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Volumn 10, Issue 21, 2004, Pages 7365-7374

Potent antitumor activity of novel iron chelators derived from di-2-pyridylketone isonicotinoyl hydrazone involves fenton-derived free radical generation

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACID; BENZOIC ACID; CATALASE; DEFEROXAMINE; DI 2 PYRIDYLKETONE 3 BROMOBENZOYLHYDRAZONE; DI 2 PYRIDYLKETONE 4 AMINOBENZOYLHYDRAZONE; DI 2 PYRIDYLKETONE 4 HYDROXYBENZOYLHYDRAZONE; DI 2 PYRIDYLKETONE BENZOYLHYDRAZONE; DI 2 PYRIDYLKETONE ISONICOTINOYLHYDRAZONE; DI 2 PYRIDYLKETONE THIOPHENECARBOXYLHYDRAZONE; DNA TOPOISOMERASE; EBSELEN; EDETIC ACID; FREE RADICAL; HYDRAZONE DERIVATIVE; HYDROGEN PEROXIDE; IRON CHELATING AGENT; PLASMID DNA; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

EID: 8444235919     PISSN: 10780432     EISSN: None     Source Type: Journal    
DOI: 10.1158/1078-0432.CCR-04-0865     Document Type: Article
Times cited : (123)

References (41)
  • 1
    • 0038324398 scopus 로고    scopus 로고
    • The role of iron chelation in cancer therapy
    • Buss JL, Torti FM, Torti SV. The role of iron chelation in cancer therapy. Curr Med Chem 2003;10:1021-34.
    • (2003) Curr Med Chem , vol.10 , pp. 1021-1034
    • Buss, J.L.1    Torti, F.M.2    Torti, S.V.3
  • 3
    • 0037986658 scopus 로고    scopus 로고
    • Iron chelators as anti-neoplastic agents: Current developments and promise of the PIH class of chelators
    • Lovejoy DB, Richardson DR. Iron chelators as anti-neoplastic agents: current developments and promise of the PIH class of chelators. Curr Med Chem 2003;10:1035-49.
    • (2003) Curr Med Chem , vol.10 , pp. 1035-1049
    • Lovejoy, D.B.1    Richardson, D.R.2
  • 5
    • 0024343393 scopus 로고
    • Antileukemic effects of deferoxamine on human myeloid leukemia cell lines
    • Becton DL, Roberts B. Antileukemic effects of deferoxamine on human myeloid leukemia cell lines. Cancer Res 1989;49:4809-12.
    • (1989) Cancer Res , vol.49 , pp. 4809-4812
    • Becton, D.L.1    Roberts, B.2
  • 6
    • 0035036499 scopus 로고    scopus 로고
    • Syntheses and antitumor activities of potent inhibitors of ribonucleotide reductase: 3-Amino-4-methylpyridine-2-carboxaldehyde-thiosemicarba-zone (3-AMP), 3-amino-pyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) and its water-soluble prodrugs
    • Li J, Zheng LM, King I, Doyle TW, Chen SH. Syntheses and antitumor activities of potent inhibitors of ribonucleotide reductase: 3-amino-4-methylpyridine-2-carboxaldehyde-thiosemicarba-zone (3-AMP), 3-amino-pyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) and its water-soluble prodrugs. Curr Med Chem 2001;8:121-33.
    • (2001) Curr Med Chem , vol.8 , pp. 121-133
    • Li, J.1    Zheng, L.M.2    King, I.3    Doyle, T.W.4    Chen, S.H.5
  • 7
    • 0029177913 scopus 로고
    • Structure-function relationships for a new series of pyridine-2- carboxaldehyde thiosemicarbazones on ribonucleotide reductase activity and tumor cell growth in culture and in vivo
    • Cory JG, Cory AH, Rappa G, et al. Structure-function relationships for a new series of pyridine-2-carboxaldehyde thiosemicarbazones on ribonucleotide reductase activity and tumor cell growth in culture and in vivo. Adv Enzyme Regul 1995;35:55-68.
    • (1995) Adv Enzyme Regul , vol.35 , pp. 55-68
    • Cory, J.G.1    Cory, A.H.2    Rappa, G.3
  • 8
    • 0029449149 scopus 로고
    • Therapeutic iron chelators and their potential side effects
    • Singh S, Khodr H, Taylor MI, Hider RC. Therapeutic iron chelators and their potential side effects. Biochem Soc Symp 1995;61:127-37.
    • (1995) Biochem Soc Symp , vol.61 , pp. 127-137
    • Singh, S.1    Khodr, H.2    Taylor, M.I.3    Hider, R.C.4
  • 9
    • 0035181433 scopus 로고    scopus 로고
    • Inhibition of malignant cell growth by 311, a novel iron chelator of the pyridoxal isonicotinoyl hydrazone class: Effect on the R2 subunit of ribonucleotide reductase
    • Green DA, Antholine WE, Wong SJ, Richardson DR, Chitambar CR. Inhibition of malignant cell growth by 311, a novel iron chelator of the pyridoxal isonicotinoyl hydrazone class: effect on the R2 subunit of ribonucleotide reductase. Clin Cancer Res 2001;7:3574-9.
    • (2001) Clin Cancer Res , vol.7 , pp. 3574-3579
    • Green, D.A.1    Antholine, W.E.2    Wong, S.J.3    Richardson, D.R.4    Chitambar, C.R.5
  • 10
    • 0037100453 scopus 로고    scopus 로고
    • Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells
    • Lovejoy DB, Richardson DR. Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells. Blood 2002;100:666-76.
    • (2002) Blood , vol.100 , pp. 666-676
    • Lovejoy, D.B.1    Richardson, D.R.2
  • 12
    • 0033975268 scopus 로고    scopus 로고
    • Triapine (3-aminopyridine-2-carboxaldehyde-thiosemicarbazone): A potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity
    • Finch RA, Liu M, Grill SP, et al. Triapine (3-aminopyridine-2- carboxaldehyde-thiosemicarbazone): a potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity. Biochem Pharmacol 2000;59:983-91.
    • (2000) Biochem Pharmacol , vol.59 , pp. 983-991
    • Finch, R.A.1    Liu, M.2    Grill, S.P.3
  • 13
    • 0037237032 scopus 로고    scopus 로고
    • Examination of the antiproliferative activity of iron chelators: Multiple cellular targets and the different mechanism of action of triapine compared with desferrioxamine and the potent pyridoxal isonicotinoyl hydrazone analogue 311
    • Chaston TB, Lovejoy DB, Watts RN, Richardson DR. Examination of the antiproliferative activity of iron chelators: multiple cellular targets and the different mechanism of action of triapine compared with desferrioxamine and the potent pyridoxal isonicotinoyl hydrazone analogue 311. Clin Cancer Res 2003;9:402-14.
    • (2003) Clin Cancer Res , vol.9 , pp. 402-414
    • Chaston, T.B.1    Lovejoy, D.B.2    Watts, R.N.3    Richardson, D.R.4
  • 14
    • 0028891974 scopus 로고
    • The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents
    • Richardson DR, Tran EH, Ponka P. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents. Blood 1995;86:4295-306.
    • (1995) Blood , vol.86 , pp. 4295-4306
    • Richardson, D.R.1    Tran, E.H.2    Ponka, P.3
  • 15
    • 0033230124 scopus 로고    scopus 로고
    • Development of novel aroylhydrazone ligands for iron chelation therapy: 2-Pyridylcarboxaldehyde isonicotinoyl hydrazone analogs
    • Becker E, Richardson DR. Development of novel aroylhydrazone ligands for iron chelation therapy: 2-pyridylcarboxaldehyde isonicotinoyl hydrazone analogs. J Lab Clin Med 1999;134:510-21.
    • (1999) J Lab Clin Med , vol.134 , pp. 510-521
    • Becker, E.1    Richardson, D.R.2
  • 16
    • 0037351292 scopus 로고    scopus 로고
    • Identification of the di-pyridyl ketone isonicotinoyl hydrazone (PKIH) analogues as potent iron chelators and anti-tumour agents
    • Becker EM, Lovejoy DB, Greer JM, Watts R, Richardson DR. Identification of the di-pyridyl ketone isonicotinoyl hydrazone (PKIH) analogues as potent iron chelators and anti-tumour agents. Br J Pharmacol 2003;138:819-30.
    • (2003) Br J Pharmacol , vol.138 , pp. 819-830
    • Becker, E.M.1    Lovejoy, D.B.2    Greer, J.M.3    Watts, R.4    Richardson, D.R.5
  • 17
    • 0038814301 scopus 로고    scopus 로고
    • Interactions of the pyridine-2-carboxaldehyde isonicotinoyl hydrazone class of chelators with iron and DNA: Implications for toxicity in the treatment of iron overload disease
    • Chaston TB, Richardson DR. Interactions of the pyridine-2-carboxaldehyde isonicotinoyl hydrazone class of chelators with iron and DNA: implications for toxicity in the treatment of iron overload disease. J Biol Inorg Chem 2003;8:427-38.
    • (2003) J Biol Inorg Chem , vol.8 , pp. 427-438
    • Chaston, T.B.1    Richardson, D.R.2
  • 18
    • 0028784211 scopus 로고
    • Effects of nitrogen monoxide species on cellular proliferation and transferrin and iron uptake by erythroleukemia (K562) cells
    • Richardson DR, Neumannova V, Nagy E, Ponka P. Effects of nitrogen monoxide species on cellular proliferation and transferrin and iron uptake by erythroleukemia (K562) cells. Blood 1995;86:3211-9.
    • (1995) Blood , vol.86 , pp. 3211-3219
    • Richardson, D.R.1    Neumannova, V.2    Nagy, E.3    Ponka, P.4
  • 19
    • 0028215081 scopus 로고
    • The action of nine chelators on iron-dependent radical damage
    • Dean RT, Nicholson P. The action of nine chelators on iron-dependent radical damage. Free Radic Res 1994;20:83-101.
    • (1994) Free Radic Res , vol.20 , pp. 83-101
    • Dean, R.T.1    Nicholson, P.2
  • 20
    • 0025324250 scopus 로고
    • Superoxide-dependent formation of hydroxyl radicals from ferric-complexes and hydrogen peroxide: An evaluation of fourteen iron chelators
    • Gutteridge JM. Superoxide-dependent formation of hydroxyl radicals from ferric-complexes and hydrogen peroxide: an evaluation of fourteen iron chelators. Free Radic Res Commun 1990;9:119-25.
    • (1990) Free Radic Res Commun , vol.9 , pp. 119-125
    • Gutteridge, J.M.1
  • 21
    • 0032533742 scopus 로고    scopus 로고
    • The iron chelator pyridoxal isonicotinoyl hydrazone (PIH) protects plasmid pUC-18 DNA against *OH-mediated strand breaks
    • Hermes-Lima M, Nagy E, Ponka P, Schulman HM. The iron chelator pyridoxal isonicotinoyl hydrazone (PIH) protects plasmid pUC-18 DNA against *OH-mediated strand breaks. Free Radic Biol Med 1998;25:875-80.
    • (1998) Free Radic Biol Med , vol.25 , pp. 875-880
    • Hermes-Lima, M.1    Nagy, E.2    Ponka, P.3    Schulman, H.M.4
  • 22
    • 0345714575 scopus 로고    scopus 로고
    • Cytotoxic iron chelators: Characterization of the structure, solution chemistry and redox activity of ligands and iron complexes of the di-2-pyridylketone isonicotinoyl hydrazone (HPKIH) analogues
    • Bernhardt PV, Caldwell LM, Chaston TB, Chin P, Richardson DR. Cytotoxic iron chelators: characterization of the structure, solution chemistry and redox activity of ligands and iron complexes of the di-2-pyridylketone isonicotinoyl hydrazone (HPKIH) analogues. J Biol Inorg Chem 2003;8:866-80.
    • (2003) J Biol Inorg Chem , vol.8 , pp. 866-880
    • Bernhardt, P.V.1    Caldwell, L.M.2    Chaston, T.B.3    Chin, P.4    Richardson, D.R.5
  • 23
    • 0002779914 scopus 로고    scopus 로고
    • Synthesis and DNA binding studies of cobalt (III) mixed-polypyridyl complex
    • Jin L, Yang P. Synthesis and DNA binding studies of cobalt (III) mixed-polypyridyl complex. J Inorg Biochem 1997;68:79-83.
    • (1997) J Inorg Biochem , vol.68 , pp. 79-83
    • Jin, L.1    Yang, P.2
  • 24
    • 0035916429 scopus 로고    scopus 로고
    • Oxidative mutagenesis of doxorubicin-Fe(III) complex
    • Kostoryz EL, Yourtee DM. Oxidative mutagenesis of doxorubicin-Fe(III) complex. Mutat Res 2001;490:131-9.
    • (2001) Mutat Res , vol.490 , pp. 131-139
    • Kostoryz, E.L.1    Yourtee, D.M.2
  • 25
    • 0032531740 scopus 로고    scopus 로고
    • Identification and hydropathic characterization of structural features affecting sequence specificity for doxorubicin intercalation into DNA double-stranded polynucleotides
    • Kellogg GE, Scarsdale JN, Fornari FA Jr. Identification and hydropathic characterization of structural features affecting sequence specificity for doxorubicin intercalation into DNA double-stranded polynucleotides. Nucleic Acids Res 1998;26:4721-32.
    • (1998) Nucleic Acids Res , vol.26 , pp. 4721-4732
    • Kellogg, G.E.1    Scarsdale, J.N.2    Fornari Jr., F.A.3
  • 26
    • 0033006172 scopus 로고    scopus 로고
    • A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics Adriamycin and daunorubicin
    • Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics Adriamycin and daunorubicin. Biochem Pharmacol 1999;57:727-41.
    • (1999) Biochem Pharmacol , vol.57 , pp. 727-741
    • Gewirtz, D.A.1
  • 27
    • 0023899205 scopus 로고
    • DNA precipitation assay: A rapid and simple method for detecting DNA damage in mammalian cells
    • Olive PL. DNA precipitation assay: a rapid and simple method for detecting DNA damage in mammalian cells. Environ Mol Mutagen 1988;11:487-95.
    • (1988) Environ Mol Mutagen , vol.11 , pp. 487-495
    • Olive, P.L.1
  • 29
    • 4444248453 scopus 로고    scopus 로고
    • Novel di-2-pyridyl-derived iron chelators with marked and selective anti-tumor activity: In vitro and in vivo assessment
    • Yuan J, Lovejoy DB, Richardson DR. Novel di-2-pyridyl-derived iron chelators with marked and selective anti-tumor activity: in vitro and in vivo assessment. Blood 2004;104:1450-8.
    • (2004) Blood , vol.104 , pp. 1450-1458
    • Yuan, J.1    Lovejoy, D.B.2    Richardson, D.R.3
  • 30
    • 0032771646 scopus 로고    scopus 로고
    • Crystal and molecular structure of 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone (NIH) and its iron(III) complex: An iron chelator with anti-tumour activity
    • Richardson DR, Bernhardt PV. Crystal and molecular structure of 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone (NIH) and its iron(III) complex: an iron chelator with anti-tumour activity. J Biol Inorg Chem 1999;4:266-73.
    • (1999) J Biol Inorg Chem , vol.4 , pp. 266-273
    • Richardson, D.R.1    Bernhardt, P.V.2
  • 31
    • 0035854916 scopus 로고    scopus 로고
    • Synthesis and DNA binding of novel water-soluble cationic methylcobalt porphyrins
    • Trommel JS, Marzilli LG. Synthesis and DNA binding of novel water-soluble cationic methylcobalt porphyrins. Inorg Chem 2001;40:4374-83.
    • (2001) Inorg Chem , vol.40 , pp. 4374-4383
    • Trommel, J.S.1    Marzilli, L.G.2
  • 32
    • 0026517627 scopus 로고
    • Determinants of response to the DNA topoisomerase II inhibitors doxorubicin and etoposide in human lung cancer cell lines
    • Kasahara K, Fujiwara Y, Sugimoto Y, et al. Determinants of response to the DNA topoisomerase II inhibitors doxorubicin and etoposide in human lung cancer cell lines. J Natl Cancer Inst (Bethesda) 1992;84:113-8.
    • (1992) J Natl Cancer Inst (Bethesda) , vol.84 , pp. 113-118
    • Kasahara, K.1    Fujiwara, Y.2    Sugimoto, Y.3
  • 33
    • 0037379680 scopus 로고    scopus 로고
    • Anthracyclines induce accumulation of ferritin iron in normal and neoplastic cells: Inhibition of the ferritin Fe mobilization pathway
    • Kwok JC, Richardson DR. Anthracyclines induce accumulation of ferritin iron in normal and neoplastic cells: inhibition of the ferritin Fe mobilization pathway. Mol Pharmacol 2003;63:849-61.
    • (2003) Mol Pharmacol , vol.63 , pp. 849-861
    • Kwok, J.C.1    Richardson, D.R.2
  • 34
    • 0033567224 scopus 로고    scopus 로고
    • Cell-permeable superoxide dismutase and glutathione peroxidase mimetics afford superior protection against doxorubicin-induced cardiotoxicity: The role of reactive oxygen and nitrogen intermediates
    • Konorev EA, Kennedy MC, Kalyanaraman B. Cell-permeable superoxide dismutase and glutathione peroxidase mimetics afford superior protection against doxorubicin-induced cardiotoxicity: the role of reactive oxygen and nitrogen intermediates. Arch Biochem Biophys 1999;368:421-8.
    • (1999) Arch Biochem Biophys , vol.368 , pp. 421-428
    • Konorev, E.A.1    Kennedy, M.C.2    Kalyanaraman, B.3
  • 35
    • 0033566305 scopus 로고    scopus 로고
    • The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents III: The effect of the ligands on molecular targets involved in proliferation
    • Darnell G, Richardson DR. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents III: the effect of the ligands on molecular targets involved in proliferation. Blood 1999;94:781-92.
    • (1999) Blood , vol.94 , pp. 781-792
    • Darnell, G.1    Richardson, D.R.2
  • 36
    • 0032746172 scopus 로고    scopus 로고
    • The therapeutic potential of iron chelators
    • Richardson DR. The therapeutic potential of iron chelators. Exp Opin Investig Drugs 1999;8:2141-58.
    • (1999) Exp Opin Investig Drugs , vol.8 , pp. 2141-2158
    • Richardson, D.R.1
  • 37
    • 0021360269 scopus 로고
    • In vivo formation of single-strand breaks in DNA by hydrogen peroxide is mediated by the Haber-Weiss reaction
    • Mello Filho AC, Meneghini R. In vivo formation of single-strand breaks in DNA by hydrogen peroxide is mediated by the Haber-Weiss reaction. Biochim Biophys Acta 1984;781:56-63.
    • (1984) Biochim Biophys Acta , vol.781 , pp. 56-63
    • Mello Filho, A.C.1    Meneghini, R.2
  • 38
    • 0024335402 scopus 로고
    • Iron ion-dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/xanthine oxidase
    • Aruoma OI, Halliwell B, Dizdaroglu M. Iron ion-dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/xanthine oxidase. J Biol Chem 1989;264:13024-8.
    • (1989) J Biol Chem , vol.264 , pp. 13024-13028
    • Aruoma, O.I.1    Halliwell, B.2    Dizdaroglu, M.3
  • 39
    • 0024468481 scopus 로고
    • DNA topoisomerase II-mediated interaction of doxorubicin and daunorubicin congeners with DNA
    • Bodley A, Liu LF, Israel M, et al. DNA topoisomerase II-mediated interaction of doxorubicin and daunorubicin congeners with DNA. Cancer Res 1989;49:5969-78.
    • (1989) Cancer Res , vol.49 , pp. 5969-5978
    • Bodley, A.1    Liu, L.F.2    Israel, M.3
  • 40
    • 0037356211 scopus 로고    scopus 로고
    • Structural variations and formation constants of first row transition metal complexes of biologically active aroylhydrazones
    • Armstrong CM, Bernhardt PV, Chin P, Richardson DR. Structural variations and formation constants of first row transition metal complexes of biologically active aroylhydrazones. Eur J Inorg Chem 2003;1145-56.
    • (2003) Eur J Inorg Chem , pp. 1145-1156
    • Armstrong, C.M.1    Bernhardt, P.V.2    Chin, P.3    Richardson, D.R.4
  • 41
    • 0026575576 scopus 로고
    • Evaluation of the iron chelation potential of hydrazones of pyridoxal, salicylaldehyde and 2-hydroxy-1-naphthylaldehyde using the hepatocyte in culture
    • Baker E, Richardson DR, Gross S, Ponka P. Evaluation of the iron chelation potential of hydrazones of pyridoxal, salicylaldehyde and 2-hydroxy-1-naphthylaldehyde using the hepatocyte in culture. Hepatology 1992;15:492-501.
    • (1992) Hepatology , vol.15 , pp. 492-501
    • Baker, E.1    Richardson, D.R.2    Gross, S.3    Ponka, P.4


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