Fresh platinum complexes with promising antitumor activity

Anti-Cancer Agents in Medicinal Chemistry

Volumn 10, Issue 5, 2010, Pages 396-411

  Wang, Xiaoyong ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Antitumor drug; Drug design; Drug resistance; Platinum complex

Indexed keywords

BBR 3464; BBR 3537; BBR 3571; BBR 3610; CARBOPLATIN; CISPLATIN; OXALIPLATIN; PLATINUM COMPLEX; SATRAPLATIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER RESISTANCE; COMPLEX FORMATION; DNA DAMAGE; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG DNA BINDING; DRUG EFFICACY; DRUG MECHANISM; HUMAN; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 77953759573     PISSN: 18715206     EISSN: None     Source Type: Journal    
DOI: 10.2174/1871520611009050396     Document Type: Article

References (139)

1. 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.
2. Muggia, F. Platinum compounds 30 years after the introduction of cisplatin: Implications for the treatment of ovarian cancer. Gynecol. Oncol., 2009, 112, 275-281.
3. Rabik, C. A.; Dolan, M. E. Molecular mechanisms of resistance and toxicity associated with platinating agents. Cancer Treat. Rev., 2007, 33, 9-23.
4. Galanski, M.; Jakupec, M. A.; Keppler, B. K. Update of the preclinical situation of anticancer platinum complexes: novel design strategies and innovative analytical approaches. Curr. Med. Chem., 2005, 12, 2075-2094.
5. Wang, D.; Lippard, S. J. Cellular processing of platinum anticancer drugs. Nat. Rev. Drug Discov., 2005, 4, 307-320.
6. Argyriou, A. A.; Polychronopoulos, P.; Iconomou, G.; Chroni, E.; Kalofonos, H. P. A review on oxaliplatin-induced peripheral nerve damage. Cancer Treat. Rev., 2008, 34, 368-377.
7. Barabas, K.; Milner, R.; Lurie, D.; Adin, C. Cisplatin: a review of toxicities and therapeutic applications. Vet. Comp. Oncol., 2008, 6, 1-18.
8. McWhinney, S. R.; Goldberg, R. M.; McLeod, H. L. Platinum neurotoxicity pharmacogenetics. Mol. Cancer Ther., 2009, 8, 10-16.
9. Montaña, Á. M.; Batalla, C. The rational design of anticancer platinum complexes: the importance of the structure-activity relationship. Curr. Med. Chem., 2009, 16, 2235-2260.
10. Koshiyama, M.; Kinezaki, M.; Uchida, T.; Sumitomo, M. Chemo sensitivity testing of a novel platinum analog, nedaplatin (254-S), in human gynecological carcinomas: a comparison with cisplatin. Anticancer Res., 2005, 25, 4499-4502.
11. Hanada, K.; Asano, K.; Nishimura, T.; Chimata, T.; Matsuo, Y.; Tsuchiya, M.; Ogata, H. Use of a toxicity factor to explain differences in nephrotoxicity and myelosuppression among the platinum antitumour derivatives cisplatin, carboplatin and nedaplatin in rats. J. Pharm. Pharmacol., 2008, 60, 317-322.
12. Martin, L. P.; Hamilton, T. C.; Schidler, R. J. Platinum resistance: the role of DNA repair pathways. Clin. Cancer Res., 2008, 14, 1291-1295.
13. Bruijnincx, P. C. A.; Sadler, P. J. New trends for metal complexes with anticancer activity. Curr. Opin. Chem. Biol., 2008, 12, 197-206.
14. Lovejoy, K. S.; Lippard, S. J. Non-traditional platinum compounds for improved accumulation, oral bioavailability, and tumor targeting. Dalton Trans., 2009, 10651-10659.
15. Sun, R. W. -Y.; 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.
16. Wang, X. Y.; Guo, Z. J. Towards the rational design of platinum(II) and gold(III) complexes as antitumour agents. Dalton Trans., 2008, 1521-1532.
17. Cossa, G.; Gatti, L.; Zunino, F.; Perego, P. Strategies to improve the efficacy of platinum compounds. Curr. Med. Chem., 2009, 16, 2355-2365.
18. Martelli, L.; Di Mario, F.; Botti, P.; Ragazzi, E.; Martelli, M.; Kelland, L. Accumulation, platinum-DNA adduct formation and cytotoxicity of cisplatin, oxaliplatin and satraplatin in sensitive and resistant human osteosarcoma cell lines, characterized by p53 wildtype status. Biochem. Pharmacol., 2007, 74, 20-27.
19. Monti, E.; Gariboldi, M.; Maiocchi, A.; Marengo, E.; Cassino, C.; Gabano, E.; Osella, D. Cytotoxicity of cis-Platinum(II) Conjugate Models. The effect of chelating arms and leaving groups on cytotoxicity: A quantitative structure-activity relationship approach. J. Med. Chem., 2005, 48, 857-866.
20. Dietrich, A.; Mueller, T.; Paschke, R.; Kalinowski, B.; Behlendorf, T.; Reipsch, F.; Fruehauf, A.; Schmoll, H.-J.; Kloft, C.; Voigt, W. 2-(4-(Tetrahydro-2H-pyran-2-yloxy)-undecyl)-propane-1,3-diamminedichloroplatinum(II): A novel platinum compound that overcomes cisplatin resistance and induces apoptosis by mechanisms different from that of cisplatin. J. Med. Chem., 2008, 51, 5413-5422.
21. van Rijt, S.; van Zutphen, S.; den Dulk, H.; Brouwer, J.; Reedijk, J. Structure-activity relationship studies for three new asymmetric cis-platinum(II) aminoethanol-based complexes. Inorg. Chim. Acta, 2006, 359, 4125-4129.
22. Silva, H.; Barra, C. V.; da Costa, C. F.; de Almeida, M. V.; César, E. T.; Silveira, J. N.; Garnier-Suillerot, A.; de Paula, F. C. S.; Pereira-Maia, E. C.; Fontes, A. P. S. Impact of the carbon chain length of novel platinum complexes derived from N-alkylpropanediamines on their cytotoxic activity and cellular uptake. J. Inorg. Biochem., 2008, 102, 767-772.
23. Schobert, R.; Biersack, B.; Dietrich, A.; Grotemeier, A.; Müller, T.; Kalinowski, B.; Knauer, S.; Voigt, W.; Paschke, R. Monoterpenes as Drug Shuttles: Cytotoxic (6-Aminomethylnicotinate) dichloridoplatinum(II) complexes with potential to overcome cisplatin resistance. J. Med. Chem., 2007, 50, 1288-1293.
24. Kelland, L. The resurgence of platinum-based cancer chemotherapy. Nat. Rev. Cancer, 2007, 7, 573-584.
25. Ciesielska, E.; Szulawska, A.; Studzian, K.; Ochocki, J.; Malinowska, K.; Kik, K.; Szmigiero, L. Comparative studies on the mechanism of cytotoxic action of novel platinum II complexes with pyrazole ligands. J. Inorg. Biochem., 2006, 100, 1579-1585.
26. Mandal, S.; Bérubé, G.; Asselin, É.; Richardson, V. J.; Church, J. G.; Bridson, J.; Pham, T. N. Q.; Pramanik, S. K.; Mandal, S. K. A new platinum complex of triazine demonstrates G1 arrest with novel biological profile in human breast cancer cell line, MDAMB-468. Bioorg. Med. Chem. Lett., 2007, 17, 2139-2145.
27. Wheate, N. J.; Brodie, C. R.; Collins, J. G.; Kempa, 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.
28. de Mier-Vinué, J.; Gay, M.; Montaña, Á. M.; Sáez, R. -I.; Moreno, V.; Kasparkova, J.; Vrana, O.; Heringova, P.; Brabec, V.; Boccarelli, A.; Coluccia, M.; Natile, G. Synthesis, biophysical studies, and antiproliferative activity of platinum(II) complexes having 1,2-bis(aminomethyl)carbobicyclic ligands. J. Med. Chem., 2008, 51, 424-431.
29. Gümüş, F.; Eren, G.; Açik, L.; Çelebi, A.; Öztürk, F.; Yilmaz, Ş.; Saǧkan, R. I.; Gür, S.; Özkul, A.; Elmali, A.; Elerman Y. Synthesis, cytotoxicity, and DNA interactions of new cisplatin analogues containing substituted benzimidazole ligands. J. Med. Chem., 2009, 52, 1345-1357.
30. Tian, T.; Mutikainen, I.; van Wezel, G. P.; Aliaga-Alcalde, N.; Reedijk J. Chemical, structural and biological studies of cis-[Pt(3-Acpy)2Cl2]. J. Inorg. Biochem., 2009, 103, 1221-1227.
31. Marzano, C.; Sbovata, S. M.; Gandin, V.; Michelin, R. A.; Venzo, A.; Bertani, R.; Seraglia, R. Cytotoxicity of cis-platinum(II) cycloaliphatic amidine complexes: Ring size and solvent effects on the biological activity. J. Inorg. Biochem., 2009, 103, 1113-1119.
32. Roy, S.; Westmaas, J. A.; Buda, F.; Reedijk J. Platinum(II) compounds with chelating ligands based on pyridine and pyrimidine: Synthesis, characterizations, DFT calculations, cytotoxic assays and binding to a DNA model base. J. Inorg. Biochem., 2009, 103, 1278-1287.
33. Safaei, R.; Katano, K.; Larson, B. J.; Samimi, G.; Holzer, A. K.; Naerdemann, W.; Tomioka, M.; Goodman, M.; Howell, S. B. Intracellular localization and trafficking of fluorescein-labeled cisplatin in human ovarian carcinoma cells. Clin. Cancer Res., 2005, 11, 756-767.
34. Marqués-Gallego, P.; den Dulk, H.; Brouwer, J.; Kooijman, H.; Spek, A. L.; Roubeau, O.; Teat, S. J.; Reedijk, J. Synthesis, crystal structure, studies in solution and cytotoxicity of two new fluorescent platinum(II) compounds containing anthracene derivatives as a carrier ligand. Inorg. Chem., 2008, 47, 11171-11179.
35. Marqués-Gallego, P.; Kalayda, G. V.; Jaehde, U.; den Dulk, H.; Brouwer, J.; Reedijk, J. Cellular accumulation and DNA platination of two new platinum(II) anticancer compounds based on anthracene derivatives as carrier ligands. J. Inorg. Biochem., 2009, 103, 791-796.
36. Habala, L.; Galanski, M.; Yasemi, A.; Nazarov, A. A.; von Keyserlingk, N. G.; Keppler, B. K. Synthesis and structure-activity relationships of mono- and dialkyl-substituted oxaliplatin derivatives. Eur. J. Med. Chem., 2005, 40, 1149-1155.
37. Galanski, M.; Yasemi, A.; Jakupec, M. A.; Keyserlingk, N. G. V.; Keppler, B. K. Synthesis, cytotoxicity, and structure-activity relationships of new oxaliplatin derivatives. Mon. Chem., 2005, 136, 693-700.
38. Cui, K.; Wang, L. H.; Zhu, H. B.; Gou, S. H.; Liu, Y. Novel cisplatin- type platinum complexes and their cytotoxic activity. Bioorg. Med. Chem. Lett., 2006, 16, 2937-2942.
39. Ye, Q. -S.; Lou, L. -G.; Liu, Z. -Y.; Liu, W. -P.; Hou, S. -Q.; Chen, X. -Z.; Yu, Y. Synthesis, characterization and cytotoxicity of diam(m)ine platinum(II) complexes containing β-phenylisosuccinate ligand. Arch. Pharm. Chem. Life Sci., 2007, 340, 599-602.
40. Ye, Q. -S.; Lou, L. -G.; Liu, W. -P.; Yu, Y.; Chen, X. -Z.; Hou, S. - Q.; Gao, W. -Q.; Liu, Y. Synthesis and in vitro cytotoxicity of novel lipophilic (diamine)platinum(II) complexes of salicylate derivatives. Bioorg. Med. Chem. Lett., 2007, 17, 2144-2147.
41. Lovejoy, K. S.; Todd, R. C.; Zhang, S.; McCormick, M. S.; D'Aquino, J. A.; Reardon, J. T.; Sancar, A.; Giacomini, K. M.; Lippard, S. J. cis-Diammine(pyridine)chloroplatinum(II), a monofunctional platinum(II) antitumor agent: Uptake, structure, function, and prospects. Proc. Natl. Acad. Sci. USA, 2008, 105, 8902-8907.
42. Margiotta, N.; Natile, G.; Capitelli, F.; Fanizzi, F. P.; Boccarelli, A.; De Rinaldis, P. Giordano, D.; Coluccia, M. Sterically hindered complexes of platinum(II) with planar heterocyclic nitrogen donors. A novel complex with 1-methyl-cytosine has a spectrum of activity different from cisplatin and is able of overcoming acquired cisplatin resistance. J. Inorg. Biochem., 2006, 100, 1849-1857.
43. Gao, X. L.; Wang, X. Y.; Ding, J.; Lin, L. P.; Li, Y. Z.; Guo, Z. J. Antitumor active monofunctional platinum(II) complexes: Synthesis, structural characterization and reactivity towards biomolecules. Inorg. Chem. Commun., 2006, 9, 722-726.
44. Guddneppanavar, R.; Bierbach, U. Adenine-N3 in the DNA minor groove - an emerging target for platinum containing anticancer pharmacophores. Anticancer Agents Med. Chem., 2007, 7, 125-138.
45. Barry, C. G.; Day, C. S.; Bierbach, U. Duplex-promoted platination of adenine-N3 in the minor groove of DNA: Challenging a longstanding bioinorganic paradigm. J. Am. Chem. Soc., 2005, 127, 1160-1169.
46. Baruah, H.; Wright, M. W.; Bierbach, U. Solution structural study of a DNA duplex containing the guanine-N7 adduct formed by a cytotoxic platinum-acridine hybrid agent. Biochemistry, 2005, 44, 6059-6070.
47. Budiman, M. E.; Bierbach, U.; Alexander, R. W. DNA minor groove adducts formed by a platinum-acridine conjugate inhibit association of TATA-binding protein with its cognate sequence. Biochemistry, 2005, 44, 11262-11268.
48. Hess, S. M.; Anderson, J. G.; Bierbach, U. A non-crosslinking platinum-acridine hybrid agent shows enhanced cytotoxicity compared to clinical BCNU and cisplatin in glioblastoma cells. Bioorg. Med. Chem. Lett., 2005, 15, 443-446.
49. Guddneppanavar, R.; Saluta, G.; Kucera, G. L.; Bierbach, U. Synthesis, biological activity, and DNA-damage profile of platinumthreading intercalator conjugates designed to target adenine. J. Med. Chem., 2006, 49, 3204-3214.
50. Hess, S. M.; Mounce, A. M.; Sequeira, R. C.; Augustus, T. M.; Ackley, M. C.; Bierbach, U. Platinum-acridinylthiourea conjugates show cell line-specific cytotoxic enhancement in H460 lung carcinoma cells compared to cisplatin. Cancer Chemother. Pharmacol., 2005, 56, 337-343.
51. Guddneppanavar, R.; Choudhury, J. R.; Kheradi, A. R.; Steen, B. D.; Saluta, G.; Kucera, G. L.; Day, C. S.; Bierbach, U. Effect of the diamine nonleaving group in platinum-acridinylthiourea conjugates on DNA damage and cytotoxicity. J. Med. Chem., 2007, 50, 2259-2263.
52. Ma, Z.; Choudhury, J. R.; Wright, M. W.; Day, C. S.; Saluta, G.; Kucera, G. L.; Bierbach, U. A non-cross-linking platinum-acridine agent with potent activity in non-small-cell lung cancer. J. Med. Chem., 2008, 51, 7574-7580.
53. Ma, Z.; Rao, L.; Bierbach, U. Replacement of a thiourea-s with an amidine-nh donor group in a platinum-acridine antitumor compound reduces the metal's reactivity with cysteine sulfur. J. Med. Chem., 2009, 52, 3424-3427.
54. Gao, J.; Woolley, F. R.; Zingaro, R. A. In vitro anticancer activities and optical imaging of novel intercalative non-cisplatin conjugates. J. Med. Chem., 2005, 48, 7192-7197.
55. Jaramillo, D.; Wheate, N. J.; Ralph, S. F.; Howard, W. A.; Tor, Y.; Aldrich-Wright, J. R. Polyamide platinum anticancer complexes designed to target specific DNA sequences. Inorg. Chem., 2006, 45, 6004-6013.
56. Nováková, O.; Malina, J.; Kašpárková, J.; Halámiková, A.; Bernard, V.; Intini, F.; Natile, G.; Brabec, V. Energetics, conformation, and recognition of DNA duplexes modified by methylated analogues of [PtCl(dien)]+. Chem. Eur. J., 2009, 15, 6211-6221.
57. Qu, Y.; Tran, M. -C.; Farrell, N. P. Structural consequences of a 3' → 3' DNA interstrand cross-link by a trinuclear platinum complex: unique formation of two such cross-links in a 10-mer duplex. J. Biol. Inorg. Chem., 2009, 14, 969-977.
58. Hensing, T. A.; Hanna, N. H.; Gillenwater, H. H.; Camboni, M. G.; 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.
59. Jakupec, M. A.; Galanski, M.; Arion, V. B.; Hartinger, C. G.; Keppler, B. K. Antitumour metal compounds: more than theme and variations. Dalton Trans., 2008, 183-194.
60. Billecke, C.; Finniss, S.; Tahash, L.; Miller, C.; Mikkelsen, T.; Farrell, N. P.; Bögler, O. Polynuclear agents are more potent than cisplatin and induce cell cycle arrest in giloma. Neuro-Oncology, 2006, 8, 215-226.
61. Mitchell, C.; Kabolizadeh, P.; Ryan, J.; Roberts, J. D.; Yacoub, A.; Curiel, D. T.; Fisher, P. B.; Hagan, M. P.; Farrell, N. P.; Grant, S.; Dent, P. Low-dose BBR3610 toxicity in colon cancer cells is p53-independent and enhanced by inhibition of epidermal growth factor receptor (ERBB1)-phosphatidyl inositol 3 kinase signaling. Mol. Pharmacol., 2007, 72, 704-714.
62. Liu, Q.; Qu, Y.; van Antwerpen, R.; Farrell, N. Mechanism of the membrane interaction of polynuclear platinum anticancer agents. Implications for cellular uptake. Biochemistry, 2006, 45, 4248-4256.
63. Hegmans, A.; Kasparkova, J.; Vrana, O.; Kelland, L. R.; Brabec, V.; Farrell, N. P. Amide-based prodrugs of spermidine-bridged dinuclear platinum. Synthesis, DNA binding, and biological activity. J. Med. Chem., 2008, 51, 2254-2260.
64. Montero, E. I.; Benedetti, B. T.; Mangrum, J. B.; Oehlsen, M. J.; Qu, Y.; Farrell, N. P. Pre-association of polynuclear platinum anticancer agents on a protein, human serum albumin. Dalton Trans., 2007, 4938-4942.
65. 4. Eur. J. Med. Chem., 2006, 41, 896-903.
66. 4 in ovarian cancer cell lines. ChemMedChem., 2008, 3, 145-151.
67. 4 (TH8). Med. Chem., 2009, 5, 372-381.
68. Kalayda, G. V.; Jansen, B. A. J.; Wielaard, P.; Tanke, H. J.; Reedijk, J. Dinuclear platinum anticancer complexes with fluorescent N,N'-bis(aminoalkyl)-1,4-diaminoanthraquinones: cellular processing in two cisplatin-resistant cell lines reflects the differences in their resistance profiles. J. Biol. Inorg. Chem., 2005, 10, 305-315.
69. Kalayda, G. V.; Zhang, G. F.; Abraham, T.; Tanke, H. J.; Reedijk, J. Application of fluorescence microscopy for investigation of cellular distribution of dinuclear platinum anticancer drugs. J. Med. Chem., 2005, 48, 5191-5202.
70. Oehlsen, M. E.; Hegmans, A.; Qu, Y.; Farrell, N. A surprisingly stable macrochelate formed from the reaction of cis dinuclear platinum antitumor compounds with reduced glutathione. Inorg. Chem., 2005, 44, 3004-3006.
71. Oehlsen, M. E.; Hegmans, A.; Qu, Y.; Farrell, N. Effects of geometric isomerism in dinuclear antitumor platinum complexes on their interactions with N-acetyl-L-methionine. J. Biol. Inorg. Chem., 2005, 10, 433-442.
72. Fan, D. M.; Yang, X. L.; Wang, X. Y.; Zhang, S. C.; Mao, J. F.; Ding, J.; Lin, L. P.; Guo, Z. J. A dinuclear monofunctional platinum(II) complex with an aromatic linker shows low reactivity towards glutathione but high DNA binding ability and antitumor activity. J. Biol. Inorg. Chem., 2007, 12, 655-665.
73. Zhu, J. H.; Lin, M. X.; Fan, D. M.; Wu, Z. Y.; Chen, Y. C.; Zhang, J. F.; Lu, Y.; Guo, Z. J. The role of bridging ligands in determining DNA-binding ability and cross-linking patterns of dinuclear platinum(II) antitumour complexes. Dalton Trans., 2009, 10889-10895.
74. Zhao, Y. M.; He, W. J.; Shi, P. F.; Zhu, J. H.; Qiu, L.; Lin, L. P.; Guo, Z. J. A positively charged trinuclear 3N-chelated monofunctional platinum complex with high DNA affinity and potent cytotoxicity. Dalton Trans., 2006, 2617-2619.
75. Zhu, J. H.; Zhao, Y. M.; Zhu, Y. Y.; Wu, Z. Y.; Lin, M. X.; He, W. J.; Wang, Y.; Chen, G. J.; Dong, L.; Zhang, J. F.; Lu, Y.; Guo, Z. J. DNA cross-linking patterns induced by an antitumor-active trinuclear platinum complex and comparison with its dinuclear analogue. Chem. Eur. J., 2009, 15, 5245-5253.
76. Rubino, S.; Portanova, P.; Albanese, A.; Calvaruso, G.; Orecchio, S.; Fontana, G.; Stocco, G. C. Mono- and polynuclear complexes of Pt(II) with polypyridyl ligands: Synthesis, spectroscopic and structural characterization and cytotoxic activity. J. Inorg. Biochem., 2007, 101, 1473-1482.
77. 4+ (BBR3464) with its noncovalent congeners. Mol. Pharmacol., 2006, 69, 666-672.
78. Harris, A. L.; Yang, X.; Hegmans, A.; Povirk, L.; Ryan, J. J.; Kelland, L.; Farrell, N. P. Synthesis, characterization, and cytotoxicity of a novel highly charged trinuclear platinum compound. Enhancement of cellular uptake with charge. Inorg. Chem., 2005, 44, 9598-9600.
79. Komeda, S.; Moulaei, T.; Woods, K. K.; Chikuma, M.; Farrell, N. P.; Williams, L. D. A third mode of DNA binding: Phosphate clamps by a polynuclear platinum complex. J. Am. Chem. Soc., 2006, 128, 16092-16103.
80. Zhang, J. C.; Liu, L.; Gong, Y. Q.; Zheng, X. M.; Yang, M. S.; Cui, J. R.; Shen, S. G. Synthesis, characterization and antitumor activity of new type binuclear platinum(II) complexes. Eur. J. Med. Chem., 2009, 44, 2322-2327.
81. Gao, E.; Zhu, M.; Yin, H.; Liu, L.; Wu, Q.; Sun, Y. Synthesis, characterization, interaction with DNA and cytotoxicity in vitro of dinuclear Pd(II) and Pt(II) complexes dibridged by 2,2'-azanediyldibenzoic acid. J. Inorg. Biochem. 2008, 102, 1958-1964.
82. Kapp, T.; Dullin, A.; Gust, R. Mono- and Polynuclear [Alkylamine] platinum(II) Complexes of [1,2-Bis(4-fluorophenyl) ethylenediamine] platinum(II): Synthesis and investigations on cytotoxicity, cellular distribution, and DNA and protein binding. J. Med. Chem., 2006, 49, 1182-1190.
83. Margiotta, N.; Ostuni, R.; Gandin, V.; Marzano, C.; Piccinonna, S.; Natile, G. Synthesis, characterization, and cytotoxicity of dinuclear platinum-bisphosphonate complexes to be used as prodrugs in the local treatment of bone tumours. Dalton Trans., 2009, 10904-10913.
84. Kalinowska-Lis, U.; Ochocki, J.; Matlawska-Wasowska, K. Trans geometry in platinum antitumor complexes. Coord. Chem. Rev., 2008, 252, 1328-1345.
85. Coluccia, M.; Natile, G. Trans-platinum complexes in cancer therapy. Anti-Cancer Agents Med. Chem., 2007, 7, 111-123.
86. Brabec, V.; Kasparkova, J. DNA Interactions of Platinum Anticancer Drugs. Recent Advances and Mechanisms of Action. Pérez, J. M.; Fuertes, M. A.; Alonso, C.; Eds. In: Metal Compounds in Cancer Chemotherapy, Research Signpost, Kerala, India, 2005, pp. 187-281.
87. Heringova, P.; Woods, J.; Mackay, F. S.; Kasparkova, J.; Sadler, P. J.; Brabec, V. Transplatin is cytotoxic when photoactivated: Enhanced formation of DNA cross-links. J. Med. Chem., 2006, 49, 7792-7798.
88. Boccarelli, A.; Giordano, D.; Natile, G.; Coluccia, M. Differential processing of antitumour-active and antitumour-inactive trans platinum compounds by SKOV-3 ovarian cancer cells. Biochem. Pharmacol., 2006, 72, 280-292.
89. Suchánková, T.; Vojtíšková, M.; Reedijk, J.; Brabec, V.; Kašpárková, J. DNA and glutathione interactions in cell-free media of asymmetric platinum(II) complexes cis- and trans-[PtCl2(isopropylamine)(1-methylimidazole)]: relations to their different antitumor effects. J. Biol. Inorg. Chem., 2009, 14, 75-87.
90. Aris, S. M.; Farrell, N. P. Towards antitumor active trans-platinum compounds. Eur. J. Inorg. Chem. 2009, 1293-1302.
91. Boccarelli, A.; Intini, F. P.; Sasanelli, R.; Sivo, M. F.; Coluccia, M.; Natile, G. Synthesis and in vitro antitumor activity of platinum acetonimine complexes. J. Med. Chem., 2006, 49, 829-837.
92. Zorbas-Seifried, S.; Jakupec, M. A.; Kukushkin, N. V.; Groessl, M.; Hartinger, C. G.; Semenova, O.; Zorbas, H.; Kukushkin, V. Y.; Keppler, B. K. Reversion of structure-activity relationships of antitumor platinum complexes by acetoxime but not hydroxylamine ligands. Mol. Pharmacol., 2007, 71, 357-365.
93. Quiroga, A. G.; Cubo, L.; de Blas, E.; Aller, P.; Navarro-Ranninger, C. Trans platinum complexes design: One novel water soluble oxime derivative that contains aliphatic amines in trans configuration. J. Inorg. Biochem., 2007, 101, 104-110.
94. Martínez, A.; Lorenzo, J.; Prieto, M. J.; de Llorens, R.; Font-Bardia, M.; Solans, X.; Avilés, F. X.; Moreno, V. Synthesis, characterization and biological activity of trans-platinum(II) and transplatinum(IV) complexes with 4-hydroxymethylpyridine. ChemBio-Chem., 2005, 6, 2068-2077.
95. 3(4-hydroxymethylpyridine)] by tumor suppressor protein p53 and character of DNA adducts of this cytotoxic complex. FEBS J., 2006, 273, 301-314.
96. Martínez, A.; Lorenzo, J.; Prieto, M. J.; Font-Bardia, M.; Solans, X.; Avilés, F. X.; Moreno, V. Influence of the position of substituents in the cytotoxic activity of trans platinum complexes with hydroxymethyl pyridines. Bioorg. Med. Chem., 2007, 15, 969-979.
97. Bulluss, G. H.; Knott, K. M.; Ma, E. S. F.; Aris, S. M.; Alvarado, E.; Farrell, N. trans-Platinum planar amine compounds with [N2O2] ligand donor sets: Effects of carboxylate leaving groups and steric hindrance on chemical and biological properties. Inorg. Chem., 2006, 45, 5733-5735.
98. Ma, E. S. F.; Bates, W. D.; Edmunds, A.; Kelland, L. R.; Fojo, T.; Farrell, N. Enhancement of aqueous solubility and stability employing a trans acetate axis in trans planar amine platinum compounds while maintaining the biological profile. J. Med. Chem., 2005, 48, 5651-5654.
99. Quiroga, A. G.; Pérez, J. M.; Alonso, C.; Navarro-Ranninger, C.; Farrell, N. Novel transplatinum(II) complexes with [N2O2] donor sets. Cellular pharmacology and apoptosis induction in Pam 212-ras cells. J. Med. Chem., 2006, 49, 224-231.
100. van Zutphen, S.; Pantoja, E.; Soriano, R.; Soro, C.; Tooke, D.M.; Spek, A. L.; den Dulk, J.; Brouwer, J.; Reedijk, J. New antitumour active platinum compounds containing carboxylate ligands in trans geometry: synthesis, crystal structure and biological activity. Dalton Trans., 2006, 1020-1023.
101. Ramos-Lima, F. J.; Vrána, O.; Quiroga, A. G.; Navarro-Ranninger, C.; Halámiková, A.; Rybnícčková, H.; Hejmalová, L.; Brabec, V. Structural characterization, DNA interactions, and cytotoxicity of new transplatin analogues containing one aliphatic and one planar heterocyclic amine ligand. J. Med. Chem., 2006, 49, 2640-2651.
102. Pantoja, E.; Gallipoli, A.; van Zutphen, S.; Komeda, S.; Reddy, D.; Jaganyi, D.; Lutz, M.; Tooke, D. M.; Spek, A. L.; Navarro-Ranninger, C.; Reedijk, J. Three new asymmetric transamine(azole)dichloridoplatinum complexes that overcome cisplatin resistance and their reactions with 5􀀑-GMP. J. Inorg. Biochem., 2006, 100, 1955-1964.
103. Jawbry, S.; Freikman, I.; Najajreh, Y.; Perez, J. M.; Gibson, D. Preparation, cytotoxicity and interactions with nucleophiles of three isomeric transplatinum complexes containing methylpiperidine ligands. J. Inorg. Biochem., 2005, 99, 1983-1991.
104. Najajreh, Y.; Kasparkova, J.; Marini, V.; Gibson, D.; Brabec, V. Structural characterization and DNA interactions of new cytotoxic transplatin analogues containing one planar and one nonplanar heterocyclic amine ligand. J. Biol. Inorg. Chem., 2005, 10, 722-731.
105. Ramos-Lima, F. J.; Quiroga, A. G.; García-Serrelde, B.; Blanco, F.; Carnero, A.; Navarro-Ranninger, C. New trans-platinum drugs with phosphines and amines as carrier ligands induce apoptosis in tumor cells resistant to cisplatin. J. Med. Chem., 2007, 50, 2194-2199.
106. Kalinowska, U.; Matławska, K.; Checińska, L.; Domagała, M.; Kontek, R.; Osiecka, R.; Ochocki, J. Synthesis, spectroscopy and antiproliferative activity of cis- and trans-platinum(II) complexes with diethyl(pyridin-4-ylmethyl)phosphate. X-ray crystal structure of trans-Pt(II) complex. J. Inorg. Biochem., 2005, 99, 2024-2031.
107. Coley, H. M.; Sarju, J.; Wagner, G. Synthesis and characterization of platinum(II) oxadiazoline complexes and their in vitro antitumor activity in platinum-sensitive and -resistant cancer cell lines. J. Med. Chem., 2008, 51, 135-141.
108. Najajreh, Y.; Khazanov, E.; Jawbry, S.; Ardeli-Tzaraf, Y.; Perez, J. M.; Kasparkova, J.; Brabec, V.; Barenholz, Y.; Gibson, D. Cationic nonsymmetric transplatinum complexes with piperidinopiperidine ligands. Preparation, characterization, in vitro cytotoxicity, in vivo toxicity, and anticancer efficacy studies. J. Med. Chem., 2006, 49, 4665-4673.
109. Halámiková, A.; Heringová, P.; Kašpárková, J., Intini, F. P.; Natile, G.; Nemirovski, A.; Gibson, D.; Brabec, V. Cytotoxicity, mutagenicity, cellular uptake, DNA and glutathione interactions of lipophilic trans-platinum complexes tethered to 1-adamantylamine. J. Inorg. Biochem., 2008, 102, 1077-1089.
110. 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.
111. Berners-Price, S. J.; Ronconi, L.; Sadler, P. J. Insights into the mechanism of action of platinum anticancer drugs from multinuclear NMR spectroscopy. Prog. Nucl. Magn. Reson. Spectrosc., 2006, 49, 65-98.
112. Davies, M. S.; Hall, M. D.; Berners-Price, S. J.; Hambley, T. W. [1H, 15N] Heteronuclear single quantum coherence NMR study of the mechanism of aquation of platinum(IV) ammine complexes. Inorg. Chem., 2008, 47, 7673-7680.
113. Mellor, H. R.; Snelling, S.; Hall, M. D.; Modok, S.; Jaffar, M.; Hambley, T. W.; Callaghan, R. The influence of tumour microenvironmental factors on the efficacy of cisplatin and novel platinum(IV) complexes. Biochem. Pharmacol., 2005, 70, 1137-1146.
114. Nemirovski, A.; Kasherman, Y.; Tzaraf, Y.; Gibson, D. Reduction of cis,trans,cis-[PtCl2(OCOCH3)2(NH3)2] by aqueous extracts of cancer cells. J. Med. Chem., 2007, 50, 5554-5556.
115. Kelland, L. Broadening the clinical use of platinum drug-based chemotherapy with new analogues: satraplatin and picoplatin. Expert. Opin. Investig. Drugs, 2007, 16, 1009-1021.
116. 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.
117. Martelli, L.; Di Mario, F.; Ragazzi, E.; Apostoli, P.; Leone, R.; Perego, P.; Fumagalli, G. Different accumulation of cisplatin, oxaliplatin and JM216 in sensitive and cisplatin-resistant human cervical tumour cells. Biochem. Pharmacol., 2006, 72, 693-700.
118. Sternberg, C. N.; Whelan, P.; Hetherington, J.; Paluchowska, B.; Slee, P. H.; Vekemans, K.; Van Erps, P.; Theodore, C.; Koriakine, O.; Oliver, T.; Lebwohl, D.; Debois, M.; Zurlo, A.; Collette, L. Phase III trial of satraplatin, an oral platinum plus prednisone vs. prednisone alone in patients with hormone-refractory prostate cancer. Oncology, 2005, 68, 2-9.
119. Latif, T.; Wood, L.; Connell, C.; Smith, D. C.; Vaughn, D.; Lebwohl, D.; Peereboom, D. Phase II study of oral bis (aceto) ammine dichloro (cyclohexamine) platinum (IV) (JM-216, BMS-182751) given daily x 5 in hormone refractory prostate cancer (HRPC). Invest. New Drugs, 2005, 23, 79-84.
120. Carr, J. L.; Tingle, M. D.; McKeage, M. J. Satraplatin activation by haemoglobin, cytochrome C and liver microsomes in vitro. Cancer Chemother. Pharmacol., 2006, 57, 483-490.
121. Choy, H.; Park, C.; Yao, M. Current status and future prospects for satraplatin, an oral platinum analogue. Clin. Cancer Res., 2008, 14, 1633-1638.
122. Choy, H. Satraplatin: an orally available platinum analog for the treatment of cancer. Expert Rev. Anticancer Ther., 2006, 6, 973-982.
123. Kozubík, A.; Horváth, V.; Švihálková-Šindlerová, L.; Souček, K.; Hofmanová, J.; Sova, P.; Kroutil, A.; Žák, F.; Mistr, A.; Turánek, 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.
124. Kašpárková, J.; Nováková, O.; Vrána, O.; Intini, F.; Natile, G.; Brabec, V. Molecular aspects of antitumor effects of a new platinum(IV) drug. Mol. Pharmacol., 2006, 70, 1708-1719.
125. Sova, P.; Mistr, A.; Kroutil, A.; Zak, F.; Pouckova, P.; Zadinova, M. Comparative anti-tumor efficacy of two orally administered platinum(IV) drugs in nude mice bearing human tumor xenografts. Anti-Cancer Drugs, 2006, 17, 201-206.
126. Reithofer, M. R.; Valiahdi, S. M.; Jakupec, M. A.; Arion, V. B.; Egger, A.; Galanski, M.; Keppler, B. K. Novel di- and tetracarboxylatoplatinum(IV) complexes. Synthesis, characterization, cytotoxic activity, and DNA platination. J. Med. Chem., 2007, 50, 6692-6699.
127. Reithofer, M. R.; Schwarzinger, A.; Valiahdi, S. M.; Galanski, M.; Jakupec, M. A.; Keppler, B. K. Novel bis(carboxylato) dichlorido(ethane-1,2-diamine)platinum(IV) complexes with exceptionally high cytotoxicity. J. Inorg. Biochem., 2008, 102, 2072-2077.
128. Reithofer, M.; Galanski, M.; Roller, A.; Keppler, B. K. An entry to novel platinum complexes: Carboxylation of dihydroxoplati num(IV) complexes with succinic anhydride and subsequent derivatization. Eur. J. Inorg. Chem., 2006, 2612-2617.
129. Dyson, P. J.; Sava, G. Metal-based antitumour drugs in the post genomic era. Dalton Trans., 2006, 1929-1933.
130. 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.
131. Ang, W. H.; Pilet, S.; Scopelliti, R.; Bussy, F.; Juillerat-Jeanneret, L.; Dyson, P. J. Synthesis and characterization of platinum(IV) anticancer drugs with functionalized aromatic carboxylate ligands: Influence of the ligands on drug efficacies and uptake. J. Med. Chem., 2005, 48, 8060-8069.
132. Bednarski, P. J.; Mackay, F. S.; Sadler, P. J. Photoactivatable platinum complexes. Anti-Cancer Agents Med. Chem., 2007, 7, 75-93.
133. Ronconi, L.; Sadler, P. J. Using coordination chemistry to design new medicines. Coord. Chem. Rev., 2007, 251, 1633-1648.
134. Bednarski, P. J.; Grünert, R.; Zielzki, M.; Wellner, A.; Mackay, F. S.; Sadler, P. J. Light-activated destruction of cancer cell nuclei by platinum diazide complexes. Chem. Biol., 2006, 13, 61-67.
135. Mackay, F. S.; Woods, J. A.; Moseley, H.; Ferguson, J.; Dawson, A.; Parsons, S.; Sadler, P. J. A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin. Chem. Eur. J., 2006, 12, 3155-3161.
136. Phillips, H. I. A.; Ronconi, L.; Sadler, P. J. Photoinduced reactions of cis,trans,cis-[PtIV(N3)2(OH)2(NH3)2] with 1-methylimidazole. Chem. Eur. J., 2009, 15, 1588-1596.
137. Ronconi, L.; Sadler, P. J. Unprecedented carbon-carbon bond formation induced by photoactivation of a platinum(IV)-diazido complex. Chem. Commun., 2008, 235-237.
138. 2]: Insights from DFT calculations. Phys. Chem. Chem. Phys., 2009, 11, 10311-10316.
139. Mackay, F. S.; Woods, J. A.; Heringová, P.; Kašpárková, J.; Pizarro, A. M.; Moggach, S. A.; Parsons, S.; Brabec, V.; Sadler, P. J. A potent cytotoxic photoactivated platinum complex. Proc. Natl. Acad. Sci. USA, 2007, 104, 20743-20748.