메뉴 건너뛰기




Volumn 42, Issue 13, 1999, Pages 2383-2393

Structure-activity relationships for substituted bis(acridine-4- carboxamides): A new class of anticancer agents

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; BISNAFIDE MESYLATE; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE INHIBITOR; GLYCOPROTEIN P; IMIDACRINE; LU 79553; MITONAFIDE; N (2 DIMETHYLAMINOETHYL) 4 ACRIDINECARBOXAMIDE; UNCLASSIFIED DRUG; WMC 26;

EID: 0033168506     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980687m     Document Type: Article
Times cited : (164)

References (38)
  • 1
    • 0016376516 scopus 로고
    • A new antitumoral agent: 9-hydroxyellipticine. Possibility of a rational design of anticancerous drugs in the series of DNA intercalating drugs
    • Le Pecq, J.-B.; Dat-Xuong, N.; Gosse, C.; Paoletti, C. A new antitumoral agent: 9-hydroxyellipticine. Possibility of a rational design of anticancerous drugs in the series of DNA intercalating drugs. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 5078-5082.
    • (1974) Proc. Natl. Acad. Sci. U.S.A. , vol.71 , pp. 5078-5082
    • Le Pecq, J.-B.1    Dat-Xuong, N.2    Gosse, C.3    Paoletti, C.4
  • 2
    • 0019860652 scopus 로고
    • Potential antitumor agents. Part 35. Quantitative relationships between antitumor (L1210) potency and DNA binding for 4′-(9-acridinylamino)methanesulfon-m-anisidide analogues
    • Baguley, B. C.; Denny, W. A.; Atwell, G. J.; Cain, B. F. Potential Antitumor Agents. Part 35. Quantitative relationships between antitumor (L1210) potency and DNA binding for 4′-(9-acridinylamino)methanesulfon-m-anisidide analogues. J. Med. Chem. 1981, 24, 520-525.
    • (1981) J. Med. Chem. , vol.24 , pp. 520-525
    • Baguley, B.C.1    Denny, W.A.2    Atwell, G.J.3    Cain, B.F.4
  • 3
    • 0023890156 scopus 로고
    • Characteristics of the interaction of anthrapyrazole anticancer agents with deoxyribonucleic acids: Structural requirements for DNA binding, intercalation and photosensitization
    • Hartley, J. A.; Reszka, K.; Zuo, E. T.; Wilson, W. D.; Morgan, A. R.; Lown, J. W. Characteristics of the interaction of anthrapyrazole anticancer agents with deoxyribonucleic acids: structural requirements for DNA binding, intercalation and photosensitization. Mol. Pharmacol. 1988, 33, 265-271.
    • (1988) Mol. Pharmacol. , vol.33 , pp. 265-271
    • Hartley, J.A.1    Reszka, K.2    Zuo, E.T.3    Wilson, W.D.4    Morgan, A.R.5    Lown, J.W.6
  • 4
    • 0024805768 scopus 로고
    • DNA-intercalating agents as antitumour drugs: Prospects for future design
    • Denny, W. A. DNA-Intercalating agents as antitumour drugs: prospects for future design. Anti-Cancer Drug Des. 1989, 4, 241-263.
    • (1989) Anti-cancer Drug Des. , vol.4 , pp. 241-263
    • Denny, W.A.1
  • 5
    • 0021226708 scopus 로고
    • Effects of new antitumor bifunctional intercalators derived from 7H-pyridocarbazole on sensitive and resistant L110 cell lines
    • Esnault, C.; Roques, P. B.; Jacquemin-Sablon, A.; Le Pecq, J.-B. Effects of new antitumor bifunctional intercalators derived from 7H-pyridocarbazole on sensitive and resistant L110 cell lines. Cancer Res. 1984, 44, 4355-4360.
    • (1984) Cancer Res. , vol.44 , pp. 4355-4360
    • Esnault, C.1    Roques, P.B.2    Jacquemin-Sablon, A.3    Le Pecq, J.-B.4
  • 6
    • 0022376055 scopus 로고
    • Potential antitumor agents. Part 44. Synthesis and antitumor activity of new classes of diacridines. The importance of linker chain rigidity for DNA binding kinetics and biological activity
    • Denny, W. A.; Atwell, G. J.; Baguley, B. C.; Wakelin, L. P. G. Potential Antitumor Agents. Part 44. Synthesis and antitumor activity of new classes of diacridines. The importance of linker chain rigidity for DNA binding kinetics and biological activity. J. Med. Chem. 1985, 28, 1568-1574.
    • (1985) J. Med. Chem. , vol.28 , pp. 1568-1574
    • Denny, W.A.1    Atwell, G.J.2    Baguley, B.C.3    Wakelin, L.P.G.4
  • 7
    • 0022445682 scopus 로고
    • Polyfunctional DNA intercalating agents
    • Wakelin, L. P. G. Polyfunctional DNA intercalating agents. Med. Res. Rev. 1986, 6, 276-340.
    • (1986) Med. Res. Rev. , vol.6 , pp. 276-340
    • Wakelin, L.P.G.1
  • 8
    • 0019351587 scopus 로고
    • Current results of the screening program at the Division of Cancer Treatment, National Cancer Institute
    • Goldin, A.; Vendetti, M. M.; McDonald, J. S.; Muggia, F. M.; Henney, J. E.; DeVita, V. T. Current results of the screening program at the Division of Cancer Treatment, National Cancer Institute. Eur. J. Cancer 1981, 17, 129-142.
    • (1981) Eur. J. Cancer , vol.17 , pp. 129-142
    • Goldin, A.1    Vendetti, M.M.2    McDonald, J.S.3    Muggia, F.M.4    Henney, J.E.5    DeVita, V.T.6
  • 10
    • 0023801422 scopus 로고
    • Selective loss of mitochondrial DNA after treatment of cells with ditercalinium (NSC 335153), an antitumor bis-intercalating agent
    • Segal-Bendirjian, E.; Coulaud, D.; Roques, B. P.; Le Pecq, J.-B. Selective loss of mitochondrial DNA after treatment of cells with ditercalinium (NSC 335153), an antitumor bis-intercalating agent. Cancer Res. 1988, 48, 4982-4992.
    • (1988) Cancer Res. , vol.48 , pp. 4982-4992
    • Segal-Bendirjian, E.1    Coulaud, D.2    Roques, B.P.3    Le Pecq, J.-B.4
  • 11
    • 0026634064 scopus 로고
    • Echinomycin (NSC-526417) in recurrent and metastatic squamous cell carcinoma of the cervix - A phase II trial of the Gynecologic Oncology Group (GOG)
    • Muss, H. B.; Blessing, J. A.; Eddy, G. L.; McGehee, R. Echinomycin (NSC-526417) in Recurrent and metastatic squamous cell carcinoma of the cervix - A Phase II trial of the Gynecologic Oncology Group (GOG). Invest. New Drugs 1992, 10, 25-26.
    • (1992) Invest. New Drugs , vol.10 , pp. 25-26
    • Muss, H.B.1    Blessing, J.A.2    Eddy, G.L.3    McGehee, R.4
  • 13
    • 0028641646 scopus 로고
    • Phase I study of mitonafide with a 3-day administration schedule: Early interruption due to severe central nervous system toxicity
    • Diaz-Rubio, E.; Martin, M.; Lopez-Vega, J. M.; Casado, A.; Benavides, A. Phase I study of mitonafide with a 3-day administration schedule: early interruption due to severe central nervous system toxicity. Invest. New Drugs 1994, 12, 277-281.
    • (1994) Invest. New Drugs , vol.12 , pp. 277-281
    • Diaz-Rubio, E.1    Martin, M.2    Lopez-Vega, J.M.3    Casado, A.4    Benavides, A.5
  • 16
    • 0029556551 scopus 로고
    • Comparative efficacy of DMP 840 against mouse and human solid tumor models
    • LoRusso, P.; Demchik, L.; Dan, M.; Polin, L.; Gross, J. L.; Corbett, T. H. Comparative efficacy of DMP 840 against mouse and human solid tumor models. Invest. New Drugs 1995, 13, 195-203. Robinson, C. P.; Robinson, K. A.; Castaner, J. Bisnafide mesylate. Antineoplastic DMP-840 (NSC D640430). Drugs Future 1996, 21, 239-244.
    • (1995) Invest. New Drugs , vol.13 , pp. 195-203
    • LoRusso, P.1    Demchik, L.2    Dan, M.3    Polin, L.4    Gross, J.L.5    Corbett, T.H.6
  • 17
    • 0029945099 scopus 로고    scopus 로고
    • Bisnafide mesylate. Antineoplastic DMP-840 (NSC D640430)
    • LoRusso, P.; Demchik, L.; Dan, M.; Polin, L.; Gross, J. L.; Corbett, T. H. Comparative efficacy of DMP 840 against mouse and human solid tumor models. Invest. New Drugs 1995, 13, 195-203. Robinson, C. P.; Robinson, K. A.; Castaner, J. Bisnafide mesylate. Antineoplastic DMP-840 (NSC D640430). Drugs Future 1996, 21, 239-244.
    • (1996) Drugs Future , vol.21 , pp. 239-244
    • Robinson, C.P.1    Robinson, K.A.2    Castaner, J.3
  • 19
    • 0001273448 scopus 로고    scopus 로고
    • Interstrand cross-linking of DNA in tumor cells by a new group of antitumor imidazoacridinones
    • abstract 2800
    • Dziegielewski, J.; Konopa, J. Interstrand cross-linking of DNA in tumor cells by a new group of antitumor imidazoacridinones. Proc. Am. Assoc. Cancer Res. 1996, 37, 410 (abstract 2800).
    • (1996) Proc. Am. Assoc. Cancer Res. , vol.37 , pp. 410
    • Dziegielewski, J.1    Konopa, J.2
  • 20
    • 0029133981 scopus 로고
    • Bisimidazoacridones and related compounds: New antineoplastic agents with high selectivity against colon tumours
    • Cholody, W. M.; Hernandez, L.; Hassner, L.; Scuderio, D. A.; Djurickovic, D. B.; Michejda, C. J. Bisimidazoacridones and related compounds: new antineoplastic agents with high selectivity against colon tumours. J. Med. Chem. 1995, 38, 3043-3052.
    • (1995) J. Med. Chem. , vol.38 , pp. 3043-3052
    • Cholody, W.M.1    Hernandez, L.2    Hassner, L.3    Scuderio, D.A.4    Djurickovic, D.B.5    Michejda, C.J.6
  • 21
    • 0029040519 scopus 로고
    • Experimental solid tumour activity of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide
    • Baguley, B. C.; Zhuang, L.; Marshall, E. M. Experimental solid tumour activity of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. Cancer Chemother. Pharmacol. 1995, 36, 244-248.
    • (1995) Cancer Chemother. Pharmacol. , vol.36 , pp. 244-248
    • Baguley, B.C.1    Zhuang, L.2    Marshall, E.M.3
  • 22
    • 0029893321 scopus 로고    scopus 로고
    • From amsacrine to DACA (N-[2-(dimethylamino)ethyl]acridine-4-carboxamide): Selectivity for topoisomerases I and II among acridine derivatives
    • Finlay, G. J.; Riou, J.-F.; Baguley, B. C. From amsacrine to DACA (N-[2-(dimethylamino)ethyl]acridine-4-carboxamide): selectivity for topoisomerases I and II among acridine derivatives. Eur. J. Cancer 1996, 32A, 708-714.
    • (1996) Eur. J. Cancer , vol.32 A , pp. 708-714
    • Finlay, G.J.1    Riou, J.-F.2    Baguley, B.C.3
  • 23
    • 0023733388 scopus 로고
    • Cell line selectivity and DNA breakage properties of the antitumour agent N-[2-(dimethylamino)ethyl]-acridine-4-carboxamide: Role of DNA topoisomerase II
    • Schneider, E.; Darkin, S. A.; Lawson, P. A.; Ching, L.-M.; Ralph, R. K.; Baguley, B. C. Cell line selectivity and DNA breakage properties of the antitumour agent N-[2-(dimethylamino)ethyl]-acridine-4-carboxamide: role of DNA topoisomerase II. Eur. J. Cancer Clin. Oncol. 1988, 24, 1783-1790.
    • (1988) Eur. J. Cancer Clin. Oncol. , vol.24 , pp. 1783-1790
    • Schneider, E.1    Darkin, S.A.2    Lawson, P.A.3    Ching, L.-M.4    Ralph, R.K.5    Baguley, B.C.6
  • 24
    • 0023251054 scopus 로고
    • Potential antitumor agents. 50. In vivo solid tumor activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide
    • Atwell, G. J.; Rewcastle, G. W.; Baguley, B. C.; Denny, W. A. Potential antitumor agents. 50. In vivo solid tumor activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. J. Med. Chem. 1987, 30, 664-669.
    • (1987) J. Med. Chem. , vol.30 , pp. 664-669
    • Atwell, G.J.1    Rewcastle, G.W.2    Baguley, B.C.3    Denny, W.A.4
  • 25
    • 0027447244 scopus 로고
    • In vitro assessment of N-[2-(dimethylamino)ethyl]-acridine-4-carboxamide (DACA), a DNA intercalating antitumor drug with reduced sensitivity to multidrug resistance
    • Finlay, G. J.; Marshall, E. S.; Matthews, J. H. L.; Paull, K. D.; Baguley, B. C. In vitro assessment of N-[2-(dimethylamino)ethyl]-acridine-4-carboxamide (DACA), a DNA intercalating antitumor drug with reduced sensitivity to multidrug resistance. Cancer Chemother. Pharmacol. 1993, 31, 401-406.
    • (1993) Cancer Chemother. Pharmacol. , vol.31 , pp. 401-406
    • Finlay, G.J.1    Marshall, E.S.2    Matthews, J.H.L.3    Paull, K.D.4    Baguley, B.C.5
  • 26
    • 0025238402 scopus 로고
    • Multiple patterns of resistance of human leukemia cell sublines to analogues of amsacrine
    • Finlay, G. J.; Baguley, B. C.; Snow, K.; Judd, W. Multiple patterns of resistance of human leukemia cell sublines to analogues of amsacrine. J. Natl. Cancer Inst. 1990, 82, 662-667.
    • (1990) J. Natl. Cancer Inst. , vol.82 , pp. 662-667
    • Finlay, G.J.1    Baguley, B.C.2    Snow, K.3    Judd, W.4
  • 28
    • 0031034670 scopus 로고    scopus 로고
    • A new synthesis of substituted acridine-4-carboxylic acids and the anticancer drug N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA)
    • Gamage, S. A.; Spicer, J. A.; Rewcastle, G. W.; Denny, W. A. A new synthesis of substituted acridine-4-carboxylic acids and the anticancer drug N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA). Tetrahedron Lett. 1997, 38, 699-702.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 699-702
    • Gamage, S.A.1    Spicer, J.A.2    Rewcastle, G.W.3    Denny, W.A.4
  • 29
    • 0031004973 scopus 로고    scopus 로고
    • Structure-activity relationships for acridine-substituted analogues of the mixed topo I/II inhibitor N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA)
    • Spicer, J. A.; Gamage, S. A.; Atwell, G. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. Structure-activity relationships for acridine-substituted analogues of the mixed topo I/II inhibitor N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA). J. Med. Chem. 1997, 40, 1919-1929.
    • (1997) J. Med. Chem. , vol.40 , pp. 1919-1929
    • Spicer, J.A.1    Gamage, S.A.2    Atwell, G.J.3    Finlay, G.J.4    Baguley, B.C.5    Denny, W.A.6
  • 30
    • 0028289870 scopus 로고
    • Comparison of the effects of genistein and amsacrine on leukemia cell proliferation
    • Finlay, G. J.; Holdaway, K. M.; Baguley, B. C. Comparison of the effects of genistein and amsacrine on leukemia cell proliferation. Oncol. Res. 1994, 6, 33-37.
    • (1994) Oncol. Res. , vol.6 , pp. 33-37
    • Finlay, G.J.1    Holdaway, K.M.2    Baguley, B.C.3
  • 31
    • 0018879554 scopus 로고
    • Viability of cultured lewis lung cell populations exposed to β-retinoic acid (40753)
    • Wilkoff, L. J.; Dulmadge, E.; Chopra, D. P. Viability of cultured Lewis lung cell populations exposed to β-retinoic acid (40753). Proc. Soc. Exp. Biol. Med. 1980, 163, 233-236.
    • (1980) Proc. Soc. Exp. Biol. Med. , vol.163 , pp. 233-236
    • Wilkoff, L.J.1    Dulmadge, E.2    Chopra, D.P.3
  • 32
    • 0020033516 scopus 로고
    • Potential antitumor agents. Part 36. Quantitative relationships between antitumor potency, toxicity and structure for the general class of 9-anilinoacridine antitumor agents
    • Denny, W. A.; Atwell, G. J.; Cain, B. F.; Leo, A.; Panthananickal, A.; Hansch, C. Potential Antitumor Agents. Part 36. Quantitative relationships between antitumor potency, toxicity and structure for the general class of 9-anilinoacridine antitumor agents. J. Med. Chem. 1982, 25, 276-316.
    • (1982) J. Med. Chem. , vol.25 , pp. 276-316
    • Denny, W.A.1    Atwell, G.J.2    Cain, B.F.3    Leo, A.4    Panthananickal, A.5    Hansch, C.6
  • 33
    • 0344293612 scopus 로고    scopus 로고
    • 5,7-Disubstituted analogues of the mixed topoisomerase I/II poison N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA)
    • submitted
    • Spicer, J. A.; Finlay, G. J.; Baguley, B. C.; Velea, L.; Graves, D. E.; Denny, W. A. 5,7-Disubstituted analogues of the mixed topoisomerase I/II poison N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA). Anti-Cancer Drug Des., submitted.
    • Anti-cancer Drug Des.
    • Spicer, J.A.1    Finlay, G.J.2    Baguley, B.C.3    Velea, L.4    Graves, D.E.5    Denny, W.A.6
  • 34
    • 0025933915 scopus 로고
    • Cytosol mediated metabolism of the experimental antitumor agent acridine carboxamide to the 9-acridone derivative
    • Robertson, I. G. C.; Palmer, B. D.; Officer, M.; Siegers, D. J.; Paxton, J. W.; Shaw, G. J. Cytosol mediated metabolism of the experimental antitumor agent acridine carboxamide to the 9-acridone derivative. Biochem. Pharmacol. 1991, 42, 1879-1884.
    • (1991) Biochem. Pharmacol. , vol.42 , pp. 1879-1884
    • Robertson, I.G.C.1    Palmer, B.D.2    Officer, M.3    Siegers, D.J.4    Paxton, J.W.5    Shaw, G.J.6
  • 36
    • 0031305020 scopus 로고    scopus 로고
    • Differential actions of aclarubicin and doxorubicin: The role of topoisomerase I
    • Bridewell, D. J. A.; Finlay, G. J.; Baguley, B. C. Differential actions of aclarubicin and doxorubicin: the role of topoisomerase I. Oncol. Res. 1997, 9, 535-542.
    • (1997) Oncol. Res. , vol.9 , pp. 535-542
    • Bridewell, D.J.A.1    Finlay, G.J.2    Baguley, B.C.3
  • 37
    • 0026602982 scopus 로고
    • Microculture-based chemosensitivity testing: A feasibility study comparing freshly explanted melanoma cells with human melanoma cell lines
    • Marshall, E. S.; Finlay, G. J.; Matthews, J. H. L.; Shaw, J. H. F.; Nixon, J.; Baguley, B. C. Microculture-based chemosensitivity testing: a feasibility study comparing freshly explanted melanoma cells with human melanoma cell lines. J. Natl. Cancer Inst. 1992, 84, 340-345.
    • (1992) J. Natl. Cancer Inst. , vol.84 , pp. 340-345
    • Marshall, E.S.1    Finlay, G.J.2    Matthews, J.H.L.3    Shaw, J.H.F.4    Nixon, J.5    Baguley, B.C.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.