Synthesis and in vitro pharmacological behavior of platinum(II) complexes containing 1,2-diamino-1-(4-fluorophenyl)-2-alkanol ligands

Journal of Medicinal Chemistry

Volumn 56, Issue 20, 2013, Pages 7951-7964

  Würtenberger, Irene ^a   Angermaier, Bernhard ^b   Kircher, Brigitte ^c   Gust, Ronald ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b UNIVERSITY OF REGENSBURG   (Germany)

^c INNSBRUCK MEDICAL UNIVERSITY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; PLATINUM COMPLEX; UNCLASSIFIED DRUG; [THREO 1,2 DIAMINO 1 (4 FLUOROPHENYL)PROPAN]DICHLORIDOPLATINUM; [THREO 2,3 DIAMINO 3 (4 FLUOROPHENYL)PROPAN 1 OL]DICHLORIDOPLATINUM;

ARTICLE; DRUG ACCUMULATION; DRUG CYTOTOXICITY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LIPOPHILICITY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CISPLATIN; DRUG RESISTANCE, NEOPLASM; HUMANS; LIGANDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NEOPLASMS; ORGANOPLATINUM COMPOUNDS; PLATINUM; U937 CELLS;

EID: 84886523195     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400967z     Document Type: Article

References (40)

1. Rosenberg, B.; Vancamp, L.; Krigas, T. Inhibition of Cell Division in Escherichia Coli by Electrolysis Products from a Platinum Electrode Nature 1965, 205, 698-699
2. Kelland, L. The Resurgence of Platinum-Based Cancer Chemotherapy Nat. Rev. Cancer 2007, 7, 573-584
3. Reedijk, J. Increased Understanding of Platinum Anticancer Chemistry Pure Appl. Chem. 2011, 83, 1709-1719
4. Wang, X.; Guo, Z. New Trends and Future Developments of Platinum-Based Antitumor Drugs Bioinorg. Med. Chem. 2011, 97-149
5. Stein, A.; Arnold, D. Oxaliplatin: A Review of Approved Uses Expert Opin. Pharmacother. 2012, 13, 125-137
6. Ott, I.; Gust, R. Preclinical and Clinical Studies on the Use of Platinum Complexes for Breast Cancer Treatment Anti-Cancer Agents Med. Chem. 2007, 7, 95-110
7. Gust, R.; Beck, W.; Jaouen, G.; Schoenenberger, H. Optimization of Cisplatin for the Treatment of Hormone Dependent Tumoral Diseases. A Review. Part 1: Use of Steroidal Ligands Coord. Chem. Rev. 2009, 253, 2742-2759
8. Gust, R.; Beck, W.; Jaouen, G.; Schoenenberger, H. Optimization of Cisplatin for the Treatment of Hormone-Dependent Tumoral Diseases. A Review. Part 2: Use of Non-Steroidal Ligands Coord. Chem. Rev. 2009, 253, 2760-2779
9. Jennerwein, M.; Wappes, B.; Gust, R.; Schoenenburger, H.; Engel, J.; Seeber, S.; Osieka, R. Influence of Ring Substituents on the Antitumor Effect of Dichloro(1,2-diphenylethylenediamine)platinum(II) Complexes J. Cancer Res. Clin. Oncol. 1988, 114, 347-358
10. Spruss, T.; Gust, R.; Mueller, R.; Engel, J.; Schoenenberger, H. Mammary-Tumor-Inhibiting Properties of (S,S)-[1,2- Bis (4-hydroxyphenyl) ethylenediamine]dichloroplatinum(II) Arch. Pharm. 1990, 323, 99-102
11. Reile, H.; Spruss, T.; Mueller, R.; Gust, R.; Bernhardt, G.; Schoenenberger, H.; Engel, J. Tumor-Inhibiting [1,2- Bis (fluorophenyl) ethylenediamine]platinum(II) Complexes. III. Evaluation of the Mammary Tumor-Inhibiting Properties Arch. Pharm. 1990, 323, 301-306
12. Gust, R.; Schnurr, B.; Krauser, R.; Bernhardt, G.; Koch, M.; Schmid, B.; Hummel, E.; Schoenenberger, H. Stability and Cellular Studies of [ rac -1,2- Bis (4-fluorophenyl)ethylenediamine][cyclobutane-1,1-dicarboxylato]platinum(II), a Novel, Highly Active Carboplatin Derivative J. Cancer Res. Clin. Oncol. 1998, 124, 585-597
13. Kapp, T.; Dullin, A.; Gust, R. Mono- and Polynuclear [Alkylamine] platinum(II) Complexes of [1,2- Bis (4-fluorophenyl)ethylenediamine]platinum(II) : Synthesis and Investigations on Cytotoxicity, Cellular Distribution, and DNA and Protein Binding J. Med. Chem. 2006, 49, 1182-1190
14. Gust, R.; Krauser, R.; Schmid, B.; Schoenenberger, H. 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 1996, 250, 203-218
15. Gust, R.; Krauser, R.; Schmid, B.; Schoenenberger, H. Synthesis and Antitumor Activity of [1,2- Bis (4-fluorophenyl)ethylenediamine][dicarboxylato] platinum(II) Complexes Arch. Pharm. 1998, 331, 27-35
16. Gust, R.; Heinrich, H.; Krauser, R.; Schoenenberger, H. [ meso-and rac -1,2- Bis (4-fluorophenyl)ethylenediamine]chloro[sulfinylbis(methane)-S] platinum(II) Chloride New Water Soluble Platinum Complexes with High Anti-Breast Cancer Activities Inorg. Chim. Acta 1999, 285, 184-189
17. 2 Z. Kristallogr. 1996, 211, 970
18. Dufrasne, F.; Gelbcke, M.; Schnurr, B.; Gust, R. Synthesis and Antitumor Activity of Enantiomerically Pure [1,2-Diamino-1-(4-fluorophenyl)propane] dichloroplatinum(II) Complexes Arch. Pharm. 2002, 335, 229-239
19. Dullin, A.; Dufrasne, F.; Gelbcke, M.; Gust, R. Enantiomerically Pure [1,2-Diamino-1-(4-fluorophenyl)butane]platinum(II) Complexes: Synthesis and Antitumor Activity against MCF-7 and MDA-MB 231 Breast Cancer and LnCaP/FGC Prostate Cancer Cell Lines Arch. Pharm. 2004, 337, 654-667
20. Dullin, A.; Dufrasne, F.; Gelbcke, M.; Gust, R. Synthesis and Cytotoxicity of Enantiomerically Pure [1,2-Diamino-1-(4-fluorophenyl)-3- methylbutane]platinum(II) Complexes ChemMedChem 2006, 1, 644-653
21. vom Orde, H. D.; Reile, H.; Mueller, R.; Gust, R.; Bernhardt, G.; Spruss, T.; Schoenenberger, H.; Burgemeister, T.; Mannschreck, A. Tumor-Inhibiting [1,2- Bis (fluorophenyl)ethylenediamine]platinum(II) Complexes. V. Synthesis and Evaluation of Enantiomeric [1,2- Bis -(4-fluorophenyl)ethylenediamine] dichloroplatinum(II) Complexes J. Cancer Res. Clin. Oncol. 1990, 116, 434-438
22. Mueller, R.; Gust, R.; Jennerwein, M.; Reile, H.; Laske, R.; Krischke, W.; Bernhardt, G.; Spruss, T.; Engel, J.; Schoenenberger, H. Tumor Inhibiting [1,2- Bis (fluorophenylethylenediamine]platinum(II) Complexes. Part I. Synthesis Eur. J. Med. Chem. 1989, 24, 341-348
23. Berger, G.; Gasper, R.; Lamoral-Theys, D.; Wellner, A.; Gelbcke, M.; Gust, R.; Jean, N.; Kiss, R.; Goormaghtigh, E.; Dufrasne, F. Fourier Transform Infrared (FTIR) Spectroscopy to Monitor the Cellular Impact of Newly Synthesized Platinum Derivatives Int. J. Oncol. 2010, 37, 679-686
24. Wittig, G.; Schoellkopf, U. Triphenylphosphinemethylene as an Olefin-Forming Reagent. I Chem. Ber. 1954, 87, 1318-1330
25. Hands, A. R.; Mercer, A. J. H. 2,2,2-Triphenyl-1,2-oxaphosph(V)olane and -oxaars(V)olane J. Chem. Soc. C 1967, 1099-1100
26. Luo, J. K.; Castle, S. L.; Castle, R. N. The Synthesis of Difluoro[1]benzothieno[2,3-c]quinolines and their N -Methyl Quaternary Salts J. Heterocycl. Chem. 1990, 27, 2047-2052
27. Jorgenson, M. J. Selective Reductions with Aluminum Hydride Tetrahedron Lett. 1962, 559-562
28. Swift, G.; Swern, D. Chemistry of Epoxy Compounds. XX. Stereospecific Syntheses of cis-and trans -1,2-Diaminocyclohexanes and Aliphatic Vicinal Diamines J. Org. Chem. 1967, 32, 511-517
29. Anderson, W. K.; Veysoglu, T. Simple Procedure for the Epoxidation of Acid Sensitive Olefinic Compounds with m-Chloroperbenzoic Acid in an Alkaline Biphasic Solvent System J. Org. Chem. 1973, 38, 2267-2268
30. Brois, S. J.; Beardsley, G. P. Aziridines. VII. Proton Coupling Constants in Styrenimines Tetrahedron Lett. 1966, 5113-5119
31. Hassner, A.; Matthews, G. J.; Fowler, F. W. Stereochemistry. XLI. Reduction of β-Iodo Azides. Stereospecific Synthesis of Aziridines J. Am. Chem. Soc. 1969, 91, 5046-5054
32. Gust, R.; Burgemeister, T.; Mannschreck, A.; Schoenenberger, H. Aqua[1-(2,6-dichloro-4-hydroxyphenyl)-2-phenylethylenediamine](sulfato) platinum(II) Complexes with Variable Substituents in the 2-Phenyl Ring. 1. Synthesis and Antitumor and Estrogenic Properties J. Med. Chem. 1990, 33, 2535-2544
33. Zenker, A.; Galanski, M.; Bereuter, T. L.; Keppler, B. K.; Lindner, W. Time-Dependent Interactions of Platinum(II) Complexes with 5'-GMP under Simulated Physiological Conditions Studied by Capillary Electrophoresis J. Biol. Inorg. Chem. 2000, 5, 498-504
34. Leo, A.; Hansch, C.; Elkins, D. Partition Coefficients and Their Uses Chem. Rev. 1971, 71, 525-616
35. Test No. 107: Partition Coefficient (n-Octanol/Water): Shake Flask Method; OECD Guideline; OECD Publishing: Paris, 1995.
36. Tetko, I. V.; Jaroszewicz, I.; Platts, J. A.; Kuduk-Jaworska, J. Calculation of Lipophilicity for Pt(II) Complexes: Experimental Comparison of Several Methods J. Inorg. Biochem. 2008, 102, 1424-1437
37. Souchard, J. P.; Ha, T. T. B.; Cros, S.; Johnson, N. P. Hydrophobicity Parameters for Platinum Complexes J. Med. Chem. 1991, 34, 863-864
38. Zou, J.; Yang, X. d.; An, F.; Wang, K. Relationship between Cellular Uptake Rate and Chemical Behavior of Diammine/Diaminocyclohexane Platinum(II) Complexes with Oxygen-Ligating Anionic Groups J. Inorg. Biochem. 1998, 70, 227-232
39. Du, X.; Wang, X.; Li, H.; Sun, H. Comparison between Copper and Cisplatin Transport Mediated by Human Copper Transporter 1 (hCTR1) Metallomics 2012, 4, 679-685
40. Bradford, M. M. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding Anal. Biochem. 1976, 72, 248-254