Unsymmetric mono- and dinuclear platinum(IV) complexes featuring an ethylene glycol moiety: Synthesis, characterization, and biological activity

Journal of Medicinal Chemistry

Volumn 55, Issue 24, 2012, Pages 11052-11061

  Pichler, Verena ^a   Heffeter, Petra ^a,b,c   Valiahdi, Seied M ^a   Kowol, Christian R ^a,c   Egger, Alexander ^a   Berger, Walter ^a,b,c   Jakupec, Michael A ^a,c   Galanski, Markus ^a   Keppler, Bernhard K ^a,c  

^a UNIVERSITY OF VIENNA   (Austria)

^b MEDICAL UNIVERSITY OF VIENNA   (Austria)

^c MEDICAL UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

(3 CARBOXYPROPANOATO)DICHLORIDO(N,N DIMETHYLETHANE 1,2 DIAMINE)METHOXIDOPLATINUM; ANTINEOPLASTIC AGENT; CISPLATIN; DIAMMINE(3 CARBOXYPROPANOATO)DICHLORIDOMETHOXIDOPLATINUM; DIAMMINEDICHLORIDOHYDROXIDO METHOXIDOPLATINUM; DICHLORIDO(N,N DIMETHYLETHANE 1,2 DIAMINE)[4 (2 HYDROXYETHOXY) 4 OXOBUTANOATO]METHOXIDOPLATINUM; DICHLORIDO(N,N DIMETHYLETHANE 1,2 DIAMINE)HYDROXIDO[4 (2 HYDROXYETHOXY) 4 OXOBUTANOATO]PLATINUM; DICHLORIDO(N,N DIMETHYLETHANE 1,2 DIAMINE)HYDROXIDOMETHOXIDOPLATINUM; DICHLORIDO(N,N DIMETHYLETHANE 1,2 DIAMINE)METHOXIDO(4 METHOXY 4 OXOBUTANOATO)PLATINUM; ETHYLENE GLYCOL; IPROPLATIN; LA 12; MU[4,4' [ETHANE 1,2 DIYLBIS(OXY)]BIS(4 OXOBUTANOATO)]BIS[DICHLORIDO(N,N DIMETHYLETHANE 1,2 DIAMINE)HYDROXIDOPLATINUM; MU[4,4' [ETHANE 1,2 DIYLBIS(OXY)]BIS(4 OXOBUTANOATO)]BIS[DICHLORIDO(N,N DIMETHYLETHANE 1,2 DIAMINE]METHOXIDOPLATINUM; PLATINUM; PLATINUM COMPLEX; SATRAPLATIN; TETRAPLATIN; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER RESISTANCE; CELL CYCLE ARREST; COMPLEX FORMATION; CONTROLLED STUDY; CYTOTOXICITY TEST; DNA SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; MASS SPECTROMETRY; NITROBLUE TETRAZOLIUM TEST; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, REVERSE-PHASE; CISPLATIN; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; ETHYLENE GLYCOLS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLATINUM; PRODRUGS; SOLUBILITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84871662928     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301645g     Document Type: Article

References (58)

1. Lebwohl, D.; Canetta, R. Clinical development of platinum complexes in cancer therapy: an historical perspective and an update Eur. J. Cancer 1998, 34, 1522-1534 (Pubitemid 28446332)
2. O'Dwyer, P. J.; Stevenson, J. P.; Johnson, S. W. Clinical Status of Cisplatin, Carboplatin, and Other Platinum-Based Antitumor Drugs. In Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug; Lippert, B., Ed.; Helvetica Chimica Acta: Zurich, Switzerland, 1999; pp 31-69.
3. Jakupec, M. A.; Galanski, M.; Keppler, B. K. Tumour-inhibiting platinum complexes-state of the art and future perspectives Rev. Physiol. Biochem. Pharmacol. 2003, 146, 1-53
4. Jakupec, M. A.; Galanski, M.; Arion, V. B.; Hartinger, C. G.; Keppler, B. K. Antitumour metal compounds: more than theme and variations Dalton Trans. 2008, 2, 183-194 (Pubitemid 350278321)
5. Fricker, S. P. Metal based drugs: from serendipity to design Dalton Trans. 2007, 43, 4903-4917 (Pubitemid 350015415)
6. Kartalou, M.; Essigmann, J. M. Mechanisms of resistance to cisplatin Mutat. Res., Fundam. Mol. Mech. Mutagen. 2001, 478, 23-43 (Pubitemid 32530848)
7. Brabec, V.; Kasparkova, J. Molecular aspects of resistance to antitumor platinum drugs Drug Resist. Updates 2002, 5, 147-161 (Pubitemid 35033806)
8. Heffeter, P.; Jungwirth, U.; Jakupec, M.; Hartinger, C.; Galanski, M.; Elbling, L.; Micksche, M.; Keppler, B. K.; Berger, W. Resistance against novel anticancer metal compounds: differences and similarities Drug Resist. Updates 2008, 11, 1-16
9. Wong, E.; Giandomenico, C. M. Current status of platinum-based antitumor drugs Chem. Rev. 1999, 99, 2451-2466
10. Galanski, M.; Jakupec, M. A.; Keppler, B. K. Update of the preclinical situation of anticancer platinum complexes: novel design strategies and innovative analytical approaches Curr. Med. Chem. 2005, 12, 2075-2094 (Pubitemid 41093559)
11. Lovejoy, K. S.; Lippard, S. J. Non-traditional platinum compounds for improved accumulation, oral bioavailability, and tumor targeting Dalton Trans. 2009, 48, 10651-10659
12. Wheate, N. J.; Walker, S.; Craig, G. E.; Oun, R. The status of platinum anticancer drugs in the clinic and in clinical trials Dalton Trans. 2010, 39, 8113-8127
13. Olszewski, U.; Hamilton, G. A better platinum-based anticancer drug yet to come Anti-Cancer Agents Med. Chem. 2010, 10, 293-301
14. Harper, B. W.; Krause-Heuer, A. M.; Grant, M. P.; Manohar, M.; Garbutcheon-Singh, K. B.; Aldrich-Wright, J. R. Advances in platinum chemotherapeutics Chem.-Eur. J. 2010, 16, 7064-7077
15. Chawla, S. P.; Yap, B. S.; Tenney, D. M.; Bodey, G. P.; Benjamin, R. S. Phase I study of weekly-administered iproplatin [cis-dichloro-trans-dihydroxy- bis-isopropylamine platin (chip, JM9)] Invest. New Drugs 1988, 6, 311-317 (Pubitemid 19010330)
16. Harstrick, A.; Casper, J.; Guba, R.; Wilke, H.; Poliwoda, H.; Schmoll, H. J. Comparison of the antitumor activity of cisplatin, carboplatin, and iproplatin against established human testicular cancer cell lines in vivo and in vitro Cancer 1989, 63, 1079-1083 (Pubitemid 19074735)
17. Screnci, D.; McKeage, M. J. Platinum neurotoxicity: clinical profiles, experimental models and neuroprotective approaches J. Inorg. Biochem. 1999, 77, 105-110 (Pubitemid 30089089)
18. Schilder, R. J.; LaCreta, F. P.; Perez, R. P.; Johnson, S. W.; Brennan, J. M.; Rogatko, A.; Nash, S.; McAleer, C.; Hamilton, T. C.; Roby, D. Phase I and pharmacokinetic study of ormaplatin (tetraplatin, NSC 363812) administered on a day 1 and day 8 schedule Cancer Res. 1994, 54, 709-717 (Pubitemid 24068326)
19. Poon, G. K.; Mistry, P.; Raynoud, F. I.; Harrap, K. R.; Murrer, B. A.; Barnard, C. F. J. Determination of metabolites of a novel platinum anticancer drug JM216 in human plasma ultrafitrates J. Pharm. Biomed. Anal. 1995, 13, 1493-1498 (Pubitemid 26026990)
20. Choy, H.; Park, C.; Yao, M. Current status and future prospects for satraplatin, an oral platinum analogue Clin. Cancer Res. 2008, 14, 1633-1638 (Pubitemid 351469447)
21. Sternberg, C. N.; Petrylak, D. P.; Sartor, O.; Witjes, J. A.; Demkow, T.; Ferrero, J.-M.; Eymard, J.-C.; Falcon, S.; Calabro, F.; James, N.; Bodrogi, I.; Harper, P.; Wirth, M.; Berry, W.; Petrone, M. E.; McKearn, T. J.; Noursalehi, M.; George, M.; Rozencweig, M. Multinational, double-blind, phase III study of prednisone and either satraplatin or placebo in patients with castrate-refractory prostate cancer progressing after prior chemotherapy: the SPARC trial J. Clin. Oncol. 2009, 27, 5431-5438
22. Prochazka, L.; Turanek, J.; Tesarik, R.; Knotigova, P.; Polaskova, P.; Andrysik, Z.; Kozubik, A.; Zak, F.; Sova, P.; Neuzil, J.; Machala, M. Apoptosis and inhibition of gap-junctional intercellular communication induced by LA-12, a novel hydrophobic platinum(IV) complex Arch. Biochem. Biophys. 2007, 462, 54-61 (Pubitemid 46755141)
23. Sova, P.; Mistr, A.; Kroutil, A.; Zak, F.; Pouckova, P.; Zadinova, M. Comparative anti-tumor efficacy of two orally administered platinum(IV) drugs in nude mice bearing human tumor xenografts Anti-Cancer Drugs 2006, 17, 201-206
24. Weaver, E. L; Bose, R. N. Platinum(II) catalysis and radical intervention in reductions of platinum(IV) antitumor drugs by ascorbic acid J. Inorg. Biochem. 2003, 95, 231-239 (Pubitemid 36773619)
25. Lemma, K.; Berglund, J.; Farrell, N.; Elding, L. I. Kinetics and mechanism for reduction of anticancer-active tetrachloroam(m)ine platinum(IV) compounds by glutathione J. Biol. Inorg. Chem. 2000, 5, 300-306 (Pubitemid 30407888)
26. Lemma, K.; Sargeson, A. M.; Elding, L. I. Kinetics and mechanism for reduction of oral anticancer platinum(IV) dicarboxylate compounds by l -ascorbate ions J. Chem. Soc., Dalton Trans. 2000, 1167-1172
27. 3(5′-GMP)] by NMR spectroscopy and ESI-MS Inorg. Chim. Acta 2000, 300-302, 783-789
28. Zhang, J. Z.; Wexselblatt, E.; Hambley, T. W.; Gibson, D. Pt(IV) analogs of oxaliplatin that do not follow the expected correlation between electrochemical reduction potential and rate of reduction by ascorbate Chem. Commun. 2012, 48, 847-849
29. Hall, M. D.; Hambley, T. W. Platinum(IV) antitumour compounds: their bioinorganic chemistry Coord. Chem. Rev. 2002, 232, 49-67
30. Hall, M. D.; Mellor, H. R.; Callaghan, R.; Hambley, T. W. Basis for design and development of platinum(IV) anticancer complexes J. Med. Chem. 2007, 50, 3403-3411 (Pubitemid 47195446)
31. Reithofer, M. R.; Bytzek, A. K.; Valiahdi, S. M.; Kowol, C. R.; Groessl, M.; Hartinger, C. G.; Jakupec, M. A.; Galanski, M.; Keppler, B. K. Tuning of lipophilicity and cytotoxic potency by structural variation of anticancer platinum(IV) complexes J. Inorg. Biochem. 2011, 105, 46-51
32. Jungwirth, U.; Kowol, C. R.; Keppler, B. K.; Hartinger, C. G.; Berger, W.; Heffeter, P. Anticancer activity of metal complexes: involvement of redox processes Antioxid. Redox Signaling 2011, 15, 1085-1127
33. Matsumoto, S.; Tanaka, T.; Kurokawa, H.; Matsuno, K.; Hayashida, Y.; Takahashi, T. Effect of copper and role of the copper transporters ATP7A and CTR1 in intracellular accumulation of cisplatin Anticancer Res. 2007, 2209-2216 (Pubitemid 47228055)
34. Oldfield, S. P.; Hall, M. D.; Platts, J. A. Calculation of lipophilicity of a large, diverse dataset of anticancer platinum complexes and the relation to cellular uptake J. Med. Chem. 2007, 50, 5227-5237 (Pubitemid 47585720)
35. Olszewski, U.; Ach, F.; Ulsperger, E.; Baumgartner, G.; Zeillinger, R.; Bednarski, P.; Hamilton, G. In Vitro Evaluation of Oxoplatin: An Oral Platinum(IV) Anticancer Agent Met.-Based Drugs 2009, 10.1155/2009/348916
36. Lee, Y.; Yoo, K. H.; Jung, O.-S. Oxidation of Pt(II) to Pt(IV) complex with hydrogen peroxide in glycols Inorg. Chem. Commun. 2003, 249-251
37. Feazell, R. P.; Nakayama-Ratchford, N.; Dai, H.; Lippard, S. J. Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design J. Am. Chem. Soc. 2007, 129, 8438-8439 (Pubitemid 47066504)
38. Lee, Y.; Jung, S. M.; Kang, S. W.; Jung, O.-S. Hydrogen peroxide oxidation of di(hydroxo)platinum(II) species in carboxylic acids Transition Met. Chem. 2004, 710-713 (Pubitemid 40003547)
39. Dhar, S.; Daniel, W. L.; Giljohann, D. A.; Mirkin, C. A.; Lippard, S. J. Polyvalent oligonucleotide gold nanoparticle conjugates as delivery vehicles for platinum(IV) warheads J. Am. Chem. Soc. 2009, 131, 14652-14653
40. Pichler, V.; Valiahdi, S. M.; Jakupec, M. A.; Arion, V. B.; Galanski, M.; Keppler, B. K. Mono-carboxylated diaminedichloridoplatinum(IV) complexes-selective synthesis, characterization, and cytotoxicity Dalton Trans. 2011, 40, 8187-8192
41. Reithofer, M. R.; Valiahdi, S. M.; Jakupec, M. A.; Arion, V. B.; Egger, A.; Galanski, M.; Keppler, B. K. Novel di- and tetracarboxylatoplatinum(IV) complexes. Synthesis, characterization, cytotoxic activity, and DNA platination J. Med. Chem. 2007, 50, 6692-6699 (Pubitemid 350309106)
42. 195Pt NMR-theory and application Chem. Soc. Rev. 2007, 36, 665-686
43. Valkó, K. Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution J. Chromatogr., A 2004, 1037, 299-310 (Pubitemid 38591346)
44. Varbanov, H.; Valiahdi, S. M.; Legin, A. A.; Jakupec, M. A.; Roller, A.; Galanski, M.; Keppler, B. K. Synthesis and characterization of novel bis(carboxylato)dichloridobis(ethylamine)platinum(IV) complexes with higher cytotoxicity than cisplatin Eur. J. Med. Chem. 2011, 46, 5456-5464
45. Heffeter, P.; Pirker, C.; Kowol, C. R.; Herrman, G.; Dornetshuber, R.; Miklos, W.; Jungwirth, U.; Koellensperger, G.; Keppler, B. K.; Berger, W. Impact of terminal dimethylation on the resistance profile of alpha-N-heterocyclic thiosemicarbazones Biochem. Pharmacol. 2012, 83, 1623-1633
46. Jansen, B. A.; Brouwer, J.; Reedijk, J. Glutathione induces cellular resistance against cationic dinuclear platinum anticancer drugs J. Inorg. Biochem. 2002, 89, 197-202 (Pubitemid 34327260)
47. Hector, S.; Bolanowska-Higdon, W.; Zdanowicz, J.; Hitt, S.; Pendyala, L. In vitro studies on the mechanisms of oxaliplatin resistance Cancer Chemother. Pharmacol. 2001, 48, 398-406 (Pubitemid 33027997)
48. -)-cotransport activity and cisplatin-induced early membrane blebbing Cell. Physiol. Biochem. 2008, 22, 45-56
49. Kalimutho, M.; Minutolo, A.; Grelli, S.; Federici, G.; Bernardini, S. Platinum(IV)-derivative satraplatin induced G2/M cell cycle perturbation via p53-p21(waf1/cip1)-independent pathway in human colorectal cancer cells Acta Pharmacol. Sin. 2011, 32, 1387-1396
50. SAINT-Plus, version 7.06a, and APEX2; Bruker-Nonius AXS Inc.: Madison, WI, 2004.
51. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
52. Johnson, G. K. Report ORNL-5138; OAK Ridge National Laboratory; Oak Ridge, TN, 1976.
53. Kuiper, C. M.; Broxterman, H. J.; Baas, F.; Schuurhuis, G. J.; Haisma, H. J.; Scheffer, G. L.; Lankelma, J.; Pinedo, H. M. Drug transport variants without P-glycoprotein overexpression from a human squamous lung cancer cell line after selection with doxorubicin J. Cell. Pharmacol. 1990, 1, 35-41
54. Egger, A.; 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
55. Heffeter, P.; Jakupec, M. A.; Koerner, W.; Wild, S.; Von Keyserlingk, N. G.; Elbling, L.; Zorbas, H.; Korynevska, A.; Knasmueller, S.; Sutterluety, H.; Micksche, M.; Keppler, B. K.; Berger, W. Multidrug-resistant cancer cells are preferential targets of the new antineoplastic lanthanum compound KP772 (FFC24) Biochem. Pharmacol. 2007, 73, 1873-1886 (Pubitemid 46677901)
56. Berger, W.; Elbling, L.; Micksche, M. Expression of the major vault protein LRP in human non-small-cell lung cancer cells: activation by short-term exposure to antineoplastic drugs Int. J. Cancer 2000, 88, 293-300
57. Heffeter, P.; Jakupec, M. A.; Koerner, W.; Wild, S.; Von Keyserlingk, N. G.; Elbling, L.; Zorbas, H.; Korynevska, A.; Knasmueller, S.; Sutterluety, H.; Micksche, M.; Keppler, B. K.; Berger, W. Anticancer activity of the lanthanum compound [tris(1,10-phenanthroline)lanthanum(III)]trithiocyanate (KP772; FFC24) Biochem. Pharmacol. 2006, 71, 426-440 (Pubitemid 43077077)
58. OECD Guidelines for the Testing of Chemicals: Partition Coefficient (n -Octanol/Water), High Performance Liquid Chromatography (HPLC) Method. 13.04.2004. OECD: Paris, France.