Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2017 (2017), Article ID 4736321, 6 pages
https://doi.org/10.1155/2017/4736321
Research Article

Influence of the Number of Axial Bexarotene Ligands on the Cytotoxicity of Pt(IV) Analogs of Oxaliplatin

1Department of Medicinal Chemistry and Fine Organic Synthesis, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia
2Blokhin Cancer Research Center, 24 Kashirskoye Shosse, Moscow 115478, Russia
3Institute for Energy Problems of Chemical Physics, Russian Academy of Sciences, Leninsky Pr. 38, Bld.2, Moscow 119334, Russia
4I.M. Sechenov First Moscow State Medical University, Moscow, Russia
5Faculty of Chemistry, Institute of Inorganic Chemistry, University of Vienna, Waehringer Str. 42, 1019 Vienna, Austria

Correspondence should be addressed to Alexey A. Nazarov; moc.em@vorazan.yexela

Received 5 April 2017; Revised 4 June 2017; Accepted 8 June 2017; Published 19 July 2017

Academic Editor: Giovanni Natile

Copyright © 2017 Yulia N. Nosova et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. B. Rosenberg, L. van Camp, and T. Krigas, “Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode,” Nature, vol. 205, no. 4972, pp. 698-699, 1965. View at Publisher · View at Google Scholar · View at Scopus
  2. M. A. Whiteside, C. J. Piyathilake, T. M. Bushell, and G. L. Johanning, “Intrinsic cisplatin resistance in lung and ovarian cancer cells propagating in medium acutely depleted of folate,” Nutrition and Cancer, vol. 54, no. 2, pp. 274–284, 2006. View at Publisher · View at Google Scholar · View at Scopus
  3. Z. H. Siddik, “Cisplatin: mode of cytotoxic action and molecular basis of resistance,” Oncogene, vol. 22, no. 47, pp. 7265–7279, 2003. View at Publisher · View at Google Scholar · View at Scopus
  4. A.-M. Florea and D. Büsselberg, “Cisplatin as an anti-tumor drug: cellular mechanisms of activity, drug resistance and induced side effects,” Cancers, vol. 3, no. 1, pp. 1351–1371, 2011. View at Publisher · View at Google Scholar · View at Scopus
  5. A. S. Abu-Surrah and M. Kettunen, “Platinum group antitumor chemistry: design and development of new anticancer drugs complementary to cisplatin,” Current Medicinal Chemistry, vol. 13, no. 11, pp. 1337–1357, 2006. View at Publisher · View at Google Scholar · View at Scopus
  6. M. J. Hannon, Pure and Applied Chemistry, vol. 79, no. 12, pp. 2243–2261, 2009.
  7. J. J. Wilson and S. J. Lippard, “Synthesis, characterization, and cytotoxicity of platinum(IV) carbamate complexes,” Inorganic Chemistry, vol. 50, no. 7, pp. 3103–3115, 2011. View at Publisher · View at Google Scholar · View at Scopus
  8. J. J. Wilson and S. J. Lippard, “Synthetic methods for the preparation of platinum anticancer complexes,” Chemical Reviews, vol. 114, no. 8, pp. 4470–4495, 2014. View at Publisher · View at Google Scholar · View at Scopus
  9. N. J. Wheate, S. Walker, G. E. Craig, and R. Oun, “The status of platinum anticancer drugs in the clinic and in clinical trials,” Dalton Transactions, vol. 39, no. 35, pp. 8113–8127, 2010. View at Publisher · View at Google Scholar · View at Scopus
  10. G. Doshi, G. Sonpavde, and C. N. Sternberg, “Clinical and pharmacokinetic evaluation of satraplatin,” Expert Opinion on Drug Metabolism and Toxicology, vol. 8, no. 1, pp. 103–111, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. D. Gibson, “Platinum(IV) anticancer prodrugs-hypotheses and facts,” Dalton Transactions, vol. 45, no. 33, pp. 12983–12991, 2016. View at Publisher · View at Google Scholar · View at Scopus
  12. S. Dhar, Z. Liu, J. Thomale, H. Dai, and S. J. Lippard, “Targeted single-wall carbon nanotube-mediated Pt(IV) prodrug delivery using folate as a homing device,” Journal of the American Chemical Society, vol. 130, no. 34, pp. 11467–11476, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. K. R. Barnes, A. Kutikov, and S. J. Lippard, “Synthesis, characterization, and cytotoxicity of a series of estrogen-tethered platinum(IV) complexes,” Chemistry and Biology, vol. 11, no. 4, pp. 557–564, 2004. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Mukhopadhyay, C. M. Barnés, A. Haskel, S. M. Short, K. R. Barnes, and S. J. Lippard, “Conjugated platinum(IV)-peptide complexes for targeting angiogenic tumor vasculature,” Bioconjugate Chemistry, vol. 19, no. 1, pp. 39–49, 2008. View at Publisher · View at Google Scholar · View at Scopus
  15. H. A. Wee, I. Khalaila, C. S. Allardyce, L. Juillerat-Jeanneret, and P. J. Dyson, “Rational design of platinum(IV) compounds to overcome glutathione-S-transferase mediated drug resistance,” Journal of the American Chemical Society, vol. 127, no. 5, pp. 1382-1383, 2005. View at Publisher · View at Google Scholar · View at Scopus
  16. J. Zajac, H. Kostrhunova, V. Novohradsky et al., “Potentiation of mitochondrial dysfunction in tumor cells by conjugates of metabolic modulator dichloroacetate with a Pt(IV) derivative of oxaliplatin,” Journal of Inorganic Biochemistry, vol. 156, pp. 89–97, 2016. View at Publisher · View at Google Scholar · View at Scopus
  17. E. Wexselblatt, R. Raveendran, S. Salameh, A. Friedman-Ezra, E. Yavin, and D. Gibson, “On the stability of Pt(IV) pro-drugs with haloacetato ligands in the axial positions,” Chemistry (Weinheim an der Bergstrasse, Germany), vol. 21, no. 7, pp. 3108–3114, 2015. View at Publisher · View at Google Scholar · View at Scopus
  18. T. C. Johnstone, N. Kulak, E. M. Pridgen, O. C. Farokhzad, R. Langer, and S. J. Lippard, “Nanoparticle encapsulation of mitaplatin and the effect thereof on in vivo properties,” ACS Nano, vol. 7, no. 7, pp. 5675–5683, 2013. View at Publisher · View at Google Scholar · View at Scopus
  19. J. Yang, X. Sun, W. Mao, M. Sui, J. Tang, and Y. Shen, “Conjugate of Pt(IV)-histone deacetylase inhibitor as a prodrug for cancer chemotherapy,” Molecular Pharmaceutics, vol. 9, no. 10, pp. 2793–2800, 2012. View at Publisher · View at Google Scholar · View at Scopus
  20. M. Alessio, I. Zanellato, I. Bonarrigo, E. Gabano, M. Ravera, and D. Osella, “Antiproliferative activity of Pt(IV)-bis(carboxylato) conjugates on malignant pleural mesothelioma cells,” Journal of Inorganic Biochemistry, vol. 129, pp. 52–57, 2013. View at Publisher · View at Google Scholar · View at Scopus
  21. V. Novohradsky, L. Zerzankova, J. Stepankova et al., “Antitumor platinum(IV) derivatives of oxaliplatin with axial valproato ligands,” Journal of Inorganic Biochemistry, vol. 140, pp. 72–79, 2014. View at Publisher · View at Google Scholar · View at Scopus
  22. Q. Cheng, H. Shi, H. Wang, Y. Min, J. Wang, and Y. Liu, “The ligation of aspirin to cisplatin demonstrates significant synergistic effects on tumor cells,” Chemical Communications, vol. 50, no. 56, pp. 7427–7430, 2014. View at Publisher · View at Google Scholar · View at Scopus
  23. W. Neumann, B. C. Crews, L. J. Marnett, and E. Hey-Hawkins, “Conjugates of cisplatin and cyclooxygenase inhibitors as potent antitumor agents overcoming cisplatin resistance,” ChemMedChem, vol. 9, no. 6, pp. 1150–1153, 2014. View at Publisher · View at Google Scholar · View at Scopus
  24. W. Neumann, B. C. Crews, M. B. Sárosi et al., “Conjugation of cisplatin analogues and cyclooxygenase inhibitors to overcome cisplatin resistance,” ChemMedChem, vol. 10, no. 1, pp. 183–192, 2015. View at Publisher · View at Google Scholar · View at Scopus
  25. Y. N. Nosova, L. S. Foteeva, I. V. Zenin et al., “Enhancing the Cytotoxic Activity of Anticancer PtIV Complexes by Introduction of Lonidamine as an Axial Ligand,” European Journal of Inorganic Chemistry, vol. 12, pp. 1785–1791, 2017. View at Publisher · View at Google Scholar · View at Scopus
  26. L. Ma, R. Ma, Y. Wang et al., “Chalcoplatin, a dual-targeting and p53 activator-containing anticancer platinum,” Chemical Communications, vol. 51, no. 29, pp. 6301–6304, 2015. View at Publisher · View at Google Scholar
  27. L. Qi, Y. Guo, P. Zhang, X. Cao, and Y. Luan, “Preventive and therapeutic effects of the retinoid x receptor agonist bexarotene on tumors,” Current Drug Metabolism, vol. 17, no. 2, pp. 118–128, 2016. View at Publisher · View at Google Scholar · View at Scopus
  28. M. Duvic, A. G. Martin, Y. Kim et al., Archives of Dermatology, vol. 137, no. 5, pp. 581–593, 2001.
  29. W. Kempf, N. Kettelhack, M. Duvic, and G. Burg, “Topical and systemic retinoid therapy for cutaneous T-cell lymphoma,” Hematology/Oncology Clinics of North America, vol. 17, no. 6, pp. 1405–1419, 2003. View at Publisher · View at Google Scholar · View at Scopus
  30. Y. N. Nosova, D. S. Karlov, S. A. Pisarev, I. A. Shutkov et al., “New highly cytotoxic organic and organometallic bexarotene derivatives,” Journal of Organometallic Chemistry, vol. 839, pp. 91–97, 2017. View at Publisher · View at Google Scholar
  31. G. M. Cruise, C. G. Harris, and M. J. Constant, “Polymers including active agents for occlusion of vascular sites and cavities within the body,” US20150306227A1, 2015.
  32. B. Moreau, M. T. Bilodeau, K. Whalen et al., “Platinum compounds, compositions for Cancer therapy,” WO2015200250A1, 2015.
  33. C. E. Wagner, P. W. Jurutka, P. A. Marshall et al., “Modeling, synthesis and biological evaluation of potential Retinoid X Receptor (RXR) selective agonists: Novel analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene),” Journal of Medicinal Chemistry, vol. 52, no. 19, pp. 5950–5966, 2009. View at Publisher · View at Google Scholar · View at Scopus
  34. U. Jungwirth, D. N. Xanthos, J. Gojo et al., “Anticancer activity of methyl-substituted oxaliplatin analogs,” Molecular Pharmacology, vol. 81, no. 5, pp. 719–728, 2012. View at Publisher · View at Google Scholar · View at Scopus
  35. H. Xiao, D. Zhou, S. Liu et al., Macromolecular Bioscience, vol. 3, pp. 367–373, 2012.
  36. M. R. Reithofer, S. M. Valiahdi, M. A. Jakupec et al., “Novel di- and tetracarboxylatoplatinum(IV) complexes. Synthesis, Characterization, cytotoxic activity, and DNA platination,” Journal of Medicinal Chemistry, vol. 50, no. 26, pp. 6692–6699, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. J. Banfić, A. A. Legin, M. A. Jakupec, M. Galanski, and B. K. Keppler, “Platinum(IV) complexes featuring one or two axial ferrocene bearing ligands - Synthesis, characterization, and cytotoxicity,” European Journal of Inorganic Chemistry, vol. 3, pp. 484–492, 2014. View at Publisher · View at Google Scholar · View at Scopus
  38. S. G. Awuah, Y.-R. Zheng, P. M. Bruno, M. T. Hemann, and S. J. Lippard, “A Pt(IV) Pro-drug Preferentially Targets Indoleamine-2,3-dioxygenase, Providing Enhanced Ovarian Cancer Immuno-Chemotherapy,” Journal of the American Chemical Society, vol. 137, no. 47, pp. 14854–14857, 2015. View at Publisher · View at Google Scholar · View at Scopus