Recent developments in the field of anticancer metallopharmaceuticals

International Journal of PharmTech Research

Volumn 1, Issue 4, 2009, Pages 1406-1420

  Bharti, Sanjay K ^a   Singh, Sushil K ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

Chelation; Encapsulation; Metal based drugs; Prodrug; Resistance

Indexed keywords

AMMINEDICHLORO(2 METHYLPYRIDINE)PLATINUM; ANTINEOPLASTIC METAL COMPLEX; ARSENIC TRIOXIDE; ASCORBIC ACID; BBR 3464; CARBOPLATIN; CISPLATIN; COBALT DERIVATIVE; DNA; GALLIUM DERIVATIVE; GOLD DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDAZOLIUM TETRACHLOROBIS(INDAZOLE)RUTHENATE; INDAZOLIUM TRANS[TETRACHLORO(1H INDAZOLE)RUTHENATE III]; INTERFERON; IPROPLATIN; LOBAPLATIN; MACROGOL; NEDAPLATIN; NICKEL COMPLEX; ORGANOTIN COMPOUND; OXALIPLATIN; RHODIUM DERIVATIVE; RUTHENIUM DERIVATIVE; SATRAPLATIN; SINGLE WALLED NANOTUBE; TETRAPLATIN; TITANIUM DERIVATIVE; TRANSCRIPTION FACTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANADIUM DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; BILIRUBIN BLOOD LEVEL; BLADDER CANCER; CANCER THERAPY; CELL LEVEL; CLINICAL TRIAL; COLON CANCER; COLORECTAL CANCER; CREATININE BLOOD LEVEL; DNA REPAIR; DRUG APPROVAL; DRUG DELIVERY SYSTEM; DRUG DNA BINDING; DRUG EFFICACY; DRUG METABOLISM; DRUG PROTEIN BINDING; DRUG RESEARCH; DRUG SAFETY; DRUG SENSITIVITY; DRUG STRUCTURE; DRUG TOLERABILITY; DRUG UPTAKE; ESOPHAGUS CARCINOMA; GENE MUTATION; HEAD AND NECK CANCER; HEART ARRHYTHMIA; HUMAN; LIVER TOXICITY; LUNG SMALL CELL CANCER; NEPHROTOXICITY; NEUROTOXICITY; NONHODGKIN LYMPHOMA; NONHUMAN; OTOTOXICITY; OVARY CANCER; PROMYELOCYTIC LEUKEMIA; PROSTATE CANCER; PROTEIN EXPRESSION; PROTEIN FUNCTION; REVIEW; SIDE EFFECT; STOMACH ADENOCARCINOMA; STRUCTURE ANALYSIS; TESTIS CANCER; UNSPECIFIED SIDE EFFECT; UTERINE CERVIX CANCER;

EID: 77953416162     PISSN: None     EISSN: 09744304     Source Type: Journal    
DOI: None     Document Type: Review

References (163)

1. Orvig, C.; Abrams, M.J. Medicinal Inorganic Chemistry: Introduction, Chem. Rev., 1999, 99, 2201-2204
2. Keppler B.K.; (Ed.), Metal complexes in cancer chemotherapy, VCH, Weinheim, 1993, p. 159.
3. Maier, P.K. Complexes of metals other than platinum as antitumour agents. Eur. J. Clin. Pharmacol, 1994, 47, 1-16.
4. Sadler, P.J; Guo, Z. Metal complexes in medicine: Design and mechanism of action. Pure and Appl.Chem., 1998, 70, 863-871 (Pubitemid 128484355)
5. Kastenholz, B. Important contributions of a new quantitative preparative native continuous polyacrylamide gel electrophoresis (QPNC-PAGE) procedure for elucidating metal cofactor metabolisms in protein-misfolding diseases - a theory. Protein Pept. Lett. 2006, 13, 503-508
6. Kastenholz, B. Important contributions of a new quantitative preparative native continuous polyacrylamide gel electrophoresis (QPNC-PAGE) procedure for elucidating metal cofactor metabolisms in protein-misfolding diseases - a theory. Electroanalysis, 2006, 18, 103-106
7. Kastenholz, B. New Hope for the Diagnosis and Therapy of Alzheimer's disease. Protein & Peptide Letters, 2007, 14, 389-393 (Pubitemid 46570910)
8. Kwiatek, W.M.; Drewniak, T.; Gajda, M.; Galka, M.; Hanson, A.L.; Cichocki, T. Preliminary study on the distribution of selected elements in cancerous and non-cancerous kidney tissues. J. Trace Elem. Med. Biol., 2002, 16, 155-160
9. Klofutar C.; Paljk S.; Krasovec F.; Suhae P., Chem Abstr., 1976, 84, p. 84739.
10. Sanchez-Delgado, R.A.; Lazardi, K.; Rincon, L.; Urbina, J.A. Toward a novel metal-based chemotherapy against tropical diseases. 1. Enhancement of the efficacy of clotrimazole against Trypanosoma cruzi by complexation to ruthenium in RuCl2(clotrimazole)2. J. Med. Chem., 1993, 36, 2041-2045
11. Frausto da Silva J. J. R.; Williams R.J.P., Biological Chemistry of the Elements, The Inorganic Chemistry of Life, ed. by Clarendon Press, Oxford, 1991.
12. Lippard S.J.; Beng J.M., Principles of Bioinorganic Chemistry, University Science Books, Mile Valley, California, 1994.
13. Barnard P. J.; Berners-Price S. J., Targeting the mitochondrial cell death pathway with gold compounds, Coordination Chemistry Reviews 2007, 251, 1889-1902.
14. Abu-Surrah, A.S.; Kettunen, M. Platinum group antitumor chemistry:design and development of new anticancer drugs complementary to cisplatin, Curr. Med. Chem., 2006, 13, 1337-1357
15. Muggia, F.M.; Fojo, T. Platinums: extending their therapeutic spectrum, J. Chemotherapy, 2004, 16, 77.
16. Eastman, A. In Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug; Lippert, B. Ed.; Wiley-VCH: Weinheim, 1999, pp, 111.
17. Gonzalez, V.M.; Fuertes, M. A.; Alonso, C.; Perez, J. M. Is Cisplatin-Induced Cell Death Always Produced by Apoptosis? Mol. Pharmacol., 2001, 59, 657-663 (Pubitemid 32273993)
18. Poon, G.K.; Raynaud, F.I.; Mistry, P.; Odell, D.E.; Kelland, L.R.; Harrap, K.R.; Barnard C.F.; Murrer, B.A. Metabolic studies of an orally active platinum anticancer drug by liquid chromatographyelectrospray ionization mass spectrometry. J. Chromatogr., 1995, 712, 61-66.
19. Raynaud, F.I.; Mistry, P.; Donaghue, A.; Poon, G.K.; Kelland, L.R.; Barnard, C.F.; Murrer, B.A.; Harrap, K.R.Biotransformation of the platinum drug JM216 following oral administration to cancer patients. Cancer Chemother. Pharmacol., 1996, 38, 155-162.
20. Kelland, L. Broadening the clinical use of platinum drug-based chemotherapy with new analogues. Satraplatin and picoplatin. Expert Opin. Invest. Drugs, 2007, 16, 1009-1021. (Pubitemid 47074157)
21. Brabec, V.; Kasparkova, J.; Vrana, O.; Novakova, O.; Cox, J.W.; Qu, Y.; Farrell, N. DNA modifications by a novel bifunctional trinuclear platinum phase I anticancer agent. Biochemistry, 1999, 38, 6781-6790 (Pubitemid 129514979)
22. Perego, P.; Caserini, C.; Gatti, L.; Carenini, N.; Romanelli, S.; Supino, R.; Colangelo, D.; Viano, I.; Leone, R.; Spinelli, S.; Pezzoni, G.; Manzotti, C.; Farrell, N.; Zunino, F. A novel trinuclear platinum complex overcomes cisplatin resistance in an osteosarcoma cell system. Mol. Pharmacol., 1999, 55, 528-534 (Pubitemid 29128110)
23. Pratesi, G.; Perego, P.; Polizzi, D.; Righetti, S.C.; Supino, R.; Caserini, C.; Manzotti, C.; Giuliani, F.C.; Pezzoni, G.; Tognella, S.; Spinelli, S.; Farrell, N.; Zunino, F. A novel charged trinuclear platinum complex effective against cisplatin-resistant tumours: hypersensitivity of p53-mutant human tumour xenografts. Br. J. Cancer, 1999, 80, 1912-1919 (Pubitemid 29391274)
24. Jodrell, D.I.; Evans, T.R.; Steward, W.; Cameron, D.; Prendiville, J.; Aschele, C.; Noberasco, C.; Lind, M.; Carmichael, J.; Dobbs, N.; Camboni, G.; Gatti, B. De Braud, F. Phase II studies of BBR3464, a novel trinuclear platinum complex, in patients with gastric or gastro-oesophageal adenocarcinoma. Eur. J. Cancer, 2004, 40, 1872-1877
25. Hensing, T.A.; Hanna, N.H.; Gillenwater, H.H.; Gabriella C.M.; Allievi, C.; Socinski, M.A. Phase II study of BBR 3464 as treatment in patients with sensitive or refractory small cell lung cancer. Anticancer Drugs, 2006, 17, 697-704. (Pubitemid 44265869)
26. Yang, Z.; Wang, X.Y.; Diao, H. J.; Zhang, J. F.; Li, H.Y.; Sun, H. Z.; Guo, Z.J. Encapsulation of platinum anticancer drugs by apoferritin. Chem. Commun., 2007, 3453-3455 (Pubitemid 47283709)
27. MacDiarmid, J.A.; Mugridge, N.B.; Weiss, J.C.; Phillips, L.; Burn, A. L.; Paulin, R. P.; Haasdyk, J. E.; Dickson, K. A.; Brahmbhatt, V. N.; Pattison, S.T.; James, A.C.; Al Bakri, G.; Straw, R.C.; Stillman, B.; Graham, R.M.; Brahmbhatt, H. Bacterially derived 400 nm particles for encapsulation and cancer cell targeting of chemotherapeutics. Cancer cell, 2007, 11,431-445 (Pubitemid 46670079)
28. Hall, M. D.; Mellor, H. R.; Callaghan, R.; Hambley, T. W. Basis for design and development of platinum (IV) anticancer complexes. J Med Chem, 2007, 50, 3403-3411 (Pubitemid 47195446)
29. Nishiyama, N; Kato, Y; Sugiyama, Y; Kataoka, K. Cisplatin-loaded polymer-metal complex micelle with time-modulated decaying property as a novel drug delivery system. Pharm Res, 2001, 18, 1035-1041 (Pubitemid 32799952)
30. Neuse, E.W.; Mphephu, N.; Netshifhefhe, H.M.; Johnson M.T. Synthesis and preliminary in vitro evaluation of polymeric dicarboxylatoand dihydroxylatoplatinum(II) chelates as antiproliferative agents. Polym Adv Technol, 2002, 13, 884-895
31. Ohya, Y.; Oue, H.; Nagatomi, K.; Ouchi, T. Design of macromolecular prodrug of cisplatin using dextran with branched galactose units as targeting moieties to hepatoma cells. Biomacromolecules, 2001, 2, 927-933 (Pubitemid 32894651)
32. Barnes, K.R.; Kutikov, A.; Lippard, S.J. Synthesis, characterization,and cytotoxicity of a series of estrogen-tethered platinum(IV)complexes. Chem Biol, 2004, 11, 557-564
33. Ang, W.H.; Khalaila, I.; Allardyce, C.S.; Juillerat-Jeanneret, L.; Dyson, P.J. Rational design of platinum(IV) compounds to overcome glutathione- Stransferase mediated drug resistance. J Am Chem Soc, 2005, 127, 1382-1383
34. Holmes, R.J.; McKeage, M.J.; Murray, V.; Denny, W.A.; McFadyen, W.D. cis-Dichloroplatinum (II) complexes tethered to 9-aminoacridine-4-carboxamides: synthesis and action in resistant cell lines in vitro. J Inorg Biochem, 2001, 85, 209-217
35. Feazell, R.P.; Nakayama-Ratchford, N.; Dai, H.; Lippard, S.J. Soluble single-walled carbon nanotubes as longboat delivery systems for platinum (IV) anticancer drug design. J Am Chem Soc 2007, 129, 8438-8439
36. Lee, K.B.; Wang, D.; Lippard, S.J.; Sharp, P.A. Transcription-coupled and DNA damage-dependent ubiquitination of RNA polymerase II in vitro. Proc Natl Acad Sci USA, 2002, 99, 4239-4244
37. Ali, H.; van Lier, J.E. Metal complexes as photo-and radiosensitizers. Chem Rev 1999, 99, 2379-2450.
38. Reisner, E.; Arion, V.B.; Keppler, B.K.; Pombeiro, A.J. Electron-transfer activated metal-based anticancer drugs. Inorganica Chemica Acta, 2008, 361, 1569-1583
39. Habtemariam, A.; Melchart, M.; Fernandez, R.; Parsons, S.; Oswald, I.D.; Parkin, A.; Fabbiani, F.P.; Davidson, J.E.; Dawson, A.; Aird, R.E.; Jodrell, D.I.; Sadler, P.J. Structure-activity relationships for cytotoxic ruthenium(II) arene complexes containing N, N-, N,O-, and O,O-chelating ligands. J Med Chem, 2006, 49, 6858-6868
40. Yan, Y.K.; Melchart, M.; Habtemariam, A.; Sadler, P.J. Organometallic chemistry, biology and medicine: ruthenium arene anticancer complexes. Chem Commun, 2005, 4764-4776
41. Peacock, A.F.; Parsons, S.; Sadler, P.J. Tuning the hydrolytic aqueous chemistry of osmium arene complexes with N,O-chelating ligands to achieve cancer cell cytotoxicity. J Am Chem Soc, 2007, 129, 3348-3357
42. Antman, K.H. Introduction: The History of Arsenic Trioxide in Cancer Therapy. The Oncologist, 2001,6,1-2.
43. Waxman, S.; Anderson, K.C. History of the Development of Arsenic Derivatives in Cancer Therapy. The Oncologist, 2001,6,3-10. (Pubitemid 32405843)
44. Shen, Z.X.; Chen, G.Q.; Ni, J.H.; Li, X.S.; Xiong, S.M.; Qiu, Q.Y.; Zhu, J.; Tang, W.; Sun, G.L.; Yang, K.Q.; Chen, Y.; Zhou, L.; Fang, Z.W.; Wang, Y.T.; Ma, J.; Zhang, P.; Zhang, T.D.; Chen, S.J.; Chen, Z.; Wang, Z.Y. Use of arsenic trioxide (As2O3) in the treatment of acute promyelocytic leukemia (APL). II. Clinical efficacy and pharmacokinetics in relapsed patients. Blood, 1997, 89, 3354-3360 (Pubitemid 27229822)
45. Soignet, S.L.; Maslak, P.; Wang, Z.G.; Jhanwar, S.; Calleja, E.; Dardashti, L. J.; Corso, D.; DeBlasio, A.; Gabrilove, J.; Scheinberg, D.A.; Pandolfi, P.P.; Warrell, R.P. Complete remission after treatment of acute promyelocytic leukemia with arsenic trioxide. New Engl. J. Med., 1998, 339, 1341-1348 (Pubitemid 28509343)
46. Dilda, P.J.; Hogg, P.J. Arsenical-based cancer drugs. Cancer Treat. Rev., 2007, 33, 542-564
47. Bahlis, N.J.; McCafferty-Grad, J.; Jordan-McMurry, I.; Neil, J.; Reis, I.; Kharfan-Dabaja, M.; Eckman, J.; Goodman, M.; Fernandez, H.F.; Boise, L.H.; Lee, K.P. Feasibility and correlates of arsenic trioxide combined with ascorbic acid-mediated depletion of intracellular glutathione for the treatment of relapsed/refractory multiple myeloma. Clin. Cancer Res., 2002, 8, 3658-3668
48. Munshi, N.C. Arsenic trioxide: an emerging therapy for multiple myeloma. The Oncologist, 2001, 6, 2, 17-21. (Pubitemid 32405845)
49. Karlsson, J.; Edsjo, A.; Pahlman, S.; Pettersson, H.M. Multidrugresistant neuroblastoma cells are responsive to arsenic trioxide at both normoxia and hypoxia. Mol. Cancer Ther., 2005, 4, 1128-1135
50. Yang, C.H.; Kuo, M.L.; Chen, J.C.; Chen Y.C. Arsenic trioxide sensitivity is associated with low level of glutathione in cancer cells. Br.J.Cancer, 1999, 81, 796-799
51. McNeely, S.C.; Xu, X.; Taylor, B. F.; Zacharias, W.; McCabe, J.; States, J.C. Exit from arsenite-induced mitotic arrest is p53 dependent. Environ Health Perspect, 2006, 114, 1401-1406
52. Ma, X. D.; Qiao, D. F.; Tian, X. M.; Yan, F.; Ma, A. D. Mechanism of opening of mitochondrial permeability transition pore induced by arsenic trioxide, AiZhang, 2006, 25, 17 [in Chinese].
53. Lu, J.; Chew, E.H.; Holmgren, A. Targeting thioredoxin reductase is a basis for cancer therapy by arsenic trioxide. Proc. Natl. Acad. Sci. U.S.A., 2007, 104, 12288-12293 (Pubitemid 47206130)
54. Apseloff, G.Therapeutic uses of gallium nitrate: past, present, and future. Am.J.Ther., 1999, 6, 327-339
55. Collery, P.; Lechenault, F.; Cazabat, A.; Juvin, E.;Khassanova, L.; Evangelou, A.; Keppler, B., Inhibitory effects of gallium chloride and tris (8-quinolinolato) gallium III on A549 human malignant cell line Anticancer Res. 2000, 20, 955-958
56. Arion, V.B.;jakupec,M.A.;galanski,M.;Unfried,P.; Keppler, B.K.,Synthesis, structure, spectroscopic and in vitro antitumour studies of a novel gallium(III) complex with 2-acetylpyridine (4)N-dimethylthiosemicarbazone J.Inorg.Biochem, 2002, 91, 298-305.
57. Knorr, G. M.; Chitambar, C. R. Gallium-pyridoxal isonicotinoyl hydrazone (Ga-PIH), a novel cytotoxic gallium complex. A comparative study with gallium nitrate. Anticancer Res.1998, 18, 1733-1737
58. IV-Protein Complex: Potential Relevance to Anticancer Activity of Titanocenes Angew Chem., Int. Ed. Engl. 1998, 37, 1577-1579
59. Christodoulou, C. V.; Ferry, D. R.; Fyfe, D. W.; Young, A.; Doran, J.; Sheehan, T. M.; Eliopoulos, A.; Hale, K.; Baumgart, J.; Sass, G.; Kerr, D. J. Phase I trial of weekly scheduling and pharmacokinetics of titanocene dichloride in patients with advanced cancer. J. Clin. Oncol. 1998, 16, 2761-2769 (Pubitemid 28363042)
60. Korfel, A.; Scheulen, M. E.; Schmoll, H. J.; Grundel, O.; Harstrick, A.; Knoche, M.; Fels, L. M.; Skorzec, M.; Bach, F.; Baumgart, J.; Sass, G.; Seeber, S.; Thiel, E.; Berdel, W. E. Phase I clinical and pharmacokinetic study of titanocene dichloride in adults with advanced solid tumors. Clin.Cancer Res. 1998, 4, 2701-2708 (Pubitemid 28523495)
61. Keppler, B. K.; Friesen, C.; Moritz, H. G.; Vongerichten, H.;Vogel, E. Struct. Bonding 1991, 78, 97.
62. Schilling, T.; Keppler, K. B.; Heim, M. E.; Niebch, G.; Dietzfelbinger,H.; Rastetter, J.; Hanauske, A. R. Clinical phase I and pharmacokinetic trial of the new titanium complex budotitane.Invest. New Drugs 1996, 13, 327-332
63. Schwietert C. W. and McCue J. P., Coordination compounds in medicinal chemistry, Coordination Chemistry Reviews, 1999, 84, 67-89.
64. Caruso F., Rossi M., Antitumor titanium compounds, Mini Rev Med Chem., 2004, 4, 49-60.
65. Schroeder, H.A.; Balassa, J.J.; Vinton, W.H. Chromium, Lead, Cadmium, Nickel and Titanium in Mice: Effect on Mortality, Tumors and Tissue Levels Jr., J. Nutr. 1964, 83, 239-250
66. Nakamura, T.M.; Morin, G.B.; Chapman, K.B.; Weinrich, S.L.; Andrews, W.H.; Linger, J.; Harley, C.B.; Cech, T.R. Telomerase catalytic subunit homologs from fission yeast and human. Science 1997, 277, 955-959
67. Meyerson, M.; Counter, C.M.; Eaton, L.E.; Ellison, L.W.; Steiner, P.; Caddle, S.D.; Ziaugra, L.; Beijersbergen, R. L.; Davidoff, M. J.; Liu, Q.; Bacchetti, S.; Haber, D.A.; Weinberg, R. A. Cell 1997, 90, 785.
68. Duffy, B.; Schwietert, C.W.; France, A.; Mann, N.; K. Culbertson,; Harmon, B.; McCue, J.P. Transition metals as protease inhibitors. Biol. Trace Elem. Res. 1998, 64, 197-213.
69. Kim, N.W.; Piatyszek, M.A.; Prowse, K.R.; Harley, C.B.; West, M.D.; Ho, P.L.; Coviello, G. M.; Wright, W. E.; Weinrich, S. L.; Shay, J.W. Specific association of human telomerase activity with immortal cells and cancer. Science 1994, 266, 2011-2015
70. Fichtinger-Schepman, A.M.; van Dijk-Knijnenburg, H.C.; van der Velde-Visser, S.D.; Berends, F.; Baan, R.A. Cisplatin- and carboplatin-DNA adducts: is Pt-AG the cytotoxic lesion? Carcinogenesis 1995, 16, 2447-2453
71. Kohlstaedt, L.A.; Wang, J.; Friedman, J.M.; Rice, P.A.; Steitz, T.A. Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science 1992, 256, 1783-1790
72. Parish, R.V.; Mack, J.; Hargreaves, L.; Wright, J.P. J. Chem. Soc. Dalton. Trans., Chemical and biological reactions of diacetato [2-(dimethylaminomethyl)-phenyl] gold (III), [Au (O2CMe)2(dmamp)] 1996, 69-74.
73. Sadler, P.J.; Sue, R.E. The Chemistry of Gold Drugs. Met. Based Drugs, 1994, 1, 107-144
74. 1H NMR studies. J Inorg Biochem., 1987, 31, 267-281
75. Berners-Price, S.J.; Mirabelli, C.K.; Johnson, R.K.; Mattern, M.R.; McCabe, F.L.; Faucette, L.F.; Sung, C.M.; Mong, S.M.; Sadler, P.J.; Crooke, S.T. In Vivo Antitumor Activity and in Vitro Cytotoxic Properties of Bis[1,2-bis(diphenylphosphino)ethane]gold(I) Chloride Cancer Res., 1986, 46, 5486-5493 (Pubitemid 17177932)
76. Mirabelli, C.K.; Johnson, R.K.; Hill, D.T.; Faucette, L.; Girard, G.R.; Kuo, G.Y.; Sung, C.M.; Crooke, S.T. Correlation of the in vitro cytotoxic and in vivo antitumor activities of gold(I) coordination complexes J. Med. Chem., 1986, 29, 218-223
77. Agrawal, K.C.; Bears, K.B.; Marcus, D.; Jonassen, H.B., Gold triphenylphosphine complexes as a new class of potential antitumor agents. Proc. Am. Assoc. Cancer Res., 1978, 18, 28.
78. Berners-Price S.J.; Mirabelli C.K.; Johnson R.K.; Mattern M.R.; McCabe F.L.; Faucette L.F.; Sung C.M.; Mong S.M.; Sadler P.J.; Crooke S.T. In vivo antitumor activity and in vitro cytotoxic properties of bis [1,2- bis(diphenylphosphino)ethane]gold(I) chloride, Cancer Res., 1986, 46, 5486.
79. Shaw III CF, in: H. Schmidbaur (Ed.), Gold-Progress in Chemistry, Biochemistry and Technology, Wiley, New York, 1999, pp.259-308.
80. 99mTcOAADT]-(CH2)2NEt2: a potential small molecule single-photon emission computed tomography probe for imaging metastatic meloma, Cancer Res., 2005, 15, 4979.
81. Pillarsetty, N.; Katti, K. K.; Hoffman, T.J.; Volkert, W.A.; Katti, K.V.; Kamei, H.; Koide, T.In vitro and in vivo antitumor properties of tetrakis ((trishydroxymethyl)phosphine) gold(I) chloride. J Med Chem, 2003, 46, 1130-1132
82. Blank, C.E.; Dabrowiak, J.C. Absorption and circular dichroism studies of gold (I)-DNA complex. J. Inorg. Biochem., 1984, 21, 21.
83. Dong, Y.; Berners-Price, S.J.; Thorburn, D.R.; Antalis, T.; Dickinson, J.; Hurst, T.; Qiu, L.; Khoo, S.K.; Parsons, P.G. Serine protease inhibition and mitochondrial dysfunction associated with cisplatin resistance in human tumor cell lines: targets for therapy. Biochem Pharmacol., 1997, 53, 1673.
84. Marcon, G.; Carotti, S.; Coronnello, M.; Messori, L.; Mini, E.; Orioli, P.; Mazzei, T.; Cinellu, M.A.; Minghetti, G. Gold (III) complexes with bipyridyl ligands: solution chemistry, cytotoxicity and DNA binding properties. J. Med. Chem., 2002, 45, 1672.
85. Mckeage, M.J.; Maharaj, L.; Berners-Price, S.J. Mechanisms of cytotoxicity and antitumor activity of gold (I) phosphine complexes: the possible role of mitochondria. Coord. Chem. Rev., 2002, 232, 127.
86. Rigobello, M.P.; Messori, L.; Marcon, G.; Cinellu, M.A.; Bragadin, M.; Folda, A.; Scutari, G.; Bindoli, A. Gold complexes inhibit mitochondrial thioredoxin reductase: consequences on mitochondrial functions. J. Inorg. Biochem., 2004, 98, 16341641. (Pubitemid 39349189)
87. Berners-Price, S.J.; Girard, G.R.; Hill, D.T.; Sutton, B.M.; Jarrett, P.S.; Faucette, L.F.; Johnson, R.K.; Mirabelli, C.K.; Sadler, P.J. J.Med. Chem., 1990, 33 1386.
88. 3. J. Am. Chem. Soc., 1987, 109, 3810.
89. 3)] (HL=pyrazoleandimidazole). J. Inorg. Biochem., 2000, 78, 363.
90. Yang, T.; Tu, C.; Zhang, J.; Lin, L.; Zhang, X.; Liu, Q.; Ding, J.; Xu, Q.; Guo, Z. Novel Au (III) complexes of aminoquinoline derivatives: crystal structure, DNA binding and cytotoxicity against melanoma and lung tumour cells. J. Chem. Soc., Dalton Trans., 2003, 3419.
91. Messori, L.; Abbate, F.; Marcon, G.; Orioli, P.; Fontani, M.; Mini, E.; Mazzei, T.; Carotti, S.; O'Connell, T.; Zanello, P. Gold (III) complexes as potential antitumor agents: Solution chemistry and cytotoxic properties of some selected gold (III) compounds. J. Med. Chem., 2000, 43, 3541.
92. Henderson, W.; McCaffery, L.J.; Nicholson, B.K. Synthesis and biological activity of platinum (II) and palladium (II) thiosalicylate complexes with mixed ancillary donor ligands. J. Chem. Soc., Dalton Trans., 2000, 2753.
93. Che, C.M.; Sun, R.W.; Yu, W.Y.; Ko, C.B.; Zhu, N.; Sun, H. Gold (III) porphyrins as a new class of anticancer drugs: Cytotoxicity, DNA binding and induction of apoptosis in human cervix epitheloid cancer cells. Chem. Commun., 2003, 1718.
94. Reisner, E.; Arion, V.B.; Keppler, B.K.; Pombeiro, A.J. Electron-transfer activated metal-based anticancer drugs, Inorganica Chemica Acta, 2008, 361, 1569.
95. Erek, A.; Rainen, L.; Whileyman, J.; Chang, I.M.; Kimball, A.P.; Bear, J. Studies of rhodium(II) carboxylates as potential antitumor agents. Proc. Soc. Exp. Bio. Med., 1974, 145, 1278.
96. Eliopoulos, A.G.; Kerr, D.J.; Herod, J.; Hodgkins, L.; Krajewski, S.; Reed, J.C.; Young, L.S. The control of apoptosis and drug resistance in ovarian cancer: influence of p53 and Bcl-2. Oncogene, 1995, 11, 1217.
97. 2+ and pH. Biochem. Biophys. Res. Communication, 1992, 186, 782.
98. 2.4EtoH (bipy=2,2′′bipyridine). Bioinorganic Chemistry and Applications, 2006, Article ID 80283, 1.
99. 2 = malonic acid) using human cancer cells. Cancer Letters, 2007, 247, 224.
100. 4 using human epithelial cell lines. Chem. Biol. Interact., 2006, 164, 115.
101. 4 (phendio = 1,10-phenanthroline-5,6-dione) and its effects on fungal and mammalian cells. Biometals, 2004, 17, 635.
102. Holzer, A.K.; Manorek, G.H.; Howell, S.B. Contribution of the major copper influx transporter CTR1 to the cellular accumulation of cisplatin, carboplatin, and oxaliplatin. Mol. Pharmacol., 2006, 70, 1390-1394
103. Kuo, M.T.; Chen, H.H.; Song, I.S.; Savaraj, N.; Ishikawa, T. The roles of copper transporters in cisplatin resistance. Cancer Metastasis Rev. 2007, 26, 71-83. (Pubitemid 46452185)
104. Borst, P., Elferink, R.O., 2002. Mammalian ABC transporters in health and disease. Annu. Rev. Biochem. 71, 537-592.
105. Calcagno, A.M.; Kim, I.W.; Wu, C.P.; Shukla, S.; Ambudkar, S.V. ABC drug transporters as molecular targets for the prevention of multidrug resistance and drug-drug interactions. Curr. Drug Deliv., 2007, 4, 324-333
106. Fojo, T.; Bates, S. Strategies for reversing drug resistance. Oncogene, 2003, 22, 7512-7523
107. Szakacs, G.; Paterson, J.K.; Ludwig, J.A.; Booth-Genthe, C.; Gottesman, M.M., Targeting multidrug resistance in cancer. Nat. Rev. Drug Discov. 2006, 5, 219-234.
108. Wosikowski, K.; Lamphere, L.; Unteregger, G.; Jung, V.; Kaplan, F.; Xu, J. P.; Rattel B.; Caligiuri, M. Preclinical antitumor activity of the oral platinum analog satraplatin. Cancer Chemother.Pharmacol., 2007, 60, 589-600. (Pubitemid 47084271)
109. Jedlitschky, G.; Hoffmann, U.; Kroemer, H.K. Structure and function of the MRP2 (ABCC2) protein and its role in drug disposition. Expert Opin. Drug Metab. Toxicol., 2006, 2, 351-366
110. Salerno, M.; Petroutsa, M.; Garnier-Suillerot, A. The MRP1-mediated effluxes of arsenic and antimony do not require arsenic-glutathione and antimony-glutathione complex formation. J. Bioenerg. Biomembr., 2002, 34, 135-145 (Pubitemid 34477976)
111. Seo, T.; Urasaki, Y.; Ueda, T. Establishment of an arsenic trioxideresistant human leukemia cell line that shows multidrug resistance. Int.J. Hematol., 2007, 85, 26-31. (Pubitemid 46193286)
112. Tachiwada, T.; Chen, Z.S.; Che, X.F., et al., Isolation and characterization of arsenite-resistant human epidermoid carcinoma KB cells. Oncol.Rep., 2007, 18, 721-727
113. Vernhet, L.; Allain, N.; Le Vee, M.; Morel, F.; Guillouzo, A.; Fardel, O. Blockage of multidrug resistance-associated proteins potentiates the inhibitory effects of arsenic trioxide on CYP1A1 induction by polycyclic aromatic hydrocarbons. J. Pharmacol. Exp. Ther., 2003, 304, 145-155 (Pubitemid 36008922)
114. Vernhet, L.; Allain, N.; Payen, L.; Anger, J.P.; Guillouzo, A.; Fardel, O. Resistance of human multidrug resistance-associated protein 1-overexpressing lung tumor cells to the anticancer drug arsenic trioxide.Biochem. Pharmacol. Biochem. Pharmacol., 2001, 61, 1387-1391 (Pubitemid 32452354)
115. Takeshita, A.; Shinjo, K.; Naito, K.; et al., Pglycoprotein (P-gp) and multidrug resistanceassociated protein 1 (MRP1) are induced by arsenic trioxide (As(2)O(3)), but are not the main mechanism of As2O3-resistance in acute promyelocytic leukemia cells.Leukemia, 2003, 17, 648-650
116. Vock, C.A.; Ang, W.H.; Scolaro, C.; et al., Development of ruthenium antitumor drugs that overcome multidrug resistance mechanisms. J. Med. Chem., 2007, 50, 2166-2175
117. Heffeter, P.; Jakupec, M.A.; Korner, W.; Chiba, P.; Pirker, C.; Dornetshuber, R.; Elbling, L.; Sutterluty, H.; Micksche, M.; Keppler, B.K.; Berger, W. Multidrug-resistant cancer cells are preferential targets of the new antineoplastic lanthanum compound KP772 (FFC24). Biochem.Pharmacol., 2007, 73, 1873-1886 (Pubitemid 46677901)
118. Mellish, K.J.; Kelland, L.R. Mechanisms of acquired resistance to the orally active platinum-based anticancer drug bis-acetato- amminedichlorocyclohexylamine platinum (i.v.) (JM216) in two human ovarian carcinoma cell lines. Cancer Res., 1994, 54, 6194-6200.
119. Perego, P.; Gatti, L.; Righetti, S.C.; Beretta, G. L.; Carenini, N.; Corna, E.; Bo, L.D.; Tinelli, S.; Colangelo, D.; Leone, R.; Apostoli, P.; Lombardi L.; Beggiolin, G.; Piazzoni, L.; Zunino, F. Development of resistance to a trinuclear platinum complex in ovarian carcinoma cells. Int. J. Cancer 2003, 105, 617-624 (Pubitemid 36687728)
120. Kasparkova, J.; Novakova, O.; Vrana, O.; Intini, F.; Natile, G.; Brabec, V. Molecular aspects of antitumor effects of a newplatinum (IV) drug.Mol. Pharmacol. Mol. Pharmacol. 2006, 70, 1708-1719 (Pubitemid 44776430)
121. Kozubik, A.; Horvath,V.; Svihalkova-Sindlerova, L.; Soucek, K.; Hofmanova, J.; Sova, P.; Kroutil, A.; Zak, F.; Mistr, A.; Turanek, J. High effectiveness of platinum(IV) complex with adamantylamine in overcoming resistance to cisplatin and suppressing proliferation of ovarian cancer cells in vitro. Biochem. Pharmacol., 2005, 69, 373-383 (Pubitemid 40094498)
122. Zhou, P.; Kalakonda, N.; Comenzo, R.L. Changes in gene expression profiles of multiple myeloma cells induced by arsenic trioxide (ATO):possible mechanisms to explain ATO resistance in vivo. Br. J. Haematol., 2005, 128, 636-644
123. Kitamura, K.; Minami, Y.; Yamamoto, K.; Akao, Y.; Kiyoi, H.; Saito,H.; Naoe, T. Involvement of CD95-independent caspase 8 activation in arsenic trioxide-induced apoptosis.Leukemia, 2000, 14, 1743-1750
124. Duechler, M.; Stanczyk, M.; Czyz, M.; Stepnik, M. Potentiation of arsenic trioxide cytotoxicity by Parthenolide and buthionine sulfoximine in murine and human leukemic cells. Cancer Chemother. Pharmacol., 2007, 61, 727-737. (Pubitemid 351302028)
125. Grad, J.M.; Bahlis, N.J.; Reis, I.; Oshiro, M.M.; Dalton, W.S.; Boise, L.H. Ascorbic acid enhances arsenic trioxide-induced cytotoxicity in multiple myeloma cells. Blood, 2001, 98, 805-813
126. Huang, R.N.; Lee, T.C. Arsenite efflux is inhibited by verapamil, cyclosporin A, and GSH-depleting agents in arsenite-resistant Chinese hamster ovary cells. Toxicol. Appl. Pharmacol., 1996, 141, 17-22.
127. Biaglow, J.E.; Miller, R.A. The thioredoxin reductase/thioredoxin system: novel redox targets for cancer therapy. Cancer Biol., Ther. 2005, 4, 6-13. (Pubitemid 41350919)
128. Urig, S.; Becker, K. On the potential of thioredoxin reductase inhibitors for cancer therapy. Semin. Cancer Biol., 2006, 16, 452-465 (Pubitemid 44780136)
129. Lu, J.; Chew, E.H.; Holmgren, A. Targeting thioredoxin reductase is a basis for cancer therapy by arsenic trioxide. Proc. Natl. Acad. Sci. U.S.A., 2007, 104, 12288-12293 (Pubitemid 47206130)
130. Witte, A.B.; Anestal, K.; Jerremalm, E.; Ehrsson, H.; Arner, E.S. Inhibition of thioredoxin reductase but not of glutathione reductase by the major classes of alkylating and platinum-containing anticancer compounds. Free Radic. Biol. Med., 2005, 39, 696-703.
131. Milacic, V.; Fregona, D.; Dou, Q.P. Gold complexes as prospective metal-based anticancer drugs. Histol. Histopathol., 2008, 23, 101-108
132. Holford, J.; Raynaud, F.; Murrer, B.A.; Grimaldi, K.; Hartley, J.A.; Abrams, M.; Kelland, L.R. Chemical, biochemical and pharmacological activity of the novel sterically hindered platinum co-ordination complex, cis-[amminedichloro(2-methylpyridine)] platinum(II) (AMD473). Anticancer Drug Des., 1998, 13, 1-18.
133. Holford, J.; Sharp, S.Y.; Murrer, B.A.; Abrams, M.; Kelland, L.R. In vitro circumvention of cisplatin resistance by the novel sterically hindered platinum complex AMD473. Br. J. Cancer, 1998, 77, 366-373
134. Ang, W.H.; Khalaila, I.; Allardyce, C.S.; Juillerat- Jeanneret, L.; Dyson, P.J. Rational design of platinum(IV) compounds to overcome glutathione-S-transferase mediated drug resistance. J. Am. Chem. Soc., 2005, 127, 1382-1383
135. Ang, W.H.; De Luca, A.; Chapuis-Bernasconi, C.; Juillerat-Jeanneret, L.; Lo Bello, M.; Dyson, P.J. Organometallic ruthenium inhibitors of glutathione-S-transferase P1-1 as anticancer drugs. ChemMedChem, 2007, 2, 1799-1806.
136. Majumder, S.; Panda, G.S.; Choudhuri, S.K. Synthesis, characterization and biological properties of a novel copper complex. Eur. J. Med.Chem., 2003, 38, 893-898 (Pubitemid 37311403)
137. Majumder, S.; Dutta, P.; Mookerjee, A.; Choudhuri, S.K. The role of a novel copper complex in overcoming doxorubicin resistance in Ehrlich ascites carcinoma cells in vivo. Biol. Interact., 2006, 159, 90-103.
138. Siddik, Z.H. Cisplatin: mode of cytotoxic action and molecular basis of resistance. Oncogene, 2003, 22, 7265-7279 (Pubitemid 37487159)
139. Silverman, A.P.; Bu, W; Cohen, S.M.; Lippard, S.J. 2.4-Å Crystal structure of the asymmetric platinum complex [Pt(ammine) (cyclohexylamine)]2+ bound to a dodecamer DNA duplex. J. Biol.Chem., 2002, 277, 49743-49749
140. Gossage, L.; Madhusudan, S. Current status of excision repair cross complementing-group 1 (ERCC1) in cancer. Cancer Treat. Rev., 2007, 33, 565-577 (Pubitemid 47355341)
141. Alt, A.; Lammens, K.; Chiocchini, C.; Lammens, A.; Pieck, J.C.; Kuch, D.; Hopfner, K.P.; Carell, T. Bypass of DNA lesions generated during anticancer treatment with cisplatin by DNApolymerase eta. Science, 2007, 318, 967-970 (Pubitemid 350098991)
142. Chaney, S.G.; Campbell, S.L.; Bassett, E.; Wu, Y. Recognition and processing of cisplatin- and oxaliplatin-DNA adducts. Crit. Rev. Oncol.Hematol., 2005, 53, 3-11.
143. Chaney, S.G.; Vaisman, A. Specificity of platinum-DNA adduct repair. J. Inorg. Biochem., 1999, 77, 71-81.
144. Fink, D.; Nebel, S.; Aebi, S.; Zheng, H.; Cenni, B.; Nehme, A.; Christen, R.D.; Howell, S.B. The role of DNA mismatch repair in platinum drug resistance. Cancer Res., 1996, 56, 4881-4886 (Pubitemid 26374423)
145. Kelland, L. The resurgence of platinum-based cancer chemotherapy. Nat. Rev. Cancer, 2007, 7, 573-584
146. Colella, G.; Pennati, M.; Bearzatto, A.; Leone, R.; Colangelo, D.; Manzotti, C.; Daidone, M.G.; Zaffaroni, N. Activity of a trinuclear platinum complex in human ovarian cancer cell lines sensitive and resistant to cisplatin: cytotoxicity and induction and gene-specific repair of DNA lesions. Br. J. Cancer, 2001, 84, 1387-1390 (Pubitemid 32522109)
147. Perego, P.; Gatti, L.; Caserini, C.; Supino, R.; Colangelo, D. Leone, R.; Spinelli, S.; Farrell, N.; Zunino, F. The cellular basis of the efficacy of the trinuclear platinum complex BBR 3464 against cisplatinresistant cells. J. Inorg. Biochem., 1999, 77, 59-64. (Pubitemid 30089083)
148. Hayward, R.L.; Macpherson, J.S.; Cummings, J.; Monia, B.P.; Smyth, J.F.; Jodrell, D.I. Enhanced oxaliplatin-induced apoptosis following antisense Bcl-xl down-regulation is p53 and Bax dependent: genetic evidence for specificity of
149. Stewart, D.J. Mechanisms of resistance to cisplatin and carboplatin. Crit. Rev. Oncol. Hematol., 2007, 63, 12-31.
150. Zhang, Y.; Lei, X.Y. Effect of bcl-2 antisense oligodeoxynucleotides on drug sensitivity of leukemic cells. Hematol. J., 2003, 4, 187-197 (Pubitemid 36789973)
151. Silva, C.M.; Shupnik, M.A. Integration of steroid and growth factor pathways in breast cancer: focus on signal transducers and activators of transcription and their potential role in resistance. Mol. Endocrinol., 2007, 21, 1499-1512.
152. Steelman, L.S.; Pohnert, S.C.; Shelton, J.G.; Franklin, R.A.; Bertrand, F.E.; McCubrey, J.A. JAK/STAT, Raf/MEK/ERK, PI3K/Akt and BCR-ABL in cell cycle progression and leukemogenesis. Leukemia, 2004, 18,189-218.
153. Roberts, D.; Schick, J.; Conway, S.; Biade, S.; Laub, P.B.; Stevenson, J.P.; Hamilton, T.C.; O'Dwyer, P.J.; Johnson, S.W. Identification of genes associated with platinum drug sensitivity and resistance in human ovarian cancer cells. Br. J. Cancer, 2005, 92, 1149-1158
154. Gariboldi, M.B.; Ravizza, R.; Molteni, R.; Osella, D.; Gabano, E.; Monti, E. Inhibition of STAT3 increases doxorubicin sensitivity in a human metastatic breast cancer cell line. Cancer Lett., 2007, 258, 181-188 (Pubitemid 350101017)
155. Anagnostopoulou, A.; Vultur, A.; Arulanandam, R.; Cao, J.; Turkson, J.; Jove, R.; Kim, J.S.; Glenn, M.; Hamilton, A.D.; Raptis, L. Differential effects of STAT3 inhibition in sparse vs confluent normal and breast cancer cells. Cancer Lett., 2006, 242, 120-132 (Pubitemid 44485298)
156. Turkson, J.; Zhang, S.; Palmer, J.; Kay, H.; Stanko, J.; Mora, L.B.; Sebti, S.; Yu, H.; Jove, R. Inhibition of constitutive signal transducer and activator of transcription 3 activation by novel platinum complexes with potent antitumor activity. Mol. Cancer Ther., 2004, 3, 1533-1542 (Pubitemid 40136708)
157. Wetzler, M.; Brady, M.T.; Tracy, E.; Li, Z.R.; Donohue, K.A.; O'Loughlin, K.L.; Cheng, Y.; Mortazavi, A.; McDonald, A. A.; Kunapuli, P.; Wallace, P. K.; Baer, M. R.; Cowell, J.K.; Baumann, H. Arsenic trioxide affects signal transducer and activator of transcription proteins through alteration of protein tyrosine kinase phosphorylation. Clin. Cancer Res., 2006, 12, 6817-6825 (Pubitemid 44876852)
158. Katsman, A.; Umezawa, K.; Bonavida, B. Reversal of resistance to cytotoxic cancer therapies: DHMEQ as a chemosensitizing and immuno-sensitizing agent. Drug Resist. Updat., 2007, 10, 1-12. (Pubitemid 46636380)
159. Mathas, S.; Lietz, A.; Janz, M.; Hinz, M.; Jundt, F.; Scheidereit, C.; Bommert, K.; Dorken, B. Inhibition of NF-kappaB essentially contributes to arsenic-induced apoptosis. Blood, 2003, 102, 1028-1034 (Pubitemid 36917800)
160. Kapahi, P.; Takahashi, T.; Natoli, G.; Adams, S.R.; Chen, Y.; Tsien, R.Y.; Karin, M. Inhibition of NF-kappa B activation by arsenite through reaction with a critical cysteine in the activation loop of Ikappa B kinase. J. Biol. Chem., 2000, 275, 36062-36066 (Pubitemid 30841151)
161. Balamurugan, K.; Schaffner, W. Copper homeostasis in eukaryotes: teetering on a tightrope. Biochim. Biophys. Acta, 2006, 1763, 737-746 (Pubitemid 44189543)
162. Laity, J.H.; Andrews, G.K. Understanding the mechanisms of zincsensing by metal-response element binding transcription factor-1 (MTF-1). Arch. Biochem. Biophys., 2007, 463, 201-210
163. Palmiter, R.D. Protection against zinc toxicity by metallothionein and zinc transporter 1. Proc. Natl. Acad. Sci. U.S.A., 2004, 101, 4918-4923 (Pubitemid 38469178)