Interactions of platinum complexes containing cationic, bicyclic, nonplanar piperidinopiperidine ligands with biological nucleophiles

Journal of Medicinal Chemistry

Volumn 49, Issue 15, 2006, Pages 4674-4683

  Najajreh, Yousef ^a   Ardeli Tzaraf, Yael ^b   Kasparkova, Jana ^c   Heringova, Pavla ^c   Prilutski, Dmitri ^d   Balter, Liliana ^b   Jawbry, Seba ^b   Khazanov, Elena ^d   Perez, Jose Manuel ^e   Barenholz, Yechezkel ^d   Brabec, Viktor ^c   Gibson, Dan ^b,f  

^a AL QUDS UNIVERSITY   (Palestine)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c INSTITUTE OF BIOPHYSICS   (Czech Republic)

^d HEBREW UNIVERSITY   (Israel)

^e UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^f HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BUTYLAMINE; CATION; CISPLATIN; CYCLOHEXYLAMINE DERIVATIVE; DIMETHYLAMINE; GLUTATHIONE; LIGAND; METHIONINE; METHYLAMINE; PIPERIDINE DERIVATIVE; PLATINUM COMPLEX; PROPYLAMINE; TRANSPLATIN; UBIQUITIN;

ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CATTLE; CIRCULAR DICHROISM; COMPLEX FORMATION; COVALENT BOND; CROSS LINKING; CRYSTAL STRUCTURE; DRUG CONFORMATION; MOLECULAR STABILITY; PROTEIN DNA BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

AMINES; ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; CATIONS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; DNA; GLUTATHIONE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; PIPERIDINES; TRANSITION TEMPERATURE; UBIQUITIN;

EID: 33746714979     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060238j     Document Type: Article

References (39)

1. Najajreh, Y.; Khazanov, E.; Jawbry, S.; Ardeli-Tzaraf, Y.; Perez, J. M.; Kasparkova, J.; Brabec, V.; Barenholz, Y.; Gibson, D. Cationic nonsymmetric transplatinum complexes with piperidinopiperidine ligands. Preparation, characterization, in vitro cytotoxicity, in vivo toxicity, and anticancer efficacy studies. J. Med. Chem. 2006, 49, 4665-4673.
2. Siddik, Z. H. Cisplatin: mode of cytotoxic action and molecular basis of resistance. Oncogene 2003, 22, 7265-7279.
3. Wong, E.; Giandomenico, C. M. Current status of platinum-based antitumor drugs. Chem. Rev. 1999, 99, 2451-2466.
4. Jamieson, E. R.; Lippard, S. J. Structure, recognition, and processing of cisplatin-DNA adducts. Chem. Rev. 1999, 99, 2467-2498.
5. Fuertes, M. A.; Castilla, J.; Alonso, C.; Perez, J. M. Cisplatin biochemical mechanism of action: From cytotoxicity to induction of cell death through interconnections between apoptotic and necrotic pathways. Curr. Med. Chem. 2003, 10, 257-266.
6. Fuertes, M. A.; Alonso, C.; Perez, J. M. Biochemical modulation of cisplatin mechanisms of action: Enhancement of antitumor activity and circumvention of drug resistance. Chem. Rev. 2003, 103, 645-662.
7. Chaney, S. G.; Campbell, S. L.; Bassett, E.; Wu, Y. Recognition and processing of cisplatin- and oxaliplatin-DNA adducts. Crit. Rev. Oncol. Hematol. 2005, 53, 3-11.
8. Kartalou, M.; Essigmann, J. M. Mechanisms of resistance to cisplatin. Mutat. Res. 2001, 478, 23-43.
9. Brabec, V.; Kasparkova, J. Molecular aspects of resistance to antitumor platinum drugs. Drug Resist. Updates 2002, 5, 147-161.
10. Momekov, G.; Bakalova, A.; Karaivanova, M. Novel approaches towards development of non-classical platinum-based antineoplastic agents: design of platinum complexes characterized by an alternative DNA-binding pattern and/or tumor-targeted cytotoxicity. Curr. Med. Chem. 2005, 12, 2177-2191.
11. Brabec, V.; Kasparkova, J. Modifications of DNA by platinum complexes. Relation to resistance of tumors to platinum antitumor drugs. Drug Resist. Updates 2005, 8, 131-146.
12. Kasparkova, J.; Marini, V.; Najajreh, Y.; Gibson, D.; Brabec, V. DNA binding mode of the cis and trans geometries of new antitumor nonclassical platinum complexes containing piperidine, piperazine, or 4-picoline ligand in cell-free media. Relations to their activity in cancer cell lines. Biochemistry 2003, 42, 6321-6332.
13. Kasparkova, J.; Novakova, O.; Marini, V.; Najajreh, Y.; Gibson, D.; et al. Activation of trans geometry in bifunctional mononuclear platinum complexes by a piperidine ligand. Mechanistic studies on antitumor action. J. Biol. Chem. 2003, 278, 47516-47525.
14. Boulikas, T.; Vougiouka, M. Cisplatin and platinum drugs at the molecular level. Oncol Rep. 2003, 10, 1663-1682.
15. Wang, D.; Lippard, S. J. Cellular processing of platinum anticancer drugs. Nat. Rev. Drug Discovery 2005, 4, 307-320.
16. Tacka, K. A.; Szalda, D.; Souid, A. K.; Goodisman, J.; Dabrowiak, J. C. Experimental and theoretical studies on the pharmacodynamics of cisplatin in jurkat cells. Chem. Res. Toxicol. 2004, 17, 1434-1444.
17. Appleton, T. G. Donor atom preferences in complexes of platinum and palladium with amino acids and related molecules. Coord. Chem. Rev. 1997, 166, 313-359.
18. Reedijk, J. Why does cisplatin reach guanine-N7 with competing S-donor ligands available in the cell? Chem. Rev. 1999, 99, 2499-2510.
19. Behrens, B. C.; Hamilton, T. C.; Masuda, H.; Grotzinger, K. R.; Whang-Peng, J.; Louie, K. G.; Knutsen, T.; McKoy, W. M.; Young, R. C.; Ozols, R. F. Characterization of a cis-diamminedichloroplatinum(II)-resistant human ovarian cancer cell line and its use in evaluation of platinum analogues. Cancer Res. 1987, 47, 414-418.
20. Kelland, L. R.; Abel, G.; McKeage, M. J.; Jones, M.; Goddard, P. M.; Valenti, M.; Murrer, B. A.; Harrap, K. R. Preclinical antitumor evaluation of bis-acetato-aramine-dichloro-cyclohexylamine platinum(IV): an orally active platinum drug. Cancer Res. 1993, 53, 2581-2586.
21. Vrana, O.; Brabec, V. L-Methionine inhibits reaction of DNA with anticancer cis-diamminedichloroplatinum(II). Biochemistry 2002, 41, 10994-10999.
22. Marchan, V.; Moreno, V.; Pedroso, E.; Grandas, A. Towards a better understanding of the cisplatin mode of action. Chem.-Eur. J. 2001, 7, 808-815.
23. 2 cross-links. Chem.-Eur. J. 2004, 10, 5369-5375.
24. Barnham, K. J.; Djuran, M. I.; Murdoch, P. D.; Sadler, P. J. Intermolecular displacement of S-bound L-methionine on platinum(II) by guanosine 5′-monophosphate. Implications for the mechanism of action of anticancer drugs. J. Chem. Soc., Chem. Commun. 1994, 721-722.
25. 2+ model adducts. Inorg. Chem. 1999, 38, 1450-1455.
26. Najajreh, Y.; Prilutski, D.; Ardeli-Tzaraf, Y.; Perez, J. M.; Khazanov, E.; et al. Structure and unique interactions with DNA of a cationic trans-platinum complex with the nonplanar bicyclic piperidinopiperidine ligand. Angew. Chem., Int. Ed. 2005, 44, 2885-2887.
27. Kasparkova, J.; Novakova, O.; Marini, V.; Najajreh, Y.; Gibson, D.; et al. Activation of trans geometry in bifunctional mononuclear platinum complexes by a piperidine ligand. Mechanistic studies on antitumor action. J. Bioi. Chem. 2003, 278, 47516-47525.
28. Prokop, R.; Kasparkova, J.; Novakova, O.; Marini, V.; Pizarro, A. M.; et al. DNA interactions of new antitumor platinum complexes with trans geometry activated by a 2-methylbutylamine or secbutylamine ligand. Biochem. Pharmacol. 2004, 67, 1097-1109.
29. Brabec, V.; Kasparkova, J.; Vrana, O.; Novakova, O.; Cox, J. W.; et al. DNA modifications by a novel bifunctional trinuclear platinum phase I anticancer agent. Biochemistry 1999, 38, 6781-6790.
30. Chen, Y.; Guo, Z. J.; Parkinson, J. A.; Sadler, P. J. Kinetic control of reactions of a sterically hindered platinum picoline anticancer complex with guanosine 5′-monophosphate and glutathione. J. Chem. Soc., Dalton Trans. 1998, 3577-3585.
31. Brabec, V.; Leng, M. DNA interstrand cross-links of trans- diamminedichloroplatinum(II) are preferentially formed between guanine and complementary cytosine residues. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5345-5349.
32. Zaludova, R.; Kleinwachter, V.; Brabec, V. The effect of ionic strength on melting of DNA modified by platinum(II) complexes. Biophys. Chem. 1996, 60, 135-142.
33. Peleg-Shulman, T.; Najajreh, Y.; Gibson, D. Interactions of cisplatin and transplatin with proteins. Comparison of binding kinetics, binding sites and reactivity of the Pt-protein adducts of cisplatin and transplatin towards biological nucleophiles. J. Inorg. Biochem. 2002, 91, 306-311.
34. Najajreh, Y.; Shulman, T. P.; Moshel, O.; Farrell, N.; Gibson, D. Ligand effects on the binding of cis- and trans-PtCl(2)Am1Am2 to proteins. J. Biol. Inorg. Chem. 2003, 8, 167-175.
35. Peleg-Shulman, T.; Gibson, D. Cisplatin-protein adducts are efficiently removed by glutathione but not by 5′-guanosine monophosphate. J. Am. Chem. Soc. 2001, 123, 3171-3172.
36. 2(Am)(piperidinopiperidine)]·HCl complexes with ubiquitin. Rapid Commun. Mass Spectrom. 2005, 19, 3666-3672.
37. Bancroft, D. P.; Lepre, C. A.; Lippard, S. J. Pt-195 NMR kinetic and mechanistic studies of cis-diamminedichloroplatinum and transdiamminedichloroplatinum(II) binding to DNA. J. Am. Chem. Soc. 1990, 112, 6860-6871.
38. Brabec, V.; Kleinwächter, V.; Butour, J. L.; Johnson, N. P. Biophysical studies of the modification of DNA by antitumour platinum coordination complexes. Biophys. Chem. 1990, 35, 129-141.
39. Keck, M. V.; Lippard, S. J. Unwinding of supercoiled DNA by platinum ethidium and related complexes. J. Am. Chem. Soc. 1992, 114, 3386-3390.