Drugs. Annu. Rev. Biochem. 1989, 58, 351-375.
15. Chen, S. F.; Behrens, D. L.; Behrens, C. H.; Czerniak, P. M.; Dexter, D. L.; Dusak, B. A.; Fredericks, J. R.; Gale, K. C.; Gross, J. L.; Jiang, J. B.; Kirshenbaum, M. R.; McRipley, R. J.; Papp, L. M.; Patten, A. D.; Perrella, F. W.; Seitz, S. P.; Stafford, M. P.; Sun, J. H.; Sun, T.; Von Hoff, D. D. XB596, a Promising Bisnaphthalimide Anticancer Agent. Anti-Cancer Drugs 1993, 4, 447-457.