Ring-substituted [1, 2-bis(4-hydroxyphenyl)ethylenediamine]dichloroplatinum(ii) complexes: Compounds with a selective effect on the hormone-dependent mammary carcinoma

Journal of Medicinal Chemistry

Volumn 31, Issue 1, 1988, Pages 72-83

  Karl, Johann ^a   Gust, Ronald ^a   Sprues, Thilo ^a   Schneider, Martin R ^a   Schönenberger, Helmut ^a   Engel, Jürgen ^b   Wrobel, Karl Heinz ^a   Lux, Franz ^c   Trebert Haeberlin, Susanne ^c  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b EVONIK INDUSTRIES AG   (Germany)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; ESTROGEN RECEPTOR; PLATINUM [1,2 BIS(2,6 DICHLORO 4 HYDROXYPHENYL)ETHYLENEDIAMINE] DIAQUA SULFATE; PLATINUM [1,2 BIS(4 HYDROXYPHENYL)ETHYLENEDIAMINE] DICHLORIDE DERIVATIVE; TAMOXIFEN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; BIOLOGICAL MODEL; BREAST CARCINOMA; CELL CULTURE; CYTOTOXICITY; DNA SYNTHESIS; HUMAN; HUMAN CELL; INFRARED SPECTROPHOTOMETRY; MOUSE; NEPHROTOXICITY; RAT; SUBCUTANEOUS DRUG ADMINISTRATION;

ANIMAL; BREAST NEOPLASMS; CELL LINE; CISPLATIN; COMPARATIVE STUDY; FEMALE; HUMAN; MAMMARY NEOPLASMS, EXPERIMENTAL; ORGANOPLATINUM COMPOUNDS; RATS; RATS, INBRED STRAINS; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; TUMOR CELLS, CULTURED;

EID: 0023858412     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00396a012     Document Type: Article

References (56)

1. Wappes, B.; Jennetwein, M.; von Angerer, E.; Schönenberger, H.; Engel, J.; Berger, M.; Wrobel, K.-H. J. Med. Chem. 1984, 27, 1280.
2. Wappes, B. Ph.D. Thesis, University of Regensburg, 1982.
3. Hartmann, R. W.; Heindl, A.; Schwarz, W.; Schönenberger, H. J. Med. Chem. 1984, 27, 819.
4. Von Angerer, E. J. Med. Chem. 1982, 25, 1374.
5. Mylonas, S.; Valavanidis, A.; Voukouvalidis, V.; Polyssiou, M. Inorg. Chim. Acta 1981, 55, 125.
6. Yano, S.; Tukada, T.; Saburi, M.; Yoshikana, S. Inorg. Chem. 1978, 17, 2520.
7. Noji, M.; Gohchi, Y.; Kidani, Y. Chem.-Biol. Interact. 1984, 57, 37.
8. Schwartz, P.; Meischen, S. J.; Gale, G. R. Cancer Treat. Rep. 1977, 61, 1519.
9. Leopold, W. R.; Batzinger, R. P.; Miller, E. C.; Miller, J. A.; Earhart, R. H. Cancer Res. 1981, 41, 4368.
10. Speer, R. J.; Ridgway, H.; Stewart, D. P.; Hall, L. M.; Zapata, A.; Hill, J. M. J. Clin. Hematol. Oncol. 1977, 7, 210.
11. Eskenazi, R.; Raskovan, J.; Levitus, R. J. Inorg. Nucl. Chem. 1966, 28, 521.
12. Gullotti, M.; Pasini, A.; Ugo, R. Inorg. Chim. Acta 1984, 91, 223.
13. Nakamoto, K. Infrared Spectra of Inorganic and Coordination Compounds, 2nd ed.; Wiley-Interscience: New York, 1970.
14. Oleare, M. J.; Hydes, P. C.; Malerbi, B. W.; Watkins, D. M. Biochimie 1978, 60, 835.
15. Vögtle, F.; Goldschmitt, E. Chem. Ber. 1976, 109, 1.
16. Von Angerer, E.; Taneja, A. K.; Ringshandl, R.; Schönenberger, H. Liebigs Ann. Chem. 1980, 409.
17. Nelson, D. J.; Uschak, E. A. J. Org. Chem. 1977, 42, 3308.
18. Olah, G. A.; Arvanaghi, M. Angew. Chem. 1981, 93, 925.
19. Voss, W. Justus Liebigs Ann. Chem. 1930, 485, 283.
20. Plaumann, H. P.; Keay, B. A.; Rodrigo, R. Tetrahedron Lett. 1979, 4921.
21. Quinkert, G.; Weber, W. D.; Schwartz, U.; Dünner, G. Angew. Chem. 1980, 92, 1060.
22. Davis, C. T.; Geissman, T. A. J. Am. Chem. Soc. 1954, 76, 3507.
23. Postmus, C., Jr.; Kaye, I. A.; Craig, C. A.; Matthews, R. S. J. Org. Chem. 1964, 29, 2693.
24. Kranzfelder, G.; Schneider, M.; Von Angerer, E.; Schönenberger, H. J. Cancer Res. Clin. Oncol. 1980, 97, 167.
25. Rubin, B. L.; Dorfman, A. S.; Black, L.; Dorfman, R. J. Endocrinology (Baltimore) 1951, 49, 429.
26. Huggins, C. H.; Jensen, E. V. J. Exp. Med. 1955, 102, 335.
27. Dawe, C. J.; Potter, M. Pathologists and Bacteriologists 1957, 33, 603.
28. Cailleau, R.; Young, R.; Olivé, M.; Reeves, W. R., Jr. J. Natl. Cancer Inst. (U.S.) 1974, 53, 661.
29. Soule, H. D.; Vazquez, J.; Long, A.; Albert, S.; Brennan, M. J. Natl. Cancer Inst. (U.S.) 1973, 51, 1409.
30. Watson, C.; Medina, D.; Clark, J. J. Cancer Res. 1977, 37, 3344.
31. Selby, P.; Bizzari, J.-P.; Buick, R. N. Cancer Treat. Rep. 1983, 67, 659.
32. Knobl, S.; Lux, F. In Instrumentelle Multielementanalyse; Sansoni, B., Ed.; VCH Verlagsgesellschaft: Weinheim, 1985.
33. Huggins, C.; Yang, N. C. Science (Washington, D.C.) 1962, 137, 257.
34. Karl, J.F.-X. Ph.D. Thesis, University of Regensburg, 1985.
35. Inagaki, K.; Kidani, S.; Suzuki, K.; Tashiro, T. Chem. Pharm. Bull. 1980, 28, 2286.
36. Inagaki, K.; Kidani, S. Inorg. Chim. Acta 1980, 46, 35.
37. Harder, H. C.; Rosenberg, B. Int. J. Cancer 1970, 6, 207.
38. Howie, J. A.; Gale, G. R. Biochem. Pharmacol. 1970, 19, 2757.
39. Pinto, A. L.; Lippard, S. J. Biochim. Biophys. Acta 1985, 780, 167.
40. Haddow, A. L.; Watkinson, J. M.; Patterson, E.; Koller, E. Br. Med. J. 1944, 2, 393.
41. Hartmann, R. W., Eur. J. Cancer Clin. Oncol. 1983, 19, 959.
42. Rennie, P. S. In Drug and Hormone Resistance in Neoplasia; Bruchovsky, N., Goldie, J. H., Eds.; CRC: Boca Raton, FL, 1982; Vol. I, p 95.
43. Bruchovsky, N.; Lesser, B.; VanDoorn, E.; Craven, S. Vitam. Horm. (IV. V.) 1975, 33, 61.
44. Bruchovsky, N.; Lesser, B. Adv. Sex Horm. Res. 1976, 2, 1.
45. Bruchovsky, N.; Rennie, P. S.; VanDoorn, E.; Noble, R. L. J. Toxicol. Environ. Health 1978, 4, 391.
46. Bruchovsky, N.; VanDoorn, E. In Recent Results in Cancer Research; St. Arneault, G., Band, P., Israeli, L., Eds.; Springer-Verlag: Berlin, 1976; Vol. 57, p 121.
47. Bruchovsky, N.; Rennie, P. S. UICC Techn. Rep. Ser. 1979, 48, 134.
48. Hartmann, R. W.; Schönenberger, H.; Wrobel, K.-H. J. Cancer Res. Clin. Oncol. 1982, 103, 241.
49. Vorherr, H. The Breast; Academic: New York, 1974.
50. Korenman, S. G. J. Clin. Endocrinol. Metab. 1968, 28, 127.
51. EORTC Breast Cancer Cooperative Group Eur. J. Cancer Clin. Oncol. 1973, 9, 379.
52. Lippman, M.; Monaco, M. E.; Bolan, G. Cancer Res. 1977, 37, 1901.
53. Gerau, R. T.; Greenberg, N. H.; Macdonald, M. M.; Schumacher, A. H.; Abbott, B. J. Cancer Chemother. Rep., Part 3 1972, 3, N 2.1.
54. Hartmann, R. W.; Kranzfelder, G.; Von Angerer, E.; Schönenberger, H. J. Med. Chem. 1980, 23, 841.
55. Lux, F.; Trebert Haeberlin, S. Fresenius' Z. Anal. Chem. 1986, 323, 833.
56. Trebert Haeberlin, S. Ph.D. Thesis, Technische Universität München, 1986.