Anticancer metal compounds in NCI's tumor-screening database: Putative mode of action

Biochemical Pharmacology

Volumn 69, Issue 7, 2005, Pages 1009-1039

  Huang, Ruili ^a   Wallqvist, Anders ^a   Covell, David G ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Cancer; Data mining; Drug discovery; Mechanism of action; Metal compounds; NCI tumor screen

Indexed keywords

2,2' BIPYRIDINE DERIVATIVE; 8 QUINOLINOL DERIVATIVE; ANTIMONY DERIVATIVE; ANTINEOPLASTIC AGENT; ARSONIC ACID DERIVATIVE; AURANOFIN; BISMUTH DERIVATIVE; BORONIC ACID DERIVATIVE; BORTEZOMIB; CHELATING AGENT; CHROMIUM DERIVATIVE; DIBUTYLDICHLOROTIN; GOLD DERIVATIVE; HYDRAZONE DERIVATIVE; LEAD; MERCURY DERIVATIVE; METAL DERIVATIVE; OXIME DERIVATIVE; PLATINUM DERIVATIVE; PORPHYRIN DERIVATIVE; REACTIVE OXYGEN METABOLITE; SALICYLALDEHYDE; SEMICARBAZONE DERIVATIVE; THIOL DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE; TIN DERIVATIVE; TITANIUM DERIVATIVE; TRIS(DIETHYLDITHIOCARBAMATO)BISMUTH; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANADIUM DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING KINETICS; CANCER CENTER; CANCER INHIBITION; CANCER SCREENING; CHELATION; CORRELATION ANALYSIS; CYTOTOXICITY; DATA BASE; DRUG ACTIVITY; DRUG BINDING; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG TARGETING; GENE EXPRESSION PROFILING; LIPOPHILICITY; PRIORITY JOURNAL; SENSITIVITY ANALYSIS; STRUCTURE ACTIVITY RELATION; TARGET CELL DESTRUCTION; TUMOR CELL;

EID: 14844293088     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.01.001     Document Type: Article

References (156)

1. B. Desoize Cancer and metals and metal compounds. Part II. Cancer treatment Crit Rev Oncol Hematol 42 3 2002 213 215
2. A.Y. Louie, and T.J. Meade Metal complexes as enzyme inhibitors Chem Rev 99 9 1999 2711 2734
3. A. Albert, S.D. Rubbo, R.J. Goldacre, and B.G. Balfour The influence of chemical constitution on antibacterial activity III. A study of 8-hydroxyquinoline (oxine) and related compounds Br J Exp Pathol 28 1947 69 87
4. B. Desoize Cancer and metals and metal compounds. Part I. Carcinogenesis Crit Rev Oncol Hematol 42 1 2002 1 3
5. F. Caruso, M. Rossi, and C. Pettinari Anticancer titanium agents Expert Opin Ther Pat 11 6 2001 969 979
6. S.M. Cohen, and S.J. Lippard Cisplatin: from DNA damage to cancer chemotherapy Prog Nucl Acid Res Mol Biol 67 2001 93 130
7. E. Wong, and C.M. Giandomenico Current status of platinum-based antitumor drugs Chem Rev 99 9 1999 2451 2466
8. A.A. Rabow, R.H. Shoemaker, E.A. Sausville, and D.G. Covell Mining the National Cancer Institute's tumor-screening database: identification of compounds with similar cellular activities J Med Chem 45 4 2002 818 840
9. T. Kohonen Self-organizing maps 1995 Springer Verlag Berlin, Germany
10. K.D. Paull, R.H. Shoemaker, L. Hodes, A. Monks, D.A. Scudiero, and L. Rubinstein Display and analysis of patterns of differential activity of drugs against human tumor cell lines: development of mean graph and COMPARE algorithm J Natl Cancer Inst 81 14 1989 1088 1092
11. R.G. Pearson Acids and bases Science 151 3707 1966 172 177
12. R.B. Martin Practical hardness scales for metal ion complexes Inorg Chim Acta 339 2002 27 33
13. N. Ballatori Mechanisms of metal transport across liver cell plasma membranes Drug Metab Rev 23 1991 83 132
14. A. Naganuma, M. Anderson, and A. Meister Cellular glutathione as a determinant of sensitivity to mercuric chloride toxicity. Prevention of toxicity by giving glutathione monoester Biochem Pharmacol 40 1990 693 697
15. L. Canesi, A. Viarengo, C. Leonzio, M. Filippelli, and G. Gallo Heavy metals and glutathione metabolism in mussel tissues Aquat Toxicol 46 1 1999 67 76
16. G. Hennighausen, and J. Merkord Nonprotein sulfhydryl groups and glutathione S-transferases in acute poisoning by di-n-alkyltin dichlorides in mice and rats Pharmazie 40 6 1985 415 416
17. R.A. Henry, and K.H. Byington Inhibition of glutathione-S-aryltransferase from rat liver by organogermanium, lead and tin compounds Biochem Pharmacol 25 20 1976 2225 2291
18. J.D. Robertson, and S. Orrenius Role of mitochondria in toxic cell death Toxicology 181/182 2002 491 496
19. K.R. Siebenlist, and F. Taketa Inactivation of yeast hexokinase B by triethyltin bromide and reactivation by dithiothreitol and glucose Biochemistry 22 20 1983 4642 4646
20. S.C. Srivastava In vivo effects of di-n-butyltin dichloride on some enzymes and lipids of rat liver plasma membrane Toxicol Lett 52 3 1990 287 291
21. +-ATPase activity J Appl Toxicol 18 5 1998 383 386
22. L. Pellerito, and L. Nagy Organotin(IV)n+ complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects Coord Chem Rev 224 2002 111 150
23. C.F. Shaw III Gold-based therapeutic agents Chem Rev 99 1999 2589 2600
24. E.R.T. Tiekink Antimony and bismuth compounds in oncology Crit Rev Oncol Hematol 42 2002 217 224
25. K.-I. Jeon, M.-S. Byun, and D.-M. Jue Gold compound auranofin inhibits IkB kinase (IKK) by modifying Cys-179 of IKKb subunit Exp Mol Med 35 2 2003 61 66
26. M. Yamashita, S. Ashino, Y. Oshima, S. Kawamura, K. Ohuchi, and M. Takayanagi Inhibition of TP A-induced NF-κB nuclear translocation and production of NO and PGE2 by the anti-rheumatic gold compounds J Pharm Pharmacol 55 2 2003 245 251
27. S. Gromer, L.D. Arscott, C.H. Williams Jr., R.H. Schirmer, and K. Becker Human placenta thioredoxin reductase. Isolation of the selenoenzyme, steady state kinetics, and inhibition by therapeutic gold compounds J Biol Chem 273 32 1998 20096 20101
28. A.D. Smith, C.A. Guidry, V.C. Morris, and O.A. Levander Aurothioglucose inhibits murine thioredoxin reductase activity in vivo J Nutr 129 1 1999 194 198
29. M.J. McKeage Gold opens mitochondrial pathways to apoptosis Br J Pharmacol 136 8 2002 1081 1082
30. M.P. Rigobello, G. Scutari, R. Boscolo, and A. Bindoli Induction of mitochondrial permeability transition by auranofin, a gold(I)-phosphine derivative Br J Pharmacol 136 8 2002 1162 1168
31. Z. Guo, and P.J. Sadler Metals in medicine Angew Chem Int Ed 38 1999 1512 1531
32. M.L. Cunningham, and A.H. Fairlamb Trypanothione reductase from Leishmania donovani. Purification, characterization and inhibition by trivalent antimonials Eur J Biochem 230 2 1995 460 468
33. N. Katsaros, and A. Anagnostopoulou Rhodium and its compounds as potential agents in cancer treatment Crit Rev Oncol Hematol 42 2002 297 308
34. M.J. Clarke, F. Zhu, and D.R. Frasca Non-platinum chemotherapeutic metallopharmaceuticals Chem Rev 99 1999 2511 2533
35. K. Becker, C. Herold-Mende, J.J. Park, G. Lowe, and R.H. Schirmer Human thioredoxin reductase is efficiently inhibited by (2,2′:6′,2″ -terpyridine)platinum(H) complexes. Possible implications for a novel antitumor strategy J Med Chem 44 17 2001 2784 2792
36. 15N] HMQC NMR J Chem Soc, Dalton Trans 18 2002 3489 3495
37. E.S.J. Arner, H. Nakamura, T. Sasada, J. Yodoi, A. Holmgren, and G. Spyrou Analysis of the inhibition of mammalian thioredoxin, thioredoxin reductase, and glutaredoxin by cis-diamminedichloroplatinum (II) and its major metabolite, the glutathione-platinum complex Free Radic Biol Med 31 10 2001 1170 1178
38. S. Fakih, V.P. Munk, M.A. Shipman, P.dS. Murdoch, J.A. Parkinson, and P.J. Sadler Novel adducts of the anticancer drug oxaliplatin with glutathione and redox reactions with glutathione disulfide Eur J Inorg Chem 6 2003 1206 1214
39. R.N. Bose Biomolecular targets for platinum antitumor drugs Mini-Rev Med Chem 2 2 2002 103 111
40. T. Audesirk, D. Shugarts, L. Cabell-Kluch, and K. Wardle The effects of triethyl lead on the development of hippocampal neurons in culture Cell Biol Toxicol 11 1 1995 1 10
41. K. Munter, M. Athanasiou, and C. Stournaras Inhibition of cellular activities by triethyllead. Role of glutathione and accumulation of triethyllead in vitro Biochem Pharmacol 38 22 1989 3941 3945
42. J. Adams Potential for proteasome inhibition in the treatment of cancer Drug Discov Today 8 7 2003 307 315
43. T. Audesirk, C. Pedersen, G. Audesirk, and M. Kern Low levels of inorganic lead noncompetitively inhibit calpain Toxicology 131 2,3 1998 169 174
44. J.L. Buss, F.M. Torti, and S.V. Torti The role of iron chelation in cancer therapy Curr Med Chem 10 12 2003 1021 1034
45. M. Sproull, M. Brechbiel, and K. Camphausen Antiangiogenic therapy through copper chelation Expert Opin Ther Targets 7 3 2003 405 409
46. T.F. Tarn, R. Leung-Toung, W. Li, Y. Wang, K. Karimian, and M. Spino Iron chelator research: past, present, and future Curr Med Chem 10 12 2003 983 995
47. A.M. Tsimberidou, Y. Alvarado, and F.J. Giles Evolving role of ribonucleoside reductase inhibitors in hematologic malignancies Expert Rev Anticancer Ther 2 4 2002 437 448
48. K.C. Agrawal, and A.C. Sartorelli The chemistry and biological activity of alpha-(N)-heterocyclic carboxaldehyde thiosemicarbazones Prog Med Chem 15 1978 321 356
49. F.J. Giles, P.M. Fracasso, H.M. Kantarjian, J.E. Cortes, R.A. Brown, and S. Verstovsek Phase I and pharmacodynamic study of Triapine, a novel ribonucleotide reductase inhibitor, in patients with advanced leukemia Leuk Res 27 12 2003 1077 1083
50. G. Nocentini, and A. Barzi Antitumor activity of 2,2′-bipyridyl-6- carbothioamide: a ribonucleotide reductase inhibitor Gen Pharmacol 29 5 1997 701 706
51. J.G. Cory, A.H. Cory, G. Rappa, A. Lorico, M.C. Liu, and T.S. Lin 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 35 1995 55 68
52. J. Easmon, G. Puerstinger, T. Roth, H.H. Fiebig, M. Jenny, and W. Jaeger 2-Benzoxazolyl and 2-benzimidazolyl hydrazones derived from 2-acetylpyridine: a novel class of antitumor agents Int J Cancer 94 1 2001 89 96
53. I.H. Hall, B.J. Barnes, J.E. Rowell, K.A. Shaffer, S.E. Cho, and D.X. West Cytotoxicity of 2-aldo- and 2-ketopyridine-N(4)-substituted thiosemicarbazones and mode of action in human Tmolt4 cells Pharmazie 56 8 2001 648 653
54. D.B. Lovejoy, and D.R. Richardson Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells Blood 100 2 2002 666 676
55. I.H. Hall, M.C. Miller III, and D.X. West Antineoplastic and cytotoxic activities of nickel(II) complexes of thiosemicarbazones Metal-Based Drugs 4 2 1997 89 95
56. J. Easmon, G. Heinisch, G. Puerstinger, T. Langer, J.K. Oesterreicher, and H.H. Grunicke Diazinyl hydrazones derived from aryl N-heteroaryl ketones: synthesis and antiproliferative activity J Med Chem 40 26 1997 4420 4425
57. M. Jenny, J. Easmon, G. Puerstinger, G. Heinisch, and J. Hofmann Screening of new potential ribonucleotide reductase inhibitors in tissue culture Contrib Oncol 54 1999 409 417 (relevance of tumor models for anticancer drug development)
58. M. El-Mottaleb, A. Ramadan, and I.M. El-Mehasseb Synthesis, characterization and biomimetic oxygenations of manganese(II), iron(III) and copper(II) pyridyl hydrazone complexes Transition Met Chem (London) 23 2 1998 183 189
59. K.D. Paull, C.M. Lin, L. Malspeis, and E. Hamel Identification of novel antimitotic agents acting at the tubulin level by computer-assisted evaluation of differential cytotoxicity data Cancer Res 52 14 1992 3892 3900
60. L.R. Barrows, D.C. Radisky, B.R. Copp, D.S. Swaffar, R.A. Kramer, and R.L. Waiters Makaluvamines, marine natural products, are active anti-cancer agents and DNA topo II inhibitors Anticancer Drug Des 8 5 1993 333 347
61. E.W. Ainscough, A.M. Brodie, W.A. Denny, G.J. Finlay, S.A. Gothe, and J.D. Ranford Cytotoxicity of salicylaldehyde benzoylhydrazone analogs and their transition metal complexes: quantitative structure-activity relationships J Inorg Biochem 77 3-4 1999 125 133
62. L.L. Koh, O.L. Kon, K.W. Loh, Y.C. Long, J.D. Ranford, and A.L.C. Tan Complexes of salicylaldehyde acylhydrazones: cytotoxicity QSAR and crystal structure of the sterically hindered t-butyl dimer J Inorg Biochem 72 3,4 1998 155 162
63. B. Bottari, R. Maccari, F. Monforte, R. Ottana, M.G. Vigorita, and G. Bruno Nickel(II) 2,6-diacetylpyridine bis(isonicotinoylhydrazonate) and bis(benzoylhydrazonate) complexes: structure and antimycobacterial evaluation. Part XI Bioorg Med Chem 9 8 2001 2203 2211
64. N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, and M.C. Nicklaus Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching J Med Chem 40 6 1997 942 951
65. Z.D. Liu, and R.C. Hider Design of iron chelators with therapeutic application Coord Chem Rev 232 1/2 2002 151 171
66. C. Gocmen, H.S. Gokturk, P.U. Ertug, S. Onder, A. Dikmen, and F. Baysal Effect of neocuproine, a selective Cu(I) chelator, on nitrergic relaxations in the mouse corpus cavernosum Eur J Pharmacol 406 2 2000 293 300
67. L.X. Zhao, T.S. Kim, S.H. Ahn, T.H. Kim, E.K. Kim, and W.J. Cho Synthesis, topoisomerase I inhibition and antitumor cytotoxicity of 2,2′:6′,2″-, 2,2′:6′,3″- and 2,2′:6′,4″-terpyridine derivatives Bioorg Med Chem Lett 11 19 2001 2659 2662
68. H.-L. Chan, H.-Q. Liu, B.-C. Tzeng, Y.-S. You, S.-M. Peng, and M. Yang Syntheses of ruthenium(II) quinonediimine complexes of cyclam and characterization of their DNA-binding activities and cytotoxicity Inorg Chem 41 12 2002 3161 3171
69. J.L. Pierre, P. Baret, and G. Serratrice Hydroxyquinolines as iron chelators Curr Med Chem 10 12 2003 1077 1084
70. J. Nordenberg, A. Novogrodsky, E. Beery, M. Patia, L. Wasserman, and A. Warshawsky Anti-proliferative effects and phenotypic alterations induced by 8-hydroxyquinoline in melanoma cell lines Eur J Cancer 26 8 1990 905 907
71. R.T. Borchardt, D.R. Thakker, V.D. Warner, D.B. Mirth, and J.N. Sane Catechol O-methyltransferase. 8. Structure-activity relationships for inhibition by 8-hydroxyquinolines J Med Chem 19 4 1976 558 560
72. P. Collery, F. Lechenault, A. Cazabat, E. Juvin, L. Khassanova, and A. Evangelou Inhibitory effects of gallium chloride and tris(8-quinolinolato) gallium(III) on A549 human malignant cell line Anticancer Res 20 2A 2000 955 958
73. T.A.K. Al-Allaf, and L.J. Rashan Synthesis, characterization, cytotoxicity and anticomplementary activity of a novel dimethyltin(IV) cyclobutyl dicarboxylate complex of 8-hydroxyquinaldine Asian J Chem 13 4 2001 1613 1617
74. K.A. Smith, G.B. Deacon, W.R. Jackson, E.R.T. Tiekink, S. Rainone, and L.K. Webster Preparation and anti-tumor activity of some arylbismuth(III) oxine complexes Metal-Based Drugs 5 5 1998 295 304
75. J.M. Gutteridge, G.J. Quinlan, and P. Kovacic Phagomimetic action of antimicrobial agents Free Radic Res 28 1 1998 1 14
76. R.H. Holm, A.L. Balch, A. Davison, A.H. Maki, and T.E. Berry Electron-transfer complexes of the [MN2S2] type The existence of cation-stabilized free-radical complexes J Am Chem Soc 89 12 1967 2866 2874
77. I.H. Hall, C.B. Lackey, T.D. Kistler, J.S. Ives, H. Beraldo, and L.J. Ackerman The cytotoxicity of symmetrical and unsymmetrical bis(thiosemicarbazones) and their metal complexes in murine and human tumor cells. Archiv der Pharmazie (Weinheim, Germany) 333 7 2000 217 225
78. M.E. Vol'pin, G.N. Novodarova, E.M. Kolosova, N.V. Guzhova, A.A. Kononenko, and Y.N. Leikin Transition metal complexes as catalysts in biochemical systems. Interaction with electron transfer processes Inorg Chim Acta 50 1 1981 21 31
79. M. Balbaa, M. Khalifa, M. El-Sabaway, and K. Kandeel Inhibition of succinate-cytochrome C reductase by a ferromacrocyclic complex J Enzym Inhib 16 4 2001 381 390
80. K.R. Huber, R. Sridhar, E.H. Griffith, E.L. Amma, and J. Roberts Superoxide dismutase-like activities of copper(II) complexes tested in serum Biochim Biophys Acta 915 2 1987 267 276
81. E.A. Hileman, G. Achanta, and P. Huang Superoxide dismutase: an emerging target for cancer therapeutics Expert Opin Ther Targets 5 6 2001 697 710
82. P. Wardman, and L.P. Candeias Fenton chemistry: an introduction Radiat Res 145 5 1996 523 531
83. M. Patel, and B.J. Day Metalloporphyrin class of therapeutic catalytic antioxidants Trends Pharmacol Sci 20 9 1999 359 364
84. S.R. Doctrow, C. Adinolfi, M. Baudry, K. Huffman, B. Malfroy, and C.B. Marcus Salen manganese complexes, combined superoxide dismutase/catalase mimetics, demonstrate potential for treating neurodegenerative and other age-associated diseases Crit Rev Oxid Stress Aging 2 2003 1324 1343
85. N. Suzuki, S. Mashiko, M. Hamada, T. Nomoto, M. Hasegaga, and B. Yoda Antioxidative activity of biologically active compounds: measurement by Cypridina chemiluminescence method Proceedings of the Eighth International Symposium on Bioluminescence and Chemiluminescence: Fundamentals and Applied Aspects Cambridge, UK, September 5-8 1994 219 222
86. N. Kasugai, T. Murase, T. Ohse, S. Nagaoka, H. Kawakami, and S. Kubota Selective cell death by water-soluble Fe-porphyrins with superoxide dismutase (SOD) activity J Inorg Biochem 91 2 2002 349 355
87. G.S. Drummond Control of heme metabolism by synthetic metalloporphyrins Ann NY Acad Sci 514 1987 87 95
88. A.I. Goodman, M. Choudhury, J.L. da Silva, M.L. Schwartzman, and N.G. Abraham Overexpression of the heme oxygenase gene in renal cell carcinoma Proc Soc Exp Biol Med 214 1 1997 54 61
89. M.D. Maines, and P.A. Abrahamsson Expression of heme oxygenase-1 (HSP32) in human prostate: normal, hyperplastic, and tumor tissue distribution Urology 47 5 1996 727 733
90. S.K. Sahoo, T. Sawa, J. Fang, S. Tanaka, Y. Miyamoto, and T. Akaike Pegylated zinc protoporphyrin: a water-soluble heme oxygenase inhibitor with tumor-targeting capacity Bioconjug Chem 13 5 2002 1031 1038
91. J. Fang, T. Sawa, T. Akaike, T. Akuta, S.K. Sahoo, and G. Khaled In vivo antitumor activity of pegylated zinc protoporphyrin: targeted inhibition of heme oxygenase in solid tumor Cancer Res 63 13 2003 3567 3574
92. Q. Zhang, J.-J. Zhai, Y.-R. Zhang, Y.-M. Liu, L.-F. Wang, and S.-B. Li Antioxidative and antitumor properties of metal(H) solid complexes with 8-acetyl-4-methyl umbelliferone Transition Metal Chem (Dordrecht, The Netherlands) 25 1 2000 93
93. T.W. Kensler, D.M. Bush, and W.J. Kozumbo Inhibition of tumor promotion by a biomimetic superoxide dismutase Science 221 4605 1983 75 77
94. M. Marikovsky Thiram inhibits angiogenesis and slows the development of experimental tumors in mice Br J Cancer 86 5 2002 779 787
95. T. Yoshikawa, S. Kokura, K. Tainaka, Y. Naito, and M. Kondo A novel cancer therapy based on oxygen radicals Cancer Res 55 8 1995 1617 1620
96. T.D. Oberley, and L.W. Oberley Antioxidant enzyme levels in cancer Histol Histopathol 12 2 1997 525 535
97. Q. Kong, J.A. Beel, and K.O. Lillehei A threshold concept for cancer therapy Med Hypotheses 55 1 2000 29 35
98. P. Amstad, R. Moret, and P. Cerutti Glutathione peroxidase compensates for the hypersensitivity of Cu, Zn-superoxide dismutase overproducers to oxidant stress J Biol Chem 269 3 1994 1606 1609
99. G.D. Mao, P.D. Thomas, G.D. Lopaschuk, and M.J. Poznansky Superoxide dismutase (SOD)-catalase conjugates Role of hydrogen peroxide and the Fenton reaction in SOD toxicity J Biol Chem 268 1 1993 416 420
100. B.A. Omar, and J.M. McCord The cardioprotective effect of Mn-superoxide dismutase is lost at high doses in the postischemic isolated rabbit heart Free Radic Biol Med 9 6 1990 473 478
101. B.K. Keppler, C. Friesen, H. Vongerichten, and E. Vogel Budotitane, a new tumor-inhibiting titanium compound: preclinical and clinical development Met Complexes Cancer Chemother 1993 297 323
102. F. Afaq, P. Abidi, R. Matin, and Q. Rahman Cytotoxicity, pro-oxidant effects and antioxidant depletion in rat lung alveolar macrophages exposed to ultrafine titanium dioxide J Appl Toxicol 18 5 1998 307 312
103. R.M. Schapira, A.J. Ghio, R.M. Effros, J. Morrisey, U.A. Almagro, and C.A. Dawson Hydroxyl radical production and lung injury in the rat following silica or titanium dioxide instillation in vivo Am J Respir Cell Mol Biol 12 2 1995 220 226
104. D.W. Kamp, V. Panduri, S.A. Weitzman, and N. Chandel Asbestos-induced alveolar epithelial cell apoptosis: role of mitochondrial dysfunction caused by iron-derived free radicals Mol Cell Biochem 234/235 1/2 2002 153 160
105. A. Fujishima, R.X. Cai, J. Otsuki, K. Hashimoto, K. Itoh, and T. Yamashita Biochemical application of photoelectrochemistry: photokilling of malignant cells with titanium dioxide powder Electrochim Acta 38 1 1993 153 157
106. R. Konaka, E. Kasahara, W.C. Dunlap, Y. Yamamoto, K.C. Chien, and M. Inoue Irradiation of titanium dioxide generates both singlet oxygen and superoxide anion Free Radic Biol Med 27 3/4 1999 294 300
107. C. Kawasaki Photokilling of T-24 human bladder cancer cells with titanium dioxide molecules Yokohama Igaku 46 2 1995 103 110
108. M. Ushio-Fukai, K.K. Griendling, P.L. Becker, L. Hilenski, S. Halleran, and R.W. Alexander Epidermal growth factor receptor transactivation by angiotensin II requires reactive oxygen species in vascular smooth muscle cells Arterioscler Thromb Vase Biol 21 4 2001 489 495
109. M. Sundaresan, Z.X. Yu, V.J. Ferrans, D.J. Sulciner, J.S. Gutkind, and K. Irani Regulation of reactive-oxygen-species generation in fibroblasts by Racl Biochem J 318 Part 2 1996 379 382
110. G.D. Frank, S. Eguchi, T. Yamakawa, S. Tanaka, T. Inagami, and E.D. Motley Involvement of reactive oxygen species in the activation of tyrosine kinase and extracellular signal-regulated kinase by angiotensin II Endocrinology 141 9 2000 3120 3126
111. T. Nishikawa, H. Wanibuchi, M. Ogawa, A. Kinoshita, K. Morimura, and T. Hiroi Promoting effects of monomethylarsonic acid, dimethylarsinic acid and trimethylarsine oxide on induction of rat liver preneoplastic glutathione S-transferase placental form positive foci: a possible reactive oxygen species mechanism Int J Cancer 100 2 2002 136 139
112. W.A. Pott, S.A. Benjamin, and R.S. Yang Pharmacokinetics, metabolism, and carcinogenicity of arsenic Rev Environ Contam Toxicol 169 2001 165 214
113. A. Barchowsky, L.R. KJei, E.J. Dudek, H.M. Swartz, and P.E. James Stimulation of reactive oxygen, but not reactive nitrogen species, in vascular endothelial cells exposed to low levels of arsenite Free Radic Biol Med 27 11-12 1999 1405 1412
114. T. Samikkannu, C.H. Chen, L.H. Yih, A.S. Wang, S.Y. Lin, and T.C. Chen Reactive oxygen species are involved in arsenic trioxide inhibition of pyruvate dehydrogenase activity Chem Res Toxicol 16 3 2003 409 414
115. R.S. Oremland, and J.F. Stolz The ecology of arsenic Science 300 5621 2003 939 944
116. B. Nemeti, and Z. Gregus Mitochondria work as reactors in reducing arsenate to arsenite Toxicol Appl Pharmacol 182 3 2002 208 218
117. D. Bagchi, S.J. Stohs, B.W. Downs, M. Bagchi, and H.G. Preuss Cytotoxicity and oxidative mechanisms of different forms of chromium Toxicology 180 1 2002 5 22
118. A.K. Singh, B.K. Puri, and R.K. Rawlley Open shell hexamethyleneiminecarbodithioates of vanadyl(IV), chromium(III), manganese(II and III), iron(III), cobalt(II) and copper(II) - magnetic, spectral and antimicrobial investigations Indian J Chem, Sect A: Inorg, Phys, Theor Anal Chem 27A 5 1988 430 433
119. A.M. Bond, and G.G. Wallace Influence of oxygen insertion on the electrochemistry of chromium(III) dithiocarbarnate complexes Inorg Chem 23 13 1984 1858 1865
120. D. Rehder, J.C. Pessoa, C.F.G.C. Geraldes, M.M.C.A. Castro, T. Kabanos, and T. Kiss In vitro study of the insulin-mimetic behaviour of vanadium(IV, V) coordination compounds J Biol Inorg Chem 7 4/5 2002 384 396
121. J. Li, G. Elberg, D.C. Crans, and Y. Shechter Evidence for the distinct vanadyl(+4)-dependent activating system for manifesting insulin-like effects Biochemistry 35 25 1996 8314 8318
122. C. Djordjevic Antitumor activity of vanadium compounds Metal Ions Biol Syst 31 1995 595 616
123. A.M. Evangelou Vanadium in cancer treatment Crit Rev Oncol Hematol 42 3 2002 249 265
124. A.P. Bevan, P.G. Drake, J.-F. Yale, A. Shaver, and B.I. Posner Peroxovanadium compounds: biological actions and mechanism of insulin-mimesis Mol Cell Biochem 153 1,2 1995 49 58
125. M.D. Cavanaugh, S.M. Tetrick, C.J. Masi, and A.R. Cutler Preparation and characterization of the rhenium silyl esters (h5-C5Me5)(CO)(NO)ReC(O)OSiR3 (SiR3 = SiMe2Ph SiEt3) J Organomet Chem 538 1-2 1997 41 48
126. P. Kopf-Maier, and T. Klapotke Ionic rhenocene derivatives with antitumor activity Cancer Chemother Pharmacol 29 5 1992 361 366
127. J.S. Modica-Napolitano, and J.R. Aprille Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells Adv Drug Delivery Rev 49 1/2 2001 63 70
128. I. Madar, L. Weiss, and G. Izbicki Preferential accumulation of (3)H-tetraphenylphosphoniurn in non-small cell lung carcinoma in mice: comparison with (99m)Tc-MIBI J Nucl Med 43 2 2002 234 238
129. D.C. Rideout, T. Calogeropoulou, J.S. Jaworski, R. Dagnino Jr., and M.R. McCarthy Phosphonium salts exhibiting selective anti-carcinoma activity in vitro Anticaneer Drug Des 4 4 1989 265 280
130. D. Rideout, A. Bustamante, and J. Patel Mechanism of inhibition of FaDu hypopharyngeal carcinoma cell growth by tetraphenylphosphonium chloride Int J Cancer 57 2 1994 247 253
131. E.J. Delikatny, S.K. Roman, R. Hancock, T.M. Jeitner, C.M. Lander, and D.C. Rideout Tetraphenylphosphonium chloride induced MR-visible lipid accumulation in a malignant human breast cell line Int J Cancer 67 1 1996 72 79
132. Covell DG, Wallqvist A, Huang R, Thanki N, Rabow AA, Lu X-J. Linking tumor cell cytotoxicity to mechanism of drug action: an integrated analysis of gene expression, small-molecule screening and structural databases. Proteins, 2005, in press.
133. A.T. Miles, G.M. Hawksworth, J.H. Beattie, and V. Rodilla Induction, regulation, degradation, and biological significance of mammalian metallothioneins Crit Rev Biochem Mol Biol 35 1 2000 35 70
134. J.H. Kim, K.C. Park, S.S. Chung, O. Bang, and C.H. Chung Deubiquitinating enzymes as cellular regulators J Biochem (Tokyo) 134 1 2003 9 18
135. J. Adams Proteasome inhibitors as new anticancer drugs Curr Opin Oncol 14 6 2002 628 634
136. N.T. Le, and D.R. Richardson The role of iron in cell cycle progression and the proliferation of neoplastic cells Biochim Biophys Acta 1603 1 2002 31 46
137. J. Easmon Copper and iron complexes with antitumor activity Expert Opin Ther Pat 12 6 2002 789 818
138. Y. Miyamoto, Y.H. Koh, Y.S. Park, N. Fujiwara, H. Sakiyama, and Y. Misonou Oxidative stress caused by inactivation of glutathione peroxidase and adaptive responses Biol Chem 384 4 2003 567 574
139. G. Georgiou, and L. Masip Biochemistry. An overoxidation journey with a return ticket Science 300 5619 2003 592 594
140. T.J. Preston, A. Abadi, L. Wilson, and G. Singh Mitochondrial contributions to cancer cell physiology: potential for drug development Adv Drug Deliv Rev 49 1/2 2001 45 61
141. K.M. Debatin, D. Poncet, and G. Kroemer Chemotherapy: targeting the mitochondrial cell death pathway Oncogene 21 57 2002 8786 8803
142. I. Royo, N. DePedro, E. Estornell, D. Cortes, F. Pelaez, and J.R. Tormo In vitro antitumor SAR of threo/cis/threo/cis/erythro bis-THF acetogenins: correlations with their inhibition of mitochondrial complex I Oncol Res 13 12 2003 521 528
143. Anon CRC handbook of chemistry and physics 2002 CRC Press Boca Raton
144. H. Irving, and R.J.P. Williams Order of stability of metal complexes Nature (London, UK) 162 1948 746 767
145. C.P. Kulatilleke, D.B. Rorabacher, and L.A. Ochrymowycz Unique copper chelators for angiosuppression Abstracts of Papers, 224th ACS National Meeting Boston, MA, USA, August 18-22 2002
146. D.R. Richardson Therapeutic potential of iron chelators in cancer therapy Adv Exp Med Biol 509 2002 231 249
147. M. McCann, M. Geraghty, M. Devereux, D. O'Shea, J. Mason, and L. O'Sullivan Insights into the mode of action of the anti-Candida activity of 1,10-phenanthroline and its metal chelates Metal-Based Drugs 7 4 2000 185 193
148. B. Coyle, K. Kavanagh, M. McCann, M. Devereux, and M. Geraghty Mode of anti-fungal activity of 1,10-phenanthroline and its Cu(II) Mn(II) and Ag(I) complexes BioMetals 16 2 2003 321 329
149. P. Kovacic, W.J. Popp, J.R. Ames, and M.D. Ryan Anti-cancer action of metal complexes: electron transfer and oxidative stress? Anticancer Drug Des 3 3 1988 205 216
150. I. Tamburlin-Thumin, M.P. Crozet, J.C. Barriere, M. Barreau, J.F. Riou, and F. Lavelle Synthesis and biological evaluation of O-alkylated tropolones and related alpha-ketohydroxy derivatives as ribonucleotide reductase inhibitors Eur J Med Chem 36 6 2001 561 568
151. V. Kahn Tropolone - a compound that can aid in differentiating between tyrosinase and peroxidase Phytochemistry (Elsevier) 24 5 1985 915 920
152. M. Cammarata, V. Arizza, N. Parrinello, G. Candore, and C. Caruso Phenoloxidase-dependent cytotoxic mechanism in ascidian (Styela plicata) hemocytes active against erythrocytes and K562 tumor cells Eur J Cell Biol 74 3 1997 302 307
153. A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Arylsulfonyl-N,N- diethyl- dithiocarbamates: a novel class of antitumor agents Bioorg Med Chem Lett 10 16 2000 1887 1891
154. W. Beerheide, M.M. Sim, Y.-J. Tan, H.-U. Bernard, and A.E. Ting Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides Bioorg Med Chem 8 11 2000 2549 2560
155. S. Yan, K. Ding, L. Zhang, and H. Sun Complexation ofantimony(III) by trypanothione Angew Chem Int Ed 39 23 2000 4260 4262
156. G.T. Morgan, and H.D.K. Drew Residual affinity and coordination. II. Acetylacetones of selenium and tellurium J Chem Soc 117 1920 1456 1465