Summary
The enantiomeric [1,2-bis(4-fluorophenyl)ethylenediamine]dichloroplatinum(II) complexes were synthesized and tested on the hormone-sensitive human MCF7 breast cancer cell line and on the P388 leukemia of the mouse. They showed a strong and comparable activity on both tumor models.
Similar content being viewed by others
Abbreviations
- R,R/S,S :
-
racemate
- R,S :
-
meso
References
von Angerer E, Holler E, Schönenberger H, Schönenberger R (1989) Antineoplastic drugs. In: Smith DF (ed) Handbook of stereoisomers: therapeutic drugs. CRC Press, Boca Raton, Florida, pp 247–284
Dawe CJ, Potter M (1957) Lymphocytic leukemia P 388 of the DBA/2 mouse. Am J Pathol 33:603
Geran RI, Greenberg NH, Macdonald MM, Schumacher AH, Abbott B (1972) Protocols for screening chemical agents and natural products against animal tumors and other biological systems. J Cancer Chemother Rep 3:9
Gullotti M, Pacchioni G, Pasini A, Ugo R (1982) Complexes of platinum(II) with chiral diamines and guanosine. Stereochemical investigation related to the mechanism of the antitumor activity of cis-bis(amine)platinum(II) type complexes. Inorg Chem 21:2006
Gullotti M, Pasini A, Ugo R, Filippeschi ST, Marmonti L, Spreafico F (1984) Enantiomeric cisplatin analogues: an investigation on their activity towards tumors in mice. Inorg Chim Acta 91:223
Hay RJ (1988) The seed stock concept and quality control for cell lines. Anal Biochem 171:225
Jennerwein M, Gust R, Müller R, Schönenberger H, Engel J, Berger MR, Schmähl D, Seeber S, Osieka R, Atassi G, Maréchal-De-Bock D (1989a) Tumor inhibiting properties of stereoisomeric [1,2-bis(3-hydroxyphenyl)ethylenediamine]dichloroplatinum(II)-complexes: part I. Synthesis. Arch Pharm (Weinheim) 322:25
Jennerwein M, Gust R, Müller R, Schönenberger H, Engel J, Berger MR, Schmähl D, Seeber S, Osieka R, Atassi G, Maréchal-De-Brock D (1989b) Tumor inhibiting properties of stereoisomeric [1,2-bis(3-hydroxyphenyl)ethylenediamine]dichloroplatinum(II) complexes: part II. Biological properties. Arch Pharm (Weinheim) 322:67
Meric R, Vigneron J (1974) Configuration absolue de la (−)stilbenediamine. Tetrahedron Lett 24:2059, 2778
Müller R, Gust R, Jennerwein M, Reile H, Laske R, Krischke W, Bernhardt G, Spruß Th, Engel J, Schönenberger H (1989) Tumor inhibiting [1,2-bis(fluorophenyl)ethylenediamine]platinum(II) complexes: part I. Synthesis. Eur J Med Chem 24:341
Müller R, Gust R, Bernhart G, Keller Ch, Schönenberger H, Seeber S, Osieka R, Eastman A, Jennerwein M (1990) [DL-1,2-Bis(2-hydroxyphenyl)ethylenediamine]dichloroplatinum(II), a new compound for the therapy of ovarian cancer. J Cancer Res Clin Oncol 116:237
Noji M, Gohchi Y, Kidani Y (1984) Preparation of antitumor platinum(II) complexes of 1,2-diphenylethylenediamine isomers and their interactions with DNA and its purine moieties. Chem Biol Interact 51:37
Reile H, Birnböck H, Bernhardt G, Spruß Th, Schönenberger H (1990a) Computerized determination of growth kinetic curves and doubling times from cells in microculture. Anal Biochem 187:262
Reile H, Spruß Th, Müller R, Gust R, Bernhardt G, Schönenberger H, Engel J (1990b) Tumor inhibiting [1,2-bis(fluorophenyl)ethylenediamine]platinum(II) complexes: III. Evaluation of the mammary tumor inhibiting properties. Arch Pharm (Weinheim) 323:301
Reile H, Spruß Th, Bernhardt G, Müller R, Gust R, Schönenberger H (1990c) Tumor inhibiting [1,2-bis(fiuorophenyl)ethylenediamine]platinum(II) complexes: IV. Biological evaluation — in vivo studies on the P 388 leukemia. Arch Pharm (Weinheim) (in press)
Soule HD, Vazquez J, Long A, Albert S, Brennan M (1973) A human cell-line from a pleural effusion derived from a breast carcinoma. J Nat Cancer Inst 51:1409
Wappes B, Jennerwein M, von Angerer E, Schönenberger H, Engel J, Berger MR, Wrobel K-H (1984a) Dichloro[1,2-bis(4-hydroxyphenyl)ethylenediamine]platinum(II) complexes: an approach to develop compounds with a specific effect on the hormone-dependent mammary carcinoma. J Med Chem 27:1280
Wappes B, Jennerwein M, von Angerer E, Engel J, Schönenberger H, Brunner H, Schmidt M, Berger M, Schmähl D, Seeber S (1984b) The tumor inhibiting effect of isomeric dichloro(diphenylethylenediamine)platinum(II) complexes. J Cancer Res Clin Oncol 107:15
Author information
Authors and Affiliations
Additional information
Dedicated to Professor Dr. D. Schmähl on the occasion of his 65th birthday
Rights and permissions
About this article
Cite this article
vom Orde, H.D., Reile, H., Müller, R. et al. Tumor-inhibiting [1,2-bis(fluorophenyl)ethylenediamine]platinum(II) complexes. J Cancer Res Clin Oncol 116, 434–438 (1990). https://doi.org/10.1007/BF01612989
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01612989