Structural and mechanistic aspects of platinum anticancer agents

Transition Metal Chemistry

Volumn 31, Issue 8, 2006, Pages 1003-1016

  Ahmad, Saeed ^a   Isab, Anvarhusein A ^b   Ali, Saqib ^c  

^a UNIVERSITY OF ENGINEERING AND TECHNOLOGY   (Pakistan)

^b KING FAHD UNIVERSITY OF PETROLEUM AND MINERALS   (Saudi Arabia)

^c QUAID I AZAM UNIVERSITY   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; COMPLEXATION; DNA; DRUG PRODUCTS; MOLECULAR BIOLOGY; THERMODYNAMICS; TUMORS;

BIOCOORDINATION CHEMISTRY; METAL COMPOUNDS; PLATINUM ANTICANCER DRUGS; PLATINUM COMPLEXES;

PLATINUM;

EID: 33751172917     PISSN: 03404285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11243-006-0100-7     Document Type: Article

References (162)

1. (a) H. M. Pinto and J. H. Schornagel (eds), Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy, Plenum, New York, 1996.
2. (b) B. Lippert (ed.) Cisplatin - Chemistry and Biochemistry of a Leading Anticancer Drug, WILEY-VCH, Weinheim, 1999.
3. (c) M. Gielen and E. Tiekink, Metallotherapeutic Drugs and Metal Based Diagnostic Agents, Wiley, 2005.
4. D. Wong and S.J. Lippard, Nature Rev, Drug Disc., 4, 307 (2005).
5. MA. Fuertes, C. Alonso and J.M. Perez, Chem. Rev., 103, 645 (2003).
6. Y.P. HO, S.C.F. Au-Yeung and K.K.W. To, Med. Res. Rev., 23, 633 (2003).
7. C.X. Zhang and S.J. Lippard, Curr. Opin. Chem. Biol., 7, 481 (2003).
8. T. W. Hambley, J. Chem. Soc., Dalton Trans., 2711 (2001).
9. Z. Guo and P.J. Sadler, Angew. Chem. Int. Ed., 38, 1513 (1999).
10. J. Reedijk, Proc. Natl. Acad. Sci., USA, 100, 3611 (2003).
11. N. Farrell, in Platinum-Based Drugs in Cancer Therapy, L.R. Killard and N. Farrell (ed.), Humana Press Inc., Totowa, NJ, 321, 2000.
12. E. Wong and CM, Giandomenico, Chem. Rev., 99, 2451 (1999).
13. F.I. Raynaud, F.E. Boxall, P.M. Goddard, M. Valenti, M. Jones, B.A. Murrer, M. Abrams and L.R. Kelland, Clin. Cancer Res., 3, 2063 (1997).
14. A.C.G. Hotze, Y. Chen, T.W. Hambley, S. Parson, N.A. Kratochwil, J.A. Parkinson, V.P. Munk and P.J. Sadler, Eur. J. Inorg. Chem., 1035 (2002).
15. L.R. Kelland, G. Abel, M.J. Mckeage, M. Jones, P.M. Goddard, M. Valenti, B.A. Murrer and K.R. Harrap, Cancer Res., 53, 2581 (1993).
16. M.J. Bloemink, J. Reedijk, N. Farrell, Y. Qu and A.I. Stetscnko, J. Chem. Soc. Chem. Commun., 1002 (1992).
17. J.D. Roberts, J. Peroutka and N. Farrell, J. Inorg. Biochem., 77, 51 (1999).
18. P. Perego, L. Gatti, C. Caserini, R. Supino, D. Colangelo, R. Leone, S. Spinelli, N. Farrell and F. Zunino, J. Inorg. Biochem., 77, 59 (1999).
19. P. Perego, C. Caserini, L. Gatti, N. Carenini, S. Romanelli, R. Supino, D. Colangelo, I. Viano, R. Leone, S. Spinelli, G. Pezzoni, C. Manzotti, N. Farrell and F. Zunino, Mol. Pharmacol., 55, 528 (1999).
20. E. Frei III, A. Elias, C. Wheeler, P. Richardson and W. Hyrniuk, Clin. Cancer Res., 4, 2027 (1998).
21. J.J. Lokich, J.D. Ahlgren, J.J. Gullo, J.A. Philips and J.B. Fryer, J. Clin. Oncol., 7, 425 (1989).
22. X. Wang, J. Lin, X. Zhang, Q. Liu, Q. Xu, R.X. Tan and Z. Guo, J. Inorg. Biochem., 94, 186 (2003).
23. M.A, Fuertes, J. Castilla, C. Alonso and J.M. Perez, Curr. Med. Chem., 10, 257 (2003).
24. E.R. Jamieson and S.J. Lippard, Chem. Rev., 99, 2467 (1999).
25. S.G. Chaney, S.L. Campbell, E. Bassett and Y. Wu, Crit. Rev. Oncol. Hematol., 53, 3 (2005).
26. M. Kartalou and J.M. Essigmann, Mutat. Res., 478, 1 (2001).
27. Y. Zou, B.V. Houten and N. Farrell, Biochemistry, 33, 5404 (1994).
28. J. Reedjik, Chem. Rev.. 99, 2499 (1999).
29. R.N. Bose, S. Moghoddas, E.L. Weaver and E.W. Cox, Inorg. Chem., 34, 5878 (1995).
30. S.V. Zutphen and J. Reedijk, Coord. Chem. Rev., 249, 2845 (2005).
31. J. Reedjik, Chem. Commun., 801 (1996).
32. M. Green, M. Garner and D.M. Orton, Transition Met. Chem., 17, 164 (1992).
33. S.J. Lippard (ed.), Platinum, Gold and Other Metal Chemotherapeutic Agents, ACS Symposium Series, 209, 51 (1983).
34. S.E. Sherman and S.J. Lippard, Chem. Rev., 87, 1153 (1987).
35. J.M. Pasco and J.J. Roberts, Biochem. Pharm., 23, 1345 (1974).
36. R.B. Ciccarelli, M.J. Solomon, A. Varshavsky and S.J. Lippard, Biochemistry, 24, 7533 (1985).
37. J.J. Roberts and F. Friedlos, Cancer Res., 47, 31 (1987).
38. M.J. Bloemink, H. Engelking, S. Karentzopoulos, B. Krebs and J. Reedijk, Inorg. Chem., 35, 619 (1996).
39. C. Tu, X. Wu, Q. Liu, X. Wang, Q. Xu and Z. Guo, Inorg. Chim. Acta, 357, 95 (2004).
40. M. Carlone, L.G. Marzilli and G. Natile, Inorg. Chem., 43, 584 (2004).
41. E. Monti, M. Gariboldi, A. Maiocchi, E. Marcno, C. Cassino, E. Gabano and D. Osella, J. Med. Chem., 48, 857 (2005).
42. C. Bauer, T.P. Shulman, D. Gibson and A.H.J. Wang, Eur. J. Biochem., 256, 253 (1998).
43. J.P. Macquet and J.L. Butour, J. Natl. Cancer Inst., 70, 899 (1983).
44. L.S. Hollis, A.R. Amundsen and E.W. Stern, J. Med. Chem., 32, 128 (1989).
45. L.S. Hollis, W.I. Sundquist, N.J. Burstyn, J.W. Heigher-Bernays, S.F. Bellon, J.K. Ahmed, A.R. Amundsen, E.W. Stern and S.J. Lippard, Cancer Res., 51, 1875 (1991).
46. M.H. Baik, R.A. Friesner and S.J. Lippard, Inorg. Chem., 42, 8615 (2003).
47. G. Natile and M. Coluccia, Coord. Chem. Rev., 216-217, 383 (2001).
48. M.V. Beusichem and N. Farrell, Inorg. Chem., 31, 634 (1992).
49. T. Fojo, N. Farrell, W. Ortuzar, H. Tanimura, J. Weinstein and T.G. Myers, Crit. Rev. Oncol. Hematol., 53, 25 (2005).
50. Y. Najajreh, J. Kasparkova, V. Marini, D. Gibson and V. Brabec, J. Biol. Inorg. Chem., 10, 722 (2005).
51. Y. Liu, F.P. Intini, G. Natile and E. Sletten, J. Chem. Soc. Dalton Trans., 3489 (2002).
52. J. Kasparkova, O. Vrana, N. Farrell and V. Brabec, J. Inorg. Biochem., 98, 1560 (2004).
53. A. Ghezzi, M. Aceto, C. Cassino, E. Gabano and D. Osella, J. Inorg. Biochem., 98, 73 (2004).
54. X. Lin, T. Okuda, A. Holzer and S.B. Howell, Mol. Pharmacol., 62, 1154 (2002).
55. S. Ishida, J. Lee, D.J. Thiele and I. Herskowitz, Proc. Natl. Acad. Sci. USA, 99, 14298 (2002).
56. P.A. Andrews, S. Velury, S.C. Mann and S.B. Howell, Cancer Res., 48, 68 (1988).
57. S.S.G.E. van Boom and J. Reedijk, J. Chem. Soc., Chem. Commun., 1397 (1993).
58. K.J. Barnham, M.I. Djuran, P. del Socorro Muroch and P.J. Sadler, J. Chem. Soc., Chem. Commun., 721 (1994).
59. T.P. Shulman, Y. Najajreh and D. Gibson, J. Inorg. Biochem., 91, 306 (2002).
60. J.M. Dornish, J.E. Melvik and E.O. Pettersen, Anticancer Res., 6, 583 (1986).
61. J.M. Dornish, E.O. Pettersen and R. Oftebro, Cancer Res., 49, 3917 (1989).
62. J. Zou, X.D. Yang, F. An and K. Wang, J. Inorg. Biochem., 70, 227 (1998).
63. M.S. Robillard, M. Galanski, W. Zimmermann, B.K. Keppler and J. Reedijk, J. Inorg. Biochem., 88, 254 (2002).
64. M. Kartalou and J.M. Essigmann, Mutat. Res., 478, 23 (2001).
65. J. Holford, P.J. Beale, F.E. Boxall, S.Y. Sharp and L.R. Kelland, Eur. Cancer J., 36, 1984 (2000).
66. R. Fujii, M. Mutoh, K. Niwa, K. Yamada, T. Aikou, M. Nakagawa, M. Kuwano and S. Akiyama, Jpn J. Cancer Res., 85, 426 (1994).
67. K. Kawai, N. Kamatani, E. Georges and V. Ling, J. Biol. Chem., 265, 13137 (1990).
68. J. Kasparkova, O. Novakova, Y. Najajreh, D. Gibson, J.M. Perez and V. Brabec, Chem. Res. Toxicol., 16, 1424 (2003).
69. G. McGowan, S. Parsons and P.J. Sadler, Inorg. Chem., 44, 7459-7467 (2005).
70. M.S. Davies, S.J. Berners-Price and T.W. Hambley, Inorg. Chem., 39, 5603 (2000).
71. S.E. Miller and D.A. House, Inorg. Chim. Acta, 173, 53 (1990).
72. M.S. Davies, J.W. Cox, S.J. Berners-Price, W. Barklage, Y. Qu and N. Farrell, Inorg. Chem., 39, 1710 (2000).
73. M.S. Davies, D.S. Thomas, A. Hegmans, S.J. Berners-Price and N. Farrell, Inorg. Chem., 41, 1101 (2002).
74. S.J. Barton, K.J. Barnham, A. Habtemariam, R.E. Sue and P.J. Sadler, Inorg. Chim. Acta, 273, 8 (1998).
75. M. El-Khateeb, T.G. Appleton, L.R. Gahan, B.G. Charles, S.J. Berners-Price and A.M. Bolton, J. Inorg. Biochem., 77, 13 (1999).
76. R.J. Knox, F. Friedlos, D.A. Lydall and J.J. Roberts, Cancer Res., 46, 1972 (1986).
77. T.W. Hambley, Coord. Chem. Rev., 166, 181 (1997).
78. M.H. Baik, R.A. Friesner and S.J. Lippard, J. Am. Chem. Soc., 125, 14082 (2003).
79. W. Kaim and B. Schwederski, Bioinorganic Chemisty: Inorganic Elements in the Chemistry of Life, John Wiley and Sons, Inc., New York, 1994, p. 367.
80. A.M.J. Fichtinger-Schepman, J.L. Veervan der, J.H.J. Hartogden, P.H.M. Lohman and J. Reedijk, Biochemistry, 24, 707 (1985).
81. S.L. Bruhn, J.H. Toney and S.J. Lippard, Prog. Inorg. Chem., 38, 477 (1990).
82. A. Eastman, Pharmacol. Ther., 34, 155 (1987).
83. F.A. Blommaert, H.C. Dijk-Knijnenburgvan, F.J. Dijt, L. Engelseden, R.A. Baan, F. Berends and A.M. Fichtinger-Schepman, Biochemistry, 34, 8474 (1995).
84. S.G. Chancy, S.L. Campbell, B. Temple, E. Bassett, Y. Wu and M. Faldu, J. Inorg, Biochem., 98, 1551 (2004).
85. A. Hongo, S. Seki, K. Akiyama and T. Kudo, Int. J. Biochem., 26, 1009 (1994).
86. G. Los, M.J. Vugtvan, L. Engelseden and H.M. Pinedo, Biochem. Pharmacol., 46, 1229 (1993).
87. G. Admiraal, J.L. Veervan der, R.A.G. Graafde, J.H.J. Hartogdcn and J. Reedijk, J. Am. Chem. Soc., 109, 592 (1987).
88. D. Yang, S.S.G.E. Boomvan, J. Reedijk, J.H. Boomvan and A.H.J. Wang, Biochemistry, 34, 12912 (1995).
89. P.M. Takahara, A.C. Rosenzweig, C.A. Frederick and S.J. Lippard, Nature, 377, 649 (1995).
90. P.M. Takahara, C.A. Frederick and S.J. Lippard, J. Am. Chem. Soc., 118, 12309 (1996).
91. S.E. Sherman, D. Gibson, A.H.-J. Wang and S.J. Lippard, J. Am. Chem. Soc., 110, 7368 (1988).
92. K.J. Barnham, C.J. Bauer, M.I. Djuran, M.A. Mazid, T. Rau and P.J. Sadler, Inorg. Chem., 34, 2826 (1995).
93. L.G. Marzilli, J.S. Saad, Z. Kuklenyik, K.A. Keating and Y. Xu, J. Am. Chem. Soc., 123, 2764 (2001).
94. A. Gelasco and S.J. Lippard, Biochemistry, 37, 9230 (1998).
95. B. Spingler, D.A. Whittington and S.J. Lippard, Inorg. Chem., 40, 5596 (2001).
96. Y. Wu, P. Pradhan, J. Havener, G. Boysen, J.A. Swenberg, S.L. Campbell and S.G. Chaney, J. Mol. Biol., 341, 1251 (2004).
97. J.M. Woynarowski, S. Faivre, M.C.S. Herzig, B. Arnett, W.G. Chapman, A.V. Trevino, E. Raymond, S.G. Chaney, A. Vaisman, M. Verchenko and P. E. Juniewicz, Mol, Pharmacol., 58, 920 (2000).
98. M.H. Fouchet, E. Guittet, J.A.H. Cognet, J. Kozelka, C. Gauthier, M.L. Bret, K. Zimmermann and J.C. Chottard, J. Biol. Inorg. Chem., 2, 83 (1997).
99. M.S. Davies, S.J. Berners-Price and T.W. Hambley, J. Am. Chem. Soc., 120, 11380 (1998).
100. R. Gupta, J.L. Beck, M.M. Sheil and S.J. Ralph, J. Inorg. Biochem., 99, 552 (2005).
101. A. Eastman, Biochemistry, 22, 3927 (1983).
102. A. Eastman, Biochemistry, 24, 5027 (1985).
103. A. Eastman, Biochemistry, 25, 3912 (1986).
104. A.M.J. Fichtinger-Schepman, A.T.V. Oosteram, P.H.M. Lohman and F. Bereads, Cancer Res., 47, 3000 (1987).
105. V. Monjardet-Bas, S. Bombard, J.C. Chottard and J. Kozelka, Chem. Eur. J., 9, 4739 (2003).
106. J.J. Roberts and F. Friedlos, Pharmacol. Therap., 34, 215 (1987).
107. F. Coste, J.M. Malinge, L. Serre, W. Shepard, M. Roth, M. Leng and C. Zelwer, Nucl. Acid Res., 27, 1837 (1999).
108. F. Paquet, C. Perez, M. Leng, G. Lancelot and J.M. Malinge, J. Biomol. Struct. Dynamics, 14, 67 (1996).
109. H. Huang, L. Zhu, B.R. Reid, G.P. Drobny and P.B. Hopkins, Science, 270, 1842 (1995).
110. A. Eastman and M.A. Barry, Biochemistry, 26, 3303 (1987).
111. A. Eastman, M.M. Jennerwein and D.L. Nagel, Chem. Biol. Interact., 67, 71 (1988).
112. V. Brabec and M. Leng, Proc. Natl. Acad. Sci. USA, 90, 5345 (1993).
113. F. Paquet, M. Boudvillain, G. Lancelot and M. Leng, Nucl. Acid Res., 27, 4261 (1999).
114. J. Kasparkova, V. Marini, Y. Najajreh, D. Gibson and V. Brabec, Biochemistry, 42, 6321 (2003).
115. C.J. Garderenvan and L.P. Houtevan, Eur. J. Biochem., 225, 1169 (1994).
116. J.M. Teuben, C. Bauer, A.H. Wang and J. Reedijk, Biochemistry, 38, 12305 (1999).
117. S.F. Bellon, J.H. Coleman and S.J. Lippard, Biochemistry, 30, 8026 (1991).
118. J.M. Malinge, C. Perez and M. Leng, Nucl. Acid Res., 22, 3834 (1994).
119. J. Zehnulova, J. Kasparkova, N. Farrell and V. Barbec, J. Biol. Chem., 276, 22191 (2001).
120. V. Brabec, J. Kasparkova, O. Varana, O. Novakova, J.W. Vox, Y. Qu and N. Farrell, Biochemistry, 38, 6781 (1999).
121. M.B.G. Kloster, H.C. Hannis, D.C. Muddiman and N. Farrell, Biochemistry, 38, 14731 (1999).
122. G. Obmolova, C. Ban, P. Hsieh and W. Yang, Nature, 407, 703 (2000).
123. U.M. Ohndorf, A.M. Rould, Q. He, C.O. Pabo and S.J. Lippard, Nature, 399, 708 (1999).
124. D.B. Zamble, Y. Mikata, C.H. Eng, K.E. Sandman and S.J. Lippard, J. Inorg. Biochem., 91, 451 (2002).
125. M.M. Mcanulty and S.J. Lippard, Mutat. Res.-DNA Repair, 362, 75 (1996).
126. D.B. Zamble, D. Mu, J.T. Reardon, A. Sancar and S.J. Lippard, Biochemistry, 35, 10004 (1996).
127. J.T. Reardon, A. Vaisman, S.G. Chancy and A. Sancar, Cancer Res., 59, 3968 (1999).
128. D.T. Kirkpatrick and T.D. Petes, Nature, 387, 929 (1997).
129. M. Yamada, E. O'Regan, R. Brown and P. Karran, Nucl. Acids Res., 25, 491 (1997).
130. M.H. Lamers, A. Perrakis, J.H. Enzlin, H.H.K. Winterwerp, N.D. Wind and T.K. Sixma, Nature, 407, 711 (2000).
131. P.M. Pil and S.J. Lippard, Science, 256, 234 (1992).
132. J.H. Toney, B.A. Donahue, P.J. Kellwtt, S.L. Bruhn, J.M. Essigmann and S.J. Lippard, Proc. Natl. Acad. Sci, USA, 86, 8328 (1989).
133. J. Kasparkova, O. Novakova, V. Marini, Y. Najajreh, D. Gibson, J.M. Perez and V. Brabec, J. Biol. Chem., 278, 47516 (2003).
134. S. Mansy, G.Y.H. Chu, R.E. Duncan and R.S. Tobias, J. Am. Chem. Soc., 100, 607 (1978).
135. D.P. Bancroft, C.A. Lepre and S.J. Lippard, J. Am. Chem. Soc., 112, 6860 (1990).
136. Y. Chen, Z. Gou, J.A. Parkinson and P.J. Sadler, J. Chem. Soc., Dalton Trans., 3577 (1998).
137. J.M. Teuben, M.R. Zubiri and J. Reedijk, J. Chem. Soc., Dalton Trans., 369 (2000).
138. N.P. Johnson, A.M. Mazard, J. Escalier and J.P. Macquet, J. Am. Chem. Soc., 107, 6376 (1985).
139. P.J. Sadler and Z. Guo, Pure Appl. Chem., 70, 863 (1998).
140. S.J. Barton, K.J. Barnham, U. Frey, A. Habtemariam, R.E. Sue and P.J. Sadler, Aust. J. Chem., 52, 173 (1999).
141. J.C. Dabrowiak, J. Goodisman and A.K. Souid, Drug Met. Disposition, 30, 1378 (2002).
142. P.D. Sadowitz, B.A. Hubbard, J.C. Dabrowiak, J. Goodisman, K.A. Tacka, M.K. Aktas, M.J. Cunningham, R.L. Dubowy and A.K. Souid, Drug Met. Disposition, 30, 183 (2002).
143. E. Volckova, L.P. Dudones and R.N. Bose, Pharm. Res., 19, 124-131 (2002).
144. M.I. Djuran, E.L.M. Lampers and J. Reedijk, Inorg. Chem., 30, 2468 (1991).
145. B.J. Cordon, Inorg. Chim. Acta, 137, 125 (1987).
146. T.G. Appleton, J.W. Conner, J.R. Hall and P.D. Prenzler, Inorg. Chem., 28, 2030 (1989).
147. K.J. Barnham, M.I. Djuran, P.S. Murdoch, J.D. Ranford and P.J. Sadler, Inorg. Chem., 35, 1065 (1996).
148. R.E. Norman, J.D. Ranford and P.J. Sadler, Inorg. Chem., 31, 877 (1992).
149. A.I. Ivanov, J. Christodoulou, J.A. Parkinson, K.J. Barnham, A. Tucker, J. Woodrow and P.J. Sadler, J. Biol. Chem., 273, 14721 (1998).
150. E.L.M. Lempers, K. Inagaki and J. Reedijk, Inorg. Chim. Acta, 152, 201 (1988).
151. K.M. Williams, C. Rowan and J. Mitchell, Inorg. Chem., 43, 1190 (2004).
152. M.E. Oehlsen, Y. Qu and N. Farrell, Inorg. Chem., 42, 5498 (2003).
153. Y. Chen, J.A. Parkinson, Z. Gou, T. Brown and P.J. Sadler, Angew. Chem., Int. Ed., 38, 2060 (1999).
154. A.J. Zelazowski, J.S. Garvey and J.D. Hoeshele, Arch. Biochem. Biophys., 229, 246 (1984).
155. Y. Saga, H. Hashimoto, S. Yachiku, T. Iwata and M. Tokumitsu, Int. J. Urol., 11, 407 (2004).
156. T.G. Appleton, Coord. Chem. Rev., 166, 313 (1997).
157. J.D. Holding, W.E. Lindup, C.V. Laer, G.C.M. Vreeburg, V. Schiling, J.A. Wilson and P.M. Stell, Brit. J. Clin. Pharmacol, 33, 75 (1992).
158. D. Screnci and M.J. Mckeage, J. Inorg, Biochem, 77, 105 (1999).
159. J.E. Huheey, E.A. Keiter and R.L. Keiter, Inorganic Chemisiry-Principles of Structure and Reactivity, Pearson Education, Inc., Delhi, India, p. 958, 2000.
160. J.G. Zhang and W.E. Lindup Biochem. Pharmacol. 47, 1127 (1994).
161. D.L. Bodnner, P.C. Dedon, P.C. Keng and R.F. Borech, Cancer Res., 46, 2745 (1986).
162. U. Bierbach, T.W. Hambley and N. Farrell, Inorg. Chem., 37, 708 (1998).