Abstract
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.
Key words: (R,R)- and (S,S)-[1,2-bis(4-fluorophenyl)ethylenediamine]dichloroplatinum(II); Synthesis; MCF7 breast cancer cell line; P388 murine leukemia
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 [Google Scholar]
- Dawe CJ, Potter M (1957) Lymphocytic leukemia P 388 of the DBA/2 mouse. Am J Pathol 33:603 [Google Scholar]
- 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 [Google Scholar]
- 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 [Google Scholar]
- 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 [Google Scholar]
- Hay RJ (1988) The seed stock concept and quality control for cell lines. Anal Biochem 171:225 [DOI] [PubMed] [Google Scholar]
- 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 [DOI] [PubMed] [Google Scholar]
- 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 [DOI] [PubMed] [Google Scholar]
- Meric R, Vigneron J (1974) Configuration absolue de la (−)stilbenediamine. Tetrahedron Lett 24:2059, 2778 [Google Scholar]
- 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 [Google Scholar]
- 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 [DOI] [PMC free article] [PubMed] [Google Scholar]
- 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 [DOI] [PubMed] [Google Scholar]
- 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 [DOI] [PubMed] [Google Scholar]
- 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 [DOI] [PubMed] [Google Scholar]
- 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) [DOI] [PubMed]
- 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 [DOI] [PubMed] [Google Scholar]
- 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 [DOI] [PubMed] [Google Scholar]
- 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 [DOI] [PMC free article] [PubMed] [Google Scholar]