References
- Adhireksan, Z., Davey, G. E., Campomanes, P., Groessl, M., Clavel, C. M., Yu, H., … Davey, C. A. (2014). Ligand substitutions between ruthenium-cymene compounds can control protein versus DNA targeting and anticancer activity. Nature Communications, 5(1), 1–5.
- Alessio, E. (2011). Bioinorganic medicinal chemistry. Weinheim: Wiley-VCH Verlag & Co. KGaA.
- Allardyce, C. S., & Dyson, P. J. (2001). Ruthenium in medicine: Current clinical uses and future prospects. Platinum Metal Review, 45(2), 62–69.
- Batchelor, L. K., Păunescu, E., Soudani, M., Scopelliti, R., & Dyson, P. J. (2017). Influence of the linker length on the cytotoxicity of homobinuclear ruthenium(II) and gold(I) complexes. Inorganic Chemistry, 56(16), 9617–9633.
- Battin, E. E., & Brumaghim, J. L. (2009). Antioxidant activity of sulfur and selenium: A review of reactive oxygen species scavenging, glutathione peroxidase, and metal-binding antioxidant mechanisms. Cell Biochemistry and Biophysics, 55(1), 1–23.
- Berndsen, R. H., Weiss, A., Abdul, U. K., Wong, T. J., Meraldi, P., Griffioen, A. W., … Nowak–Sliwinska, P. (2017). Combination of ruthenium (II)-arene complex [Ru(η6-p-cymene)Cl2(pta)]-(RAPTA-C) and the epidermal growth factor receptor inhibitor erlotinib results in efficient angiostatic and antitumor activity. Scientific Reports, 7(1), 1–7.
- Čanović, P., Simović, A. R., Radisavljević, S., Bratsos, I., Demitri, N., Mitrović, M., … Bugarčić, ŽD. (2017). Impact of aromaticity on ́anticancer activity of polypyridyl ruthenium(II) complexes: Synthesis, structure, DNA/protein binding, lipophilicity and anticancer activity. JBIC Journal of Biological Inorganic Chemistry, 22(7), 1007–1028.
- Caruso, F., Monti, E., Matthews, J., Rossi, M., Gariboldi, M. B., Pettinari, C., … Marchetti, F. (2014). Synthesis, characterization, and antitumor activity of water-soluble (arene)ruthenium(II) derivatives of 1,3-dimethyl-4-acylpyrazolon-5-ato ligands. First example of Ru(arene)(ligand) antitumor species involving simultaneous Ru-N7(guanine) bonding and ligand intercalation to DNA. Inorganic Chemistry, 53(7), 3668–3677.
- Cheng, L.‐Y., Fang, M., Bai, A.‐M., Ouyang, Y., & Hu, Y. J. (2017). Insights into the interaction of methotrexate and human serum albumin: A spectroscopic and molecular modeling approach. Luminescence, 32(5), 873–879.
- Clarke, M. J. (2003). Ruthenium metallopharmaceuticals. Coordination Chemistry Reviews, 236(1–2), 209–233.
- Clavel, C. M., Paunescu, E., Nowak-Sliwinska, P., Griffioen, A. W., Scopelliti, R., & Dyson, P. J. (2015). Modulating the anticancer activity of ruthenium (II)-arene complexes. Journal of Medicinal Chemistry, 58(8), 3356–3365.
- Cui, F., Yan, Y., Zhang, Q., Du, J., Yao, X., Qu, G., & Lu, Y. (2009). Characterization of the interaction between 2′-deoxyuridine and human serum albumin. Carbohydrate Research, 344(5), 642–647.
- Cushnie, T. P. T., & Lamb, A. J. (2005). Antimicrobial activity of flavonoids. International Journal of Antimicrobial Agents, 26(5), 343–356.
- Divsalar, A., Bagheri, M. J., Saboury, A. A., Mansoori-Torshizi, H., & Amani, M. (2009). Investigation on the interaction of newly designed anticancer pd(ii) complexes with different aliphatic tails and human serum albumin. The Journal of Physical Chemistry B, 113(42), 14035–14042.
- Dyson, P. J. (2007). Systematic design of a targeted organometallic antitumour drug in pre-clinical development. CHIMIA International Journal for Chemistry, 61(11), 698–703.
- Fonseca, S. F., Lima, D. B., Alves, D., Jacob, R. G., Perin, G., Lenardao, E. J., & Savegnago, L. (2015). Synthesis, characterization and antioxidant activity of organoselenium and organotellurium compound derivatives of chrysin. New Journal of Chemistry, 39(4), 3043–3050.
- Frik, M., Martínez, A., Elie, B. T., Gonzalo, O., Ramírez de Mingo, D., Sanaú, M., … Contel, M. (2014). In vitro and in vivo evaluation of water-soluble iminophosphorane ruthenium(II) compounds. A potential chemotherapeutic agent for triple negative breast cancer. Journal of Medicinal Chemistry, 57(23), 9995–10012.
- Fu, X. B., Liu, D. D., Lin, Y., Hu, W., Mao, Z. W., & Le, X. Y. (2014). Water-soluble DNA minor groove binders as potential chemotherapeutic agents: synthesis, characterization, DNA binding and cleavage, antioxidation, cytotoxicity and HSA interactions. Dalton Transactions, 43(23), 8721–8737.
- Grazul, M., & Budzisz, E. (2009). Biological activity of metal ions complexes of chromones, coumarins and flavones. Coordination Chemistry Reviews, 253(21–22), 2588–2598.
- Guichard, S. M., Else, R., Reid, E., Zeitlin, B., Aird, R., Muir, M., … Jodrell, D. I. (2006). Anti-tumour activity in non-small cell lung cancer models and toxicity profiles for novel ruthenium(II) based organo-metallic compounds. Biochemical Pharmacology, 71(4), 408–415.
- Hall, J. P., Beer, H., Buchner, K., Cardin, D. J., & Cardin, C. J. (2015). The structural effect of methyl substitution on the binding of polypyridyl Ru-dppz complexes to DNA. Organometallics, 34(11), 2481–2486.
- Hartinger, C. G., Jakupec, M. A., Zorbas-Seifried, S., Groessl, M., Egger, A., Berger, W., … Keppler, B. K. (2008). KP1019, a new redox-active anticancer agent preclinical development and results of a clinical phase I study in tumor patients. Chemistry & Biodiversity, 5(10), 2140–2155.
- Hartinger, C. G., Zorbas-Seifried, S., Jakupec, M. A., Kynast, B., Zorbas, H., & Keppler, B. K. (2006). From bench to bedside preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A). Journal of Inorganic Biochemistry, 100(5–6), 891–904.
- He, X. M., & Carter, D. C. (1992). Atomic structure and chemistry of human serum albumin. Nature, 358(6383), 209–214.
- Hosoya, N., & Miyagawa, K. (2014). Targeting DNA damage response in cancer therapy. Cancer Science, 105(4), 370–388.
- Hu, K., Wang, W., Cheng, H., Pan, S., & Ren, J. (2011). Synthesis and cytotoxicity of novel chrysin derivatives. Medicinal Chemistry Research, 20(7), 838–846.
- Janakiram, N. B., Mohammed, A., Ravillah, D., Choi, C. I., Zhang, Y., Desai, D., … Rao, C. V. (2013). Chemopreventive effects of PBI-Se, a selenium-containing analog of PBIT, on AOM-induced aberrant crypt foci in F344 rats. Oncology Reports, 30(2), 952–960.
- Jaouen, G., & Metzler-Nolte, N. (2010). Medicinal organometallic chemistry. Topics in organometallic chemistry (Vol. 32, p. 32). Berlin, Heidelberg: Springer-Verlag.
- Karami, K., Lighvan, Z. M., Farrokhpour, H., Jahromi, M. D., & Momtazi-Borojeni, A. A. (2017). Synthesis and spectroscopic characterization study of new palladium complexes containing bioactive O,O-chelated ligands: Evaluation of the DNA/protein BSA interaction, in vitro antitumoral activity and molecular docking. Journal of Biomolecular Structure and Dynamics. doi:10.1080/07391102.2017.1391125.
- Kelland, L. (2007). The resurgence of platinum-based cancer chemotherapy. Nature Reviews Cancer, 7(8), 573–584.
- Kljun, J., Bratsos, I., Alessio, E., Psomas, G., Repnik, U., Butinar, M., … Ture, I. (2013). New uses for old drugs: Attempts to convert quinolone antibacterials into potential anticancer agents containing ruthenium. Inorganic Chemistry, 52(15), 9039–9052.
- Kubanik, M., Tu, J. K. Y., Sohnel, T., Hejl, M., Jakupec, M. A., Kandioller, W., … Hartinger, C. G. (2015). Expanding on the structural diversity of flavone derived ruthenium II(ƞ6-arene) anticancer agents. Metallodrugs, 1, 24–35.
- Kumar, P., Dasari, S., & Patra, A. K. (2017). Ruthenium(II) complexes of saccharin with dipyridoquinoxaline and dipyridophenazine: Structures, biological interactions and photoinduced DNA damage activity. European Journal of Medicinal Chemistry, 136, 52–62.
- Kurzwernhart, A., Kandioller, W., Bachler, S., Bartel, C., Martic, S., Buczkowska, M., … Hartinger, C. G. (2012a). Structure-activity relationships of targeted RuII(η6-p-cymene) anticancer complexes with flavonol-derived ligands. Journal of Medicinal Chemistry, 55(23), 10512–10522.
- Kurzwernhart, A., Kandioller, W., Bartel, C., Bachler, S., Trondl, R., Mu¨hlgassner, G., … Hartinger, C. G., (2012b). Targeting the DNA-topoisomerase complex in a double-strike approach with a topoisomerase inhibiting moiety and covalent DNA binder. Chemical Communications, 48, 4839–4841.
- Kurzwernhart, A., Kandioller, W., Enyedy, É. A., Novak, M., Jakupec, M. A., Keppler, B. K., & Hartinger, C. G. (2013). Hydroxyflavones vs. 3-hydroxyquinolinones: Structure-activity relationships and stability studies on RuII(arene) anticancer complexes with biologically active ligands. Dalton Transaction, 42(17), 6193–6202.
- Lakowicz, J. R. (2006). Principles of fluorescence spectroscopy, 3rd ed. New York: Springer.
- Lee, S. S., Park, J. M., Kim, D. Y., Jung, J. H., & Cho, M. H. (1995). Multi-podands. Ag(I) complexation with mono- to quadru-podands having sulfur donor. Chemistry Letters, 24(11), 1009–1010.
- Liu, Z. C., Wang, B. D., Li, B., Wang, Q., Yang, Z. Y., Li, T. R., & Li, Y. (2010). Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases. European Journal of Medicinal Chemistry, 45(11), 5353–5361.
- Long, E. C., & Barton, J. K. (1990). On demonstrating DNA intercalation. Accounts of Chemical Research, 23(9), 271–273.
- Marmur, J. (1961). A procedure for the isolation of deoxyribonucleic acid from micro-organisms. Journal of Molecular Biology, 3(2), 208–218.
- Martins, I. L., Miranda, J. P., Oliveira, N. G., Fernandes, A. S., Goncalves, S., & Antunes, A. M. (2013). Synthesis and biological activity of 6-selenocaffeine: potential modulator of chemotherapeutic drugs in breast cancer cells. Molecules, 18(5), 5251–5264.
- Middleton, E., Kandaswami, C., & Theoharides, T. C. (2000). The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacological Reviews, 52(4), 673–751.
- Moradi, Z., Khorasani-Motlagh, M., Rezvani, A. R., & Noroozifar, M. (2018). Evaluation of DNA, BSA binding, and antimicrobialactivity of new synthesized neodymium complex containing 29-dimethyl 110-phenanthroline. Journal of Biomolecular Structure and Dynamics, 36(3), 779–794.
- Mustard, D., & Ritchie, D. W. (2005). Docking essential dynamics Eigen structures. Proteins: Structure, Function, and Bioinformatics, 60(2), 269–274.
- Nazarov, A. A., Hartinger, C. G., & Dyson, P. J. (2014). Opening the lid on piano-stool complexes: An account of ruthenium (II)-arene complexes with medicinal applications. Journal of Organometallic Chemistry, 45(23), 260.
- Nguyen, N., Sharma, A., Nguyen, N., Sharma, A. K., Desai, D., Huh, S. J., … Robertson, G. P. (2011). Melanoma chemoprevention in skin reconstructs and mouse xenografts using isoselenocyanate-4. Cancer Prevention Research (Philadelphia, PA), 4(2), 248–258.
- Noffke, A. L., Habtemariam, A., Pizarro, A. M., & Sadler, P. J. (2012). Designing organometallic compounds for catalysis and therapy. Chemical Communications, 48(43), 5219–5246.
- Norden, B., & Tjerneld, F. (1982). Structure of methylene blue-DNA complexes studied by linear and circular dichroism spectroscopy. Biopolymers, 21(9), 1713–1734.
- Nowak-Sliwinska, P., van Beijnum, J. R., Casini, A., Nazarov, A. A., Wagnieres, G., van den Bergh, H., … Griffioen, A. W. (2011). Organometallic ruthenium(II) arene compounds with antiangiogenic activity. Journal of Medicinal Chemistry, 54(11), 3895–3902.
- Pasternack, R. F., Gibbs, E. J., & Villafranca, J. J. (1983). Interactions of porphyrins with nucleic acids. Biochemistry, 22(10), 2406–2414.
- Păunescu, E., McArthur, S., Soudani, M., Scopelliti, R., & Dyson, P. J. (2016). Nonsteroidal anti-inflammatory-organometallic anticancer compounds. Inorganic Chemistry, 55(4), 1788–1808.
- Pawar, S., Tandel, R., Kunabevu, R., & Jaldappagari, S. (2018). Spectroscopic and computational approaches to unravel the mode of binding between a isoflavone, biochanin-A and calf thymus DNA. Journal of Biomolecular Structure and Dynamics. doi:10.1080/07391102.2018.1442748.
- Pettinari, C., Pettinari, R., Fianchini, M., Marchetti, F., Skelton, B. W., & White, A. H. (2005). Syntheses, structures, and reactivity of new pentamethylcyclopentadienyl-rhodium(III) and -iridium(III) 4-acyl-5-pyrazolonate complexes. Inorganic Chemistry, 44(22), 7933–7942.
- Pichichero, E., Cicconi, R., Mattei, M., & Canini, A. (2011). Chrysin induced apoptosis is mediated through p38 and Bax activation in B16-F1 and A375 melanoma cells. International Journal of Oncology, 38, 473–483.
- Qi, Y., Fu, X., Xiong, Z., Zhang, H., Hill, S. M., Rowan, B. G., & Dong, Y. (2012). Methylseleninic acid enhances paclitaxel efficacy for the treatment of triple-negative breast cancer. PLoS One, 7(2), e31539.
- Rademaker-Lakhai, J. M., Van Den, B., D., Pluim, D., Beijnen, J. H., & Schellens, J. H. M. (2004). A phase I and pharmacological study with imidazolium-trans-DMSO-imidazole-tetrachlororuthenate, a novel ruthenium anticancer agent. Clinical Cancer Research, 10(11), 3717–3727.
- Rahmanto, A. S., & Davies, M. J. (2012). Selenium-containing amino acids as direct and indirect antioxidants. International Union of Biochemistry and Molecular Biology Life, 64(11), 863–871.
- Raja, D. S., Bhuvanesh, N. S. P., & Natarajan, K. (2011). Biological evaluation of a novel water soluble sulphur bridged binuclear copper(II) thiosemicarbazone complex. European Journal of Medicinal Chemistry, 46(9), 4584–4594.
- Rajendiran, V., Karthik, R., Palaniandavar, M., Stoeckli–Evans, H., Periasamy, V. S., Akbarsha, M. A., … Krishnamurthy, H. (2007). Mixed-ligand copper(II)-phenolate complexes: Effect of coligand on enhanced DNA and protein binding, DNA cleavage, and anticancer activity. Inorganic Chemistry, 46(20), 8208–8221.
- Ramachandran, E., Raja, D. S., Bhuvanesh, N. S. P., & Natarajan, K. (2012). Mixed ligand palladium(II) complexes of 6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde 4N-substituted thiosemicarbazones with triphenylphosphine co-ligand: Synthesis, crystal structure and biological properties. Dalton Transactions, 41(43), 13308–13323.
- Raut, K. B., & Wender, S. H. (1960). Synthesis of certain chalcones and 3-hydroxychromones. The Journal of Organic Chemistry, 25(1), 50–52.
- Reedijk, J. (1996). Improved understanding in platinium antitumour chemistry. Chemical Communications, 7, 801–806.
- Rehman, M. U., Tahir, M., Khan, A. Q., Khan, R., Lateef, A., Oday-O-Hamiza, … Sultana, S. (2013). Chrysin suppresses renal carcinogenesis via amelioration of hyperproliferation, oxidative stress and inflammation: plausible role of NF-κB. Toxicology Letters, 216, 146–158.
- Riedl, C. A., Flocke, L. S., Hejl, M., Roller, A., Klose, M. H., Jakupec, M. A., … Keppler, B. K. (2017). Introducing the 4-phenyl-1,2,3-triazole moiety as a versatile scaffold for the development of cytotoxic ruthenium(II) and osmium(II) arene cyclometalates. Inorganic Chemistry, 56 (1), 528–541.
- Sahoo, B. K., Ghosh, K. S., Bera, R., & Dasgupta, S. (2008). Studies on the interaction of diacetylcurcumin with calf thymus-DNA. Chemical Physics, 351(1–3), 163–169.
- Samari, F., Hemmateenejad, B., Shamsipur, M., Rashidi, M., & Samouei, H. (2012). Affinity of two novel five-coordinated anticancer Pt(II) complexes to human and bovine serum albumins: A spectroscopic approach. Inorganic Chemistry, 51(6), 3454–3464.
- Sanmartín, C., Plano, D., & Palop, J. A. (2008). Selenium compounds and apoptotic modulation: A new perspective in cancer therapy. Mini-Reviews in Medicinal Chemistry, 8(10), 1020–1031.
- Sanmartin, C., Plano, D., Sharma, A. K., & Palop, J. A. (2012). Selenium compounds, apoptosis and other types of cell death: An overview for cancer therapy. International Journal of Molecular Sciences, 13(8), 9649–9672.
- Sarkar, B. (1989). Metal-protein interactions in transport, accumulation, and excretion of metals. Biological Trace Element Research, 21(1), 137–144.
- Singh, M., Kaur, M., & Silakari, O. (2014). Flavones: An important scaffold for medicinal chemistry. European Journal of Medicinal Chemistry, 84, 206–239.
- Soares, S., Mateus, N., & de Freitas, V. (2007). Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary α-amylase (HSA) by fluorescence quenching. Journal of Agricultural and Food Chemistry, 55(16), 6726–6735.
- Stephanos, J. J. (1996). Drug-protein interactions: Two-site binding of heterocyclic ligands to a monomeric hemoglobin. Journal of Inorganic Biochemistry, 62(3), 155–169.
- Tanzadehpanah, H., Mahaki, H., Moghadam, N. H., Salehzadeh, S., Rajabi, O., Najafi, R., … Saidijam, M. (2018). Binding site identification of anticancer drug gefitinib to HSA and DNA in the presence of five different probes. Journal of Biomolecular Structure and Dynamics. doi:10.1080/07391102.2018.1441073.
- Wang, F., Habtemariam, A., van der Geer, E. P., Fernandez, R., Melchart, M., Deeth, R. J., … Sadler, P. J. (2005). Controlling ligand substitution reactions of organometallic complexes: Tuning cancer cell cytotoxicity. Proceedings of the National Academy of Sciences of the United States of America, 102(51), 18269–18274.
- Wang, Y., Wang, X., Wang, J., Zhao, Y., He, W., & Guo, Z. (2011). Noncovalent interactions between a trinuclear monofunctional platinum complex and human serum albumin. Inorganic Chemistry, 50(24), 12661–11266.
- Weiss, A., Berndsen, R. H., Dubois, M., Mu¨Ller, C., Schibli, R., Griffioen, A. W., … Nowak-Sliwinska, P. (2014). In vivo anti-tumor activity of the organometallic ruthenium (II)-arene complex [Ru(η6-p-cymene)Cl2(pta)](RAPTA-C) in human ovarian and colorectal carcinomas. Chemical Science, 5(12), 4742–4748.
- Weiss, A., Ding, X., van Beijnum, J. R., Wong, I., Wong, T. J., Berndsen, R. H., … Nowak-Sliwinska, P. (2015). Rapid optimization of drug combinations for the optimal angiostatic treatment of cancer. Angiogenesis, 18(3), 233–244.
- Wheate, N. J., Walker, S., Craig, G. E., & Oun, R. (2010). The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Transactions (Cambridge, England: 2003), 39(35), 8113–8127.
- Wolfe, A., Shimer, G. H., & Meehan, T. (1987). Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry, 26(20), 6392–6396.
- Yamasaki, K., Chuang, V. T. G., Maruyama, T., & Otagiri, M. (2013). Albumin-drug interaction and its clinical implication. Biochimica et Biophysica Acta, 1830(12), 5435–5443.
- Yang, B., Huang, J., Xiang, T., Yin, X., Luo, X., Huang, J., … Ren, G. (2014). Chrysin inhibits metastatic potential of human triple-negative breast cancer cells by modulating matrix metalloproteinase-10, epithelial to mesenchymal transition, and PI3K/Akt signaling pathway. Journal of Applied Toxicology, 34(1), 105–112.
- Zeng, H., Cheng, W. H., & Johnson, L. K. (2013). Methylselenol, aselenium metabolite, modulates p53 pathway and inhibits the growth of colon cancer xenografts in Balb/c mice. Journal of Nutritional Biochemistry, 24(5), 776–780.
- Zhang, Y. Z., Chen, X.-X., Dai, J., Zhang, X.-P., Liu, Y.-X., & Liu, Y. (2008). Spectroscopic studies on the interaction of lanthanum(III) 2‐oxo‐propionic acid salicyloyl hydrazone complex with bovine serum albumin. Luminescence, 23(3), 150–156.
- Zhao, X., Liu, R., Chi, Z., Teng, Y., & Qin, P. (2010). New insights into the behavior of bovine serum albumin adsorbed onto carbon nanotubes: Comprehensive spectroscopic studies. The Journal of Physical Chemistry B, 114(16), 5625–5631.