Palladium(II) complexes of dialkyl α-anilinobenzylphosphonates. Synthesis, characterization, and cytostatic activity

Journal of Inorganic Biochemistry

Volumn 63, Issue 2, 1996, Pages 125-142

  Curic M ^a   Tusek Bozic Lj ^a   Vikic Topic D ^a   Scarcia, V ^b   Furlani, A ^b   Balzarini, J ^c   De Clercq, E ^c  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b UNIVERSITY OF TRIESTE   (Italy)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AZOBENZENE DERIVATIVE; CISPLATIN; LIGAND; METAL COMPLEX; ORGANOPHOSPHORUS COMPOUND; PHOSPHONIC ACID DERIVATIVE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CYTOSTASIS; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; TUMOR CELL LINE;

EID: 0030221718     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/0162-0134(95)00199-9     Document Type: Article

References (52)

1. 1. A. W. Prestayko, S. T. Crooke, and S. K. Carter (Eds.), Cisplatin: Current Status and New Developments, Academic, New York, 1980.
2. 2. M. P. Hacker, E. B. Douple, and I. H. Krakoff (Eds.), Platinum Coordination Complexes in Cancer Chemotherapy, Martinus Nijhoff, Boston, 1984.
3. 3. H. Krakoff, in Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy: Clinical Applications of Platinum Complexes, E. M. Nicolini, Ed., Martinus Nijhoff, Boston, 1988, p. 351.
4. 4. J. H. Burchenal, K. Kalahar, T. Toole, and J. Chisholm, Cancer Res. 37, 3455 (1977); G. R. Gale, A. B. Smith, and P. Schwartz, J. Clin. Hematol. Oncol. 217 (1979); J. P. Macquet, S. Cros, and J. P. Armand, Cancer Res. 44, 3736 (1984).
5. 4. J. H. Burchenal, K. Kalahar, T. Toole, and J. Chisholm, Cancer Res. 37, 3455 (1977); G. R. Gale, A. B. Smith, and P. Schwartz, J. Clin. Hematol. Oncol. 217 (1979); J. P. Macquet, S. Cros, and J. P. Armand, Cancer Res. 44, 3736 (1984).
6. 4. J. H. Burchenal, K. Kalahar, T. Toole, and J. Chisholm, Cancer Res. 37, 3455 (1977); G. R. Gale, A. B. Smith, and P. Schwartz, J. Clin. Hematol. Oncol. 217 (1979); J. P. Macquet, S. Cros, and J. P. Armand, Cancer Res. 44, 3736 (1984).
7. 5. A. Furlani, V. Scarcia, G. Faraglia, L. Sindellary, L. Trincia, and M. Nicolini, Eur. J. Med. Chem. - Chim. Ther. 21, 261 (1986).
8. 6. S. Mylonas, A. Valavanidis, K. Dimitropoulos, M. Polissiou, A. S. Tsiftsoglou, and S. Vizirianakis, J. Inorg. Biochem. 34, 265 (1988); R. Mital, N. Jain, and T. S. Srivastava, Inorg. Chim. Acta 166, 135 (1989).
9. 6. S. Mylonas, A. Valavanidis, K. Dimitropoulos, M. Polissiou, A. S. Tsiftsoglou, and S. Vizirianakis, J. Inorg. Biochem. 34, 265 (1988); R. Mital, N. Jain, and T. S. Srivastava, Inorg. Chim. Acta 166, 135 (1989).
10. 7. A. R. Khokhar and G. J. Lumetta, Inorg. Chim. Acta 153, 255 (1988).
11. 8. F. L. Wimmer, S. Wimmer, P. Castan, S. Cros, N. Johnson, and E. Colacio-Rodrigues, Anticancer Res. 9, 791 (1989); P. Castan, E. Colacio-Rodriguez, A. L. Beauchamp, S. Cros, and S. Wimmer, J. Inorg. Biochem. 38, 225 (1990).
12. 8. F. L. Wimmer, S. Wimmer, P. Castan, S. Cros, N. Johnson, and E. Colacio-Rodrigues, Anticancer Res. 9, 791 (1989); P. Castan, E. Colacio-Rodriguez, A. L. Beauchamp, S. Cros, and S. Wimmer, J. Inorg. Biochem. 38, 225 (1990).
13. 9. D. Higgins III, L. Neely and S. Fricker, J. Inorg. Biochem. 49, 149 (1993).
14. 10. I. Haiduc and C. Silvestru, In Vivo 3, 285 (1989); G. Sava, S. Pacor, V. Ceschia, G. Zassinovich, and G. Mestroni, Anticancer Res. 9, 878 (1989).
15. 10. I. Haiduc and C. Silvestru, In Vivo 3, 285 (1989); G. Sava, S. Pacor, V. Ceschia, G. Zassinovich, and G. Mestroni, Anticancer Res. 9, 878 (1989).
16. 11. E. Alessio, G. Menstroni, G. Nardin, W. M. Attia, M. Calligaris, G. Sava, and S. Zorzet, Inorg. Chem. 27, 4099 (1988); S. K. Chattopadhyay and S. Ghosh, J. Inorg. Biochem. 43, 613 (1988).
17. 11. E. Alessio, G. Menstroni, G. Nardin, W. M. Attia, M. Calligaris, G. Sava, and S. Zorzet, Inorg. Chem. 27, 4099 (1988); S. K. Chattopadhyay and S. Ghosh, J. Inorg. Biochem. 43, 613 (1988).
18. 12. G. M. Kolodny and C. Rose, Cancer Res. 43, 3101 (1983); G. Sava, T. Giraldi, G. Mestroni, and G. Zassinovich, Chem. Biol. Interactions 45, 1 (1983).
19. 12. G. M. Kolodny and C. Rose, Cancer Res. 43, 3101 (1983); G. Sava, T. Giraldi, G. Mestroni, and G. Zassinovich, Chem. Biol. Interactions 45, 1 (1983).
20. 13. Lj. Tušek-Božić, I. Matijašić, G. Bocelli, G. Calestani, A. Furlani, V. Scarcia, and A. Papaioannou, J. Chem. Soc., Dalton Trans. 195 (1991).
21. 14. Lj. Tušek-Božić, I. Matijašić, G. Bocelli, P. Sgarabotto, A. Furlani, V. Scarcia, and A. Papaioannou, Inorg. Chim. Acta 185, 229 (1991).
22. 15. Lj. Tušek-Božić, M. Ćurić, J. Balzarini, and E. De Clercq, Nucleosides Nucleotides 14, 777 (1995).
23. 16. V. Jagodić, Croat. Chem. Acta 48, 325 (1976); E. K. Fields, J. Am. Chem. Soc. 74, 1528 (1952).
24. 16. V. Jagodić, Croat. Chem. Acta 48, 325 (1976); E. K. Fields, J. Am. Chem. Soc. 74, 1528 (1952).
25. 17. M. Ćurić, Lj. Tušek-Božić, and D. Vikić-Topić, Magn. Reson. Chem. 14, 27 (1995).
26. 18. V. Jagodić and Lj. Tušek, J. Org. Chem. 37, 222 (1972).
27. 19. F. R. Hartley, The Chemistry of Platinum and Palladium, Wiley, New York, 1993.
28. 20. H. Eagle, Proc. Soc. Exp. Biol. Med. 89, 362 (1955).
29. 21. D. J. Hutchinson, O. L. Ittensohn, and M. R. Bjerregaard, Exp. Cell Res. 42, 157 (1966).
30. 22. E. De Clercq, J. Balzarini, P. F. Torrence, M. P. Mertes, C. L. Schmit, D. Shugar, P. J. Baar, A. S. Jones, G. Verhelst, and R. T. Walker, Mol. Pharmacol. 19, 321 (1981).
31. 23. H. Eagle, Science 130, 432 (1952).
32. 24. G. E. Moore, R. E. Gerner, and H. A. Franklin, J. Am. Med. Assoc. 199, 519 (1967).
33. 25. R. I. Geran, N. H. Greenberg, M. M. McDonald, A. M. Schumacher, and B. J. Abbot, Cancer Chemother. Rep. 3, 1 (1972).
34. 26. R. J. Tallarida and R. B. Murray, Manual of Pharmacological Calculations with Computer Programs, Springer, New York, 1987.
35. 27. A. C. Cope and R. W. Siekman, J. Am. Chem. Soc. 87, 3272 (1965); J. M. Kliegman and A. C. Cope, J. Organomet. Chem. 16, 309 (1969); A. M. Manotti Lanfredi, F. Ugozzoli, M. Ghedini, and S. Licoccia, Inorg. Chim. Acta 86, 165 (1984).
36. 27. A. C. Cope and R. W. Siekman, J. Am. Chem. Soc. 87, 3272 (1965); J. M. Kliegman and A. C. Cope, J. Organomet. Chem. 16, 309 (1969); A. M. Manotti Lanfredi, F. Ugozzoli, M. Ghedini, and S. Licoccia, Inorg. Chim. Acta 86, 165 (1984).
37. 27. A. C. Cope and R. W. Siekman, J. Am. Chem. Soc. 87, 3272 (1965); J. M. Kliegman and A. C. Cope, J. Organomet. Chem. 16, 309 (1969); A. M. Manotti Lanfredi, F. Ugozzoli, M. Ghedini, and S. Licoccia, Inorg. Chim. Acta 86, 165 (1984).
38. 28. D. Suton, Chem. Rev. 93, 995 (1993).
39. 29. M. I. Bruce, B. L. Goodall, and F. G. A. Stone, J. Chem. Soc., Dalton Trans. 687 (1978); M. Ghedini, S. Licoccia, and S. Armentano, Mol. Cryst. Liq. Cryst. 108, 269 (1984).
40. 29. M. I. Bruce, B. L. Goodall, and F. G. A. Stone, J. Chem. Soc., Dalton Trans. 687 (1978); M. Ghedini, S. Licoccia, and S. Armentano, Mol. Cryst. Liq. Cryst. 108, 269 (1984).
41. 30. P. J. Steel and G. B. Caygill, J. Organomet. Chem. 327, 101 (1987).
42. 31. V. Jagodić and Lj. Tušek, Croat. Chem. Acta 44, 445 (1972); V. Jagodić, Croat. Chem. Acta 49, 127 (1977).
43. 31. V. Jagodić and Lj. Tušek, Croat. Chem. Acta 44, 445 (1972); V. Jagodić, Croat. Chem. Acta 49, 127 (1977).
44. 32. A. L. Balch and D. Petridis, Inorg. Chem. 8, 2247 (1969).
45. 33. L. C. Thomas, Interpretation of Infrared Spectra of Organophosphorus Compounds, Heyden & Son Ltd., 1974.
46. 34. A. J. Klaus and P. Rys, Helv. Chim. Acta 64, 1452 (1981); I. Omae, Chem. Rev. 79, 287 (1979).
47. 34. A. J. Klaus and P. Rys, Helv. Chim. Acta 64, 1452 (1981); I. Omae, Chem. Rev. 79, 287 (1979).
48. 35. G. P. Khare, R. G. Little, J. T. Veal, and R. J. Doedens, Inorg. Chem. 14, 2475 (1975).
49. 36. J. F. Van Baar, K. Vrieze, and D. J. Stufkens, J. Organomet. Chem. 81, 247 (1974).
50. 37. C. G. van Kralingen, J. Reedijk, and A. L. Spek, Inorg. Chem. 19, 1481 (1980).
51. 38. M. Coluccia, A. Nassi, F. Loseto, A. Boccarelli, M. A. Mariggio, D. Giordano, F. P. Intini, P. Caputo, and G. Natile, J. Med. Chem. 36, 510 (1993).
52. 39. J. Reedijk, A. M. J. Fichtinger-Schepman, A. T. von Oasteron, and P. von de Putte, Structure and Bonding 67, Springer-Verlag, Berlin-Heidelberg, 1987.