Stability and cellular studies of [rac-1,2-bis(4-fluorophenyl)- ethylenediamine][cyclobutane-1,1-dicarboxylato]platinum (II), a novel, highly active carboplatin derivative

Journal of Cancer Research and Clinical Oncology

Volumn 124, Issue 11, 1998, Pages 585-597

  Gust, Ronald ^a   Schnurr, Beate ^a   Krauser, Rudolf ^b   Bernhardt, Günther ^b   Koch, Marion ^b   Schmid, Beate ^b   Hummel, Evelyn ^b   Schönenberger, Helmut ^b  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Accumulation; Breast and ovarian cancer cell lines; Reactivity; Stability; Synthesis

Indexed keywords

[1,2 BIS(4 FLUOROPHENYL)ETHYLENEDIAMINE](CYCLOBUTANE 1,1 DICARBOXYLATO)PLATINUM II; ANTINEOPLASTIC AGENT; CARBOPLATIN; CISPLATIN; HUMAN SERUM ALBUMIN; PLATINUM COMPLEX; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; CONTROLLED STUDY; DIASTEREOISOMER; DRUG EFFECT; DRUG STABILITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; OVARY CANCER; PRIORITY JOURNAL;

BREAST NEOPLASMS; CARBOPLATIN; CELL SIZE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG SCREENING ASSAYS, ANTITUMOR; DRUG STABILITY; FEMALE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; OVARIAN NEOPLASMS; PLATINUM; SERUM ALBUMIN; SOLUBILITY; TUMOR CELLS, CULTURED;

EID: 0031775412     PISSN: 01715216     EISSN: None     Source Type: Journal    
DOI: 10.1007/s004320050220     Document Type: Article

References (33)

1. Bednarski PJ, Trümbach B (1994) Rate constants of dichloro[1,2-diarylethylenediamine]platinum(II) complexes. Transition Met Chem 19:513
2. Bernhardt G, Reile H, Spruß T, Koch M, Gust R, Schönenberger H, Hollstein M, Lux F, Engel J (1991) (±)-(D,L)-[1,2-Bis(4-fluorophenyl)ethylenediamine]dichloroplatinum(II). Drugs Fut 16:899
3. Bernhardt G, Reile H, Birnböck H, Spruß T, Schönenberger H (1992) Standardized kinetik microassay to quantify differential chemosensitivity on the basis of proliferative activity. J Cancer Res Clin Oncol 118:35
4. Bitha P, Child RG, Hlavka JJ, Lang SA, Lin Y, Haltiwanger RC, Pierpont CG (1988) Structural characterization on two (diamine)(1,1-cyclobutanedicarboxylato)platinum(II) antitumor drugs. Inorg Chim Acta 151:89
5. Bradford MM (1976) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248
6. Cocconi G, Bisagni G, Bacchi M, Boni C, Bartolucci R, Ceci G, Colozza MA, De Lisi V, Lottici R, Mosconi AM (1991) Cisplatin and etoposide as first-line chemotherapy for metastatic breast carcinoma: a prospective randomized trial of the Italian Oncology Group for Clinical Research. J Clin Oncol 9:664
7. Conte PF, Ragni N, Rosso R, Vermorken JB (1989) Multimodal treatment of ovarian cancer. Raven, New York
8. de Valeriola D, Forrest A, Dodion P, Crespeigne N, Piccart M, Rastogi R, Kantrowitz JD, Egorin MJ (1991) Clinical and pharmacokinetic studies on the new complex zeniplatin. In: Howell SB (ed) Platinum and other metal coordination compounds in cancer chemotherapy. Plenum, New York, p 357
9. Frost AA, Pearson ARG (1961) Kinetics and mechanism. Wiley, New York
10. Gonias SL, Pizzo SV (1983) Complexes of serum albumin and cis-dichlorodiammineplatinum(II). J Biol Chem 258:5764
11. Gust R, Bernhardt G, Spruß T, Krauser R, Koch M, Schönenberger H, Bauer KH, Schertl S, Lu Z (1995) Development of a parenterally administrable hydrosol preparation of the "third generation platinum complex" [(±)-1,2-bis(4-fluorophenyl)ethylenediamine]dichloroplatinum(II). I. Preparation and studies on the stability and antitumor activity. Arch Pharm (Weinheim) 328:645
12. Gust R, Krauser R, Schmidt B, Schönenberger H (1996) Breast cancer inhibiting diastereomeric diacetato[1,2-bis(4-fluorophenyl)ethylenediamine]platinum(II) derivatives - synthesis and studies on the relationship between reactivity and antitumor activity. Inorg Chim Acta 250:203
13. Hay RJ (1988) The seed stock concept and quality control for cell lines. Anal Biochem 171:225
14. Holding JD, Lindup WE, van Laer C, Vreeburg GCM, Schilling V, Wilson JA, Stell PM (1992) Phase I trial of a cisplatin-albumin complex for the treatment of cancer of head and neck. Br J Clin Pharmacol 33:75
15. Khokhar AR, Lumetta GJ (1989) Synthesis and characterization of a series of platinum(II) and palladium(II) complexes containing the bidentate ligand meso-1,2-diphenylethylenediamine or meso-1,2-bis(4-chlorophenyl)ethylenediamine. J Coord Chem 19:321
16. Koch M (1993) PhD thesis, Optimierung analytischer Methoden (AAS, HPLC) zur Weiterentwicklung neuartiger Platin (II)-komplexe. University of Regensburg, Germany
17. Kolaric K, Vukas D (1991) Carboplatin activity in untreated metastatic breast cancer - a phase II trial. Cancer Chemother Pharmacol 27:409
18. Krauser R (1995) PhD thesis, Synthese, Struktur, Reaktivität von [1,2-Diaryl ethylene diamin] platin (II)-komplexen sowie von Bendamistin hydrochlorid University of Regensburg, Germany
19. Lippard SJ (1987) Chemistry and molecular biology of platinum anticancer drugs. Pure Appl Chem 59:731
20. Lippard SJ (1994) Metals in medicine. In: Bertini I, Gray HB, Lippard SJ, Valentine JS (eds) Bioinorganic chemistry. University Science Books, Mill Valley, p 519
21. Müller R, Gust R, Jennerwein M, Reile H, Laske R, Krischke W, Bernhardt G, Spruß T, Engel J, Schönenberger H (1989) Tumor inhibiting [1,2-bis(4-fluorophenyl)ethylenediamine]platinum(II) complexes. I. Synthesis. Eur J Med Chem 24:341
22. Nash JD, Young RC (1988) Gynecologic malignancies. Cancer Chemother Biol Response Modif 10:291
23. Noji M, Suzuki K, Tashiro T, Suzuki M, Harada KI, Masuda K, Kidani Y (1987) Syntheses and antitumor activities of 1R,2R-cyclohexanediamine Pt(II) complexes containing dicarboxylates Chem Pharm Bull (Tokyo) 35:221
24. Prestayko AW, Crooke ST, Carter SK (eds) (1980) Cisplatin current status and new developments. Academic Press, New York
25. Reile H, Birnböck H, Bernhardt G, Spruß T, Schönenberger H (1990a) Computerized determination of growth kinetik curves and doubling times from cells in microculture. Anal Biochem 187:262
26. Reile H, Spruß T, Müller R, Gust R, Bernhardt G, Schönenberger H, Engel J (1990b) Tumor inhibiting [1,2-bis(4-fluorophenyl)ethylenediamine]platinum(II) complexes. III. Evaluation of the mammary tumor inhibiting properties. Arch Pharm (Weinheim) 323:301
27. Reile H, Bernhardt G, Koch M, Schönenberger H, Hollstein M, Lux F (1992) Chemosensitivity of human MCF-7 breast cancer cells to diastereomeric diaqua[1,2-diphenylethylenediamine] platinum(II) sulfates and specific platinum accumulation. Cancer Chemother Pharmacol 30:113
28. Repta AJ, Long DF (1980) Reaction of cisplatin with human plasma and plasma fraction. In: Prestayko AW, Crooke ST, Carter SK (eds) Cisplatin, current status and new developments. Academic Press, New York, p 285
29. Schilder RJ, Godfrey SA, Young RC (1992) Gynecological malignancies. Cancer Chemother Biol Response Modif 13:541
30. Siddik ZH, Dible SE, Boxall FE, Harrap KR (1985) Biochemical mechanism of platinum antitumor drugs. In: McBrien DCH, Slater TF (eds) Biochemical mechanism of platinum antitumor drugs. IRL Press, Oxford, p 171
31. Sigel A, Sigel H (eds) (1996) Metal ions in biological systems, vol 32. Dekker, New York, Basel, Hong Kong, p 641, p 687
32. Vogelzang NJ (1984) Continuous infusion chemotherapy: a critical review. J Clin Oncol 2:1289
33. Wander HE (1984) Prognosefaktoren beim metastasierenden Mammakarzinom. In: Nagel GA (ed) Mammakarzinome. Zuckschwerdt, Munich, p 1