Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N-dimethyl-2(R)-aminomethylpyrrolidine)

European Journal of Medicinal Chemistry

Volumn 44, Issue 7, 2009, Pages 2807-2814

  Diakos, Connie I ^a   Zhang, Mei ^b   Beale, Philip J ^b   Fenton, Ronald R ^a   Hambley, Trevor W ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b ROYAL PRINCE ALFRED HOSPITAL   (Australia)

Author keywords

Anti tumor; Cytotoxic activity; Enantioselectivity; Platinum; Structure activity

Indexed keywords

AMINO ACID; AMINOMETHYLPYRROLIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; CISPLATIN; MIBOPLATIN; N CARBOBENZOXY S PROLINE 4 NITROPHENOL ESTER; N,N DIMETHYL 2 AMINOMETHYLPYRROLIDINE; PLATINUM DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; OVARY CANCER; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; HUMANS; LIGANDS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; PLATINUM; PROLINE; PYRROLIDINES; STEREOISOMERISM;

EID: 67349234832     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.12.022     Document Type: Article

References (46)

1. Siafaca K. Technology, Markets and Service Opportunities. Fut. Oncol. 5 2/3 (1999) 1041-1071
2. Wong E., and Giandomenico C.M. Chem. Rev. 99 9 (1999) 2451-2466
3. Hambley T.W. J. Chem. Soc., Dalton Trans. (2001) 2711-2718
4. Kelland L.R. Nat. Rev. Cancer 7 (2007) 573-584
5. Hambley T.W. Coord. Chem. Rev. 166 (1997) 181-223
6. Sandman K.E., and Lippard S.J. Methods for Screening the Potential Antitumour Activity of Platinum Compounds in Combinatorial Libraries. In: Lippert B. (Ed). Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug (1999), Verlag Helvetica Chimica Acta, Zurich 523-536
7. Natile G., and Marzilli L.G. Coord. Chem. Rev. 250 11-12 (2006) 1315-1331
8. Burchenal J.H., Kalaher K., O'Toole T., and Chisholm J. Cancer Res. 37 (1977) 3455-3457
9. Burchenal J.H., Kalaher K., Dew K., Lokys L., and Gale G. Biochimie 60 (1978) 961-965
10. Burchenal J.H., Kalaher K., Dew K., and Lokys L. Cancer Treat. Rep. 63 9-10 (1979) 1493-1498
11. Kidani Y., Inagaki K., and Tsukagoshi S. Gann 67 (1976) 921-922
12. Tashiro T., Kawada Y., Sakurai Y., and Kidani Y. Biomed. Pharmacother. 43 (1989) 251-260
13. Kidani Y., Inagaki K., Saito R., and Tsukagoshi S. J. Clin. Hematol. Oncol. 7 1 (1977) 197-209
14. Kidani Y., Noji M., and Tashiro T. Gann 71 (1980) 637-643
15. Noji M., Okamoto K., Kidani Y., and Tashiro T. J. Med. Chem. 24 (1981) 508-515
16. Speer R.J., Hall L.M., Stewart D.P., Ridgeway H.J., Hill J.M., Kidani Y., Inagaki K., Noji M., and Tsukagoshi S. J. Clin. Hematol. Oncol. 8 2 (1978) 44-50
17. Yamashita T., Hirose J., Noji M., Saito R., Tomida H., and Kidani Y. Biol. Pharm. Bull. 16 10 (1993) 1014-1018
18. Inagaki K., Ninomiya C., and Kidani Y. Chem. Lett. (1986) 233-236
19. Inagaki K., and Kidani Y. Inorg. Chem. 25 1 (1986) 1-3
20. Pendyala L., Kidani Y., Perez R., Wilkes J., Bernacki R.J., and Creaven P.J. Cancer Lett. 97 2 (1995) 177-184
21. Brunner H., Schmidt M., and Schonenberger H. Inorg. Chim. Acta 123 (1986) 201-207
22. Morikawa K., Honda M., Endoh K.-I., Matsumoto T., Akamatsu K.-I., Mitsui H., and Koizumi M. J. Pharm. Sci. 79 8 (1990) 750-753
23. Morikawa K., Honda M., Endoh K.-I., Matsumoto T., Akamatsu K.-I., Mitsui H., and Koizumi M. Chem. Pharm. Bull. 38 4 (1990) 930-935
24. Morikawa K., Honda M., Endoh K.-I., Matsumoto T., Akamatsu K.-I., Mitsui H., and Koizumi M. J. Pharm. Sci. 80 9 (1991) 837-842
25. Akamatsu K.-I., Endo K., Matsumoto T., Morikawa K., Koizumi M., Koizumi K., and Mitsui H. Jpn. J. Cancer Res. 82 (1991) 724-731
26. Matsumoto T., Endoh K., Akamatsu K., Kamisango K., Mitsui H., Koizumi K., Morikawa K., Koizumi M., and Matsuno T. Brit. J. Cancer 64 (1991) 41-46
27. Berger A., Kurta J., and Katchalski E. J. Am. Chem. Soc. 76 (1954) 5552-5554
28. Bodanszky M., and du Vigneaud V. J. Am. Chem. Soc. 81 (1959) 5688-5691
29. Fenton R.R., Stephens F.S., Vagg R.S., and Williams P.A. Inorg. Chim. Acta 197 (1992) 233-242
30. R.R. Fenton, PhD Thesis, Department of Chemistry, Macquarie University, Sydney, 1990.
31. Fenton R.R., Easdale W.J., Er H.M., O'Mara S.M., McKeage M.J., Russell P.J., and Hambley T.W. J. Med. Chem. 40 (1997) 1090-1098
32. Fanizzi F.P., Intini F.P., Maresca L., Natile G., Quaranta R., Coluccia M., di Bari L., Giordano D., and Mariggio M.A. Inorg. Chim. Acta 137 (1987) 45-51
33. Price J.H., Williamson A.N., Schramm R.F., and Wayland B.B. Inorg. Chem. 11 6 (1972) 1280-1284
34. Fenton R.R., Stephens F.S., Vagg R.S., and Williams P.A. Inorg. Chim. Acta 201 (1992) 157-164
35. Texsan, Molecular Structure Corporation, 1985 and 1992.
36. Sheldrick G.M. In: Sheldrick G.M., Kruger C., and Goddard R. (Eds). SHELXS-86. Crystallographic Computing vol. 3 (1986), Oxford University Press, Oxford 175-189
37. ORTEP, C.K. Johnson, Oak Ridge National Laboratories, Oak Ridge, 1965.
38. Hypercube, Enraf Nonius, 1985.
39. Hambley T.W. MOMEC-SG, Programme for Strain Energy Minimisation (1991), The University of Sydney
40. Hambley T.W. Inorg. Chem. 30 (1991) 937-942
41. Carmichael J., DeGraff W.G., Gazdar A.F., Minna J.D., and Mitchell J.B. Cancer Res. 47 (1987) 936-942
42. Brunner H., Schmidt M., Unger G., and Schonenberger H. Eur. J. Med. Chem. 20 6 (1985) 509-512
43. Brunner H., Kroiβ R., Schmidt M., and Schonenberger H. Eur. J. Med. Chem. 21 4 (1986) 333-338
44. Weeks C.L., Turner P., Fenton R.R., and Lay P.A. J. Chem. Soc., Dalton Trans. 6 (2002) 931-940
45. Rezler E.M., Fenton R.R., Esdale W.J., McKeage M.J., Russell P.J., and Hambley T.W. J. Med. Chem. 40 (1997) 3508-3515
46. Yonei M., Murata H., Itoh M., Watanabe Y., Ochi K., Honda M., and Nawata Y. Acta Crystallogr. C46 (1990) 137-138