In vitro cytotoxicity and DNA damage production in Chinese hamster ovary cells and topoisomerase II inhibition by 2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1, 3-diones with substitutions at the 6 and 7 positions (azonafides)

Anti-Cancer Drugs

Volumn 8, Issue 3, 1997, Pages 245-256

  Mayr, Craig A ^a,b   Sami, Salah M ^a   Dorr, Robert T ^b  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

Author keywords

alkaline elution; anthracene; azonafide; intercalation; strand breaks

Indexed keywords

ANTHRACENE DERIVATIVE; ANTINEOPLASTIC AGENT; AZONAFIDE DERIVATIVE; DNA; DNA TOPOISOMERASE (ATP HYDROLYSING); TETRAZOLIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL CULTURE; CELL NUCLEUS; CHO CELL; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; CYTOPLASM; CYTOTOXICITY; DNA CROSS LINKING; DNA DAMAGE; DNA STRAND BREAKAGE; DNA SYNTHESIS; DRUG DISTRIBUTION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; PRIORITY JOURNAL; RNA SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; CELL-FREE SYSTEM; CHO CELLS; CRICETINAE; DIMETHYLAMINES; DNA DAMAGE; DNA TOPOISOMERASES, TYPE II; DNA, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; ISOQUINOLINES; MICROSCOPY, CONFOCAL; NEOPLASM PROTEINS; PLASMIDS; TETRAZOLIUM SALTS; THIAZOLES;

EID: 0030933706     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/00001813-199703000-00005     Document Type: Article

References (25)

1. Brana MF, Castellano JM, Roldan CM, Vasquez D, Jiminez A. Synthesis and mode(s) of action of a new series of imide derivatives of 3-nitro-1,8-naphthoic acid. Cancer Chemother Pharmacol 1980; 4: 61-6.
2. Brana MF, Sanz AM, Castellano JM, Roldan CM, Roldan C. Synthesis and cytostatic activity of benz(de)-isoquinolines-1,3-diones. Structure activity relationships. Eur J Med Chem 1981; 16: 207-12.
3. Craig J, Crawford E. Phase II trial of amonafide in advanced prostate cancer: a Southwest Oncology Group study (meeting abstract). Proc Am Soc Clin Oncol 1989; 8: 147.
4. Costanza ME, Berry D, Henderson IC. Amonafide: An active agent in the treatment of previously untreated breast cancer a Cancer and Leukemia Group B Study (CALGB 8624). Clin Cancer Res 1995; 1: 699-704.
5. Saez R, Craig JB, Kuhn JG, et al. Phase I clinical investigation of amonafide. J Clin Oncol 1989; 7: 1351-8.
6. Sami SM, Dorr RT, Alberts DS, Remers WA. 2-substituted 1,2-dihydro-3H-dibenz[de,h]isoquinoline-1 ,3-diones. A new class of antitumor agent. J Med Chem 1993; 36: 765-70.
7. Sami SM, Dorr RT, Soloyam AM, Alberts DS, Remers WA. Amino-substituted 2-[2′-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3- diones. Synthesis, antitumor activity, and quantitative structureactivity relationship. J Med Chem 1995; 38: 983-93.
8. Dorr RT, Shipp NG, Lee KM. Comparison of cytotoxicity in heart cells and tumor cells exposed to DNA intercalating agents in vitro. Anti-Cancer Driugs 1991; 2: 27-33.
9. Andersson BS, Beran M, Bakic M, Silberman LE, Newman RA, Zwelling LA. In vitro toxicity and DNA cleaving capacity of benzisoquinolinedine (nafidimide; NSC-308847) in human leukemia. Cancer Res 1987; 47: 1040-4.
10. Remers WA, Dorr RT, Sami SM, Solyomas AS, Alberts DS. Quantitative structure-activity relationships of azonafide analogs. Proc Am Ass Cancer Res 1994; 35: 337.
11. Alley MC, Scudiero DA, Monks A, Boyd MR. Feasibility of drug screening panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res 1988; 48: 589-601.
12. Li LH, Timmins LG, Wallace TL, Krueger WC, Prairie MD, Im WB. Mechanism of action of didemnin B, a depsipeptide from the sea. Cancer Lett 1984; 23: 279-288.
13. Ikegami S, Taguchi T, Ohashi M, Oguro M, Nagano H, Mano Y. Aphidicolin prevents mitotic cell division by interfering with the activity of DNA polymerase-alpha. Nature 1978; 275: 458-60.
14. Young CW, Hodas S. Acute effects of cytotoxic compounds on incorporation of precursors into DNA, RNA and protein of HeLa monolayers. Biochem Pharmacol 1965; 14: 205-14.
15. Kohn KW, Ewig RAG, Erickson LC, Zwelling LA. Measurement of strand breaks and cross-links by alkaline elution. In: Freidberg EC, Hanwalt PC, eds. DNA repair: a laboratory manual of research procedures. New York: Marcel Dekker; 1981; 1B: 379-401.
16. Kohn KW, Ewig RAG. DNA protein cross-linking by trans-platinum(II) diamminedichloride in mammalian cells, a new method of analysis. Biochem Biophys Acta 1979; 562: 32-40.
17. Fornace AJ, Kohn KW. DNA-protein cross-linking by ultraviolet radiation in normal human and xeroderma pigmentosum fibroblasts. Biochem Biophys Acta 1976; 435: 95-103.
18. Kohn KW, Grimek-Ewig RA. Alkaline elution analysis, a new approach to the study of DNA single-strand interruptions in cells. Cancer Res 1973; 33: 1849-53.
19. Ross WE, Glaubiger D, Kohn KW Qualitative and quantitative aspects of intercalator-incluced DNA strand breaks. Biochim Biophys Acta 1979; 562: 41-50.
20. Foglesong PD, Reckford C. Improved electrophoretic separation of supercoiled and relaxed DNA in the presence of ethidium bromide. Biotechniques 1992; 13: 402-4.
21. Ludwig R, Alberts DA, Miller TR, Salmon SE. Evaluation of anticancer drug schedule dependency using an in vitro tumor clonogenic assay. Cancer Chemother Pharmacol 1984; 12: 135-41.
22. Meriwether VD, Bachur NR. Inhibition of DNA and RNA metabolism by daunorubicin and Adriamycin in L1210 mouse leukemia. Cancer Res 1972; 32: 1137-42.
23. Bowden GT, Roberts R, Alberts DA, Peng Y-M, Garcia D. Comparative molecular pharmacology in leukemic L1210 cells of the anthracene anticancer drugs mitoxantrone and bisantrene. Cancer Res 1985; 45: 4915-20.
24. Ross W, Towe T, Glisson B, Yalowich J, Liu L. Role of topoisomerase II in mediating epipodophyllotoxininduced DNA cleavage. Cancer Res 1984; 44: 5857-60.
25. Dorr RT, Alberts DS, Sami SM, Remers WA. Consistent cytotoxic activity in multidrug resistant tumors for azonafide, a new anthracene analog of amonafide. Proc Am Ass Cancer Res 1991; 32: 408.