Design and synthesis of novel organometallic complexes using boronated phenylalanine derivatives as potential anticancer agents

References

• Aihara, T., et al. 2006. First clinical case of boron neutron capture therapy for head and neck malignancies using 18F‐BPA PET. Head & Neck, 28 (9), 850–855.
   PubMed Web of Science ®Google Scholar
• Aisen, P., Enns, C. and Wessling-Resnick, M. 2001. Chemistry and biology of eukaryotic iron metabolism. The International Journal of Biochemistry & Cell Biology, 33 (10), 940–959.
   PubMed Web of Science ®Google Scholar
• Alderden, R.A., Hall, M.D. and Hambley, T.W. 2006. The discovery and development of cisplatin. Journal of Chemical Education, 83 (5), 728.
   Web of Science ®Google Scholar
• Ali, I., et al. 2013. Platinum compounds: a hope for future cancer chemotherapy. Anti-Cancer Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Anti-Cancer Agents), 13 (2), 296–306.
   PubMed Web of Science ®Google Scholar
• Andreini, C., et al. 2008. Metal ions in biological catalysis: from enzyme databases to general principles. JBIC Journal of Biological Inorganic Chemistry, 13 (8), 1205–1218.
   PubMed Web of Science ®Google Scholar
• Bost, F., et al. 1999. The Jun kinase 2 isoform is preferentially required for epidermal growth factor-induced transformation of human A549 lung carcinoma cells. Molecular and Cellular Biology, 19 (3), 1938–1949.
   PubMed Web of Science ®Google Scholar
• Bostancioglu, R.B., et al. 2012. Studies on the cytotoxic, apoptotic and antitumoral effects of Au (III) and Pt (II) complexes of 1, 10-phenanthroline on V79 379A and A549 cell lines. Journal of Enzyme Inhibition and Medicinal Chemistry, 27 (3), 458–466.
   PubMed Web of Science ®Google Scholar
• Carmeliet, P. and Jain, R.K. 2000. Angiogenesis in cancer and other diseases. Nature, 407 (6801), 249–257.
   PubMed Web of Science ®Google Scholar
• Chen, D., et al. 2009. Metal complexes, their cellular targets and potential for cancer therapy. Current Pharmaceutical Design, 15 (7), 777–791.
   PubMed Web of Science ®Google Scholar
• Condeelis, J., Singer, R.H., and Segall, J.E. 2005. The great escape: when cancer cells hijack the genes for chemotaxis and motility. Annual Review of Cell and Developmental Biology, 21, 695–718.
   PubMed Web of Science ®Google Scholar
• Corte-Real, L., et al. 2014. Anticancer activity of structurally related ruthenium(II) cyclopentadienyl complexes. Journal of Biological Inorganic Chemistry, 19 (6), 853–867.
   PubMed Web of Science ®Google Scholar
• Çağır, A., et al. 2017. Evaluation of multifunctional hybrid analogs for stilbenes, chalcones and flavanones. Anti-cancer Agents in Medicinal Chemistry, 17 (14), 1915–1923.
   Web of Science ®Google Scholar
• Dart, A. 2016. Cell migration: caged for protection. Nature Reviews Cancer, 17 (1), 2.
   PubMedGoogle Scholar
• Frezza, M., Schmitt, S., and Ping Dou, Q. 2011. Targeting the ubiquitin-proteasome pathway: an emerging concept in cancer therapy. Current Topics in Medicinal Chemistry, 11 (23), 2888–2905.
   PubMed Web of Science ®Google Scholar
• Gao, E., et al. 2011. Synthesis, characterization, interaction with DNA, and cytotoxic effect in vitro of new mono-and dinuclear Pd (II) and Pt (II) complexes with benzo [d] thiazol-2-amine as the primary ligand. Inorganic Chemistry, 50 (11), 4732–4741.
   PubMed Web of Science ®Google Scholar
• Hanahan, D. and Weinberg, R.A. 2011. Hallmarks of cancer: the next generation. Cell, 144 (5), 646–674.
   PubMed Web of Science ®Google Scholar
• Heber, E.M., et al. 2006. Homogeneous boron targeting of heterogeneous tumors for boron neutron capture therapy (BNCT): chemical analyses in the hamster cheek pouch oral cancer model. Archives of Oral Biology, 51 (10), 922–929.
   PubMed Web of Science ®Google Scholar
• Henriksson, R., et al. 2008. Boron neutron capture therapy (BNCT) for glioblastoma multiforme: a phase II study evaluating a prolonged high-dose of boronophenylalanine (BPA). Radiotherapy and Oncology, 88 (2), 183–191.
   PubMed Web of Science ®Google Scholar
• Keibler, M.A., et al. 2016. Metabolic requirements for cancer cell proliferation. Cancer & Metabolism, 4 (1), 16.
   PubMedGoogle Scholar
• Komeda, S. and Casini, A. 2012. Next-generation anticancer metallodrugs. Current Topics in Medicinal Chemistry, 12 (3), 219–235.
   PubMed Web of Science ®Google Scholar
• Kreja, L. and Seidel, H.-J. 2002. On the cytotoxicity of some microbial volatile organic compounds as studied in the human lung cell line A549. Chemosphere, 49 (1), 105–110.
   PubMed Web of Science ®Google Scholar
• Liu, W. and Gust, R. 2013. Metal N-heterocyclic carbene complexes as potential antitumor metallodrugs. Chemical Society Reviews, 42 (2), 755–773.
   PubMed Web of Science ®Google Scholar
• Miyatake, S.-I., et al. 2016. Boron neutron capture therapy for malignant brain tumors. Neurologia Medico-Chirurgica, 56 (7), 361–371.
   PubMed Web of Science ®Google Scholar
• Mjos, K.D. and Orvig, C. 2014. Metallodrugs in medicinal inorganic chemistry. Chemical Reviews, 114 (8), 4540–4563.
   PubMed Web of Science ®Google Scholar
• Mosmann, T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65 (1), 55–63.
   PubMed Web of Science ®Google Scholar
• Nobili, S., et al. 2010. Gold compounds as anticancer agents: chemistry, cellular pharmacology, and preclinical studies. Medicinal Research Reviews, 30 (3), 550–580.
   PubMed Web of Science ®Google Scholar
• Ouchi, N., et al. 2004. Adiponectin stimulates angiogenesis by promoting cross-talk between AMP-activated protein kinase and Akt signaling in endothelial cells. Journal of Biological Chemistry, 279 (2), 1304–1309.
   PubMed Web of Science ®Google Scholar
• Ronconi, L., et al. 2006. Gold (III) dithiocarbamate derivatives for the treatment of cancer: solution chemistry, DNA binding, and hemolytic properties. Journal of Medicinal Chemistry, 49 (5), 1648–1657.
   PubMed Web of Science ®Google Scholar
• Rosselli, S., et al. 2012. Cytotoxic effect of eudesmanolides isolated from flowers of Tanacetum vulgare ssp. siculum. Molecules, 17 (7), 8186–8195.
   PubMed Web of Science ®Google Scholar
• Rubin, L., et al. 1991. A cell culture model of the blood-brain barrier. The Journal of Cell Biology, 115 (6), 1725–1735.
   PubMed Web of Science ®Google Scholar
• Sahai, E. 2005. Mechanisms of cancer cell invasion. Current Opinion in Genetics & Development, 15 (1), 87–96.
   PubMed Web of Science ®Google Scholar
• Serratrice, M., et al. 2012. Synthesis, structural characterization, solution behavior, and in vitro antiproliferative properties of a series of gold complexes with 2-(2′-pyridyl) benzimidazole as ligand: comparisons of gold (III) versus gold (I) and mononuclear versus binuclear derivatives. Inorganic Chemistry, 51 (5), 3161–3171.
   PubMed Web of Science ®Google Scholar
• Sun, R.W.-Y. 2013. Strategies to improve the anti-cancer properties of gold (III) complexes. Modern Chemistry & Applications, 1 (102), 2.
   Google Scholar
• Varol, M. 2016. The importance of metal-based drugs in medicinal inorganic chemistry to improve life quality of patients. Journal of Applied Pharmacy, 8 (1), 1–2.
   Google Scholar
• Varol, M., et al. 2016. Photoprotective activity of vulpinic and gyrophoric acids toward ultraviolet B‐induced damage in human keratinocytes. Phytotherapy Research, 30 (1), 9–15.
   PubMed Web of Science ®Google Scholar
• Wang, Y., et al. 2015. Metallomic and metalloproteomic strategies in elucidating the molecular mechanisms of metallodrugs. Dalton Transactions, 44 (2), 437–447.
   PubMed Web of Science ®Google Scholar
• Wheate, N.J., et al. 2010. The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Transactions, 39 (35), 8113–8127.
   PubMed Web of Science ®Google Scholar
• Yamaguchi, H., Wyckoff, J., and Condeelis, J. 2005. Cell migration in tumors. Current Opinion in Cell Biology, 17 (5), 559–564.
   PubMed Web of Science ®Google Scholar
• Yokoyama, K., et al. 2006. Pharmacokinetic study of BSH and BPA in simultaneous use for BNCT. Journal of Neuro-oncology, 78 (3), 227–232.
   PubMed Web of Science ®Google Scholar
• Zhao, Y., Butler, E.B., and Tan, M. 2013. Targeting cellular metabolism to improve cancer therapeutics. Cell Death & Disease, 4 (3), e532.
   PubMed Web of Science ®Google Scholar