Abstract
The intensive program of analogue synthesis initiated after the discovery of cisplatin has led to clinical trials for a number of second-generation complexes. Again it should be emphasized that analogue development in general has been responsible for many compounds of clinical usefulness and their study contributes to our better understanding of the parent complex.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
M. J. Cleare: Coord. Chem. Rev. 12, 479 (1974).
W. C. J. Ross, P. D. Braddock, A. R. Khokhar, and M. L. Tobe: Chem.-Biol. Interact. 5, 415 (1972).
M. J. Cleare and J. D. Hoeschele: Bioinorg. Chem. 2, 187 (1973).
P. D. Braddock, T. A. Connors, M. Jones, A. R. Khokhar, D. H. Melzack, and M. L. Tobe: Chem.-Biol. Interact. 11, 145 (1975).
M. L. Tobe and A. R. Khokhar: J. Clin. Hematol. Oncol. 7, 114 (1977).
M. J. Cleare: J. Clin. Hematol. Oncol. 7, 1 (1977).
J. J. Roberts and A. J. Thomson: Prog. Nuc. Acid Res. and Mol. Biol. 22, 71 (1979).
M. J. Cleare and P. C. Hydes: Metal Ions in Biol Syst. 11, 1 (1980).
M. J. Cleare, P. C. Hydes, D. R. Hepburn, and B. W. Malerbi: Cisplatin, Current Status and New Developments (Eds. A. W. Prestayko, S. T. Crooke, and S. K. Carter), p. 149. Academic Press, London (1980).
P. C. Hydes: Platinum Coordination Complexes in Cancer Chemotherapy (Eds. M. P. Hacker, E. B. Douple, and I. H. Krakoff), p. 216. Martinus Nijhoff, Boston (1984).
J. P. Macquet and J. L. Butour: J. Natl. Cancer Inst. 70, 899 (1983).
J. D. Hoeschele, T. A. Butler, and J. A. Roberts: Inorganic Chemistry in Biology and Medicine (ACS Symposium Series v. 140, Ed. A. E. Martell), p. 181. ACS (1980).
D. B. Brown, A. R. Khokhar, M. P. Hacker, J. J. McCormack, and R. A. Newman: in Platinum, Gold and Other Metal Chemotherapeutic Agents (ACS Symposium Series 209, Ed. S. J. Lippard), p. 265. ACS (1983).
N. Farrell, J. Williamson, and D. J. McLaren: Biochem. Pharmacol. 33, 961 (1984).
M. J. Abrams, D. H. Picker, P. H. Fackler, C. J. L. Lock, H. E. Howard-Lock, and R. Faggiani: Inorg. Chem. 25, 3980 (1986).
B. Rosenberg, L. Van Camp, J. E. Trosko, and H. V. Mansour: Nature (London) 222, 385 (1969).
M. Laverick, A. H. W. Nias, P. J. Sadler, and I. M. Ismail: Br. J. Cancer 43, 732 (1981).
L. Pendyala, J. W. Cowens, S. Madajewicz, and P. J. Creaven: Platinum Coordination Complexes in Cancer Chemotherapy (Eds. M. P. Hacker, E. B. Douple, and I. H. Krakoff), p. 114. Martinus Nijhoff (1984).
E. Rotondo, V. Fimiani, and A. Cavallaro: Tumori 69, 31 (1983).
S. Mong, D. C. Eubanks, A. W. Prestayko, and S. T. Crooke: Biochemistry 21, 3174 (1982).
J. F. Vollano, E. E. Blatter, and J. C. Dabrowiak: J. Am. Chem. Soc. 106, 2732 (1984).
P. C. Hydes and D. R. Hepburn: U.K. Patent Appl 2085440A (1981); C.A. 97, 61004 (1982).
R. J. Brandon and J. C. Dabrowiak: J. Med. Chem. 27, 861 (1984).
E. E. Blatter, J. F. Vollano, B. S. Krishnan, and J. C. Dabrowiak: Biochemistry 23, 4817 (1984).
N. Farrell and K. A. Skov: unpublished results.
R. K. Elespuru and S. K. Daley: Platinum Coordination Complexes in Cancer Chemotherapy (Eds. M. P. Hacker, E. B. Douple, and I. H. Krakoff), p. 58. Martinus-Nijhoff (1984).
J. L. van der Veer, A. R. Peters, and J. Reedijk: J. Inorg. Biochem. 26, 137 (1986).
H. Schöllhorn, R. Beyerle-Pfnur, U. Thewalt, and B. Lippert: J. Am. Chem. Soc. 108, 3680 (1986).
R. Kuroda, S. Neidle, I. M. Ismail, and P. J. Sadler: Inorg. Chem. 22, 3620 (1983).
R. Faggiani, B. Lippert, C. J. L. Lock, and B. Rosenberg: Can. J. Chem. 60, 529 (1982).
W. T. Bradner, W. C. Rose, and J. B. Huftalen: Cisplatin, Current Status and New Developments (Eds. A. W. Prestayko, S. T. Crooke, and S. K. Carter), p. 171. Academic Press (1980).
M. Noji, K. Okamoto, Y. Kidani, and T. Tashiro: J. Med. Chem. 24, 508 (1981).
R. H. Earhart: Cancer Treat. Rep. 62, 1105 (1978).
C. L. Litterst: Toxicol Appl Pharm. 61, 99 (1981).
R. J. Knox, F. Friedlos, D. A. Lydall, and J. J. Roberts: Cancer Res. 46, 1972 (1986).
S. D. Cutbush, R. Kuroda, S. Neidle, and A. B. Robins: J. Inorg. Biochem. 18, 213 (1983).
M. A. Bruck, R. Bau, M. Noji, K. Inagaki, and Y. Kidani: Inorg. Chim. Acta 92, 279 (1984).
C. G. van Kralingen, J. Reedijk, and A. L. Spek: Inorg. Chem. 19, 1481 (1980).
M. V. Caparelli, D. M. L. Goodgame, R. T. Riley, and A. C. Skapski: Inorg. Chim. Acta 67, L9 (1982).
J. D. Hoeschele, N. Farrell, W. R. Turner and C. D. Rithner: Inorg. Chem. 27, 4106 (1988).
D. G. Cracienescu, R. Maral, G. Mathé: Platinum Coordination Complexes in Cancer Chemotherapy (Eds. M. P. Hacker, E. B. Douple, and I. H. Krakoff), p. 256. Martinus Nijhoff (1984).
F. D. Rochon and P. C. Kong: Can. J. Chem. 64, 1894 (1986).
P. J. Andrulis, Jr. and P. Schwartz: U.S. Patent 4,565,884; C. A. 102 P: 1790652.
N. Farrell: In Platinum, Gold and Other Metal Chemotherapeutic Agents (ACS Symposium Series 209, Ed. S. J. Lippard), p. 279. ACS (1983).
R. Romeo and M. Cusumano: Inorg. Chim. Acta 49, 167 (1981).
S. Lanza, D. Minniti, R. Romeo, and M. L. Tobe: Inorg. Chem. 22, 2006 (1983).
N. Farrell, unpublished results.
J. A. Howie, G. R. Gale, and A. B. Smith: Biochem. Pharmacol. 21, 1465 (1972).
S. J. Lippard, H. M. Ushay, C. M. Merkel, and M. Poirier: Biochemistry 22, 5165 (1983).
I. Husain, S. K. Mauldin, A. Sancar, and S. G. Chaney: Proc. Am. Assoc. Cancer Res. 27, 287 (1986).
J. Burchenal, K. Kalaher, K. Dew, L. Lokys, and G. Gale: Biochimie 60, 961 (1978).
Y. Kidani, K. Inagaki, R. Saito, and S. Tsukagoshi: J. Clin. Hematol. Oncol. 7(1), 197 (1977).
C. J. L. Lock and P. Pilon: Acta Cryst. B37, 45 (1981).
K. P. Larsen and F. Toftlund: Acta Chemica Scand. A31, 182 (1977).
M. A. Bruck, R. Bau, M. Noji, K. Inagaki, and Y. Kidani: Inorg. Chim. Acta 92, 279 (1984).
F. D. Rochon, R. Melanson, J.-P. Macquet, F. Belanger-Gariepy, and A. L. Beauchamp: Inorg. Chim. Acta 108, 17 (1985).
K. Okamoto, M. Noji, T. Tashiro, and Y. Kidani: Chem. Pharm. Bull. 29, 929 (1981).
K. Inagaki and Y. Kidani: Inorg. Chem. 25, 1 (1986).
M. Gullotti, A. Pasini, R. Ugo, S. Filippeschi, L. Marmonti, and F. Spreafico: Inorg. Chim. Acta 91, 223 (1984).
M. Gulotti, G. Pacchioni, A. Pasini, and R. Ugo: Inorg. Chem. 21, 2006 (1982).
K. Inagaki, K. Tajima, Y. Kidani, T. Tashiro, and S. Tsukagoshi: Inorg. Chim. Acta 37, L547 (1979).
A. Shulman and F. P. Dwyer: Metal Chelates in Biological Systems (Chelating Agents and Metal Chelates, Eds. E. P. Dwyer and D. P. Mellor), pp. 383–431. Academic Press (1964).
A. B. Robins: J. Clin. Hematol. Oncol. 7(1), 266 (1978).
R. E. Cramer, P. L. Dahlstrom, M. J. T. Seu, T. Norton, and M. Kashiwagi: Inorg. Chem. 19, 148 (1980).
S. J. Meischen, G. R. Gale, and M. B. Naff: J. Clin. Hematol Oncol. 12, 67 (1982).
Pt compound NSC 356135, NCI antitumour screening data.
A. Pasini, G. Pratesi, G. Savi and F. Zunino: Inorg. Chim. Acta 137, 123 (1987).
S. Yolles, R. M. Roat, M. F. Sartori, and C. L. Washburne: ACS Symposium Series 186, 223 (1982).
W. Beck, B. Purucker, M. Girnth, H. Schoenenberger, H. Siedenberger, and G. Ruckdeshel: Z. Naturforsch., Teil 3:31, 832 (1976).
E. Bersanetti, A. Pasini, G. Pezzoni, G. Pratesi, G. Savi, R. Supino, and F. Zunino: Inorg. Chim. Acta 93, 167 (1984).
A. E. Martell Chelates of Ascorbic Acid. Formation and Catalytic Properties (Ascorbic Acid, Chemistry, Metabolism and Uses, Eds. P. A. Seib and B. M. Tolbert), pp. 153–178. ACS Symposium Series 200 (1982).
L. S. Hollis, A. Amundsen, and E. Stern: J. Am. Chem. Soc. 107, 274 (1985).
M. P. Hacker, A. R. Khokhar, D. B. Brown, J. J. McCormack, and I. H. Krakoff: Cancer Res. 45, 4748 (1985).
K. C. Tsou, K. F. Yip, K. W. Lo, and S. Ahmad: J. Clin. Hematol. Oncol. 7(1), 322 (1978).
M. Julliard, G. Vernin, and J. Metzger: Synthesis 49 (1982).
M. Maeda, N. Abiko, H. Uchida, and T. Sasaki: J. Med. Chem. 27, 444 (1984).
T.-s. Lin, R.-X. Zhou, K. J. Scanion, W. F. Brubaker Jr., J. J. S. Lee, K. Woods, C. Humphreys, and W. H. Prusoff: J. Med. Chem. 29, 681 (1986).
T. Tsubomura, S. Yano, K. Kobayashi, T. Sakurai, and S. Yoshikawa: J. Chem. Soc. Chem. Comm. 459 (1986).
H. Schonenberger, B. Wappes, M. Jennerwein, and M. Berger: Cancer Treat. Reviews 11 (Supp. A) 125 (1984).
O. Gandolfi, J. Blum, and F. Mandelbaum-Shavit: Inorg. Chim. Acta 91, 257 (1984).
W. D. McFayden, L. P. G. Wakelin, I. A. G. Roos, and V. A. Leopold: J. Med. Chem. 28, 1113 (1985).
E. Hurwitz, R. Kashi, and M. Wilchek: J. Natl. Cancer Inst. 69, 47 (1982).
M. Cais: Methods Enzymol. 92, 445 (1983).
M. Cais, S. Dani, Y. Eden, O. Gandolfi, M. Horn, E. Isaacs, Y. Josephi, Y. Saar, E. Slovin, and L. Snarsky: Nature (London) 270, 534 (1977).
C. Hansch: Acc. Chem. Res. 2, 232 (1969).
P. G. Abdul-Ahad and G. A. Webb: Int. J. Quantum Chem. 21, 1105 (1982).
T. P. Carsey and E. A. Boudreaux: Chem.-Biol. Interactions 30, 189 (1980).
R. Romeo and M. L. Tobe: Inorg. Chem. 13, 1991 (1974).
P. D. Braddock, R. Romeo, and M. L. Tobe: Inorg. Chem. 13, 1170 (1974).
R. B. Martin: Hydrolytic Equilibria and N7 Versus NI Binding in Purine Nucleosides of cis-Diamminedichloroplatinum(II): Palladium(II) as a Guide to Platinum(II) Reactions at Equilibrium (Platinum, Gold, and Other Metal Chemotherapeutic Agents, ACS Symposium Series 209, Ed. S. J. Lippard), pp. 231–244 (1983).
M. E. Howe-Grant and S. J. Lippard: Metal Ions in Biological Systems 11, 63 (1980).
M. C. Lim and R. B. Martin: J. Inorg. Nucl. Chem. 38, 1915 (1976).
K. J. Scanlon, R. L. Safirstein, H. Thies, R. B. Gross, S. Waxman, and J. B. Guttenplan: Cancer Res. 43, 4211 (1983).
R. Faggiani, B. Lippert, C. J. L. Lock, and B. Rosenberg: J. Am. Chem. Soc. 99, 777 (1977).
J. A. Stanko, L. S. Hollis, J. A. Schriefels, and J. D. Hoeschele: J. Clin. Hematol. Oncol. 7(1), 138 (1977).
R. Faggiani, B. Lippert, C. J. L. Lock, and B. Rosenberg: Inorg. Chem. 17, 1941 (1978).
J.-P. Macquet, S. Cros, and A. L. Beauchamp: J. Inorg. Biochem. 25, 197 (1985).
J. C. Dabrowiak, M. S. Balakrishnan, J. Clardy, G. D. van Duyne, and L. Silviera: NMR and Crystallographic Studies on a Second Generation Cisplatin Analogue (Platinum Coordination Complexes in Cancer Chemotherapy, Eds. M. P. Hacker, E. B. Douple, and I. H. Krakoff), p. 63. Martinus-Nijhoff (1984).
B. Rosenberg: Biochimie 60, 859 (1978).
D. S. Gill and B. Rosenberg: J. Am. Chem. Soc. 104, 4598 (1982).
C. J. Boreham, J. A. Broomhead, and D. P. Fairlie: Aust. J. Chem. 34, 659 (1981).
M. Chikuma and R. J. Pollock: J. Magn. Res. 47, 324 (1982).
P. S. Pregosin: Coord. Chem. Rev. 44, 247 (1982).
T. G. Appleton, R. D. Berry, C. A. Davis, J. R. Hall, and H. A. Kimlin: Inorg. Chem. 23, 3514 (1984).
T. G. Appleton, J. R. Hall, and S. F. Ralph: Inorg. Chem. 24, 4685 (1985).
L. G. Marzilli, Y. Hayden, and M. D. Reily: Inorg. Chem. 25, 974 (1986).
G. Annibale, L. Canovese, L. Cattalini, G. Marangoni, G. Michelon, and M. L. Tobe: Inorg. Chem. 23, 2705 (1984).
C. M. Riley, L. A. Sternson, and A. J. Repta: Anal. Biochem. 130, 203 (1983).
P. Melius and M. E. Friedman: Inorg. Perspect. Biol. Med. 1, 1 (1978).
B. Odenheimer and W. Wolf: Inorg. Chim. Acta 66, L41 (1982).
A. Meister and M. E. Anderson: Ann. Rev. Biochem. 52, 711 (1983).
B. A. Arrick and C. F. Nathan: Cancer Res. 44, 4224 (1984).
K. Micetich, L. A. Zwelling, and K. W. Kohn: Cancer Res. 43, 3609 (1983).
A. Eastman and V. M. Richon: Chem.-Biol. Inter. 61, 241 (1987).
P. A. Andrews, M. P. Murphy, and S. B. Howell: Cancer Res. 45, 6250 (1985).
A. Eastman and E. Bresnick: Biochem. Pharmacol. 30, 2721 (1981).
I. M. Ismail and P. J. Sadler: 195 Pt and 15 N-NMR Studies of Antitumour Complexes (Platinum, Gold and Other Metal Chemotherapeutic Agents, Ed. S. J. Lippard), pp. 171–190. ACS Symposium Series 209, Washington (1983).
A. B. Robins and M. O. Leach: Cancer Treat. Rep. 67, 245 (1983).
E. Segal and J.-B. lePecq: Cancer Res. 45, 492 (1985).
L. S. Hollis, A. R. Amundsen, and E. W. Stern: J. Med. Chem. 32, 128 (1989).
L. S. Hollis, E. W. Stern, A. R. Amundsen, A. V. Miller, and S. L. Doran: J. Am. Chem. Soc. 109, 3596 (1987).
N. Farrell, S. G. de Almeida, and K. A. Skov: J. Am. Chem. Soc. 110, 5018 (1988).
R. F. Borch: ‘The Platinum Anti-Tumour Drugs’ in Metabolism and Action of Anti-Cancer Drugs (Eds. G. Powis and R. A. Prough), p. 163. Taylor and Francis, London (1987).
S. K. Maudlin, I. Husain, A. Sancar, and S. G. Chaney: Cancer Res. 46, 2876 (1986).
S. K. Maudlin, F. A. Richard, M. Plescia, S. D. Wyrick, A. Sancar, and S. G. Chaney: Anal. Biochem. 157, 129 (1986).
J. D. Bell, R. E. Norman, and P. J. Sadler: J. Inorg. Biochem. 31, 241 (1987).
F. D. Rochon and P. C. Kong: J. Clin. Hematol. Oncol. 12, 39 (1987).
A. J. Canty and E. A. Stevens: Inorg. Chim. Acta 55, 157 (1981).
L. Kumar, N. R. Kandasamy, T. S. Srivastava, A. J. Amonkar, M. K. Adwanka, and M. P. Chitnis: J. Inorg. Biochem. 23, 1 (1985).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1989 Kluwer Academic Publishers
About this chapter
Cite this chapter
Farrell, N. (1989). Structure—Activity Relationships of Platinum—Amine Complexes. In: Transition Metal Complexes as Drugs and Chemotherapeutic Agents. Catalysis by Metal Complexes, vol 11. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-7568-5_4
Download citation
DOI: https://doi.org/10.1007/978-94-011-7568-5_4
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-011-7570-8
Online ISBN: 978-94-011-7568-5
eBook Packages: Springer Book Archive