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Volumn 7, Issue 2, 2009, Pages 196-209

Deoxyamphimedine, a pyridoacridine alkaloid, damages DNA via the production of reactive oxygen species

Author keywords

Amphimedine; Deoxyamphimedine; Neoamphimedine; Pyridoacridine; Reactive oxygen species

Indexed keywords

ACRIDINE DERIVATIVE; ALKALOID DERIVATIVE; AMPHIMEDINE; DEOXYAMPHIMEDINE; DNA TOPOISOMERASE; DOUBLE STRANDED DNA; NEOAMPHIMEDINE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

EID: 66449103251     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md7020196     Document Type: Article
Times cited : (20)

References (41)
  • 1
    • 0036314422 scopus 로고    scopus 로고
    • Synthesis and cytotoxic evaluation of analogues of the marine pyridoacridine amphimedine
    • Brahic, C.; Darro, F.; Belloir, M.; Bastide, J.; Kiss, R.; Delfourne, E. Synthesis and cytotoxic evaluation of analogues of the marine pyridoacridine amphimedine. Bioorg. Med. Chem. 2002, 10, 2845-2853.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 2845-2853
    • Brahic, C.1    Darro, F.2    Belloir, M.3    Bastide, J.4    Kiss, R.5    Delfourne, E.6
  • 2
    • 0035960054 scopus 로고    scopus 로고
    • Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid
    • Delfourne, E.; Darro, F.; Bontemps-Subielos, N.; Decaestecker, C.; Bastide, J.; Frydman, A.; Kiss, R. Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid. J. Med. Chem. 2001, 44, 3275-3282.
    • (2001) J. Med. Chem. , vol.44 , pp. 3275-3282
    • Delfourne, E.1    Darro, F.2    Bontemps-Subielos, N.3    Decaestecker, C.4    Bastide, J.5    Frydman, A.6    Kiss, R.7
  • 4
    • 0042343837 scopus 로고    scopus 로고
    • Synthesis and in vitro antitumor activity of phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine: Structure-activity relationship
    • Delfourne, E.; Kiss, R.; Le Corre, L.; Dujols, F.; Bastide, J.; Collignon, F.; Lesur, B.; Frydman, A.; Darro, F. Synthesis and in vitro antitumor activity of phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine: structure-activity relationship. J. Med. Chem. 2003, 46, 3536-3545.
    • (2003) J. Med. Chem. , vol.46 , pp. 3536-3545
    • Delfourne, E.1    Kiss, R.2    Le Corre, L.3    Dujols, F.4    Bastide, J.5    Collignon, F.6    Lesur, B.7    Frydman, A.8    Darro, F.9
  • 5
    • 3042793405 scopus 로고    scopus 로고
    • Synthesis and in vitro antitumor activity of ring C and D-substituted phenanthrolin- 7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine
    • Delfourne, E.; Kiss, R.; Le Corre, L.; Dujols, F.; Bastide, J.; Collignon, F.; Lesur, B.; Frydman, A.; Darro, F. Synthesis and in vitro antitumor activity of ring C and D-substituted phenanthrolin- 7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine. Bioorg. Med. Chem. 2004, 12, 3987-3994.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 3987-3994
    • Delfourne, E.1    Kiss, R.2    Le Corre, L.3    Dujols, F.4    Bastide, J.5    Collignon, F.6    Lesur, B.7    Frydman, A.8    Darro, F.9
  • 6
    • 0041333100 scopus 로고    scopus 로고
    • Synthesis and in vitro antitumor activity of an isomer of the marine pyridoacridine alkaloid ascididemin and related compounds
    • Delfourne, E.; Kiss, R.; Le Corre, L.; Merza, J.; Bastide, J.; Frydman, A.; Darro, F. Synthesis and in vitro antitumor activity of an isomer of the marine pyridoacridine alkaloid ascididemin and related compounds. Bioorg. Med. Chem. 2003, 11, 4351-4356.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 4351-4356
    • Delfourne, E.1    Kiss, R.2    Le Corre, L.3    Merza, J.4    Bastide, J.5    Frydman, A.6    Darro, F.7
  • 7
    • 34547187581 scopus 로고    scopus 로고
    • Advances in solid-phase cycloadditions for heterocyclic synthesis
    • Feliu, L.; Vera-Luque, P.; Albericio, F.; Alvarez, M. Advances in solid-phase cycloadditions for heterocyclic synthesis. J. Comb. Chem. 2007, 9, 521-565.
    • (2007) J. Comb. Chem. , vol.9 , pp. 521-565
    • Feliu, L.1    Vera-Luque, P.2    Albericio, F.3    Alvarez, M.4
  • 9
    • 11144339340 scopus 로고    scopus 로고
    • Biological activities of pyridoacridines
    • Marshall, K.M.; Barrows, L.R. Biological activities of pyridoacridines. Nat Prod. Rep. 2004, 21, 731-751.
    • (2004) Nat Prod. Rep. , vol.21 , pp. 731-751
    • Marshall, K.M.1    Barrows, L.R.2
  • 12
    • 0022472686 scopus 로고
    • Biological effects of the superoxide radical
    • Fridovich, I. Biological effects of the superoxide radical. Arch. Biochem. Biophys. 1986, 247, 1-11.
    • (1986) Arch. Biochem. Biophys. , vol.247 , pp. 1-11
    • Fridovich, I.1
  • 14
    • 0030570517 scopus 로고    scopus 로고
    • Oxidative DNA damage in human respiratory tract epithelial cells. Time course in relation to DNA strand breakage
    • Spencer, J. P.; Jenner, A.; Aruoma, O. I.; Cross, C. E.; Wu, R.; Halliwell, B. Oxidative DNA damage in human respiratory tract epithelial cells. Time course in relation to DNA strand breakage. Biochem. Biophys. Res. Commun. 1996, 224, 17-22.
    • (1996) Biochem. Biophys. Res. Commun. , vol.224 , pp. 17-22
    • Spencer, J.P.1    Jenner, A.2    Aruoma, O.I.3    Cross, C.E.4    Wu, R.5    Halliwell, B.6
  • 15
    • 0029125952 scopus 로고
    • Oxygen radical-induced single-strand DNA breaks and repair of the damage in a cell-free system
    • Sarker, A.H.; Watanabe, S.; Seki, S.; Akiyama, T.; Okada, S. Oxygen radical-induced single-strand DNA breaks and repair of the damage in a cell-free system. Mutat. Res. 1995, 337, 85-95.
    • (1995) Mutat. Res. , vol.337 , pp. 85-95
    • Sarker, A.H.1    Watanabe, S.2    Seki, S.3    Akiyama, T.4    Okada, S.5
  • 16
    • 0028609513 scopus 로고
    • Interaction between reactive oxygen species and coenzyme Q10 in an aprotic medium: A cyclic voltammetry study
    • Ferri, E.; Gattavecchia, E.; Feroci, G.; Battino, M. Interaction between reactive oxygen species and coenzyme Q10 in an aprotic medium: a cyclic voltammetry study. Mol. Aspects Med. 1994, 15 Suppl, s83-s88.
    • (1994) Mol. Aspects Med. , vol.15 , Issue.SUPPL.
    • Ferri, E.1    Gattavecchia, E.2    Feroci, G.3    Battino, M.4
  • 17
    • 0031272128 scopus 로고    scopus 로고
    • Electrochemical properties of some biologically active quinone derivatives: Furanquinones, pyridoquinones, and diplamine, a cytotoxic pyridoacridine alkaloid
    • Crawford, P.W.; Gross, J.; Lawson, K.; Cheng, C.C.; Dong, Q.; Liu, D.F.; Luo, Y.L.; Szczepankiewicz, B.G.; Heathcock, C.H. Electrochemical properties of some biologically active quinone derivatives: furanquinones, pyridoquinones, and diplamine, a cytotoxic pyridoacridine alkaloid. J. Electrochem. Soc. 1997, 144, 3710-3715.
    • (1997) J. Electrochem. Soc. , vol.144 , pp. 3710-3715
    • Crawford, P.W.1    Gross, J.2    Lawson, K.3    Cheng, C.C.4    Dong, Q.5    Liu, D.F.6    Luo, Y.L.7    Szczepankiewicz, B.G.8    Heathcock, C.H.9
  • 18
    • 0027172654 scopus 로고
    • The etiology of breast cancer. Characteristic alteration in hydroxyl radical-induced DNA base lesions during oncogenesis with potential for evaluating incidence risk
    • Malins, D.C.; Holmes, E.H.; Polissar, N.L.; Gunselman, S.J. The etiology of breast cancer. Characteristic alteration in hydroxyl radical-induced DNA base lesions during oncogenesis with potential for evaluating incidence risk. Cancer 1993, 71, 3036-3043.
    • (1993) Cancer , vol.71 , pp. 3036-3043
    • Malins, D.C.1    Holmes, E.H.2    Polissar, N.L.3    Gunselman, S.J.4
  • 19
    • 0027260350 scopus 로고
    • Cytogenetic effects of inhibition of topoisomerase I or II activities in the CHO mutant EM9 and its parental line AA8
    • Cortes, F.; Pinero, J.; Palitti, F. Cytogenetic effects of inhibition of topoisomerase I or II activities in the CHO mutant EM9 and its parental line AA8. Mutat. Res. 1993, 288, 281-289.
    • (1993) Mutat. Res. , vol.288 , pp. 281-289
    • Cortes, F.1    Pinero, J.2    Palitti, F.3
  • 20
    • 0023627729 scopus 로고
    • Induction and repair of DNA single-strand breaks in EM9 mutant CHO cells treated with hydrogen peroxide
    • Cantoni, O.; Murray, D.; Meyn, R.E. Induction and repair of DNA single-strand breaks in EM9 mutant CHO cells treated with hydrogen peroxide. Chem. Biol. Interact. 1987, 63, 29-38.
    • (1987) Chem. Biol. Interact. , vol.63 , pp. 29-38
    • Cantoni, O.1    Murray, D.2    Meyn, R.E.3
  • 21
    • 33646566825 scopus 로고    scopus 로고
    • Causes of DNA single-strand breaks during reduction of chromate by glutathione in vitro and in cells
    • Messer, J.; Reynolds, M.; Stoddard, L.; Zhitkovich, A. Causes of DNA single-strand breaks during reduction of chromate by glutathione in vitro and in cells. Free Radic. Biol. Med. 2006, 40, 1981-1992.
    • (2006) Free Radic. Biol. Med. , vol.40 , pp. 1981-1992
    • Messer, J.1    Reynolds, M.2    Stoddard, L.3    Zhitkovich, A.4
  • 22
    • 0024804442 scopus 로고
    • Sensitivity of Chinese hamster ovary mutants defective in DNA double strand break repair to topoisomerase II inhibitors
    • Jeggo, P.A.; Caldecott, K.; Pidsley, S.; Banks, G.R. Sensitivity of Chinese hamster ovary mutants defective in DNA double strand break repair to topoisomerase II inhibitors. Cancer Res. 1989, 49, 7057-7063. (Pubitemid 20016593)
    • (1989) Cancer Research , vol.49 , Issue.24 I , pp. 7057-7063
    • Jeggo, P.A.1    Caldecott, K.2    Pidsley, S.3    Banks, G.R.4
  • 23
    • 0032956510 scopus 로고    scopus 로고
    • Pyrroloquinoline and pyridoacridine alkaloids from marine sources
    • Ding, Q.; Chichak, K.; Lown, J.W. Pyrroloquinoline and pyridoacridine alkaloids from marine sources. Curr. Med. Chem. 1999, 6, 1-27.
    • (1999) Curr. Med. Chem. , vol.6 , pp. 1-27
    • Ding, Q.1    Chichak, K.2    Lown, J.W.3
  • 25
    • 0027942883 scopus 로고
    • Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: A mechanism for the apparent intercalator-induced inhibition of topoisomerase II
    • McDonald, L.A.; Eldredge, G.S.; Barrows, L.R.; Ireland, C.M. Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J. Med. Chem. 1994, 37, 3819-3827.
    • (1994) J. Med. Chem. , vol.37 , pp. 3819-3827
    • McDonald, L.A.1    Eldredge, G.S.2    Barrows, L.R.3    Ireland, C.M.4
  • 26
    • 0034603455 scopus 로고    scopus 로고
    • Mechanism of action studies of cytotoxic marine alkaloids: Ascididemin exhibits thiol-dependent oxidative DNA cleavage
    • DOI 10.1016/S0040-4039(00)00011-3, PII S0040403900000113
    • Matsumoto, S.S.; Sidford, M.H.; Holden, J.A.; Barrows, L.R.; Copp, B.R. Mechanism of action studies of cytotoxic marine alkaloids: ascididemin exhibits thiol-dependent oxidative DNA cleavage. Tetrahedron Lett. 2000, 41, 1667-1670. (Pubitemid 30131126)
    • (2000) Tetrahedron Letters , vol.41 , Issue.10 , pp. 1667-1670
    • Matsumoto, S.S.1    Sidford, M.H.2    Holden, J.A.3    Barrows, L.R.4    Copp, B.R.5
  • 27
    • 0019518585 scopus 로고
    • Reduction of chronic doxorubicin cardiotoxicity in dogs by pretreatment with (+/-)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane (ICRF-187)
    • Herman, E.H.; Ferrans, V.J. Reduction of chronic doxorubicin cardiotoxicity in dogs by pretreatment with (+/-)-1,2-bis(3,5-dioxopiperazinyl- 1-yl)propane (ICRF-187). Cancer Res. 1981, 41, 3436-3440. (Pubitemid 11063616)
    • (1981) Cancer Research , vol.41 , Issue.9 I , pp. 3436-3440
    • Herman, E.H.1    Ferrans, V.J.2
  • 28
    • 0027428534 scopus 로고
    • Identification of hydroxyl radical-induced lesions in DNA base structure: Biomarkers with a putative link to cancer development
    • Malins, D.C. Identification of hydroxyl radical-induced lesions in DNA base structure: biomarkers with a putative link to cancer development. J. Toxicol. Environ. Health 1993, 40, 247-261.
    • (1993) J. Toxicol. Environ. Health , vol.40 , pp. 247-261
    • Malins, D.C.1
  • 29
    • 0001213485 scopus 로고
    • Role of hydrogen peroxide and hydroxyl radical formation in the killing of Ehrlich tumor cells by anticancer quinones
    • Doroshow, J.H. Role of hydrogen peroxide and hydroxyl radical formation in the killing of Ehrlich tumor cells by anticancer quinones. Proc. Natl. Acad. Sci. USA 1986, 83, 4514-4518.
    • (1986) Proc. Natl. Acad. Sci. USA , vol.83 , pp. 4514-4518
    • Doroshow, J.H.1
  • 30
    • 0023028913 scopus 로고
    • Redox cycling of anthracyclines by cardiac mitochondria. II. Formation of superoxide anion, hydrogen peroxide, and hydroxyl radical
    • Doroshow, J.H.; Davies, K.J. Redox cycling of anthracyclines by cardiac mitochondria. II. Formation of superoxide anion, hydrogen peroxide, and hydroxyl radical. J. Biol. Chem. 1986, 261, 3068-3074.
    • (1986) J. Biol. Chem. , vol.261 , pp. 3068-3074
    • Doroshow, J.H.1    Davies, K.J.2
  • 31
    • 0019414005 scopus 로고
    • Prevention of doxorubicin cardiac toxicity in the mouse by N-acetylcysteine
    • Doroshow, J.H.; Locker, G.Y.; Ifrim, I.; Myers, C.E. Prevention of doxorubicin cardiac toxicity in the mouse by N-acetylcysteine. J. Clin. Invest. 1981, 68, 1053-1064.
    • (1981) J. Clin. Invest. , vol.68 , pp. 1053-1064
    • Doroshow, J.H.1    Locker, G.Y.2    Ifrim, I.3    Myers, C.E.4
  • 32
    • 0018915753 scopus 로고
    • Enzymatic defenses of the mouse heart against reactive oxygen metabolites: Alterations produced by doxorubicin
    • Doroshow, J.H.; Locker, G.Y.; Myers, C.E. Enzymatic defenses of the mouse heart against reactive oxygen metabolites: alterations produced by doxorubicin. J. Clin. Invest. 1980, 65, 128-135.
    • (1980) J. Clin. Invest. , vol.65 , pp. 128-135
    • Doroshow, J.H.1    Locker, G.Y.2    Myers, C.E.3
  • 35
    • 0017867183 scopus 로고
    • The replication of kinetoplast DNA networks in Crithidia fasciculata
    • Englund, P.T. The replication of kinetoplast DNA networks in Crithidia fasciculata. Cell 1978, 14, 157-168. (Pubitemid 8340443)
    • (1978) Cell , vol.14 , Issue.1 , pp. 157-168
    • Englund, P.T.1
  • 38
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • Mossman, T. Rapid colorimetric assay for cell growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63. (Pubitemid 14203433)
    • (1983) Journal of Immunological Methods , vol.65 , Issue.1-2 , pp. 55-63
    • Mosmann, T.1
  • 39
    • 0029995669 scopus 로고    scopus 로고
    • Differences in the topoisomerase I cleavage complexes formed by camptothecin and wakayin, a DNA-intercalating marine natural product
    • Kokoshka, J.M.; Capson, T.L.; Holden, J.A.; Ireland, C.M.; Barrows, L.R. Differences in the topoisomerase I cleavage complexes formed by camptothecin and wakayin, a DNA-intercalating marine natural product. Anticancer Drugs 1996, 7, 758-765. (Pubitemid 26388766)
    • (1996) Anti-Cancer Drugs , vol.7 , Issue.7 , pp. 758-765
    • Kokoshka, J.M.1    Capson, T.L.2    Holden, J.A.3    Ireland, C.M.4    Barrows, L.R.5
  • 41
    • 0027167775 scopus 로고
    • Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the Genus Zyzzya
    • Radisky, D.C.; Radisky, E. .; Barrows, L.R.; Copp, B.R.; Kramer, R.A.; Ireland, C.M. Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the Genus Zyzzya. J. Am. Chem. Soc. 1993, 115, 1632-1638.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1632-1638
    • Radisky, D.C.1    Radisky, E.2    Barrows, L.R.3    Copp, B.R.4    Kramer, R.A.5    Ireland, C.M.6


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