Synthesis, characterization, and representative crystal structure of lipophilic platinumii (homopiperazine)carboxylate complexes

Journal of Coordination Chemistry

Volumn 52, Issue 3, 2001, Pages 273-287

  Ali, Mohammad S ^a   Powers, Christopher A ^b   Whitmire, Kenton H ^b   Guzman Jimenez, Ilse ^b   Khokhar, Abdul R ^a  

^a UNIVERSITY OF TEXAS   (United States)

^b RICE UNIVERSITY   (United States)

Author keywords

Carboxylate; Crystal structure; Homopiperazine; Platinum(II); Synthesis

Indexed keywords

ACETIC ACID DERIVATIVE; BUTYRIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHELATE; DECANOIC ACID DERIVATIVE; HEPTANOIC ACID DERIVATIVE; HEXANOIC ACID DERIVATIVE; LAURIC ACID DERIVATIVE; MYRISTIC ACID DERIVATIVE; NONANOIC ACID; OCTANOIC ACID DERIVATIVE; OXALIC ACID DERIVATIVE; PALMITIC ACID DERIVATIVE; PIPERAZINE DERIVATIVE; PLATINUM COMPLEX; PROPIONIC ACID DERIVATIVE; TARTRONIC ACID DERIVATIVE; UNDECANOIC ACID; VALERIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; INFRARED SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0035759727     PISSN: 00958972     EISSN: None     Source Type: Journal    
DOI: 10.1080/00958970108022593     Document Type: Article

References (51)

1. B. Rosenberg, L. Van Camp, J. E. Troska and V. H. Mansour, Nature (London) 222, 385 (1969).
2. I. H. Krakoff, M. Nicolini (Eds.), Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy: Clinical Application of Platinum Complexes, Martinus Nijhoff Boston, MA, p. 351 (1988).
3. P. J. Loehrer Sr., S. D. Williams and L. H. Einhorn, J. Natl. Cancer Inst. 80, 1373 (1988).
4. P. J. Loehrer and L. H. Enihorn, Ann. Intern. Med. 100, 704 (1984).
5. I. H. Krakoff, Cancer Treat. Rep. 63, 1523 (1979).
6. J. B. Vermorken and H. M. Pinedos, Nth. J. Med. 25, 270 (1982).
7. D. D. Vonhoff, R. Schlsky and R. Reichert, Cancer Treat. Rep. 63, 1527 (1979).
8. A. Eastman and S. Illenye, Cancer Treat. Rep. 68, 1189 (1984).
9. (a) J. H. Burchenal, K. Kalaher, K. Dew and L. Lokys, Cancer Treat Rep. 63 (9-10) 1493 (1979);
10. (b) J. H. Burchenal, K. Kalaher, K. Dew, L. Lokys and G. Gale, Biochemie 60, 961 (1978);
11. (c) J. H. Burchenal, K. Kalaher, T. O'Toole and J. Chishoim, Cancer Res. 37, 3455 (1977).
12. (a) K. R. Harrap, Cancer Treat. Rev. 12, 2133 (1985);
13. (b) C. Magioni, G. Bolis, S. Pecorelli, K. Bragman, A. Epis, G. Favalli, A. Gambino, F. Landoni, M. Presti, W. Tori, W. Vassena, F. Zanaboni and S. Marsoni, J. Natl. Cancer Inst. 81, 1464 (1989);
14. (c) A. H. Calvert, S. J. Harland, D. R. Newell, Z. H. Siddik and K. R. Harrap, Cancer Treat. Rev. 12 (suppl. A) 51 (1981);
15. (d) B. W. Booth, R. B. Weiss, A. H. Korzan, W. C. Wood, R. W. Carey and L. P. Panasci, Cancer Treat. Rep. 69, 919 (1985).
16. J. M. Extra, M. Espie, F. Calvo, C. Ferme, L. Mignot and M. Marti, Cancer Chemother. Pharmacol. 25, 299 (1990).
17. G. Gregoniadis et al. (Eds.), Receptor-Mediating Targeting of Drugs, Plenum Press, New York, p. 427 (1985).
18. E. Mayhew, D. Papahadjopoulos and M. J. Ostro (Eds.), Liposomes, Marcel Deckker, New York, p. 289 (1983).
19. J. N. Weinstein and L. D. Leserman, Pharmacol Ther. 24, 207 (1984).
20. G. Poste, R. Kirch, P. Bugelski and P. S. Sunkara (Eds.), Novel Approach to Cancer Chemotherapy, Academic, Orlando, FL (1984).
21. (a) J. Freis, W. H. Mueller, P. Magerstedt and H. J. Schmoll, Arch. Int. Pharmacodyn. Ther. 258, 180 (1980);
22. (b) V. I. Kaledin, N. A. Matlenko, V. P. Nikolin, V. V. Gruntenko and V. G. Budker, J. Natl. Cancer Inst. 41, 1602 (1982);
23. (c) M. B. Yatvin, H. Muhlensiepen, W. Proschen, J. N. Weinstein and L. E. Feinendegen, Cancer Res. 258, 180 (1982).
24. (a) A. R. Khokhar, S. Al-Baker and G. J. Lumetta, J. Coord. Chem. 18, 291 (1988);
25. (b) A. R. Khokhar, S. Al-Baker, T. Brown and R. Perez-Soler, J. Med. Chem. 34, 325 (1991);
26. (c) A. R. Khokhar, Q. Xu and S. Al-Baker, J. Coord. Chem. 24, 77 (1991);
27. S. Al-Baker, R. Perez-Soler, and A. R. Khokhar, J. Inorg. Biochem. 47, 99 (1992);
28. (e) S. Al-Baker, R. Perez-Soler and A. R. Khokhar, J. Coord. Chem. 29, 1 (1993);
29. (f) Mohammad S. Ali, Kenton H. Whitmire, Zahid H. Siddik and Abdul R. Khokhar, J. Bioinorg. Chem. 77, 231-238 (1999).
30. (a) R. Perez-Soler, A. R. Khokhar and G. Lopez-Berestein, Cancer. Res. 47, 6462 (1987);
31. (b) A. R. Khokhar, S. Al-Baker and R. Perez-Soler, Anticancer Drug Des. 3, 177 (1988);
32. (c) A. R. Khokhar, S. Al-Baker, I. H. Krakoff and R. Perez-Soler, Cancer Chemother. Pharmacol. 23, 219 (1989).
33. R. Perez-Soler, G. Lopez-Berestein, J. Lauthersztain, S. Al-Baker, K. Francis, D. MaciasKiger, M. N. Raber and A. R. Khokhar, Cancer Res. 50, 4254 (1990).
34. TEXSAN: Single Crystal Analysis Software, Version 5.0; Molecular Structure Corporation: The Woodlands, TX (1989).
35. The scattering factors are part of the SHELX-93 package and can be found in the International Tables for X-ray Crystallography; Tables 4.2.6.8 and 6.1.1.4. Kluwers Academic Publishers: Dordrecht, The Netherlands, Vol. C (1992).
36. SHELXTL-PLUS PC Version 4.2; Siemens Crystallographic Research Systems; Madison, WI (1990).
37. G. M. Sheldrick, SHELXL-93; University of Gottingen: Gottingen, Germany (1993).
38. S. C. Dhara, Ind. J. Chem. 8, 193 (1970).
39. K. Nakamato, Infrared and Raman Spectra of Inorganic Coordination Compounds, 4th edn., John Wiley and Sons, New York, p. 383 (1986).
40. (a) A. R. Khokhar, S. Al-baker, T. Brown and R. Perez-Soler, J. Med. Chem. 34, 321 (1991);
41. (b) S. Al-Baker, R. Perez-Soler and A. R. Khokhar, J. Inorg. Biochem. 47, 99 (1992);
42. (c) S. Al-Baker, R. Perez-Soler and A. R. Khokhar, J. Coord. Chem. 29, 1(1993).
43. (a) J. H. Price, A. N. Williamson, R. F. Schramm and B. B. Wayland, Inorg. Chem. 11, 1280 (1972);
44. (b) P. Bita, G. O. Morton, T. S. Dunne, E. F. Delos Santos, Y. Lin, S. R. Boone, R. C. Haltiwanger and C. G. Pierpont, Inorg. Chem. 29, 645 (1990);
45. (c) A. R. Khokhar, S. Al-Baker, I. H. Krakoff and R. Perez-Soler, Cancer. Chemother. Pharmacol. 23, 219 (1989).
46. E. C. H. Ling, W. A. Gregory and T. W. Hambley, J. Am. Chem. Soc. 116, 2673 (1994).
47. M. Bruck, R. Bau, M. Noji, K. Inagaki and Y. Kidani, Inorg. Chim. Acta 92, 279 (1984).
48. S. Neidle, I. M. Ismail and P. J. Sadler, J. Inorg. Biochem. 13, 205 (1980).
49. J. D. Hoeschele, H. D. H. Showalter, A. J. Kraker, W. L. Elliott, B. J. Robert and J. W. Kampf, J. Med. Chem. 37, 2630 (1994).
50. F. D. Rochon, R. Melanson, J. P. Meacquet, F. Belanger-Gariepy and A. L. Beauchamp, J. Inorg. Chim. Acta, Chim. 108, 17 (1985).
51. P. Bitha, G. O. Morton, T. S. Dunne, E. F. Delos Santos, Y. Lin, S. R. Boone, R. Haltiwanger and C. G. Pierpont, Inorg. Chem. 29, 645 (1990).