Advance Search
You have access

More insight into the mode of action of lipophilic antitumor drugs containing a platinum (II) fragment

Cite this:
Vanchanagiri, K. (2017). More insight into the mode of action of lipophilic antitumor drugs containing a platinum (II) fragment. Journal of Medical Biomedical and Applied Sciences, 5(3). https://doi.org/10.15520/.v5i3.54
Copyright @ 2022 Interactive Protocols
RIGHTS & PERMISSIONS
Article Views
250
Altmetric
1
Citations
-
LEARN ABOUT THESE METRICS
PDF  

Abstract

Cis-Diammine(1,1-cyclobutanedicarboxylato)platinum(II)) (Carboplatin 2) is a second generation platinum anticancer drug following Cis-diamminedichloroplatinum(II) (Cisplatin 1). In the present study Cisplatin and Carboplatin analogs are attached to the acid group of the bile acid via an ester link called as ChAPt(n)Cis and ChAPt(n)Carbo. The in vitro antitumor activity of Cisplatin 1 along with the corresponding ChAPt derivatives evaluated against a panel of five tumor cell lines of different histogenic origin. A series of biological methods starting from Sulforhodamine B (SRB) assay to determine IC50, Cell cycle analysis, Annexin-V assay and Caspase assays were performed with the aim to scrutinize the anticancer mode of action on HepG2 (hepatocellular car cinoma) cell line. The compounds exerted a dose dependent antiproliferative action at micro molar concentrations and the effect of these structural variations on anticancer activity was elaborated and discussed more in detail. To summarize, several compounds revealed significant antitumor activity and surprisingly the ChAPt(11)Cis and ChAPt(11)Carbo induce programmed cell death with molecular features different from each other, suggesting that both drugs induce apoptosis through different initial pathways.
KEYWORDS:

 Additional Information

Downloads

Download data is not yet available.

Article Metrics Graph

Chart Graph | Range Graph

Content

Section

References

  1. Monti, Elena, Gariboldi, Marzia, Maiocchi, Alessandro, Marengo, Emilio, Cassino, Claudio,
  2. Gabano, Elisabetta, and Osella, Domenico. Cytotoxicity of cis-Platinum(II) Conjugate
  3. Models. The Effect of Chelating Arms and Leaving Groups on Cytotoxicity: A Quantitative
  4. Structure-Activity Relationship Approach. J.Med.Chem. 48[3], 857-866. 2005.
  5. Ye, Qing Song, Liu, Wei Ping, Chen, Xi Zhu, Yu, Yao, Chang, Qiao Wen, and Hou, Shu
  6. Qian. Synthesis and In Vitro cytotoxicity of Cis-[Pt(NH3)(NH2OH)Cl2]. Arch.Pharmacal
  7. Res. 33[6], 807-811. 2010.
  8. Larena, Monica G., Martinez-Diez, Maria C., Maclas, Rocio I. R., Dominguez, Maria F.,
  9. Serrano, Maria A., and Marin, Jose J. G. Relationship between tumor cell load and
  10. sensitivity to the cytostatic effect of two novel platinum-bile acid complexes, Bamet-D3
  11. and Bamet-UD2. J.Drug Targeting 10[5], 397-404. 2002.
  12. Barbara, Cecilia, Orlandi, Paola, Bocci, Guido, Fioravanti, Anna, Di Paolo, Antonello,
  13. Natale, Gianfranco, Del Tacca, Mario, and Danesi, Romano. In vitro and in vivo antitumour
  14. effects of novel, orally active bile acid-conjugated platinum complexes on rat hepatoma.
  15. Eur.J.Pharmacol. 549[1-3], 27-34. 2006.
  17. Biersack, Bernhard, Dietrich, Andrea, Zoldakova, Miroslava, Kalinowski, Bernd, Paschke,
  18. Reinhard, Schobert, Rainer, and Mueller, Thomas. Lipophilic Pt(II) complexes with
  19. selective efficacy against cisplatin-resistant testicular cancer cells. J.Inorg.Biochem.
  20. [12], 1630-1637. 2011.
  21. Briz, Oscar, Serrano, Maria Angeles, Rebollo, Noemi, Hagenbuch, Bruno, Meier, Peter J.,
  22. Koepsell, Hermann, and Marin, Jose J. G. Carriers involved in targeting the cytostatic bile
  23. acid-cisplatin derivatives cis-diammine-chloro-cholylglycinate-platinum(II) and cisdiammine-bisursodeoxycholate-platinum(II)
  24. toward liver cells. Mol.Pharmacol. 61[4], 853-
  25. 2002.
  26. Criado, J. J., Macias, R., I, Medarde, M., Monte, M. J., Serrano, M. A., and Marin, J. J.
  27. Synthesis and characterization of the new cytostatic complex cis-diammineplatinum(II)-
  28. chlorocholylglycinate. Bioconjug Chem 8[4], 453-458. 1997.
  29. Gabano, Elisabetta, Ravera, Mauro, and Osella, Domenico. The drug targeting and
  30. delivery approach applied to pt-antitumour complexes. A coordination point of view. Curr
  31. Med Chem 16[34], 4544-4580. 2009.
  32. Gandolfi, Ottavio, Blum, Jochanan, and Mandelbaum-Shavit, Frederika. Antitumor
  33. steroidal-cis-platinum(II)-o-catecholato conjugates: preliminary evaluation on breast
  34. cancer MCF-7 cells. Inorg.Chim.Acta 91[4], 257-261. 1984.
  35. Carrasco, J., Criado, J. J., Macias, R. I. R., Manzano, J. L., Marin, J. J. G., Medarde, M.,
  36. and Rodriguez, E. Structural characterization and cytostatic activity of
  37. chlorobischolylglycinatogold(III). J.Inorg.Biochem. 84[3-4], 287-292. 2001.
  38. Georgiadis, Minas P., Haroutounian, Serkos A., and Chondros, Kostas P. Synthesis and
  39. biological studies of steroidal cis-platinum(II) complexes. Inorg.Chim.Acta 138[3], 249-
  40. 1987.
  41. Criado, Julio J., Dominguez, Maria F., Medarde, Manuel, Fernandez, Emilio R., Macias,
  42. Rocio I. R., and Marin, Jose J. G. Structural characterization, kinetic studies, and in vitro
  43. biological activity of new cis-diamminebis-cholylglycinate(o,o') pt(II) and cis-diamminebisursodeoxycholate(o,o')
  44. pt(II) complexes. Bioconjugate Chem. 11[2], 167-174. 2000.
  45. Criado, Julio J., Manzano, Juan L., and Rodriguez-Fernandez, E. New organotropic
  46. compounds. Synthesis, characterization and reactivity of Pt(II) and Au(III) complexes with
  47. bile acids: DNA interactions and 'in vitro' anticancer activity. [Erratum to document cited in
  48. CA140:052755]. J.Inorg.Biochem. 99[10], 2092. 2005.
  50. Criado, J. J., Herrera, M. C., Palomero, M. F., Medarde, M., Rodriguez, E., and Marin, J.
  51. J. G. Synthesis and characterization of a new bile acid and platinum(II) complex with
  52. cytostatic activity. J.Lipid Res. 38[5], 1022-1032. 1997.
  53. Marin, J. J. G., Macias, R. I. R., Monte, M. J., El-Mir, M. Y., and Serrano, M. A. Liver
  54. targeting of cisplatin-derived cytostatic drugs (Bamets) by coupling to bile acids. Falk
  55. Symp. 120[Biology of Bile Acids in Health and Disease], 271-277. 2001.
  56. Tyszczuk-Rotko, K., Wojciak-Kosior, M., and Sowa, I. Voltammetric determination of
  57. betulinic acid at lead film electrode after chromatographic separation in plant material.
  58. Anal.Biochem. 436[2], 121-126. 2013.
  59. Emmerich, Daniel, Vanchanagiri, Kranthi, Baratto, Leopoldo C., Schmidt, Harry, and
  60. Paschke, Reinhard. Synthesis and studies of anticancer properties of lupane-type
  61. triterpenoid derivatives containing a cisplatin fragment. Eur.J.Med.Chem. 75, 460-466.
  63. J. Lokich, N. Anderson. Ann. Oncol. 1998, 9(1), 13-21.
  64. Dietrich, Andrea, Mueller, Thomas, Paschke, Reinhard, Kalinowski, Bernd, Behlendorf,
  65. Timo, Reipsch, Franziska, Fruehauf, Angelika, Schmoll, Hans Joachim, Kloft, Charlotte,
  66. and Voigt, Wieland. 2-(4-(tetrahydro-2H-pyran-2-yloxy)-undecyl)-propane-1,3-
  67. diamminedichloroplatinum(II): A Novel Platinum Compound that Overcomes Cisplatin
  68. Resistance and Induces Apoptosis by Mechanisms Different from that of Cisplatin.
  69. J.Med.Chem. 51[17], 5413-5422. 2008.
  70. Wagner, Jill M. and Karnitz, Larry M. Cisplatin-induced DNA damage activates replication
  71. checkpoint signaling components that differentially affect tumor cell survival.
  72. Mol.Pharmacol. 76[1], 208-214. 2009.
  73. Xie, Mingjin, Liu, Weiping, Lou, Liguang, Chen, Xizhu, Ye, Qingsong, Yu, Yao, Chang,
  74. Qiaowen, and Hou, Shuqian. Unusual Dimeric Chemical Structure for a Carboplatin
  75. Analogue as a Potential Anticancer Complex. Inorg.Chem. 49[13], 5792-5794. 2010.
  76. V. M. Gonzalez, M. A. Fuertes, C. Alonso, J. M. Perez. Mol. Pharmacol. 2001, 59(4), 657-
  78. S. Elmore. Toxicol. Pathol. 2007, 35(4), 495-516.
  79. Paschke, R., Kalbitz, J., and Paetz, C. Novel spacer linked bile acid-cisplatin compounds
  80. as a model for specific drug delivery, synthesis and characterization. Inorg.Chim.Acta
  81. [2], 241-249. 2000.
  82. Paschke, Reinhard, Kalbitz, Jutta, Paetz, Christian, Luckner, Martin, Mueller, Thomas,
  83. Schmoll, Hans Joachim, Mueller, Helmut, Sorkau, Eduard, and Sinn, Ekkehard. Cholic
  85. acid-carboplatin compounds (CarboChAPt) as models for specific drug delivery: synthesis
  86. of novel carboplatin analogous derivatives and comparison of the cytotoxic properties with
  87. corresponding cisplatin compounds. J.Inorg.Biochem. 94[4], 335-342. 2003.
  88. Kaluderovic, Goran N., Dietrich, Andrea, Kommera, Harish, Kuntsche, Judith, Maeder,
  89. Karsten, Mueller, Thomas, and Paschke, Reinhard. Liposomes as vehicles for water
  90. insoluble platinum-based potential drug: 2-(4-(Tetrahydro-2H-pyran-2-yloxy)-undecyl)-
  91. propane-1,3-diamminedichloroplatinum(II). Eur.J.Med.Chem. 54, 567-572. 2012.
  92. Paschke, Reinhard, Paetz, Christian, Mueller, Thomas, Schmoll, Hans Joachim, Mueller,
  93. Helmut, Sorkau, Eduard, and Sinn, Ekkehard. Biomolecules linked to transition metal
  94. complexes - new chances for chemotherapy. Curr.Med.Chem. 10[19], 2033-2044. 2003.
  95. J. Rohacova, M. L. Marin, A. Martinez-Romero, L. Diaz, J. E. O'Connor, M. J. GomezLechon,
  96. M. T. Donato, J. V. Castell, M. A. Miranda. ChemMedChem. 2009, 4(3), 466-472.
  97. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H.
  98. Bokesch, S. Kenney, M. R. Boyd. J. Natl. Cancer Inst. 1990, 82(13), 1107-1112.
  99. Willmann, M., Wacheck, V., Buckley, J., Nagy, K., Thalhammer, J., Paschke, R., Triche,
  100. T., Jansen, B., and Selzer, E. Characterization of NVX-207, a novel betulinic acid-derived
  101. anti-cancer compound. Eur.J.Clin.Invest. 39[5], 384-394. 2009.
  102. S. Dasari, P. B. Tchounwou. Eur. J. Pharmacol. 2014, 740, 364-378.
  103. V. Cepeda, M. A. Fuertes, J. Castilla, C. Alonso, C. Quevedo, J. M. Perez. Anticancer
  104. Agents Med. Chem. 2007, 7(1), 3-18.
  105. D. S. Alberts. Semin. Oncol. 1990, 17(4 Suppl 7), 6-8.

Source

Indexing and Abstracting

  • 1
  • 2
  • 3
  • 4
  • 5
Google Scholar Url for the Journal is not available