Biological evaluation of transdichloridoplatinum( II) complexes with 3- and 4-acetylpyridine in comparison to cisplatin

1. O’Dwyer PJ, Stevenson JP, Johnson SW. Clinical status of cisplatin, carboplatin and other platinum-based antitumor drugs. In: Lippert B, editor. Cisplatin: chemistry and biochemistry of the leading anticancer drug. Weinheim, Germany: Wiley-VCH; 1999. p. 30-70.Search in Google Scholar

2. Kelland L. The resurgence of platinum-based cancer chemotherapy. Nat RevCancer 2007; 7: 573-84.10.1038/nrc2167Search in Google Scholar

3. Desoize B, Madoulet C. Particular aspects of platinum compounds used at present in cancer treatment. Crit Rev Oncol Hematol 2002; 42: 317-25.10.1016/S1040-8428(01)00219-0Search in Google Scholar

4. Reedijk J. Metal-ligand exchange kinetics in platinum and ruthenium complexes. Platinum Metals Rev 2008; 52: 2-11.10.1595/147106708X255987Search in Google Scholar

5. Wang, X. Fresh platinum complexes with promising antitumor activity. Anti-Cancer Agents Med Chem 2010; 10: 396-411.10.2174/187152061100905039620545618Search in Google Scholar

6. Farrell N, Kelland LR, Robert JD. Van Beusichem M. Activation of the trans geometry in platinum antitumor complexes: a survey of the cytotoxicity of trans complexes containing planar ligands in murine L1210 and human tumor panels and studies on their mechanism of action. Cancer Res 1992; 52: 5065-72.Search in Google Scholar

7. Quiroga AG. Understanding trans platinum complexes as potential antitumor drugs beyond targeting DNA. J Inorg Biochem 2012; 114: 106-12.10.1016/j.jinorgbio.2012.06.00222819649Search in Google Scholar

8. Coluccia M, Nassi A, Loseto F, Boccarell A, Mariggiò MA, Giordano D, et al. A trans-platinum complex showing higher antitumor activity than the cis congeners. J Med Chem 1993; 36: 510-2.10.1021/jm00056a0128474104Search in Google Scholar

9. Radulović S, Tesić Ž, Manić, S. Trans-platinum complexes as anticancer drugs: recent developments and future prospects. Curr Med Chem 2002; 9: 1611-8.10.2174/092986702336937612171556Search in Google Scholar

10. Pérez JM, Montero EI, González AM, Solans X, Font-Bardia M, Fuertes MA, et al. X-Ray structure of cytotoxic trans-[PtCl(2)(dimethylamine)(isopropylamine)]: interstrand cross-link efficiency, DNA sequence specificity, and inhibition of the B-Z transition. J Med Chem 2000; 43: 2411-8.10.1021/jm000925p10882368Search in Google Scholar

11. Arandjelović S, Tesić Ž, Juranić Z, Radulović S, Vrvić M, Potkonjak B, et al. Antiproliferative activity of some cis-/trans-platinum(II) complexes on HeLa cells. J Exp Clin Cancer Res 2002; 21: 519-26.Search in Google Scholar

12. Aris SM, Farrell N. Towards antitumor active trans-platinum compounds. Eur J Inorg Chem 2009; 10: 1293-302.Search in Google Scholar

13. Wang, X. Fresh platinum complexes with promising antitumor activity. Anti-Cancer Agents Med Chem 2010; 10: 396-411.10.2174/1871520611009050396Search in Google Scholar

14. Cubo L, Quiroga AG, Zhang J, Thomas DS, Carnero A, Navarro-Ranninger C, et al. Influence of amine ligands on the aquation and cytotoxicity of transdiamine platinum(II) anticancer complexes. Dalton Trans 2009; 18: 3457-66.10.1039/b819301k19381408Search in Google Scholar

15. Reed E. ERCC1 and clinical resistance to platinum-based therapy. Clin CancerRes 2005; 11: 6100-2.10.1158/1078-0432.CCR-05-108316144907Search in Google Scholar

16. Manić S, Gatti L, Carenini N, Fumagalli G, Zunino F, Perego P. Mechanisms controlling sensitivity to platinum complexes: role of p53 and DNA mismatch repair. Curr Cancer Drug Targets 2003; 3: 21-9.10.2174/156800903333372712570658Search in Google Scholar

17. Kalayda GV, Wagner CH, Jaehde U. Relevance of copper transporter 1 for cisplatin resistance in human ovarian carcinoma cells. J Inorg Biochem 2012, 116: 1-10.10.1016/j.jinorgbio.2012.07.01023010323Search in Google Scholar

18. Sadler PJ. Protein recognition of platinated DNA. ChemBioChem 2009; 10: 73-4.10.1002/cbic.20080073319040246Search in Google Scholar

19. Ravera M, Gabano E, Sardi M, Ermondi G, Caron G, McGlinchey MJ, et al. Synthesis, characterization, structure, molecular modeling studies and biological activity of sterically crowded Pt(II) complexes containing bis(imidazole) ligands. J Inorg Biochem 2011; 105: 400-9.10.1016/j.jinorgbio.2010.12.00221421126Search in Google Scholar

20. Ramos-Lima FJ, Moneo V, Quiroga AG, Carnero A, Navarro-Ranninger C. The role of p53 in the cellular toxicity by active trans-platinum complexes containing isopropylamine and hydroxymethylpyridine. Eur J Med Chem 2010; 45: 134-41.10.1016/j.ejmech.2009.09.03519853978Search in Google Scholar

21. Huq F, Yu JQ, Daghriri H, Beale P. Studies on activities, cell uptake and DNA binding of four trans-planaramineplatinum(II) complexes of the form: trans- PtL(NH3)Cl2, where L=2-hydroxypyridine, imidazole, 3-hydroxypyridine and imidazo(1,2-alpha)pyridine. J Inorg Biochem 2004; 98: 1261-70.10.1016/j.jinorgbio.2004.05.01415271501Search in Google Scholar

22. Aris SM, Knott KM, Yang X, Gewirtz DA, Farrell NP. Modulation of transplanaramine platinum complex reactivity by systematic modification of carrier and leaving groups. Inorg Chim Acta 2009; 362: 929-34.10.1016/j.ica.2008.01.025Search in Google Scholar

23. Rakić GM, Grgurić-Sipka S, Kaluderović GN, Gómez-Ruiz S, Bjelogrlić SK, Radulović SS, et al. Novel trans-dichloridoplatinum(II) complexes with 3- and 4-acetylpyridine: Synthesis, characterization, DFT calculations and cytotoxicity. Eur J Med Chem 2009; 44: 1921-5.10.1016/j.ejmech.2008.11.00419070943Search in Google Scholar

24. Kim KY, Jeong SY, Won J, Ryu PD, Nam MJ. Induction of angiogenesis by expression of soluble type II transforming growth factor-beta receptor in mouse hepatoma. J Bio Chem 2001; 276: 38781-6.10.1074/jbc.M10494420011457844Search in Google Scholar

25. Muscella A, Calabriso N, Vetrugno C, Urso L, Fanizzi FP, De Pascali SA, et al. Sublethal concentrations of the platinum(II) complex [Pt(O,O’-acac) (gamma-acac)(DMS)] alter the motility and induce anoikis in MCF-7 cells. BrJ Pharmacol 2010; 160: 1362-77.10.1111/j.1476-5381.2010.00782.xSearch in Google Scholar

26. Sasanelli R, Boccarelli A, Giordano D, Laforgia M, Arnesano F, Natile G, et al.Platinum complexes can inhibit matrix metalloproteinase activity: platinum- diethyl[(methylsulfinyl)methyl]phosphonate complexes as inhibitors of matrix metalloproteinases 2, 3, 9, and 12. J Med Chem 2007; 50: 3434-41.10.1021/jm061435lSearch in Google Scholar

27. Montiel M, Urso L, de la Blanca EP, Marsigliante S, Jiménez E. Cisplatin reduces endothelial cell migration via regulation of type 2-matrix metalloproteinase activity. Cell Physiol Biochem 2009; 23: 441-8.10.1159/000218191Search in Google Scholar

28. Jacobs JP, Jones CM, Baille JP. Characteristics of a human diploid cell designated MRC-5. Nature 1970; 227: 168-70.10.1038/227168a0Search in Google Scholar

29. Gligorijević N, Aranđelović S, Filipović L, Jakovljević K, Janković R, GrgurićŠipka S, et al. Picolinate ruthenium(II)-arene complex with in vitro antiproliferative and antimetastatic properties: comparison to a series of ruthenium(II)-arene complexes with similar structure. J Inorg Biochem 2012; 108: 53-61.10.1016/j.jinorgbio.2011.12.002Search in Google Scholar

30. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl CancerInst 1990; 82: 1107-12.10.1093/jnci/82.13.1107Search in Google Scholar

31. Ormerod MG. Flow Cytometry, a Practical Approach. New York: Oxford University Press; 1994.Search in Google Scholar

32. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. AnalBiochem 1976; 72: 248-54.10.1016/0003-2697(76)90527-3Search in Google Scholar

33. Snoek-van Beurden PA, Von den Hoff JW. Zymographic techniques for the analysis of matrix metalloproteinases and their inhibitors. BioTechniques 2005; 38: 73-83.10.2144/05381RV0115679089Search in Google Scholar

34. Musetti C, Nazarov AA, Farrell NP, Sissi C. DNA reactivity profile of transplatinum planar amine derivatives. Chem Med Chem 2011; 6: 1283-90.10.1002/cmdc.20110003221472991Search in Google Scholar

35. Altaha R, Liang X, Yu JJ, Reed E. Excision repair cross complementing-group 1: gene expression and platinum resistance. Int J Mol Med 2004; 14: 959-70.Search in Google Scholar

36. Zorbas H, Keppler BK. Cisplatin damage: are DNA repair proteins saviors or traitors to the cell? Chem Bio Chem 2005; 6: 1157-66.Search in Google Scholar

37. Ramos-Lima FJ, Vrána O, Quiroga AG, Navarro-Ranninger C, Halámiková A, Rybnícková H, et al. Structural characterization, DNA interactions, and cytotoxicity of new transplatin analogues containing one aliphatic and one planar heterocyclic amine ligand. J Med Chem 2006; 49: 2640 51.10.1021/jm060251416610807Search in Google Scholar

38. Bierbach U, Sabat M, Farrell N. Inversion of the cis geometry requirement for cytotoxicity in structurally novel platinum(II) complexes containing the bidentate N,O-donor pyridin-2-yl-acetate. Inorg Chem 200; 39: 1882-90.10.1021/ic991259p11428108Search in Google Scholar

39. Wang QE, Milum K, Han C, Huang YW, Wani G, Thomale J, et al. Differential contributory roles of nucleotide excision and homologous recombination repair for enhancing cisplatin sensitivity in human ovarian cancer cells. MolCancer 2011; 10: 24.10.1186/1476-4598-10-24306465321385444Search in Google Scholar

40. Perego P, Giarola M, Righetti SC, Supino R, Caserini C, Delia D, et al. Association between cisplatin resistance and mutation of p53 gene and reduced bax expression in ovarian carcinoma cell systems. Cancer Res 1996; 56: 556-62.Search in Google Scholar

41. Todd RC, Lippard SJ. Inhibition of transcription by platinum antitumor compounds. Metallomics 2009; 1: 280-91.10.1039/b907567d275288420046924Search in Google Scholar

42. Seetharam RN, Sood A, Basu-Mallick A, Augenlicht LH, Mariadason JM, Goel S. Oxaliplatin resistance induced by ERCC1 up-regulation is abrogated by siRNA-mediated gene silencing in human colorectal cancer cells. AnticancerRes 2010; 30: 2531-8.Search in Google Scholar

43. 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: 6321-32.10.1021/bi034231512755637Search in Google Scholar

44. Arkell J, Jackson CJ. Constitutive secretion of MMP9 by early-passage cultured human endothelial cells. Cel Biochem Funct 2003; 21: 381-6.10.1002/cbf.103714624478Search in Google Scholar

45. Ulukaya E, Ari F, Dimas K, Ikitimur KI, Yilmaz VT. Anti-cancer activity of a novel palladium(II) complex on human breast cancer cells in vitro and invivo. Eur J Med Chem 2011; 46: 4957-63.10.1016/j.ejmech.2011.07.05521885165Search in Google Scholar

46. Kiran MS, Viji RI, Kumar SV, Prabhakaran AA, Sudhakaran PR. Changes in expression of VE-cadherin and MMPs in endothelial cells: Implications for angiogenesis. Vasc Cell 2011; 3: 6. 10.1186/2045-824X-3-6304535221349163Search in Google Scholar