Trans-Dichloridopalladium(II) and platinum(II) complexes with 2-(hydroxymethyl)pyridine and 2-(2-hydroxyethyl)pyridine: Synthesis, structural characterization, DNA binding and in vitro cytotoxicity studies

European Journal of Medicinal Chemistry

Volumn 60, Issue , 2013, Pages 386-394

  Icsel, Ceyda ^a   Yilmaz, Veysel T ^a   Ari, Ferda ^a   Ulukaya, Engin ^a   Harrison, William T A ^b  

^a ULUDAG UNIVERSITY   (Turkey)

^b UNIVERSITY OF ABERDEEN   (United Kingdom)

Author keywords

2 (2 Hydroxyethyl) pyridine; 2 (Hydroxymethyl)pyridine; Cytotoxic activity; DNA binding; Transplatinum complexes

Indexed keywords

CISPLATIN; DNA; PALLADIUM COMPLEX; PLASMID DNA; PLATINUM COMPLEX; PYRIDINE DERIVATIVE; TRANSPLATIN;

ABSORPTION SPECTROSCOPY; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL VIABILITY; COLON CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DNA BINDING; DNA DENATURATION; DRUG SYNTHESIS; FIBROBLAST; GEL ELECTROPHORESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; INTERACTIONS WITH DNA; NONHUMAN; RAT; STRUCTURE ANALYSIS; TITRIMETRY; ULTRAVIOLET RADIATION; VISCOSITY; X RAY DIFFRACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; BINDING SITES; CELL LINE, TUMOR; CELL PROLIFERATION; CHO CELLS; CRICETINAE; DNA; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; PALLADIUM; PLATINUM; PYRIDINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84872160407     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.12.002     Document Type: Article

References (66)

1. M. Peyrone Ueber die einwirkung des ammoniaks auf platinchlorür Ann. Chem. Pharm. 51 1844 1 29
2. B. Rosenberg, L. van Camp, and T. Krigas Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode Nature 205 1965 698 699
3. P.J. Loehrer, and L.H. Einhorn Cisplatin Ann. Int. Med. 100 1984 704 713
4. F.M. Muggia Cisplatin update Semin. Oncol. 18 1991 1 4
5. H.M. Pinedo, and J.H. Schornagel Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy 2 1996 Plenum Press New York
6. D.Z. Yang, and A.H.J. Wang Structural studies of interactions between anticancer platinum drugs and DNA Prog. Biophys. Mol. Biol. 66 1996 81 111
7. L.R. Kelland The resurgence of platinum-based cancer chemotherapy Nat. Rev. Cancer 7 2007 573 584
8. J. Reedijk Metal-ligand exchange kinetics in platinum and ruthenium complexes, significance for effectiveness as anticancer drugs Platinum Metals Rev. 52 2008 2 11
9. G.N. Kaluderovic, and R. Paschke Anticancer metallotherapeutics in preclinical development Curr. Med. Chem. 18 2011 4738 4752
10. T.A. Connors, M.J. Cleare, and K.R. Harrap Structure-activity relationships of the antitumor platinum coordination complexes Cancer Treat. Rep. 63 1979 1499 1502
11. K.M. Comess, and S.J. Lippard S. Neidle and M. Waring, Molecular Aspects of Platinum-DNA Interactions Molecular Aspects of Anticancer Drugs-dna Interactions vol. 1 1993 MacMillan Press London 134 168
12. J.M. Perez, M.A. Fuertes, C. Alonso, and C. Navarro-Ranninger Current status of the development of trans-platinum antitumor drugs Crit. Rev. Oncol. Hemat 35 2000 109 120
13. G. Natile, and M. Coluccia Current status of trans-platinum compounds in cancer therapy Coord. Chem. Rev. 216-217 2001 383 410
14. I. Kostova Platinum Complexes as anticancer agents Recent Patents Anti-cancer Drug Discov. 1 2006 1 22
15. M. Coluccia, and G. Natile Trans-platinum complexes in cancer therapy Anti-cancer Agent Med. Chem. 7 2007 111 123
16. S.M. Aris, and N.P. Farrell Towards antitumor active trans-platinum compounds Eur. J. Inorg. Chem. 10 2009 1293 1302
17. H.H. Zheng, Z.H. Xu, and K. Wang FT-Raman studies on the transformation of G-actin to F-actin, the binding of cisplatin and transplatin to F-actin and the effects of the conformation of F-actin Int. J. Biol. Macromol. 20 1997 107 113
18. 2]. A concept for activation of the trans geometry in platinum antitumor complexes Nucleic Acids Res. 31 2003 6450 6460
19. M.E. Alberto, C. Cosentino, and N. Russo Hydrolysis mechanism of anticancer Pd(II) complexes with coumarin derivatives: a theoretical investigation Struct. Chem. 23 2012 831 839
20. U. Kalinowska-Lis, J. Ochocki, and K. Matlawska-Wasowska Trans geometry in platinum antitumor complexes Coord. Chem. Rev. 252 2008 1328 1345
21. S. Grabner, M. Cemazar, N. Bukovec, and G. Sersa Syntheses and cytotoxicity of Pt(II) complexes with acyclovir Acta Chim. Slov 53 2006 153 158
22. 3(4-(hydroxymethyl)-pyridine)] Polyhedron 22 2003 3379 3381
23. A. Martinez, J. Lorenzo, M.J. Prieto, M. Font-Bardia, X. Solans, F.X. Aviles, and V. Moreno Influence of the position of substituents in the cytotoxic activity of trans platinum complexes with hydroxymethyl pyridines Bioorg. Med.Chem. 15 2007 969 979
24. F.J. Ramos-Lima, O. Vrana, A.G. Quiroga, C. Navarro-Ranninger, A. Halamikova, H. Rybnickova, L. Hejmalova, and V. Brabec Structural characterization, DNA interactions, and cytotoxicity of new transplatin analogues containing one aliphatic and one planar heterocyclic amine ligand J. Med. Chem. 49 2006 2640 2651
25. E. Guney, V.T. Yilmaz, F. Ari, O. Buyukgungor, and E. Ulukaya Synthesis, characterization, structures and cytotoxic activity of palladium(II) and platinum(II) complexes containing bis(2-pyridylmethyl)amine and saccharinate Polyhedron 30 2011 114 122
26. E. Ulukaya, F. Ari, K. Dimas, M. Sarimahmut, E. Guney, N. Sakellaridis, and V.T. Yilmaz Cell death-inducing effect of novel palladium(II) and platinum(II) complexes on non-small Cell lung cancer cells in vitro J. Cancer Res. Clin. Oncol. 137 2011 1425 1434
27. E. Ulukaya, F. Ari, K. Dimas, E.I. Ikitimur, E. Guney, and V.T. Yilmaz Anti-cancer activity of a novel palladium(II) complex on human breast cancer cells in vitro and in vivo Eur. J. Med. Chem. 46 2011 4957 4963
28. A.S. Abu-Surrah, H.H. Al-Sadoni, and M.Y. Abdalla Palladium-based chemotherapeutic agents: routes toward complexes with good antitumor activity Cancer Ther. 6 2008 1 10
29. A. Garoufis, S.K. Hadjikakou, and N. Hadjiliadis Palladium coordination compounds as anti-viral, anti-fungal, anti-microbial and anti-tumor agents Coord. Chem. Rev. 253 2009 1384 1397
30. W.J. Geary The use of conductivity measurements in organic solvents for the characterizations of coordination compounds Coord. Chem. Rev. 7 1971 81 122
31. a values for the aiaqua adduct Eur. J. Inorg. Chem. 2002 1035 1039
32. B. Viossat, N.-H. Dung, and F. Robert Structure du trans- dichlorobis(pyridine)palladium(II) Acta Cryst C49 1993 84 85
33. C.-Y. Liao, and H.M. Lee trans-Dichlorodipyridinepalladium(II) Acta Cryst E62 2006 m680 m681
34. H.M. Lee, and C.-Y. Liao A new monoclinic polymorph of trans-dichloridodipyridinepalladium(II) Acta Cryst E64 2008 m1447
35. E. Guney, V.T. Yilmaz, and O. Buyukgungor Palladium(II) and platinum(II) saccharinate complexes containing pyridine and 3-acetylpyridine: synthesis, crystal structures, fluorescence and thermal properties Polyhedron 30 2011 1968 1974
36. J.K. Barton, A.T. Danishefsky, and J.M. Goldberg Tris(phenanthroline) ruthenium(II): stereoselectivity in Binding to DNA J. Am. Chem. Soc. 106 1984 2172 2176
37. H. Chao, W. Mei, Q. Huang, and L. Ji DNA binding studies of ruthenium(II) complexes containing asymmetric tridentate ligands J. Inorg. Biochem. 92 2002 165 170
38. 2{d(pGpG)}], the principal adduct formed by cis-diamminedichloroplatinum(II) with DNA J. Am. Chem. Soc. 110 1988 7368 7381
39. L. Strekowski, and B. Wilson Noncovalent interactions with DNA: an overview Mutat. Res. 623 2007 3 13
40. F.R. Keene, J.A. Smith, and J.G. Collins Metal complexes as structure-selective binding agents for nucleic acids Coord. Chem. Rev. 253 2009 2021 2035
41. 3)(thiazole)]. Protein recognition and nucleotide excision repair of monofunctional adducts Biochemistry 42 2003 792 800
42. J. Kasparkova, O. Novakova, V. Marini, Y. Najajreh, D. Gibson, J.M. Perez, and V. Brabec Activation of trans geometry in bifunctional mononuclear platinum complexes by a piperidine ligand J. Biol. Chem. 278 2003 47516 47525
43. 3)(quinoline)] Eur. J. Biochem. 254 1998 547 557
44. V. Brabec, K. Neplechova, J. Kasparkova, and N. Farrell Steric control of DNA interstrand cross-link sites of trans platinum complexes: specificity can be dictated by planar nonleaving groups J. Biol. Inorg. Chem. 5 2000 364 368
45. E.K. Efthimiadou, A. Karaliota, and G. Psomas Metal complexes of the third-generation quinolone antimicrobial drug sparfloxacin: structure and biological evaluation J. Inorg. Biochem. 104 2010 455 466
46. A.M. Pyle, J.P. Rehmann, R. Meshoyrer, C.V. Kumar, N.J. Turro, and J.K. Barton Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA J. Am. Chem. Soc. 111 1989 3051 3058
47. S. Nafisi, and Z. Norouzi A comparative study on the interaction of cis- and trans-platin with DNA and RNA DNA Cell. Biol. 28 2009 469 477
48. S. Kundu, S. Maity, R. Bhadra, and P. Ghosh Trans-dichlorobis(N-p- tolylpyridine-2-amine)palladium(II): synthesis, structure, fluorescence features and DNA binding J. Chem. 50A 2011 1443 1449
49. M.J. Waring Complex formation between ethidium bromide and nucleic acids J. Mol. Biol. 13 1965 269 282
50. J.-B. LePecq, and C.J. Paoletti A fluorescent complex between ethidium bromide and nucleic acids. Physical-chemical characterization Mol. Biol. 27 1967 87 106
51. J. Kozelka, F. Legendre, F. Reeder, and J. Chottard Kinetic aspects of interactions between DNA and platinum complexes Coord. Chem. Rev. 190-192 1999 61 82
52. P. Jordan, and M. Carmo-Fonseca Molecular mechanisms involved in cisplatin cytotoxicity Cell. Mol. Life Sci. 57 2000 1229 1235
53. L.S. Lerman Structural considerations in the interaction of DNA and acridines J. Mol. Biol. 3 1961 18 30
54. E.C. Long, and J.K. Barton On demonstrating DNA intercalation Acc. Chem. Res. 23 1990 271 273
55. S. Satyanarayana, J.C. Dabrowiak, and J.B. Chaires Neither Δ- nor Λ-tris(phenanthroline)ruthenium(II) binds to DNA by classical intercalation Biochemistry 31 1992 9319 9324
56. R. Thomas The denaturation of DNA Gene 135 1993 77 79
57. J.-L. Mergny, and L. Lacroix Analysis of thermal melting curves Oligonucleotides 13 2003 515 537
58. J. Sambrook, and D.W. Russel Molecular Cloning: A Laboratory Manual third ed. 2001 Cold Spring Harbor Laboratory Press New York
59. 3Cl]Cl, where L = 3-hydroxypyridine, 4-hydroxypyridine and imidazo(1,2-α)pyridine J. Inorg. Biochem. 99 2005 1098 1112
60. E.J. Gao, M.C. Zhu, Y. Huang, L. Liu, H.Y. Liu, F.C. Liu, S. Ma, and C.Y. Shi New pH-dependent complexes, from mononuclear Pd(II) monomer to heteronuclear [Pd(II), K(I)]Polymer: DNA cleavage and cytotoxicity in vitro Eur. J. Med. Chem. 45 2010 1034 1041
61. I. Eryazici, C.N. Moorefield, and G.R. Newkome Square-planar Pd(II), Pt(II), and Au(III) terpyridine complexes: their syntheses, physical properties, supramolecular constructs, and biomedical activities Chem. Rev. 108 2008 1834 1895
62. J. Marmur A procedure for the isolation of deoxyribonucleic acid from micro-organisms J. Mol. Biol. 3 1961 208 218
63. M.E. Reichman, S.A. Rice, C.A. Thomas, and P. Doty A further examination of the molecular weight and size of desoxypentose nucleic Acid J. Am. Chem. Soc. 76 1954 3047 3053
64. G.M. Sheldrick A short history of SHELX Acta Crystallogr. A64 2008 112 122
65. G. Cohen, and H. Eisenberg Viscosity and sedimentation study of sonicated DNA-proflavine complexes Biopolymers 8 1969 45 55
66. E. Ulukaya, F. Ozdikicioglu, A.Y. Oral, and M. Demirci The MTT assay yields a relatively lower result of growth inhibition than the ATP assay depending on the chemotherapeutic drugs tested Toxicol. In Vitro 22 2008 232 239