Transition metal based anticancer drugs

Current Topics in Medicinal Chemistry

Volumn 11, Issue 5, 2011, Pages 521-542

  Garbutcheon Singh, K Benjamin ^a   Grant, Maxine P ^a   Harper, Benjamin W ^a   Krause Heuer, Anwen M ^a   Manohar, Madhura ^a   Orkey, Nikita ^a   Aldrich Wright, Janice R ^a  

^a UNIVERSITY OF WESTERN SYDNEY   (Australia)

Author keywords

Cobalt; Copper; Gold; Palladium; Platinum; Ruthenium; Titanium; Vanadium

Indexed keywords

1,10 PHENANTHROLINE TETRADENTATE; 9 AMINO 4 ACRIDINECARBOXAMIDE; ANTINEOPLASTIC AGENT; AURANOFIN; CARBOPLATIN; CISPLATIN; CS 292; DNA; GOLD COMPLEX; IMIDAZOLE; IPROPLATIN; METAL COMPLEX; METALLOOCENE; N [3 N (ETHYLENEDIAMINO)PROPYL]ACRIDIN 4 CARBOXAMIDEDICHLOROPLATINUM; NEDAPLATIN; OXALIPLATIN; OXOPLATIN; PALLADIUM COMPLEX; PLATINUM COMPLEX; PROFLAVINE; RUTHENIUM; SATRAPLATIN; STAUROSPORINE; TETRAPLATIN; TITANIUM DERIVATIVE; TRANS AMMINEDICHLORO(CYCLOHEXYLAMINE)DIHYDROXOPLATINUM; TRANSITION ELEMENT; TRANSPLATIN; TRIPLATIN TETRANITRATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER CELL; CANCER RESISTANCE; CANCER THERAPY; CAUSE OF DEATH; COLORECTAL CANCER; CRYSTAL STRUCTURE; DNA REPLICATION; DNA TRANSCRIPTION; DRUG BINDING; DRUG DESIGN; DRUG DNA INTERACTION; DRUG DOSE INCREASE; DRUG EFFICACY; DRUG HALF LIFE; DRUG INHIBITION; DRUG UPTAKE; GASTROINTESTINAL TOXICITY; HUMAN; LYMPHATIC LEUKEMIA; NEPHROTOXICITY; NEUTROPENIA; NONHUMAN; OVARY CANCER; PREVALENCE; STRUCTURE ACTIVITY RELATION; TESTIS CANCER; UTERINE CERVIX CANCER;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; DNA, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; NEOPLASMS; ORGANOMETALLIC COMPOUNDS; TRANSITION ELEMENTS;

EID: 79952772825     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802611794785226     Document Type: Article

References (235)

1. Jemal, A., Siegel, R., Ward, E., Murray, T., Xu, J., Smigal, C., Thun, M. J. Cancer Statistics, 2006, CA Cancer J. Clin. 2006, 56, 106-130.
2. Giaccone, G. Clinical perspectives on platinum resistance. Drugs Exp. Clin. Res., 2000, 59 (Suppl. 4), 9-17.
3. Chabner, B. A.; Allegra, C. J.; Curt, G. A.; Calabresi, P. In: Goodman and Gilman's The Pharmacological Basis of Therapeutics. Hardman, G. J.; Limbird, E. L.; Gilman, G. A. Eds.; McGraw-Hill: New York, 1996.
4. Loehrer, P. J.; Einhorn, L. H. Diagnosis and treatment: drugs five years later. Ann. Intern. Med., 1984, 100, 704-713.
5. Jamieson, E. R.; Lippard, S. J. Structure, recognition, and processing of cisplatin-DNA adducts. Chem. Rev., 1999, 99, 2467-2498.
6. Kelland, L. R. Preclinical perspectives on platinum resistance. Drugs Exp. Clin. Res., 2000, 59 (Suppl. 4), 1-8.
7. Bruijnincx, P. C. A.; Sadler, P. J. New trends for metal complexes with anticancer activity. Curr. Opin. Chem. Biol., 2008, 12, 197-206.
8. Franklin, C. A.; Fry, J. V.; Collins, J. G. NMR evidence for sequence-specific DNA minor groove binding by bis(ethylenediamine)platinum(II). Inorg. Chem., 1996, 35, 7541-7545.
9. Blackburn, G. M.; Gait, M. J. Nucleic Acids in Chemistry and Biology. Oxford University Press: New York, 1996.
10. Gessner, R. V.; Quigley, G. J.; Wang, A. H. J.; Van der Marel, G. A.; Van Boom, J. H.; Rich, A. Structural basis for stabilization of Z-DNA by cobalt hexaammine and magnesium cations. Biochemistry, 1985, 24, 237-240.
11. Neidle, S.; Jones, T. A. Crystal structure structure proflavine, a DNA binding agent. Nature, 1975, 253, 284-285.
12. Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Biver, T.; Boggioni, A.; Bonacchi, S.; Danesi, A.; Giorgi, C.; Gratteri, P.; Ingraín, Antonio M.; Secco, F.; Sissi, C.; Valtancoli, B.; Venturini, M. DNA binding by a new metallointercalator that contains a proflavine group bearing a hanging chelating unit. Chem. Eur. J., 2008, 14, 184-196.
13. Sarma, R. H. Nucleic Acid Geometry & Dynamics, Pergamon Press: Oxford, 1980.
14. Farrell, N. Transition Metal Complexes as Drugs and Chemotherapeutic Agents, Springer: USA 1989.
15. Sherman, S. E.; Gibson, D.; Wang, A. H. J.; Lippard, S. J. Crystal and Molecular Structure of cis-Pt(NH3)2{d(pGpG)}], the principal adduct formed by cis-diamminedichloroplatinum(II) with DNA. J. Am. Chem. Soc., 1988, 110, 7368-7381.
16. Huang, H.; Woo, J.; Ally, S. C.; Hopkins, P. H. DNA-DNA interstrand cross-linking by cis-diamminedichloroplatinum(II): N7(dG)-to-N7(DG) cross-linking at 5'-d(GC) in synthetic oligonucleotides. Bioorg. Med. Chem. Lett., 1995, 3, 659-669.
17. Huang, H.; Zhu, L.; Reid, B. R.; Drobny, G. P.; Hopkins, P. B. Solution structure of a cisplatin-induced DNA interstand cross link. Science, 1995, 270, 1842-1845.
18. Kasparkova, J.; Brabec, V. Recognition of DNA interstrand crosslinks of cis-diamminedichloroplatinum(II) and its trans isomer by DNA-binding proteins. Biochemistry, 1995, 34, 12379-12387.
19. Cohen, S. M.; Mikata, Y.; He, Q.; Lippard, S. J. HMG-domain protein recognition of cisplatin 1,2-intrastrand d(GpG) cross-links in purine-rich sequence contexts. Biochemistry, 2000, 39, 11771-11776.
20. Caradonna, J. P.; Lippard, S. J.; Gait, M. J.; Singh, M. The antitumor drug cis-dichlorodiammineplatinum forms an intrastrand d(GpG) crosslink upon reaction with [d(ApGpGpCpCpT)]2. J. Am. Chem. Soc., 1982, 104, 5793-5795.
21. Boulikas, T.; Vougiouka, M. Cisplatin and platinum drugs at the molecular level. Oncol. Rep., 2003, 10, 1663-1682.
22. Qu, Y.; Scarsdale, N. J.; Tran, M.-C.; Farell, N. Cooperative effects in long-range 1,4 DNA-DNA interstrand cross-links formed by polynuclear platinum complexes: an unexpected syn orientation of adenine bases outside the binding sites. J. Inorg. Biol. Chem., 2003, 8, 19-28.
23. Qu, Y.; Scarsdale, N. J.; Tran, M.-C.; Farell, N. Comparison of structural effects in 1,4 DNA-DNA interstrands cross-links formed by di and trinuclear platinum complexes. J. Inorg. Biochem., 2004, 98, 1585-1590.
24. Fuertes, M. A.; Castilla, J.; Alonso, C.; Perez, J. M. Novel concepts in the development of platinum antitumor drugs. Curr. Med.Chem.: Anti-Cancer Agents, 2002, 2, 539-551.
25. McLachlan, G. A.; Muller, J. G.; Rokita, S. E.; Burrows, C. J. Metal-mediated oxidation of guanines in DNA and RNA: A comparison of cobalt(II), nickel(II) and copper(II) complexes. Inorg. Chim. Acta, 1996, 251, 193-199.
26. Barton, J. K.; Lolis, E. Chiral discrimination in the covalent binding of bis(phenanthroline)dichlororuthenium(II) to B-DNA. J. Am. Chem. Soc., 1985, 107, 708-709.
27. Mahnken, R. E.; Billadeau, M. A.; Nikonowicz, E. P.; Morrison, H. Development of Photo cis-platinum reagents. Reaction of cisdichlorobis(1,10-phenanthroline)rhodium(III) with calf thymus DNA, nucleotides and nucleosides. J. Am. Chem. Soc., 1992, 114, 9253-9265.
28. Mahnken, R. E.; Bina, M.; Deibel, R. M.; Luebke, K.; Morrison, H. Photochemically induced binding of Rh(phen)2Cl2+ to DNA. Photochem. Photobiol., 1989, 49, 519-522.
29. Mohammad, T.; Chen, C.; Guo, P.; Morrison, H. Photoinduced cross-linking of RNA by cis-[Rh(phen)2Cl2]+ and cis- [Rh(phen)(phi)]Cl2 +: A new family of light activatable nucleic acid cross-linking agents. Bioorg. Med. Chem. Lett., 1999, 9, 1703-1708.
30. Mohammad, T.; Morrison, H. Simultaneous photoconjugation of methylene blue and cis-[Rh(phen)2Cl2]+ to DNA via a synergistic effect. Photochem. Photobiol., 2000, 71, 369-381.
31. 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.
32. Bowler, B. E.; Hollis, L. S.; Lippard, S. J. Synthesis and dna binding and photonicking properties of acridine orange linked by a polymethylene tether to (1,2-diaminoethane)dichloroplatinum(II). J. Am. Chem. Soc., 1984, 106, 6102-6104.
33. Bowler, B. E.; Ahmed, K. J.; Sundquist, W. I.; Hollis, L. S.; Whang, E. E.; Lippard, S. J. Synthesis, characterization, and DNAbinding properties of (1,2-diaminoethane)platinum(II) complexes linked to the dna intercalator acridine-orange by trimethylene and hexamethylene chains. J. Am. Chem. Soc., 1989, 111, 1299-1306.
34. Lippard, S. J.; Bowler, B. E. Modulation of platinum antitumour drug binding to DNA by linked and free intercalators. Biochemistry, 1986, 3031-3038.
35. Sundquist, W. I.; Bancroft, D. P.; Chassot, L.; Lippard, S. J. DNA promotes the reaction of cis-diamminedichloroplatinum(II) with the exocyclic amino groups of ethidium bromide. J. Am. Chem. Soc., 1988, 110, 8559-8560.
36. Grahman, D. R.; Marshall, L. E.; Reich, K. A.; Sigman, D. S. Cleavage of DNA by coordination complexes. superoxide formation in the oxidation of 1,10-phenanthroline-cuperous complexes by oxygen-relevance to DNA cleavage reactions. J. Am. Chem. Soc., 1980, 102, 5419-5421.
37. Thederahn, T. B.; Kuwabara, M. D.; Larsen, T. A.; Sigman, D. S. Activity of 1,10-phenanthroline-copper. J. Am. Chem. Soc., 1989, 111, 4941-4946.
38. Kim, S. K.; Norden, B. Methyl Green - a DNA major-groove binding drug. FEBS Lett., 1993, 315, 61-64.
39. Long, E. C.; Barton, J. K. On demonstrating DNA intercalation. Acc. Chem. Res., 1990, 23, 271-273.
40. Friedman, A. E.; Kumar, C. V.; Turro, N. J.; J.K. B. Luminescence: Evidence for intercalative binding to Z-DNA. Nucl. Acids Res., 1991, 19, 2595-2602.
41. Coury, J. E.; Anderson, J. R.; McFail-Isom, L.; Williams, L. D.; Bottomley, L. A. Scanning force microscopy of small ligandnucleic acid complexes: Tris(o-phenanthroline)ruthenium(II) as a test for a new assay. J. Am. Chem. Soc., 1997, 119, 3792-3796.
42. Eriksson, M.; Leijon, M.; Hiort, C.; Norden, B.; Graeslund, A. Minor groove binding of [Ru(phen)3]2+ to [d(CGCGATCGCG)]2 evidenced by two-dimensional NMR. J. Am. Chem. Soc., 1992, 114, 4933-4934.
43. Mei, H. Y.; Barton, J. K. Tris(tetramethylphenanthroline) ruthenium(II): A chiral probe that cleaves A-DNA conformations. Proc. Natl. Acad. Sci. USA, 1988, 85, 1339-1343.
44. Pindur, U.; Haber, M.; Sattler, K. Antitumor active drugs as intercalators of deoxyribonucleic acid: molecular models of intercalation complexes. J. Chem. Educ., 1993, 70, 263-272.
45. Lerman, L. S. Structural consideration in the interactions of DNA and acridines. J. Mol. Biol., 1961, 3, 18-30.
46. Berman, H. M.; Young, P. R. The interaction of intercalating drugs with nucleic acids. Ann. Rev. Biophys. Bioeng., 1981, 10, 87-114.
47. Odani, A.; Sekiguchi, T.; Okada, H.; Ishiguro, S.-I.; Yamauchi, O. Calormetric and 195Pt NMR studies on aromatic ring stacking between nucleotides and platinum DNA intercalators. Bull. Chem. Soc. Jpn., 1995, 68, 2093-2102.
48. Sundquist, W. I.; Lippard, S. J. The coordination chemistry of platinum anticancer drugs and related compounds with DNA. Coord. Chem. Rev., 1990, 100, 293-322.
49. Gale, E. F.; Cundliffe, E.; Reynolds, P. E.; Richmond, M. H.; Waring, M. J. In: The Molecular Basis of Antibiotic Action; John Wiley and Sons: London, 1972, pp. 173-277.
50. Cohen, G.; Eisenberg, H. Viscosity and sedimentation study of sonicated DNA-proflavine complexes. Biopolymers, 1969, 8, 45-55.
51. Chow, C. S.; Barton, J. K. Shape-Selective cleavage of tRNA Phe by transition-metal complexes. J. Am. Chem. Soc., 1990, 112, 2839-2841.
52. Waring, M. J. Complex formation between ethidium bromide and nucleic acids. J. Mol. Biol., 1965, 13, 269-282.
53. Jennette, K. W.; Gill, J. T.; Sadownick, J. A.; Lippard, S. J. Metallointercalation Reagents. synthesis, characterisation, and structural properties of thiolato(2,2',2-terpyridine)platinum(II) complexes. J. Am. Chem. Soc., 1976, 98, 6159-6168.
54. Howe-Grant, M.; Wu, K. C.; Bauer, W. R.; Lippard, S. J. Binding of platinum and palladium metallointercalation reagents and antitumour drugs to closed and open DNAs. Biochemistry, 1976, 15, 4339-4346.
55. Lippard, S. J.; Bond, P. J.; Wu, K. C.; Bauer, W. R. Stereochemical requirements for intercalation of platinum complexes into doublestranded DNA's. Science, 1976, 194, 726-728.
56. Pyle, A. M.; Barton, J. K. In: Progress in Inorganic Chemistry: Bioionorganic Chemistry, Lippard, S. J. ed.; Wiley-Interscience: New York, 1990; Vol. 38, pp. 413-475.
57. Lippard, S. J. Platinum complexes: probes of polynucleotide structure and antitumour drugs. Acc. Chem. Res., 1978, 11, 211-217.
58. Cusumano, M.; Petro, M. L. D.; Giannetto, A.; Nicolo, F.; Rotondo, E. Noncovalent interactions of platinum(II) square planar complexes containing ligands out-of-plane with DNA. Inorg. Chem., 1998, 37, 563-568.
59. Fisher, D. M. In: School of Chemistry; University of Sydney: Sydney, 2000.
60. Wang, A. H. J.; Nathans, J.; van der Marel, G.; van Boom, J. H.; Rich, A. Molecular structure of a double helical DNA fragment intercalator complex between deoxy CpG and a terpyridine platinum compound. Nature, 1978, 276, 471-474.
61. Barton, J. K.; Goldberg, J. M.; Kumar, C. V.; Turro, N. J. Binding modes and base specificity of tris(phenanthroline)ruthenium(II) enantomers with nucleic acids: Tuning the stereoselectivity. J. Am. Chem. Soc., 1986, 108, 2081-2088.
62. Neidle, S. In: Progress in Medicinal Chemistry. Ellis G. P.; West, G. B. Eds.; Elsevier: Amsterdam, 1979; Vol. 16, pp. 151-221.
63. Schwartz, H. S. Adv. Cancer Chemo., 1979, 1, 1-60.
64. Denny, W. A. Review: DNA-intercalating ligands as anti-cancer drugs: prospects for future design. Anti-Cancer Drug Des., 1989, 4, 241-263.
65. Werner, M. H.; Gronenborn, A. M.; Clore, G. M. Intercalation, DNA kinking, and the control of transcription. Science, 1996, 271, 778-784.
66. Rush, G. E.; Alberts, D. W.; Meunier, P.; Leffler, K.; Smith, P. F. In vivo and in vitro hepatotoxicity of a novel antineoplastic agents SKF101772 in male beagle dogs. Toxicologist, 1987, 7, 59.
67. Wilson, W. D.; Jones, R. L. Intercalating drugs: DNA binding and molecular pharmacology. Adv. Pharmacol. Chemother., 1981, 18, 177-222.
68. Wong, E.; Giandomenico, C. M. Current status of platinum-based antitumour drugs. Chem. Rev., 1999, 99, 2451-2466.
69. Reedijk, J. New Clues for platinum antitumour chemistry: Kinetically controlled metal binding to DNA. Proc. Natl. Acad. Sci. USA, 2003, 100, 3611-3616.
70. Alberts, D. S.; Fanta, P. T.; Running, K. L.; Adair, L. P. Jr.; Garcia, D. J.; Liu-Stevens, R.; Salmon, S. E. In Vitro Phase II comparison of the cytotoxicity of a novel platinum analog, nedaplatin (254-S), with that of cisplatin and carboplatin against fresh, human ovrian cancers. Cancer. Chemother. Pharmacol., 1997, 39, 493-497.
71. Tashiro, T.; Kawada, Y.; Sakurai, Y.; Kidani, Y. Antitumour activity of a new platinum complex, oxalato(trans-l-1,2- diaminocyclohexane)platinum(II): New experimental data. Biomed. Pharmacother., 1989, 43, 251-260.
72. Kraker, A. J.; Moore, C. W. Accumulation of cisdiamminedichloroplatinum(II) and platinum analogues by platinum-ressitant murine leukemia cells. In vitro, Cancer Res., 1988, 48, 9-13.
73. Jakupec, M. A.; Galanski, M.; Arion, V. B.; Hartinger, C. G.; Keppler, B. K. Antitumor metal compounds: More than theme and variations. Dalton Trans., 2008, 183-194.
74. Reedijk, J. The Mechanism of action of platinum anti-tumor drugs. Pure Appl. Chem., 1987, 59, 181-192.
75. Pasini, A.; Zunino, F. New cisplatin analogues - on the way to better antitumour agents. Angew. Chem. Int. Ed. Engl., 1987, 26, 615-624.
76. Alderden, R. A.; Hall, M. D.; Hambley, T. W. The discovery and development of cisplatin. J. Chem. Educ., 2006, 83, 728-734.
77. Collins, J. G.; Wheate, N. J. Potential adenine and minor groove binding platinum complexes. J. Inorg. Biochem., 2004, 98, 1578-1584.
78. Kelly, M.; Dietrich, A.; Gomez-Ruiz, S. Platinum(IV) metallacrown ethers: Synthesis, structures, host properties and anticancer evaluation. Organometallics, 2008, 27, 4917-4927.
79. Hannon, M. J. Metal-based anticancer drugs: From a past anchored in platinum chemistry to a post-genomic future of diverse chemistry and biology. Pure Appl. Chem., 2007, 79, 2243-2261.
80. Heffeter, P.; Jungwirth, U.; Jakupec, M.; Hartinger, C.; Galanski, M.; Elbling, L.; Micksche, M.; Keppler, B.; Berger, W. Resistance against novel anticancer metal compounds: Differences and similarities. Drug Resist. Updates, 2008, 11, 1-16.
81. Maksimoska, J.; Feng, L.; Harms, K.; Yi, C.; Kissil, J.; Marmorstein, R.; Meggers, E. Targeting large kinase active site with rigid, bulky octahedral ruthenium complexes. J. Am. Chem. Soc., 2008, 130, 15764-15765.
82. Reedijk, J. Metal-ligand exchange kinetics in platinum and ruthenium complexes. Significance for effectiveness as anticancer drugs. Platinum Metel. Rev., 2008, 52, 2-11.
83. Hartinger, C. G.; Jakupec, M. A.; Zorbas-Seifried, S.; Groessl, M.; Egger, A.; Berger, W.; Zorbas, H.; Dyson, P. J.; Keppler, B K., KP1019, a New redox-active anticancer agent--preclinical development and results of a clinical phase I study in tumor patients. Chem. Biodivers., 2008, 5, 2140-2155.
84. Maksimoska, J.; Williams Douglas, S.; Atilla-Gokcumen, G. E.; Smalley Keiran, S. M.; Carroll Patrick, J.; Webster Richard, D.; Filippakopoulos, P.; Knapp, S.; Herlyn, M.; Meggers, E. Similar biological activities of two isostructural ruthenium and osmium complexes. Chemistry, 2008, 14, 4816-4822.
85. Ishida, S.; Lee, J.; Thiele, D. J.; Herskowitz, I. Uptake of the anticancer drug cisplatin mediated by the copper transporter Ctr1 in yeast and mammals. Proc. Natl. Acad. Sci. USA, 2002, 99, 14298-14302.
86. De Vizcaya-Ruiz, A.; Rivero-Muller, A.; Ruiz-Ramirez, L.; Kass, G. E. N.; Kelland, L. R.; Orr, R. M.; Dobrota, M. Induction of apoptosis by a novel copper-based anticancer compound, casiopeina II, in L1210 murine leukaemia and CH1 Human ovarian carcinoma cells. Toxicol. Vitro, 2000, 14, 1-5.
87. Puthraya, K. H.; Srivastava, T. S. Some mixed ligand palladium(II) complexes of 2,2'-bipyiridne and amino acids and potential anticancer agents. J. Inorg. Biochem., 1985, 25, 207-215.
88. Casini, A.; Hartinger Christian, G.; Gabbiani, C.; Mini, E.; Dyson Paul, J.; Keppler Bernhard, K.; Messori, L. Gold(III) compounds as anticancer agents: relevance of gold-protein interactions for their mehansim of action. J. Inorg. Biochem., 2008, 102, 564-575.
89. Farrell, N. P. Preclinical perspectives on the use of platinum compounds in cancer chemotherapy. Semin. Oncol., 2004, 31, 1-9.
90. nd, Fukuoka, Dec. 6, 1997, 1998, pp. 49-58.
91. Harris, A. L.; Ryan, J. J.; Farell, N. Biological consequences of trinuclear platinum complexes: Comparison of BBR3464 with its noncovalent congeners. Mol. Pharmacol., 2005, 69, 666-672.
92. Harris, A. L.; Yang, M.; Hegmans, A.; Povirk, L.; Ryan, J. J.; Kelland, L.; Farell, N. Synthesis characterisation and cytotoxicity of a novel highly charged trinuclear platinum(II) compound. enhancement of cellular uptake with charge. Inorg. Chem., 2005, 44, 9598-9600.
93. Hegmans, A.; Berners-price, S. J.; Davies, M. S.; Cox, J. W.; Thomas, D. S.; Humphreys, A. S.; Farell, N. Long Range 1,4 and 1,6-interstrand cross-links formed by a trinuclear platinum complex. minor groove preassociation affects kinetics and mechanism of cross-link formation as well as adduct structure. J. Am. Chem. Soc., 2004, 126, 2166-2180.
94. Kasparkova, J.; Fojta, M.; Farell, N.; Brabec, V. Differential recognition by the tumor surpressor protein p53 of DNA modified by novel antitumor trinuclear Platinum drug BBR3464 and cisplatin. Nucl. Acids Res., 2004, 32, 5546-5552.
95. Nagaich, A. K.; Zhurkin, V. B.; Sakamoto, H.; Gorin, A. A.; Clore, G. M.; Gronenborn, A. M.; Appella, E.; Harrington, R. E. Architectural accommodation in the complex of four p53 DNA binding domain peptides with the p21/waf1/cip1 DNA. J. Biol. Chem., 1997, 272, 14830-14841.
96. Jakupec, M. A.; Galanski, M.; Keppler, B. K. Tumour-inhibiting platinum complexes - state of the art and future perspectives. Rev. Physiol. Biochem. Pharmacol., 2003, 146, 1-53.
97. Roberts, J. D.; Peroutka, J.; Beggiolin, G.; Manzotti, C.; Piazzoni, L.; Farrell, N. Comparison of cytotoxicity and cellular accumulation of polynuclear platinum complexes in L1210 murine leukemia cell lines. J. Inorg. Biochem., 1999, 77, 47-50.
98. 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.
99. 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 BBR3464 against cisplatin-resistant cells. J. Inorg. Biochem., 1999, 77, 59-64.
100. 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.
101. Manzotti, C.; Pratesi, G.; Menta, E.; Domenico, R. D.; Cavalletti, E.; Fiebig, H. H.; Kelland, L. R.; Farrell, N.; Polizzi, D.; Supino, R.; Pezzoni, G.; Zunino, F. BBR3464: A novel triplatinum complex, exhibiting a preclinical profile of antitumor efficacy different from cisplatin. Clin. Cancer Res., 2000, 6, 2626-2634.
102. Orlandi, L.; Colella, G.; Bearzatto, A.; Abolafio, G.; Manzotti, C.; Daidone, M. G.; Zaffaroni, N. Effects of a novel trinuclear platinum complex in cisplatin-sensitive and cisplatin-resistant human ovarian cancer cell lines: interference with cell cycle progression and induction of apoptosis. Eur. J. Cancer, 2001, 37, 649-659.
103. Farrell, N. P. In: Metal Ions in Biolgical Systems, Metal Complexes in Tumor Diagnosis and as Anticancer Agents, 2004; Vol. 42, pp. 251-296.
104. Jodrell, D. I.; Evans, T. R. J.; 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-oesophagel adenocarcinoma. Eur. J. Cancer, 2004, 40, 1872-1877.
105. Denny, W. A. Acridine derivatives as chemotherapeutic agents. Curr. Med. Chem., 2002, 9, 1655-1665.
106. Ma, Z.; Saluta, G.; Kucera, G. L.; Bierbach, U. Effect of linkage geometry on biological activity in thiourea and guanidinesubstituted acridines and platinum-acridines. Bioorg. Med. Chem. Lett., 2008, 18, 3799-3801.
107. Gibson, D.; Gean, K.-F.; Ben-Shoshan, R.; Ramu, A.; Ringel, I.; Katzhendler, J. Preparation, characterization, and anticancer activity of a series of cis-PtCl2 complexes linked to anthraquinone intercalators. J. Med. Chem., 1991, 34, 414-420.
108. Che, C.-M.; Yang, M.; Wong, K.-H.; Chan, H.-L.; Lam, W. Platinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell lines. Chem. Eur. J., 1999, 5, 3350-3356.
109. Wickham, G.; Wakelin, L.; Palmer, B.; Lee, H.; Johnson, P.; Baguley, B.; Denny, W.; McFadyen, D. Cis-diammineplatinum(II) complexes tethered to DNA-affinic ligands: antitumor activity and DNA-binding properties. Platinum Other Met. Coord. Compd. Cancer Chemother., [Proc. Int. Symp.], 1991, 6, 51-60.
110. Murray, V.; Motyka, H.; England, P. R.; Wickham, G.; Lee, H. H.; Denny, W. A.; McFadyen, W. D. An investigation of the sequencespecific interaction of cis-diamminedichloroplatinum(II) and four analogues, including two acridine-tethered complexes, with DNA inside human cells. Biochemistry, 1992, 31, 11812-11817.
111. Lee, H. H.; Palmer, B. D.; Baguley, B. C.; Chin, M.; McFadyen, W. D.; Wickham, G.; Thorsbourne-Palmer, D.; Wakelin, L. P. G.; Denny, W. A. DNA-directed alkylating agents. 5. acridinecarboxamide derivatives of (1,2-diaminoethane) dichloroplatinum(II). J. Med. Chem., 1992, 35, 2983-2987.
112. Cullinane, C.; Wickham, G.; McFadyen, W. D.; A.Denny, W.; D. Palmer, B.; R.Phillips, D. The use of bidirectional transcription footprinting to detect platinum-DNA crosslinks by acridinetethered platinum diamine complexes and cisplatin. Nucl. Acids Res., 1993, 21, 393-400.
113. Whittaker, J.; McFadyen, W. D.; Baguley, B. C.; Murray, V. The interaction of DNA-targeted platinum phenanthridinium complexes with DNA in human cells. Anticancer Drug Des., 2001, 16, 81-89.
114. Perrin, L. C.; Prenzler, P. D.; Cullinane, C.; Phillips, D. R.; Denny, W. A.; McFadyen, W. D. DNA targeted platinum complexes: synthesis, cytotoxicity and DNA interactions of cis dichloroplatinum(II) complexes tethered to phenazine-1- carboxamides. J. Inorg. Biochem., 2000, 81, 111-117.
115. Mikata, Y.; Yokoyama, M.; Mogami, K.; Kato, M.; Okura, l.; Chikira, M.; Yano, S. Intercalator-linked cisplatin: Synthesis and antitumor activity of cis-dichloroplatinum(ll) complexes connected to acridine and phenylquinolines by one methylene chain. Inorg. Chim. Acta, 1998, 279, 51-57.
116. Grokhovsky, S. L.; Surovaya, A. N.; Burckhardt, G.; Pismensky, V. F.; Chernov, B. K.; Zimmer, C.; Gursky, G. V. DNA Sequence recognition by bis-linked netropsin and distamycin derivatives. FEBS Lett., 1998, 439, 346-350.
117. Brabec, V.; Neplechova, K.; Kasparkova, J.; Farrell, N. Steric control of DNA interstrand cross-link sites of trans platinum complexes: specificity can be dictated by planar nonleaving groups. J. Biol. Inorg. Chem., 2000, 5, 364-368.
118. McFadyen, W. D.; Wakelin, L. P. G.; Roos, I. A. G.; Leopold, V. A. Activity of platinum(II) intercalating agents against murine leukemia L1210. J. Med. Chem., 1985, 28, 1113-1116.
119. Cusumano, M.; Letizia, M.; Giannetto, A. Stacking surface effect in the DNA intercalation of some polypyridine platinum(II) complexes. Inorg. Chem., 1999, 38, 1754-1758.
120. Fenton, R.R.; Aldrich-Wright, J.R. Metal Complexes and Therapeutic uses thereof, International Patent, Application Number WO/2002/066435 2002, p. 26.
121. Bulluss, G. H. Platinum compounds, DNA interactions, and their role in anti-cancer activity, PhD thesis, University of Sydney (Sydney), 2004.
122. Brodie, C.; Collins, J. G.; Aldrich-Wright, J. R. The biological activity of some square-planar platinum(II) metallointercalators. Dalton. Trans., 2004, 1145-1152.
123. Collins, J. G.; Rixon, R. M.; Aldrich-Wright, J. R. Interaction of [Pt(en)(phen)]2+ and [Pt(en)(phi)]2+ with the hexanucleotide d(GTCGAC)2: evidence for minor groove binding. Inorg. Chem., 2000, 39, 4377-4379.
124. Paul, A. K.; Mansuri-Torshizi, H.; Srivastava, T. S.; Chavan, S. J.; Chitnis, M. P. Some potential antitumor 2,2'-dipyridylamine Pt(II)/Pd(II) complexes with amino acids: Their synthesis, spectroscopy, DNA binding, and cytotoxic studies. J. Inorg. Biochem., 1993, 50, 9-20.
125. Bulluss, G.H. The synthesis and biological testing of platinum square-planar intercalators, Honuors thesis, University of Sydney (Sydney), 1999.
126. Fisher, D. M.; Bednarski, P. J.; Grunert, R.; Turner, P.; Fenton, R. R.; Aldrich-Wright, J. R. Chiral platinum(II) metallointercalators with potent in vitro cytotoxic activity. ChemMedChem, 2007, 2, 488-495.
127. Norden, B. Structure of DNA metal complexes in solution studied by linear and circular dichroism. [Pt(II)(ethylenediamine)(2,2'- dipyridine)]2+ binds strongly to DNA by intercalation. [Cu(II)(2,2'- dipyridine)2]2+ is not intercalated. Inorg. Chim. Acta, 1978, 31, 83-95.
128. Lippert, B. Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug, B. Lippert, Ed. HVCA, Zurich, Wiley-VCH, Weinheim, 1999, p379.
129. Palmer, B. D.; Lee, H. H.; Baguley, B. C.; Chin, M.; McFadyen, W. D.; Wickham, G.; Thorsbourne-Palmer, D.; Wakelin, L. P. G.; Denny, W. A. DNA-Directed alkylating agents. 5. Acridinecarboxamide derivatives of (1,2-diaminoethane)dichloroplatinum (II). J. Med. Chem., 1992, 35, 2983-2987.
130. Kumar, L.; Kandasamy, N. R.; Srivastava, T. S.; Amonkar, A. J.; Adwankar, M. K.; Chitnis, M. P. Synthesis and spectroscopic studies of potential anticancer [platinum(II)(2,2' -bipyridine)(amino acid)]n+ (n = 1 or 2) complexes. J. Inorg. Biochem., 1984, 23, 1-11.
131. Jain, N.; Mittal, R.; Srivastava, T. S.; Satyamoorthy, K.; Chitnis, M. P. Synthesis, characterization, DNA binding, and cytotoxic studies of dinuclear complexes of palladium(II) and platinum(II) with 2,2-bipyridine and [alpha],[omega]-diaminoalkane-N,N'- diacetic acid. J. Inorg. Biochem., 1994, 53, 79-94.
132. Mital, R.; Srivastava, T. S.; Parekh, H. K.; Chitnis, M. P. Synthesis, characterization, DNA binding, and cytotoxic studies of some mixed-ligand palladium(II) and platinum(II) complexes of [alpha]- diimine and amino acids. J. Inorg. Biochem., 1991, 41, 93-103.
133. Wheate, N. J.; Taleb, R. I.; Krause-Heuer, A. M.; Cook, R. L.; Wang, S.; Higgins, V. J.; Aldrich-Wright, J. R. Novel platinum(II)- based anticancer complexes and molecular hosts as their drug delivery vehicles. Dalton Trans., 2007, 5055-5064.
134. Krause-Heuer, A. M.; Gruenert, R.; Kuehne, S.; Buczkowska, M.; Wheate, N. J.; Le Pevelen, D. D.; Boag, L. R.; Fisher, D. M.; Kasparkova, J.; Malina, J.; Bednarski, P. J.; Brabec, V.; Aldrich-Wright, J. R. Studies of the mechanism of action of platinum(II) complexes with potent cytotoxicity in human cancer cells. J. Med. Chem., 2009, 52, 5474-5484.
135. Kemp, S.; Wheate, N. J.; Buck, D. P.; Nikac, M.; Collins, J. G.; Aldrich-Wright, J. R. The effect of ancillary ligand chirality and phenanthroline functional group substitution on the cytotoxicity of platinum(II)-based metallointercalators. J. Inorg. Biochem., 2007, 101, 1049-1058.
136. Morgan, G. T.; Burstall, F. H. Researches on residual affinity and co-ordination. Part XXXV. 2: 2: 2-Tripyridylplatinum salts. J. Chem. Soc., 1934, 1498-1500.
137. Jennette, K. W.; Lippard, S., J.; Vassiliades, G. A.; Bauer, W. R. Metallointercalaintercalation reagents 2-hydroxyethanethiolato (2,2',2-terpyridine)-platinum(II) monocation binds strongly to DNA by intercalation. Proc. Natl. Acad. Sci. USA, 1974, 71, 3839-3843.
138. Yu, C.; Chan, H.-Y.; K., W.; Yam, V. W. Single-stranded nucleic acid-induced helical Self-assembly of alkynylplatinum(II) terpyridyl complexes, Proc. Natl. Acad. Sci. USA, 2006, 103, 19652-19657.
139. McFadyen, W. D.; Wakelin, L. P. G.; Roos, I. A. G.; Hillcoat, B. L. Binuclear platinum(II)-terpyridine complexes. J. Biochem., 1986, 238, 757-763.
140. McFadyen, W. D.; Wakelin, L. P. G.; Roos, I. A. G.; Hillcoat, B. L. The binding of binuclear platinum(II)-terpyridine complexes to DNA. J. Biochem., 1987, 242, 177-183.
141. Jennette, K. W.; Lippard, S. J.; Vassiliades, G. A.; Bauer, W. R. Metallointercalaintercalation reagents 2-hydroxyethanethiolato (2,2',2-terpyridine)-platinum(II) monocation binds strongly to DNA by intercalation. Proc. Natl. Acad. Sci. USA, 1974, 71, 3839-3843.
142. Lowe, G.; McCloskey, J. A.; Ni, J.; Vilaivan, T. A Mass spectrometric investigation of the reaction between 4,4'- vinylenedipyridine bis[2,2':6',2-terpyridine platinum(II)] and the self-complementary oligonucleotide d(CpGpTpApCpG). Bioorg. Med. Chem., 1996, 4, 1007-1013.
143. Barton, J. K.; Lippard, S. J. Cooperative binding of a platinum metallointercalation reagent to poly(A).poly(U). Biochemistry, 1979, 18, 2661-2668.
144. Gillard, R. D.; Sengül, A. Dimorphism in a terpyridyl compound. Trans. Met. Chem., 2001, 26, 339-344.
145. Lowe, G. Terpyridine-platinum(II) complexes, International Patent, Application Number WO/1997/027202, 1997, p 62.
146. Lowe, G. Platinum(II) complexes, International Patent, Application Number WO/2000/050431, 2000, p 65.
147. Lowe, G.; Droz, A.; Vilaivan, T.; Weaver, G. W.; Tweedale, L.; Pratt, J. M.; Rock, P.; Yardley, V.; Croft, S. L. Cytotoxicity of (2,2':6',2''-terpyridine)platinum(II) complexes to Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei. J. Med. Chem., 1999, 42, 999-1006.
148. Becker, K.; Herold-Mende, C.; Park, J. J.; Lowe, G.; Schirmer, R. H. Human thioredoxin reductase is efficiently inhibited by (2,2':6',2-terpyridine)platinum(II) complexes. Possible implications for a novel antitumor strategy. J. Med. Chem., 2001, 44, 2784-2792.
149. McCoubrey, A.; Latham, H. C.; Cook, P. R.; Rodger, A.; Lowe, G. 4-Picoline-2,2':6',2-terpyridine-platinum(II) - a potent intercalator of DNA. FEBS Lett., 1996, 380, 73-78.
150. Wee, S.; O'Hair, R. A. J.; McFadyen, W. D. Can radical cations of the constituents of nucleic acids be formed in the gas phase using ternary transition metal complexes? Rapid Commun. Mass Spectrom., 2005, 19, 1797-1805.
151. Woodhouse, S. L.; Ziolkowski, E. J.; Rendina, L. M. Synthesis and anti-cancer activity of dinuclear platinum(II) complexes containing bis(thioalkyl)dicarba-closo-dodecaborane(12) ligands. Dalton Trans., 2005, 17, 2827-2829.
152. Todd, J. A.; Turner, P.; Ziolkowski, E. J.; Rendina, L. M. (2,2':6',2''-terpyridine)platinum(II) complexes containing (thioalkyl)dicarba-closo-dodecaborane(12) ligands. J. Inorg. Chem., 2005, 44, 6401-6408.
153. Ma, D.-L.; Shum, T. Y.-T.; Zhang, F.; Che, C.-M.; Yang, M. Water soluble luminescent platinum terpyridine complexes with glycosylated acetylide and arylacetylide ligands: photoluminescent properties and cytotoxicities. Chem. Commun., 2005, 37, 4675-4677.
154. Wheate, N. J.; Brodie, C. R.; Collins, J. G.; Kemp, S.; Aldrich-Wright, J. R. DNA intercalators in cancer therapy: Organic and inorganic drugs and their spectroscopic tools of analysis. Mini-Rev. Med. Chem., 2007, 7, 627-648.
155. Lowe, G.; Droz, A. S.; Park, J. J.; Waever, G. W. The design and synthesis of bis-[4'-azido-2,2':6',2''-terpyridine platinum(II)] complexes with rigid and extended linkers for studying the topology of DNA by photoaffinity labeling. Bioorg. Chem., 1999, 27, 477-486.
156. Lowe, G.; Ross, S. A.; Probert, M.; Cowley, A. The X-ray crystal structure of N,S-bis[(4'-chloro-2,2':6',2-terpyridine)platinum(II)]- 2-mercaptoimidazole tris-hexafluorophosphate and tris[(2,2':6',2- terpyridine)platinum(II)]sulfonium tetra-perchlorate. Chem. Commun., 2001, 1288-1289.
157. Lowe, G.; Droz, A. S.; Vilaivan, T.; Weaver, G. W.; Park, J. J.; Pratt, J. M.; Tweedale, L.; Kelland, L. R. Cytotoxicity of 2,2':6',2''- terpyridineplatinum(II) complexes against human ovarian carcinoma. J. Med. Chem., 1999, 42, 3167-3174.
158. Bonse, S.; Richards, J. M.; Ross, S. A.; Lowe, G.; Krauth-Siegel, R. L. (2,2':6',2''-Terpyridine)platinum(II) complexes are irreversible inhibitors of trypanosoma cruzi trypanothione reductase but not of human glutathione reductase. J. Med. Chem., 2000, 43, 4812-4821.
159. Chan, H.-L.; Ma, D.-L.; Yang, M.; Che, C.-M. Bis-intercalative dinuclear Platinum(II) 6-phenyl-2,2'-bipyridine complexes exhibit enhanced DNA affinity but similar cytotoxicity compared to the mononuclear unit. J. Biol. Inorg. Chem., 2003, 8, 761-769.
160. Lowe, G. Bis-terpyridine-platinum(II) complexes, International Patent, Application Number WO/2000/043405, 2000, p 35.
161. Rosenberg, B.; VanCamp, L.; Grimley, E. B.; Thomson, A. J. The inhibition of growth or cell division in escherichia coli by different ionic species of platinum(IV) complexes. J. Biol. Chem., 1967, 242, 1347-1352.
162. Rosenberg, B.; Camp, L. v.; Krigas, T. Inhibition of cell division in Escherichia coli by Electrolysis products from a platinum electrode. Nature, 1965, 205, 698-699.
163. Hall, M. D.; Hambley, T. W. Platinum(IV) antitumour compounds: Their bioinorganic chemistry. Coord. Chem. Rev., 2002, 232, 49-67.
164. Zaludova, R.; Zadovska, A.; Kasparkova, J. DNA interactions of bifunctional dinuclear platinum(II) antitumor agents. Eur. J. Biochem., 1997, 246, 508-517.
165. Hall, M.; Alderden, R.; Zhang, M. The fate of Pt(II) and Pt(IV) anti-cancer agents in cancer cells and tumours. J. Struct. Biol., 2006, 155, 38-44.
166. Choy, H.; Park, C.; Yao, M. Current status and future prospects for satraplatin, an oral platinum analogue. Clin. Cancer Res., 2008, 14, 1633-1638.
167. Hall, M.; Dolman, R.; Hambley, T. Metal Ions in Biological Systems, Marcel Dekker: New York, 2004.
168. Kelland, L.; Abel, G.; McKeage, M.; Jones, M.; Goddard, P.; Valenti, M.; Murrer, B.; Harrap, K. Preclinical antitumor evaluation of bis-acetatoamminedichlorocyclohexylamine Platinum(IV): an orally active platinum drug. Cancer Res., 1993, 53, 2581-2586.
169. Gurney, H.; Crowther, G.; Anderson, H.; Murphy, D.; Prendiville, J.; Ranson, M.; Mayor, P.; Swindell, R.; Buckley, C.; Tindell, V. Five year follow-up and dose delivery analysis of cisplatin, iproplatin or carboplatin in combination with cyclophosphamide in advanced ovarian carcinoma. Ann. Oncol., 1990, 1, 427-433.
170. Schilder, R.; LaCreta, F.; Perez, R.; Johnson, S.; Brennan, J.; Rogatko, A.; Nash, S.; McAleer, C.; Hamilton, T.; Roby, D.; Young, R.; Ozols, F.; O'Dwyer, P. Phase I and pharmacokinetic study of ormaplatin (tetraplatin, NSC 363812) administered on a day 1 and day 8 schedule. Cancer Res., 1994, 54, 709-717.
171. Kelland, L. R.; Barnard, C. F. J.; Mellish, K. J.; Jones, M.; Goddard, P. M.; Valenti, M.; Bryant, A.; Murrer, B. A.; Harrap, K. R. A novel trans-platinum coordination complex possessing in vitro and in vivo antitumor activity. Cancer Res., 1994, 54, 5618-5622.
172. Vetter, C.; Wagner, C.; Kaluderovic, G.; Paschke, R.; Steinborn, D. Synthesis, characterisation, and cytotoxicity of trimethyl Platinum(IV) complexes with 2-thiocytosine and 1-methyl-2- thiocytosine ligands. Inorg. Chim. Acta, 2009, 362, 189-195.
173. Krajcinovic, B.; Kaluderovic, G.; Steinborn, D. Synthesis and in vitro antitumoral activity of novel O,O'-Di-2-alkyl-(S,S)- ethylenediamine-N,N'-di-propanoate ligands and corresponding platinum(II/IV) complexes. J. Inorg. Biochem., 2008, 102, 892-900.
174. Presnov, M.; Konovalova, A.; Kozlov, A.; Brovtsyn, V.; Romanova, L. The antitumor activity of oxoplatin. Neoplasma, 1985, 32, 73-83.
175. Dwyer, F. P.; Gyarfas, E. C. Chemistry of ruthenium. VI. existence of the tris-o-phenanthroline ruthenium(II) and tris-ophenanthroline ruthenium(III) ions in enantiomorphous forms. J. Proc. R. Soc. N. S. W., 1950, 83, 170-173.
176. Dwyer, F. P.; Gyarfas, E. C.; O'Dwyer, M. F. Configurational activity. Nature, 1951, 167, 1036.
177. Bosnich, B.; Dwyer, F. P. Bis-1,10-Phenanthroline complexes of divalent ruthenium. Aust. J. Chem., 1966, 19, 2229-2233.
178. Mellor, D. P. Dwyer's Contribution to coordination chemistry. Proc. R. Aust. Chem. Inst., 1970, 37, 199-208.
179. Clarke, M. J.; Zhu, F.; Frasca, D. R. Non-platinum chemotherapeutic metallopharmaceuticals. Chem. Rev., 1999, 99, 2511-2533.
180. Sava, G.; Clerici, K.; Capozzi, I.; Cocchietto, M.; Gagliardi, R.; Alessio, E.; Mestroni, G.; Perbellini, A. Reduction of lung metastasis by ImH[trans-RuCl4(DMSO)Im]: Mechanism of the selective action investigated on mouse tumours. Anti-Cancer Drugs, 1999, 10, 129-138.
181. Bergamo, A.; Gagliardi, R.; Scarcia, V.; Furlani, A.; Alessio, E.; Mestroni, G.; Sava, G. In vitro cell cycle arrest, in vivo action on solid metastasizing tumors, and host toxicity of the antimetastatic drug NAMI-A and cisplatin. J. Pharmacol. Exp. Ther., 1999, 289, 559-564.
182. Alessio, E.; Mestroni, G.; Bergamo, A.; Sava, G. Ruthenium antimetastatic agents. Curr. Top. Med. Chem., 2004, 4, 1525-1535.
183. Alessio, E.; Mestroni, G.; Bergamo, A.; Sava, G. In: Metal Ions in the Biological Systems, Sigel, A.; Sigel, H. Eds.; Marcel Dekker Inc: Netherlands, 2004, Vol. 42, pp. 323-351.
184. Dougan, S. J.; Melchart, M.; Habtemariam, A.; Parsons, S.; Sadler, P. J. Phenylazo-pyridine and phenylazo-pyrazole chloride ruthenium(II) arene complexes: arene loss, aquation, and cancer cell cytotoxicity. Inorg. Chem., 2006, 45, 10882-10894.
185. Yan, Y. K.; Melchart, M.; Habtemariam, A.; Sadler, P. J. Organometallic chemistry, biology and medicine: ruthenium arene anticancer complexes. Chem. Commun., 2005, 4764-4776.
186. Chen, H.; Parkinson, J. A.; Parsons, S.; Coxall, R. A.; Gould, R. O.; Sadler, P. J. Organometallic ruthenium(II) diamine anticancer complexes: arene-nucleobase stacking and stereospecific hydrogenbonding in guanine adducts. J. Am. Chem. Soc., 2002, 124, 3064-3082.
187. Aird, R. E.; Cummings, J.; Ritchie, A. A.; Muir, M.; Morris, R. E.; Chen, H.; Sadler, P. J.; Jodrell, D. I. In vitro and in vivo activity and cross resistance profiles of novel ruthenium(II) organometallic arene complexes in human ovarian cancer. Br. J. Cancer, 2002, 86, 1652-1657.
188. Scolaro, C.; Bergamo, A.; Brescacin, L.; Delfino, R.; Cocchietto, M.; Laurenczy, G.; Geldbach, T. J.; Sava, G.; Dyson, P. J. In vitro and in vivo evaluation of ruthenium(II)-arene PTA complexes. J. Med. Chem., 2005, 48, 4161-4171.
189. Ang, W. H.; Daldini, E.; Scolaro, C.; Scopelliti, R.; Juillerat-Jeannerat, L.; Dyson, P. J. Development of organometallic ruthenium-arene anticancer drugs that resist hydrolysis. Inorg. Chem., 2006, 45, 9006-9013.
190. Tardito, S.; Marchio, L. Copper compounds in anticancer strategies. Curr. Med. Chem., 2009, 16, 1325-1348.
191. Lahey, M. E.; Gubler, C. J.; Chase, M. S.; Cartwright, G. E.; Wintrobe, M. M. Studies on copper metabolism ii. hematologic manifestations of copper deficiency in swine. Blood, 1952, 7, 1053-1074.
192. Cartwright, G. E.; Gubler, C. J.; Wintrobe, M. M. Studies on copper metabolism. XX. Enzyme activities and iron metabolism in copper and iron deficiencies. J. Biol. Chem., 1957, 224, 533-546.
193. Osaki, S.; Johnson, D. A.; Frieden, E. The possible significance of the ferrous oxidase acitivty of ceruloplasmin in normal human serum. J. Biol. Chem., 1966, 241, 2746-2751.
194. Safaei, R. Role of copper transporters in the uptake and efflux of platinum containing drugs. Cancer Lett., 2006, 234, 34-39.
195. Sigman, D. S.; Graham, D. R.; D'Aurora, V.; Stern, A. M. Oxygendependent cleavage of DNA by the 1,10-phenanthroline cuprous complex. J. Biol. Chem., 1979, 254, 12269-12272.
196. Pitié, M.; Burrows, C. J.; Meunier, B. Mechanisms of DNA cleavage by copper complexes of 3-clip-phen and of its conjugate with a distamycin analogue. Nucl. Acids Res., 2000, 28, 4856-4864.
197. Robertazzi, A.; Vargiu, A. V.; Magistrato, A.; Ruggerone, P.; Carloni, P.; Hoog, P. D. Reedijk, J. Copper-1,10-phenanthroline complexes binding to DNA: structural predictions from molecular simulations. J. Phys. Chem. B, 2009, 113, 10881-10890.
198. García-Giménez, J. L.; González-Álvarez, M.; Liu-González, M.; Macías, B.; Borrás, J.; Alzuet, G. Toward the development of metal-based synthetic nucleases: DNA binding and oxidative DNA cleavage of a mixed copper(II) complex with N-(9H-purin-6- yl)benzenesulfonamide and 1,10-phenantroline. antitumor activity in human caco-2 cells and jurkat T lymphocytes. Evaluation of p53 and Bcl-2 proteins in the apoptotic mechanism. J. Inorg. Biochem., 2009, 103, 923-934.
199. Zhang, S.; Zhu, Y.; Tu, C.; Wei, H.; Yang, Z.; Lin, L.; Ding, J.; Zhang, J.; Guo, Z. A novel cytotoxic ternary copper(II) complex of 1,10-phenanthroline and L-threonine with DNA nuclease activity. J. Inorg. Biochem., 2004, 98, 2099-2106.
200. Gracia-Mora, I.; Ruiz-Ramirez, L.; Gomez-Ruiz, C.; Tinoco-Mendez, M.; Marquez-Quinones, A.; Lira, L. R.-D.; Marin-Hernandez, A.; Macias-Rosales, L.; Bravo-Gomez, M. E. Knight's move in the periodic table, from copper to platinum, novel antitumor mixed chelate coppor compounds, casiopeinas, evaluated by an in vitro human and murine cancer cell line panel. Met. Based Drugs, 2001, 8, 19-28.
201. Vizcaya-Ruiz, A. D.; Rivero-Muller, A.; Ruiz-Ramirez, L.; Kass, G. E. N.; Kelland, L. R.; Orr, R. M.; Dobrota, M. Induction of apoptosis by a novel copper-based anticancer compound, casiopeina II in L1210 murine leukaemia and CH1 human ovarian carcinoma cells. Toxicol. In Vitro, 2000, 14, 1-5.
202. Vizcaya-Ruiz, A. D.; Rivero-Müller, A.; Ruiz-Ramirez, L.; Howarth, J. A.; Dobrota, M. Hematotoxicity response in rats by the novel copper-based anticancer agent: casiopeina II. Toxicology, 2003, 194, 103-113.
203. Gao, E.; Liu, C.; Zhu, M.; Lin, H.; Wu, Q.; Liu, L. Current developments of Pd(II) complexes as potential antitumor agents. Anti-Cancer Agents Med. Chem., 2009, 9, 356-368.
204. Caires, A. C. F. Recent advances involving palladium (II) complexes for the cancer therapy. Anti-Cancer Agents Med. Chem., 2007, 7, 484-491.
205. Mital, R.; Shah, G. M.; Srivastava, T. S.; Bhattacharya, R. K. The effect of some new platinum(II) and palladium(II) coordination complexes on rat hepatic nuclear transcription in vitro. Life Sci., 1992, 50, 781-790.
206. Zhao, G.; Sun, H.; Lin, H.; Zhu, S.; Su, X.; Chen, Y. Palladium(II) complexes with N,N'-dialkyl-1,10-phenanthroline-2,9-dimathanamine: synthesis, characterization and cytotoxic activity. J. Inorg. Biochem., 1998, 72, 173-177.
207. Khan, B. T.; Bhatt, J.; Najmuddin, K.; Shamsuddin, S.; Annapoorna, K. Synthesis, antimicrobial, and antitumor activity of a series of palladium(II) mixed ligand complexes. J. Inorg. Biochem., 1991, 44, 55-63.
208. Melendez, E. Titanium complexes in cancer treatment. Crit. Rev. Oncol. Hematol., 2002, 42, 309-315.
209. Keppler, B. K.; Hartmann, M. New tumor-inhibiting metal complexes. chemistry and antitumor properties. Met. Based Drugs, 1994, 1, 145-150.
210. Caruso, F.; Rossi, M.; Opazo, C.; Pettinari, C. Structural features of antitumor titanium agents and related compounds. Bioinorg. Chem. Appl., 2005, 3, 317-329.
211. Caruso, F.; Rossi, M. In: Metal Ions in Biological Systems, Sigel, A.; Sigel, H. Eds.; Marcel Dekker, Inc.: Basel, 2004; Vol. 42, pp. 353-384.
212. Köpf-Maier, P.; Köpf, H.; Wagner, W. Different inhibition pattern of the nucleic acid metabolism after in vitro treatment with titanocene and vanadocene dichlorides. Naturwissenschaften, 1981, 68, 272-273.
213. Köpf-Maier, P.; Köpf, H. Tumorhemmung durch titanocendichlorid: Erste hinweise zum wirkungsmechanismus. Naturwissenschaften, 1980, 67, 415-416.
214. Tacke, M.; Allen, L. T.; Cuffe, L.; Gallagher, W. M.; Lou, Y.; Mendoza, O.; Mueller-Bunz, H.; Rehmman, F.-J. K.; Sweeney, N. Novel titanocene anti-cancer drugs derived from fulvenes and titanium dichloride. J. Organomet. Chem., 2004, 689, 2242-2249.
215. Tacke, M.; Cuffe, L. P.; Gallagher, W. M.; Lou, Y.; Mendoza, O.; Mueller-Bunz, H.; Rehmann, J. P.; Sweeney, N. Methoxy-phenyl substituted ansa-titanocenes as potential anti-cancer drugs derived from fulvenes and titanium dichloride. J. Inorg. Biochem., 2004, 98, 1987-1994.
216. Köpf-Maier, P.; Krahl, D. Tumor inhibition by metallocenes: Ultrastructural localization of titanium and vanadium in treated tumor cells by electron energy loss spectroscopy. Chem. Biol. Interact., 1983, 44, 317-328.
217. Köpf-Maier, P.; Krahl, D. After treatment with the antitumor agent titanocene dichloride: An electron energy loss spectroscopic study. Naturwissenschaften, 1981, 68, 273-274.
218. Köpf-Maier, P. Intracellular localization of titanium within xenografted sensitive human tumors after treatment with the antitumor agent titanocene dichloride. J. Stuct. Biol., 1990, 105, 34-45.
219. Sergeant, C. D.; Ott, I.; Sniady, A.; Meneni, S.; Gust, R.; Rheingold, A. L.; Dembinski, R. Metallo-nucleosides: Synthesis and biological evaluation of hexacarbonyl dicobalt 5-alkynyl-2'-deoxyuridines. Org. Biomol. Chem., 2008, 6, 73-80.
220. Ott, I.; Kircher, B.; Schumacher, P.; Schmidt, K.; Gust, R. Antitumor-active cobalt-alkyne complexes derived from acetylsalicylic acid: Studies on the mode of drug action. J. Med. Chem., 2005, 48, 622-629.
221. Ware, D. C.; Palmer, B. D.; Wilson, W. R.; Denny, W. A. Hypoxia-selective Antitumor agents. 7. Metal complexes of aliphatic mustards as a new class of hypoxia-selective cytotoxins. synthesis and evaluation of cobalt(III) complexes of bidentate mustards. J. Med. Chem., 1993, 36, 1839-1846.
222. Ahn, G. O.; Ware, D. C.; Denny, W. A.; Wilson, W. R. Optimization of the auxiliary ligand shell of cobalt(III)(8- hydroxyquinoline) complexes as model hypoxia-selective radiation-activated prodrugs. Radiat. Res., 2004, 162, 315-325.
223. Gust, R.; Ott, I.; Posselt, D.; Sommer, K. Development of cobalt(3,4-diarylsalen) complexes as tumor therapeutics. J. Med. Chem., 2004, 47, 5837-5846.
224. Failes, T. W.; Cullinane, C.; Diakos, C. I.; Yamamoto, N.; Lyons, J. G.; Hambley, T. W. Studies of a cobalt(III) complex of the MMP inhibitor marimastat: A potential hypoxia-activated prodrug. Chem. Eur. J., 2007, 13, 2974-2982.
225. Fricker, S. P. Medical uses of gold compounds: Past, present and future. Gold Bull., 1996, 29, 53-60.
226. Barnard, P. J.; Baker, M. V.; Berners-Price, S. J.; Day, D. A. Mitochondrial permeability transition induced by dinuclear gold(I)-carbene complexes: potential new antimitochondrial antitumour agents. J. Inorg. Biochem., 2004, 98, 1642-1647.
227. Mirabelli, C. K.; Johnson, R. K.; Sung, C.-M.; Faucette, L. F.; Muirhead, K.; Crooke, S. T. Evaluation of the in vivo antitumor activity and in vitro cytotoxic properties of auranofin, a coordinated gold compound, in murine tumor models. Cancer Res., 1985, 45, 32-39.
228. Hoke, G. D.; Rush, G. E.; Bossard, G. E.; McArdle, J. V.; Jensen, C. K.; Mirabelli, C. K. Mechanism of alterations in isolated rat liver mitochondrial function induced by gold complexes of bidentate phosphines. J. Biol. Chem., 1988, 263, 11203-11210
229. Shi, P. F.; Jiang, Q.; Zhao, Y. M.; Zhang, Y. M.; Lin, J.; Lin, L. P.; Ding, J.; Guo, Z. J. DNA binding properties of novel cytotoxic gold(III) complexes of terpyridine ligands: The impact of steric and electrostatic effects. J. Biol. Inorg. Chem., 2006, 11, 745-752.
230. Wai-Yin Sun, R.; Ma, D.-L.; Wong, E. L.-M.; Che, C.-M. Some Uses of transition metal complexes as anti-cancer and anti-HIV agents. Dalton Trans., 2007, 4884-4892.
231. Boulikas, T.; Pantos, A.; Bellis, E.; Christofis, P. Designing platinum compounds in cancer: structures and mechanisms. Cancer Ther., 2007, 5, 537-583.
232. Springler, B.; Whittington, D. A.; Lippard, S. J. 2.4 Å crystal structure of an oxaliplatin 1,2-d(GpG) intrastrand cross-link in a DNA dodecamer duplex. Inorg. Chem., 2001, 40, 596-5602.
233. 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.
234. Hall, M. D.; Dolman, R. C.; Hambley, T. W. In: Metal Ions in Biological Systems, Sigel, A.; Sigel, H.; Eds.; Marcel Dekker, Inc.: Basel, 2004, Vol. 42, pp. 297-322.
235. Xie, X.; Mulcahy, S. P.; Meggers, E. Strategy for the stereochemical assignment of tris-heteroleptic Ru(II) complexes by NMR spectroscopy. Inorg. Chem., 2009, 48, 1053-1061.