5,7-Disubstituted analogues of the mixed topoisomerase I/II poison N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA): DNA binding and patterns of cytotoxicity

Anti-Cancer Drug Design

Volumn 14, Issue 1, 1999, Pages 37-45

  Spicer, Julie A ^a   Finlay, Graeme J ^a   Baguley, Bruce C ^a   Velea, Luminita ^b   Graves, David E ^b   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Anticancer drug; DACA; DNA binding; topoisomerase inhibitor

Indexed keywords

ANTINEOPLASTIC AGENT; DNA; HALOGEN; N (2 DIMETHYLAMINOETHYL) 4 ACRIDINECARBOXAMIDE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL LINE; CONTROLLED STUDY; CYCLIZATION; DRUG DNA BINDING; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ACRIDINES; ANIMALS; COLONIC NEOPLASMS; DNA TOPOISOMERASES, TYPE I; DNA TOPOISOMERASES, TYPE II; DNA, NEOPLASM; ENZYME INHIBITORS; HUMANS; INTERCALATING AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; NEOPLASM TRANSPLANTATION; TIME FACTORS; TUMOR CELLS, CULTURED;

ANIMALIA;

EID: 0032961654     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Atwell G.J., Rewcastle G.W., Baguley B.C., Denny W.A. (1987) Potential antitumor agents. 50. In vivo solid tumor activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. Journal of Medicinal Chemistry, 30, 664.
2. Baguley B.C., Zhuang L., Marshall E.M. (1995) Experimental solid tumour activity of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. Cancer Chemotherapy and Pharmacology, 36, 244.
3. Crenshaw J.M., Graves D.E., Denny W.A. (1995) Interactions of acridine antitumor agents with DNA: binding energies and groove preferences. Biochemistry, 34, 13682.
4. Denny W.A., Atwell G.J., Cain B.F., Leo A., Panthananickal A., Hansch C. (1982) Potential antitumor agents. Part 36. Quantitative relationships between antitumor potency, toxicity and structure for the general class of 9-anilino-acridine antitumor agents. Journal of Medicinal Chemistry, 25, 276.
5. Finlay G.J., Baguley B.C., Snow K., Judd W. (1990) Multiple patterns of resistance of human leukemia cell sublines to analogs of amsacrine. Journal of the National Cancer Institute, 82, 662.
6. Finlay G.J., Marshall E.S., Matthews J.H.L., Paull K.D., Baguley B.C. (1993) In vitro assessment of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA), a DNA intercalating antitumor drug with reduced sensitivity to multidrug resistance. Cancer Chemotherapy and Pharmacology, 31, 401.
7. Finlay G.J., Holdaway K.M., Baguley B.C. (1994) Comparison of the effects of genistein and amsacrine on leukemia cell proliferation. Oncology Research, 69, 33.
8. Finlay G.J., Riou J.-F., Baguley B.C. (1996) From amsacrine to DACA (N-[2-(dimethylamino)ethyl]acridine-4-carboxamide): selectivity for topoisomerases I and II among acridine derivatives. European Journal of Cancer, 32A, 708.
9. Gamage S.A., Spicer J.A., Rewcastle G.W., Denny W.A. (1997) A new synthesis of substituted acridine-4-carboxylic acids and the anticancer drug N-[2-(dimethylamino)ethyl]-acridine-4-carboxamide (DACA). Tetrahedron Letters, 38, 699.
10. Marshall E.S., Finlay G.J., Matthews J.H.L., Shaw J.H.F., Nixon J., Baguley B.C. (1992) Microculture-based chemosensitivity testing: a feasibility study comparing freshly explanted melanoma cells with human melanoma cell lines. Journal of the National Cancer Institute, 84, 340.
11. McGhee J.D., von Hippel P. (1974) Theoretical aspects of DNA-protein interactions: co-operative and non-cooperative binding of large ligands to a one-dimensional homogeneous lattice. Journal of Molecular Biology, 86, 469.
12. Rewcastle G.W., Denny W.A. (1987) The synthesis of 9-oxo-9,10-dihydroacridine-4-carboxylic acids via the Jourdan-Ullmann reaction of anthranilic acids and methyl 2-iodobenzoates. Synthetic Communications, 17, 309.
13. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., Boyd M.R. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. Journal of the National Cancer Institute, 82, 1107.
14. Spicer J.A., Gamage S.A., Atwell G.J., Finlay G.J., Baguley B.C., Denny W.A. (1997) Structure-activity relationships for acridine-substituted analogues of the mixed topo I/II inhibitor N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA). Journal of Medicinal Chemistry, 40, 1919.
15. Wilkoff L.J., Dulmadge E., Chopra D.P. (1980) Viability of cultured Lewis lung cell populations exposed to β-retinoic acid (40753). Proceedings of the Society for Experimental Biology and Medicine, 163, 233.