Preparation, characterization, and antitumor activity of new cisplatin analogues with 1-methyl-4-(methylamino)piperidine: Crystal structure of [PtII(1-methyl-4-(methylamino) piperidine)(oxalate)]

Journal of Inorganic Biochemistry

Volumn 94, Issue 1-2, 2003, Pages 179-185

  Mukhopadhyay, Uday ^a   Thurston, John ^b   Whitmire, Kenton H ^b   Siddik, Zahid H ^a   Khokhar, Abdul R ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

^b RICE UNIVERSITY   (United States)

Author keywords

1 Methyl 4 (methylamino)piperidine; Antitumor agents; Carboxylates; Crystal structure; Platinum; Synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; CISPLATIN DERIVATIVE; LIGAND; NITROGEN; OXALIC ACID; OXYGEN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; GEOMETRY; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

EID: 0037294260     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0162-0134(02)00614-1     Document Type: Article

References (42)

1. Loehrer P.J., Einhorn L. Ann. Intern. Med. 100:1984;704-713.
2. Reed E., Kohn K.W. Chabner B.A., Collins J. Cancer Chemotherapy Principles and Practice. 1990;465 J.B. Lippincott, Philadelphia, PA.
3. Pratt W.B., Ruddon R.W., Ensminger W.D., Maybaum J. The Anticancer Drugs. 1994;133 Oxford University Press, New York.
4. Krakoff I.H. Cancer Treat. Rep. 63:1979;1523-1525.
5. Vermorken J.B., Pinedos H.M. Neth. J. Med. 25:1982;270-274.
6. Krakoff I.H. Nicolini M. Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy: Clinical Applications of Platinum Complexes. 1988;351 Martinus Nijhoff, Boston.
7. Calvert A.H., Harland S.J., Newell D.R., Siddik Z.H., Harrap K.R. Cancer Treat. Rev. 12:1985;51-57.
8. Alvarez-Valdes A., Perez J.M., López-Solera I., Lannegrand R., Continente J.M., Amo-Ochoa P., Camazón M.J., Solans X., Font-Bardia M., Navarro-Ranninger C. J. Med. Chem. 45:2002;1835-1844.
9. Thomas T., Thomas T.J. Cell. Mol. Life Sci. 58:2001;244-258.
10. Taguchi T., Kurata S., Ohashi M. Cell. Biochem. Funct. 19:2001;19-26.
11. Booth B.W., Weis W.C., Korzun A.H., Wood W.C., Carey R.W., Panasci L.P. Cancer Treat. Rep. 69:1985;919-920.
12. Speer R.J., Ridgway H., Stewart D.P., Hall L.M., Zapatta A., Hill J.M. J. Clin. Hematol. Oncol. 7:1977;220.
13. Perez-Soler R., Khokhar A.R., Hacker M.P., Lopez Berestein G. Cancer Res. 46:1986;6269-6273.
14. Khokhar A.R., Al-Baker S., Krakoff I.H., Perez-Soler R. Cancer Chemother. Pharmacol. 23:1989;219-224.
15. Kidani Y. Trends Inorg. Chem. 1:1990;107.
16. Khokhar A.R., Al-Baker S., Perez-Soler R. Anticancer Drugs. 3:1992;95-100.
17. Eastman A., Illenye S. Cancer Treat. Rep. 68:1984;1189-1190.
18. Burchenal J.H., Kalaher K., Dew K., Lokys L., Gale G. Biochemie. 60:1978;961-965.
19. Burchenal J.H., Kalaher K., O'Toole T., Chrisholm J. J. Cancer Res. 37:1977;3455-3457.
20. Extra J.M., Espie M., Calvo F., Ferme C., Mignot L., Marty M. Cancer Chemother. Pharmacol. 25:1990;299-303.
21. 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;4254-4259.
22. SHELXTL 5.10 (Bruker AXS, 1997).
23. The Scattering Factors are part of the SHELXTL package and can be found in the international Tables for X-ray Crystallographic, Vol. C, Kluwer, Dordrecht, The Netherlands, 1992.
24. Siddik Z.H., Mims B., Lozano G., Thai G. Cancer Res. 58:1998;698-703.
25. Dhara S.C. Ind. J. Chem. 8:1970;193.
26. Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. 4th Edition:1986;383 Wiley, New York.
27. Khokhar A.R., Al-Baker S., Brown T., Perez-Soler R. J. Med. Chem. 34:1991;325-329.
28. Al-Baker S., Perez-solere R., Khokhar A.R. J. Inorg. Biochem. 47:1992;99-108.
29. Al-Baker S., Perez-Soler R., Khokhar A.R. J. Coord. Chem. 29:1993;1-6.
30. Ali M.S., Whitmire K.H., Toyomasu T., Siddik Z.H., Khokhar A.R. J. Inorg. Biochem. 77:1999;231-238.
31. Ramsey N.F. Phys. Rev. 78:1950;699-703.
32. Gill D.S., Rosenberg B. J. Am. Chem. Soc. 104:1982;4598-4604.
33. Khokhar A.R., Xu Q., Al-Baker S., Bear J.L. Inorg. Chim Acta. 194:1992;243-246.
34. Bruck M.A., Bau R., Noji M., Inagaki K., Kidani Y. Inorg. Chim Acta. 92:1984;279-284.
35. Neidle S., Ismail I.M., Sadler P.J. J. Inorg. Biochem. 13:1980;205-212.
36. Hoeschele J.D., Showalter H.D.H., Kraker A.J., Elliott W.L., Robert B.J., Kampf J.W. J. Med. Chem. 37:1994;2630-2636.
37. Rochon F.D., Melanson R., Macquet J.P., Belanger-Gariepy F., Beauchamp A.L. Inorg. Chim. Acta. 108:1985;17-21.
38. Rochon F.D., Gruia L.M. Inorg. Chim. Acta. 306:2000;193-204.
39. Ling E.C.H., Allen G.W., Hambley T.W. J. Am. Chem. Soc. 116:1994;2673-2674.
40. Harrap K.R. Cancer Treat. Rev. (Suppl. A). 12:1985;21-33.
41. Wiltshaw E. Cancer Treat. Rev. (Suppl. A). 12:1985;67-71.
42. Siddik Z.H., Hagopian G.S., Thai G., Tomisaki S., Toyomasu T., Khokhar A.R. J. Inorg. Biochem. 77:1999;65-70.