In vitro anticancer activity of cis-diammineplatinum(II) complexes with β-diketonate leaving group ligands

Journal of Medicinal Chemistry

Volumn 55, Issue 11, 2012, Pages 5326-5336

  Wilson, Justin J ^a   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIKETONE; [PLATINUM (1,1,1, TRIFLUOROACETYLACETONATE)(AMMONIA) 2 ](SULFATE) 0.5; [PLATINUM(4,4,4 TRIFLUOROBENZOYLACETONATE)(AMMONIA) 2 ](NITRATE); [PLATINUM(ACETYLACETONATE)(AMMONIA) 2 ](SULFATE) 0.5; [PLATINUM(BENZOYLACETONATE)(AMMONIA) 2 ](NITRATE); [PLATINUM(DIBENZOYLMETHIDE)(AMMONIA) 2 ](NITRATE); ANTINEOPLASTIC AGENT; CELL DNA; CISPLATIN; CISPLATIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CANCER CELL DESTRUCTION; CHEMOREACTIVITY; CONTROLLED STUDY; CYTOTOXICITY; DNA CROSS LINKING; DRUG DNA BINDING; DRUG EFFICACY; DRUG STABILITY; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIPOPHILICITY; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CATIONS; CELL LINE, TUMOR; CELL NUCLEUS; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; DRUG STABILITY; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KETONES; LIGANDS; MOLECULAR STRUCTURE; PLATINUM; SOLUBILITY; SOLVENTS; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 84862296306     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3002857     Document Type: Article

References (63)

1. Kelland, L. The resurgence of platinum-based cancer chemotherapy Nat. Rev. Cancer 2007, 7, 573-584
2. Cvitkovic, E. Cumulative toxicities from cisplatin therapy and current cytoprotective measures Cancer Treat. Rev. 1998, 24, 265-281
3. Boulikas, T.; Vougiouka, M. Cisplatin and platinum drugs at the molecular level Oncol. Rep. 2003, 10, 1663-1682
4. Jamieson, E. R.; Lippard, S. J. Structure, recognition, and processing of cisplatin-DNA adducts Chem. Rev. 1999, 99, 2467-2498
5. Todd, R. C.; Lippard, S. J. Inhibition of transcription by platinum antitumor compounds Metallomics 2009, 1, 280-291
6. Knox, R. J.; Friedlos, F.; Lydall, D. A.; Roberts, J. J. Mechanism of cytotoxicity of anticancer platinum drugs: Evidence that cis -diamminedichloroplatinum(II) and cis -diammine-(1,1-cyclobutanedicarboxylato) platinum(II) differ only in the kinetics of their interaction with DNA Cancer Res. 1986, 46, 1972-1979
7. Rixe, O.; Ortuzar, W.; Alvarez, M.; Parker, R.; Reed, E.; Paull, K.; Fojo, T. Oxaliplatin, tetraplatin, cisplatin, and carboplatin: Spectrum of activity in drug-resistant cell lines and in the cell lines of the National Cancer Institute's anticancer drug screen panel Biochem. Pharmacol. 1996, 52, 1855-1865
8. van der Vijgh, W. J. F. Clinical pharmacokinetics of carboplatin Clin. Pharmacokinet. 1991, 21, 242-261
9. Hollis, L. S.; Miller, A. V.; Amundsen, A. R.; Schurig, J. E.; Stern, E. W. cis -Diamineplatinum(II) complexes containing phosphono carboxylate ligands as antitumor agents J. Med. Chem. 1990, 33, 105-111
10. Pasini, A.; D'Alfonso, G.; Manzotti, C.; Moret, M.; Spinelli, S.; Valsecchi, M. Cytotoxic diamine-platinum(II) complexes with methylsulfinyl carboxylates as the leaving groups. Synthesis, characterization, and reactivity toward chloride ions, 5′-GMP, and 9-methylguanine Inorg. Chem. 1994, 33, 4140-4148
11. Zou, J.; Dou, P. Y.; Wang, K. Synthesis, antitumor activity and acute toxicity of diammine/diaminocyclohexane platinum(II) complexes with oxygen-ligating leaving group J. Inorg. Biochem. 1997, 65, 145-149
12. Ho, Y.-P.; To, K. K. W.; Au-Yeung, S. C. F.; Wang, X.; Lin, G.; Han, X. Potential new antitumor agents from an innovative combination of demethylcantharidin, a modified traditional Chinese medicine, with a platinum moiety J. Med. Chem. 2001, 44, 2065-2068
13. Aronov, O.; Horowitz, A. T.; Gabizon, A.; Gibson, D. Folate-targeted PEG as a potential carrier for carboplatin analogs. Synthesis and in vitro studies Bioconjugate Chem. 2003, 14, 563-574
14. Aronov, O.; Horowitz, A. T.; Gabizon, A.; Fuertes, M. A.; Pérez, J. M.; Gibson, D. Nuclear localization signal-targeted poly(ethylene glycol) conjugates as potential carriers and nuclear localizing agents for carboplatin analogues Bioconjugate Chem. 2004, 15, 814-823
15. Bernhardt, G.; Brunner, H.; Gruber, N.; Lottner, C.; Pushpan, S. K.; Tsuno, T.; Zabel, M. Carboplatin derivatives with superior antitumor activity compared to the parent compound Inorg. Chim. Acta 2004, 357, 4452-4466
16. Brunner, H.; Gruber, N. Carboplatin-containing porphyrin-platinum complexes as cytotoxic and phototoxic antitumor agents Inorg. Chim. Acta 2004, 357, 4423-4451
17. Warnecke, A.; Fichtner, I.; Garmann, D.; Jaehde, U.; Kratz, F. Synthesis and biological activity of water-soluble maleimide derivatives of the anticancer drug carboplatin designed as albumin-binding prodrugs Bioconjugate Chem. 2004, 15, 1349-1359
18. Mishur, R. J.; Zheng, C.; Gilbert, T. M.; Bose, R. N. Synthesis, X-ray crystallographic, and NMR characterizations of platinum(II) and platinum(IV) pyrophosphato complexes Inorg. Chem. 2008, 47, 7972-7982
19. Xie, M.; Liu, W.; Lou, L.; Chen, X.; Ye, Q.; Yu, Y.; Chang, Q.; Hou, S. Unusual dimeric chemical structure for a carboplatin analogue as a potential anticancer complex Inorg. Chem. 2010, 49, 5792-5794
20. Liu, W.; Chen, X.; Ye, Q.; Xu, Y.; Xie, C.; Xie, M.; Chang, Q.; Lou, L. A novel water-soluble heptaplatin analogue with improved antitumor activity and reduced toxicity Inorg. Chem. 2011, 50, 5324-5326
21. Sun, Y.; Gou, S.; Yin, R.; Jiang, P. Synthesis, antiproliferative activity and DNA binding study of mixed ammine/cyclohexylamine platinum(II) complexes with 1-(substituted benzyl) azetidine-3, 3-dicarboxylates Eur. J. Med. Chem. 2011, 46, 5146-5153
22. Yin, R.; Gou, S.; Liu, X.; Lou, L. Antitumor activities and interaction with DNA of oxaliplatin-type platinum complexes with linear or branched alkoxyacetates as leaving groups J. Inorg. Biochem. 2011, 105, 1095-1101
23. 3)L] (L = planar nitrogen base). Effect of L and cis/trans isomerism on sequence specificity and unwinding properties observed in globally platinated DNA Inorg. Chem. 1999, 38, 3535-3542
24. Ma, E. S. F.; Bates, W. D.; Edmunds, A.; Kelland, L. R.; Fojo, T.; Farrell, N. Enhancement of aqueous solubility and stability employing a trans acetate axis in trans planar amine platinum compounds while maintaining the biological profile J. Med. Chem. 2005, 48, 5651-5654
25. 2] donor sets. Cellular pharmacology and apoptosis induction in Pam 212- ras cells J. Med. Chem. 2005, 49, 224-231
26. 2] ligand donor sets: Effects of carboxylate leaving groups and steric hindrance on chemical and biological properties Inorg. Chem. 2006, 45, 5733-5735
27. Aris, S. M.; Knott, K. M.; Yang, X.; Gewirtz, D. A.; Farrell, N. P. Modulation of transplanaramine platinum complex reactivity by systematic modification of carrier and leaving groups Inorg. Chim. Acta 2009, 362, 929-934
28. Benedetti, B. T.; Quintal, S.; Farrell, N. P. Modulation of drug activation profiles through carboxylate ligand modification in cytotoxic trans -platinum planar amine compounds Dalton Trans. 2011, 40, 10983-10988
29. Bischoff, H.; Berger, M. R.; Keppler, B. K.; Schmähl, D. Efficacy of β-diketonato complexes of titanium, zirconium, and hafnium against chemically induced autochthonous colonic tumors in rats J. Cancer Res. Clin. Oncol. 1987, 113, 446-450
30. Schilling, T.; Keppler, K. B.; Heim, M. E.; Niebch, G.; Dietzfelbinger, H.; Rastetter, J.; Hanauske, A.-R. Clinical phase I and pharmacokinetic trial of the new titanium complex budotitane Invest. New Drugs 1995, 13, 327-332
31. Wu, A.; Kennedy, D. C.; Patrick, B. O.; James, B. R. Ruthenium(II) acetylacetonato-sulfoxide complexes Inorg. Chem. Commun. 2003, 6, 996-1000
32. Fernández, R.; Melchart, M.; Habtemariam, A.; Parsons, S.; Sadler, P. J. Use of chelating ligands to tune the reactive site of half-sandwich ruthenium(II)-arene anticancer complexes Chem.-Eur. J. 2004, 10, 5173-5179
33. Melchart, M.; Habtemariam, A.; Parsons, S.; Sadler, P. J. Chlorido-, aqua-, 9-ethylguanine- and 9-ethyladenine-adducts of cytotoxic ruthenium arene complexes containing O,O-chelating ligands J. Inorg. Biochem. 2007, 101, 1903-1912
34. + complexes (PTA = 1,3,5-triaza-7-phosphaadamantane) Eur. J. Inorg. Chem. 2008, 1661-1671
35. Schwartz, P.; Meischen, S. J.; Gale, G. R.; Atkins, L. M.; Smith, A. B.; Walker, E. M., Jr. Preparation and antitumor evaluation of water-soluble derivatives of dichloro(1,2-diaminocyclohexane)platinum(II) Cancer Treat. Rep. 1977, 61, 1519-1525
36. Cleare, M. J.; Hoeschele, J. D. Anti-tumour platinum compounds. Relationship between structure and activity Platinum Metals Rev. 1973, 17, 2-13
37. Muscella, A.; Calabriso, N.; Fanizzi, F. P.; De Pascali, S. A.; Urso, L.; Ciccarese, A.; Migoni, D.; Marsigliante, S. [Pt(O, O ′-acac)(γ- acac)(DMS)], a new Pt compound exerting fast cytotoxicity in MCF-7 breast cancer cells via the mitochondrial apoptotic pathway Br. J. Pharmacol. 2008, 153, 34-49
38. Muscella, A.; Calabriso, N.; Vetrugno, C.; Urso, L.; Fanizzi, F. P.; De Pascali, S. A.; Marsigliante, S. Sublethal concentrations of the platinum(II) complex [Pt(O, O ′-acac)(γ-acac)(DMS)] alter the motility and induce anoikis in MCF-7 cells Br. J. Pharmacol. 2010, 160, 1362-1377
39. Muscella, A.; Calabriso, N.; Vetrugno, C.; Fanizzi, F. P.; De Pascali, S. A.; Storelli, C.; Marsigliante, S. The platinum(II) complex [Pt(O,O′-acac)(γ-acac)(DMS)] alters the intracellular calcium homeostasis in MCF-7 breast cancer cells Biochem. Pharmacol. 2011, 81, 91-103
40. Muscella, A.; Calabriso, N.; Vetrugno, C.; Fanizzi, F. P.; De Pascali, S. A.; Marsigliante, S. The signalling axis mediating neuronal apoptosis in response to [Pt(O,O′-acac)(γ-acac)(DMS)] Biochem. Pharmacol. 2011, 81, 1271-1285
41. Behnke, G. T.; Nakamoto, K. Infrared spectra and structure of acetylacetonato platinum(II) complexes. I. Infrared spectra and normal coordinate analysis of potassium dichloro(acetylacetonato)platinate(II) Inorg. Chem. 1967, 6, 433-440
42. 3)(L)] J. Inorg. Biochem. 2011, 105, 652-662
43. Tetko, I. V.; Tanchuk, V. Y. Application of associative neural networks for prediction of lipophilicity in ALOGPS 2.1 program J. Chem. Inf. Comput. Sci. 2002, 42, 1136-1145
44. VCCLAB, Virtual Computational Chemistry Laboratory. http://www.vcclab.org (accessed October 2011).
45. Tetko, I. V.; Gasteiger, J.; Todeschini, R.; Mauri, A.; Livingstone, D.; Ertl, P.; Palyulin, V. A.; Radchenko, E. V.; Zefirov, N. S.; Makarenko, A. S.; Tanchuk, V. Y.; Prokopenko, V. V. Virtual computational chemistry laboratory - design and description J. Comput.-Aided Mol. Des. 2005, 19, 453-463
46. Shoemaker, R. H. The NCI60 human tumour cell line anticancer drug screen Nat. Rev. Cancer 2006, 6, 813-823
47. Pregosin, P. S. Platinum-195 nuclear magnetic resonance Coord. Chem. Rev. 1982, 44, 247-291
48. 195Pt nuclear magnetic resonance spectroscopy Appl. Spectrosc. Rev. 2006, 41, 185-226
49. 195Pt NMR-theory and application Chem. Soc. Rev. 2007, 36, 665-686
50. Yuge, H.; Miyamoto, T. K. Dual behaviour of acetylacetonate anions in the hydrogen-bonded supramolecular structure (acetylacetonato- O, O ′)[ trans -(1 R,2 R)-diaminocyclohexane- N, N ′]platinum(II) acetylacetonate Acta Crystallogr., Sect. C 1997, 53, 1816-1819
51. Leo, A.; Hansch, C.; Elkins, D. Partition coefficients and their uses Chem. Rev. 1971, 71, 525-616
52. 195Pt NMR kinetic and mechanistic studies of cis-and trans -diamminedichloroplatinum(II) binding to DNA J. Am. Chem. Soc. 1990, 112, 6860-6871
53. Canovese, L.; Cattalini, L.; Chessa, G.; Tobe, M. L. Kinetics of the displacement of cyclobutane-1,1-dicarboxylate from diammine(cyclobutane-1,1- dicarboxylato)platinum(II) in aqueous solution J. Chem. Soc., Dalton Trans. 1988, 2135-2140
54. 2(CBDCA- O)(5′-GMP- N 7)] in solution Inorg. Chem. 1993, 32, 1333-1340
55. Zhang, S.; Lovejoy, K. S.; Shima, J. E.; Lagpacan, L. L.; Shu, Y.; Lapuk, A.; Chen, Y.; Komori, T.; Gray, J. W.; Chen, X.; Lippard, S. J.; Giacomini, K. M. Organic cation transporters are determinants of oxaliplatin cytotoxicity Cancer Res. 2006, 66, 8847-8857
56. Screening Services, NCI-60 DTP Human Tumor Cell Line Screen. http://dtp.nci.nih.gov/branches/btb/ivclsp.html (accessed Nov, 2011).
57. Perez, R. P.; Godwin, A. K.; Handel, L. M.; Hamilton, T. C. A comparison of clonogenic, microtetrazolium and sulforhodamine B assays for determination of cisplatin cytotoxicity in human ovarian carcinoma cell lines Eur. J. Cancer 1993, 29, 395-399
58. APEX2, 2008-4.0; Bruker AXS, Inc.: Madison, WI, 2008.
59. Sheldrick, G. M. SADABS: Area-Detector Absorption Correction, University of Göttingen: Göttingen, Germany, 2008.
60. Sheldrick, G. M. SHELXTL-97, 6.14; University of Göttingen: Göttingen, Germany, 2000.
61. Sheldrick, G. M. A short history of SHELX Acta Crystallogr., Sect. A 2008, 64, 112-122
62. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool, 91110; Utrecht University: Utrecht, The Netherlands, 2008.
63. Egger, A. E.; Rappel, C.; Jakupec, M. A.; Hartinger, C. G.; Heffeter, P.; Keppler, B. K. Development of an experimental protocol for uptake studies of metal compounds in adherent tumor cells J. Anal. At. Spectrom. 2009, 24, 51-61