Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Lpophilicity vs. Antitumor Activity of Carboxylatoplatinum(lV) Complexes

  • Published : 20001000
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Abstract

Acylation of an intermediate tetrahydroxoplatinum(IV) complex, $[Pt(OH)_4(dach)]$ (dach = $trans-(\pm)-12-di-aminocyclohexane)$, with one or two kinds of carboxylic anhydrides in stepwise manner afforded various car-boxylatoplatinum(IV) complexes, $[Pt(O_2CR)\chi(OR’)4-\chi(dach)]$ (R = $(CH_2)_3CH_3$ or $C(CH_3)_3$, R’ = H or $OCCH_3$, and $\chi$ = 1-4) with a wide range of lipophilicity. The title complexes were subjected to bioassay using the murine leukemia L1210 cell line, and in particular, their in vivo oral antitumor activity was attempted to correlate with their lipophilicity and water solubility. The most orally active complex exhibited intermediate lipophilicity and water solubility, but it has been found that an exact relationship between the lipophilicity and oral anticancer activity could not be established, since the lipophilicity of the complexes is not the sole parameter to determine the oral activity. One of the important intermediate complexes partially substituted was subjected to X-ray anal-ysis for positit of the substituted group: $[Pt(OPiv)_3(OH)(dach)]$ crystallizes in the tetragonal sys-tem, space group $P42_1c$ with a = 21.161(3) $\AA$, b = 21.161(6) $\AA$, c = 12.816(3) $\AA$, $\alpha=\beta=$ r $=90^{\circ}$, V = 5739(2) $\AA^3$ and Z = 8.

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References

  1. Cancer REs. v.52 Kelland, L. R.;Murrer, B. A.;Abel, G.;Giandomenico, C. M.;Mistry, P.;Harrap, K. R.
  2. Cancer Chemother. Pharmacol. v.43 Kizu, R.;Nakanish, T.;Hayagawa, K.;Matsuzawa, A.;Eriguchi, M.;Takeda, Y.;Akiyama, N.;Tashiro, T.;Kidani, Y.
  3. Inorg. Chem. v.37 Choi, S.;Filotto, C.;Bisanzo, M.;Delaney, S.;Lagasee, D.;Whitworth, J. L.;Jusko, A.;Li, C.;Wood, N. A.;Willingham, J.;Schwenker, A.;Spaulding, K.
  4. Inorg. Chem. v.35 Barnard, C. F. J.;Vollano, J. F.;Chaloner, P. A.;Dewa, S. Z.
  5. Inorg. Chem. v.34 Giandomenico, C. M.;Abrams, M. J.;Murrer, B. A.;Vollano, J. F.;Rheinheimer, M. I.;Wyer, S. B.;Bossard, G. E.;Higgins Ⅲ, J. D.
  6. Inorg. Chem. v.35 Galanski, M.;Keppler, B. K.
  7. J. Med. Chem. v.40 Khokhar, A. R.;Al-Baker, S.;Shamsuddin, S.;Siddik, Z. H.
  8. Cancer Res. v.54 Yoshida, M.;Khokhar, A. R.;Siddik, Z. H.
  9. Anticancer Drug v.7 Kizu, R.;Naganish, T.;Miyazaki, M.;Tashiro, T.;Noji, M.;Matsuzawa, A.;Eriguchi, M.;Takeda, Y.;Akiyama, N.;Kidani, Y.
  10. Inorg. Chim. Acta v.292 Kim, K. M.;Lee, Y.-A.;Lee, S. S.;Shon, Y. S.
  11. J. Med. Chem. v.43 Lee, Y.-A.;Lee, S. S.;Kim, K. M.;Chung, Y. K.;Lee, C. O.;Sohn, Y. S.
  12. J. Inorg. Biochem. v.54 Khokhar, A. R.;Al-Baker, S.;Siddik, Z. H.
  13. Biol. Pharm. Bull. v.16 Yamahita, T.;Hirose, J.;Noji, M.;Saito, R.;Tomida, H.;Kidani, Y.
  14. Inorg. Chem. v.39 Song, R.;Kim, K. M.;Lee, S. S.;Shon, Y. S.
  15. SHELXS-86: A Program for Structure Determination Sheldrick, G. M.
  16. SHELXL-97: A Program for Structure Refinement Sheldrick, G. M.
  17. J. Chromatogr. A v.656 Lambert, W. J.
  18. Inorg. Chem. v.22 Kuroda, R.;Neidle, S.;Ismail, I. M.;Sadler, P. J.
  19. Chem. Pharm. Bull. v.40 Goto, M.;Hirose, J.;Noji, M.;Lee, K. I.;Saito, R.;Kidani, Y.
  20. J. Clin. Oncol. v.15 McKeage, M. J.;Raynaud, F.;Ward, J.;Berry, C.;O'Dell, D.;Kelland, L. R.;Murrer, B.;Santabarbara, P.;Harrap, K. R.;Judson, I. R.
  21. Cancer Res. v.54 Mellish, K. J.;Kelland, L. R.
  22. Antimicrob. Agents Chemother. v.37 Shimizu, K.;Saito, A.;Shimada, J.;Ohmichi, M.;Hiraga, Y.;Inamatsu, T.;Shimada, K.;Tanimura, M.;Fujita, Y.;Nishikawa, T.;Oguma, T.;Yamamoto, S.

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