Synthesis, characterization and cytotoxicity of new platinum(IV) axial carboxylate complexes: Crystal structure of potential antitumor agent [Pt(IV)(trans-1R,2R-diaminocyclohexane)trans(acetate)2Cl2]

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 3, 2000, Pages 515-521

  Ali Khan, S Rounaq ^a   Huang, Shurong ^a   Shamsuddin, S ^a   Inutsuka, Sadaaki ^a   Whitmire, Kenton H ^b   Siddik, Zahid H ^a   Khokhar, Abdul R ^a  

^a UNIVERSITY OF TEXAS   (United States)

^b RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CARBOXYLIC ACID DERIVATIVE; CHLORIDE ION; CISPLATIN; PLATINUM; PLATINUM COMPLEX; TETRAPLATIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG SYNTHESIS; GEOMETRY; HUMAN; HUMAN CELL; HYDROGEN BOND; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OVARY TUMOR; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CARBOXYLIC ACIDS; CELL SURVIVAL; CISPLATIN; CRYSTALLOGRAPHY, X-RAY; HUMANS; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; ORGANOPLATINUM COMPOUNDS; PLATINUM; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0033996086     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00313-2     Document Type: Article

References (54)

1. Loehrer P.J., Einhorn L. Ann. Intern. Med. 100:1984;704.
2. Krakoff I.H. Cancer Treat. Rep. 63:1979;1523.
3. Vermorken J.B., Pinedos H.M. Neth. J. Med. 25:1982;270.
4. Carter, S. K. In Platinum Coordination Complexes in Cancer Chemotherapy; Hacker, M. P.; Douple, E. B.; Krakoff, I. H., Eds.; Martinus Nijhoff: Boston, 1984; p 359.
5. Krakoff, I. H. In Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy: Clinical Applications of Platinum Complexes; Nicolini, M., Ed.; Martinus Nijhoff: Boston, 1988; p 351.
6. Loehrer P.J., Williams S.D. Sr., Einhorn L.H. J. Natl Cancer Inst. 80:1988;1373.
7. Calvert A.H., Harland S.J., Newell D.R., Siddik Z.H., Harrap K.R. Cancer Treat. Rev. 12:1985;51.
8. Booth B.W., Weis W.C., Korzun A.H., Wood W.C., Carey R.W., Panasci L.P. Cancer Treat. Rep. 69:1985;919.
9. Speer R.J., Ridgway H., Stewart D.P., Hall L.M., Zapata A., Hill J.M. J. Clin. Hematol. Oncol. 7:1977;220.
10. Perez-Soler R., Khokhar A.R., Hacker M.P., Lopez Berestein G. Cancer Res. 46:1986;6269.
11. Khokhar A.R., Al-Baker S., Krackoff I.H., Perez-Soler R. Cancer Chemother. Pharmacol. 23:1989;219.
12. Kidani Y. Trends Inorg. Chem. 1:1990;107.
13. Khokhar A.R., Al-Baker S., Perez-Soler R. Anticancer Drugs. 3:1992;95.
14. Eastman A., Illenye S. Cancer Treat. Rep. 68:1984;1189.
15. Burchenal J.H., Kalaher K., Dew K., Gale G. Biochemie. 60:1978;961.
16. Burchenal J.H., Kalaher K., O'Toole T., Chrisholm J. J. Cancer Res. 37:1977;3455.
17. Extra J.M., Espie M., Calvo F., Ferme C., Mignot L., Marty M. Cancer Chemother. Pharmacol. 25:1990;299.
18. Perez-Soler R., Lopez-Berestein G., Lauthersztain J., Al-Baker S., Francis K., Macias-Kiger D., Raber M.N., Khokhar A.R. Cancer Res. 50:1990;4252.
19. Prestayko, A. W.; Crooke, S. T.; Carter, S. K. Cisplatin, Current Status and New Developments; Academic: New York, 1980.
20. Al-Baker S., Vollano J.F., Dabrowaik J. J. Am. Chem. Soc. 108:1986;5443.
21. Kelland L.R., Barnard C.F.J., Evans I.G., Murrer B.A., Theobald B.R.C., Wyer S.B., Goddard P.M., Jones M., Valenti M., Bryant A., Gogers P.M., Harrap K.R. J. Med. Chem. 38:1995;3031.
22. Novakova O., Vrana O., Kiseleva V.I., Brabec V. Eur. J. Biochem. 228:1995;616.
23. Christian M.C., Kohn K., Sarosy G., Link C., Davis P., Adams D., Weiss R.B., Brewster L., Lombardo F., Reed E. Proc. Am. Soc. Clin. Oncol. 11:1992;117.
24. Judson, I.; McKeage, M.; Hanwell, J.; Berry, C; Mistey, P.; Raymand, F.; Poon, G.; Murrer, B.; Harrap, K. In Platinum and Other Metal Coordination Complexes in Cancer Chemotherapy: The Clinical Development of the Oral Platinum Anticancer Agent JM 216, H. M. Press: New York, 1996; p 83.
25. Khokhar A.R., Al-Baker S., Brown T., Perez-Soler R. J. Med. Chem. 34:1991;325.
26. Al-Baker S., Siddik Z.H., Khokhar A.R. J. Coord. Chem. 31:1994;109.
27. Khokhar A.R., Shamsuddin S., Al-Baker S., Shah S. J. Coord. Chem. 36:1995;7.
28. Shamsuddin S., Al-Baker S., Siddik Z.H., Khokhar A.R. Inorg. Chim. Acta. 241:1996;101.
29. Khokhar A.R., Al-Baker S., Shamsuddin S., Siddik Z.H. J. Med. Chem. 40:1997;112.
30. Dhara S.C. Ind. J. Chem. 8:1970;193.
31. Shamsuddin S., Santillan C.C., Stark J.L., Whitmire K.H., Siddik Z.H., Khokhar A.R. J. Inorg. Biochem. 71:1998;29.
32. Nakamoto, K. Infrared and Raman Spectra of Inorganic Coordination Compounds, 4th ed.; Wiley: New York, 1986; p 383.
33. For chemical shifts of platinum with different surroundings, see Pregosin, P. S. Coord. Chem. Rev. 1982, 44, 247 and refs 34 and 35.
34. Brandon R.J., Dabrowiak J.C. J. Med. Chem. 27:1984;861.
35. Bancroft D.P., Lepre C.A., Lippard S.J. J. Am. Chem. Soc. 112:1990;6860.
36. Khokhar A.R., Xu Q., Al-Baker S., Bear J.L. Inorg. Chim. Acta. 194:1992;243.
37. Bruck M.A., Bau R., Noji M., Inagaki K., Kidani Y. Inorg. Chim. Acta. 92:1984;279.
38. Ohba S., Sato S., Saito Y. Acta Cryst. B35:1979;957.
39. 1 2.
40. Choi H.-K.Kuei-Shang Hung, S. Bau R. Biochem. Biophys. Res. Commun. 156:1988;1125.
41. Xu Q., Khokhar A.R. J. Inorg. Biochem. 48:1992;217.
42. Khokhar A.R., Xu Q., Al-Baker S. J. Inorg Biochem. 52:1993;51.
43. Khokhar A.R., Shamsuddin S., Xu Q. Inorg. Chim. Acta. 219:1994;193.
44. Shamsuddin S., Khokhar A.R. J. Coord. Chem. 33:1994;83.
45. Hoeschele J.D., Hollis Showalter H.D., Kraker A.R., Elliot W.L., Roberts B.J., Kampf J.W. J. Med. Chem. 37:1994;2630.
46. Shamsuddin S., Van Hal J.W., Stark J.L., Whitmire K.H., Khokhar A.R. Inorg. Chem. 36:1997;25.
47. Neidle S., Snook C.F., Murrer B.A., Barnard C.F. J. Acta Cryst. C51:1995;822.
48. Nowotnik, D. P., In Radiopharmaceuticals Using Radioactive Compounds in Pharmaceutics and Medicine; Theobald, A., Ed.; John Wiley & Sons: New York, 1989; Chapter 3.
49. Siddik Z.H., Thai G., Yoshida M., Zhang Y.P., Al-Baker S., Khokhar A.R. J. Cancer Res. Clin. Oncol. 120:1994;571.
50. TEXSAN: Single Crystal Analysis Software, Version 5.0; Molecular Structure Corporation: The Woodlands, TX, 1989.
51. The scattering factors are part of the SHELX-93 package and can be found in the International Tables for X-ray Crystallography; Kluwer Academic Publishers: Dordrecht, The Netherlands, Vol. C, 1992, Tables 4.2.6.8 and 6.1.1.4.
52. SHELXTL-PLUS PC, Version 4.2; Siemens Crystallographic Research Systems; Madison, WI, 1990.
53. Sheldrick, G. M. SHELXL-93, University of Gottingen: Gottingen, Germany, 1993.
54. Siddik Z.H., Mims B., Lozano G., Thai G. Cancer Res. 58:1998;698.