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Research Article

Synthesis and spectroscopic characterization study of new palladium complexes containing bioactive O,O-chelated ligands: evaluation of the DNA/protein BSA interaction, in vitro antitumoural activity and molecular docking

, , , &
Pages 3324-3340 | Received 07 Jul 2017, Accepted 28 Sep 2017, Published online: 30 Oct 2017

References

  • Abedi, A., Mehri-Lighvan, Z., Yasan, M., & Amani, V. (2017). Novel Cu (II) complexes of bithiazole: Structure and biological study. Journal of the Iranian Chemical Society, 14(2), 491–502.10.1007/s13738-016-0997-5
  • Angeles-Boza, A. M., Bradley, P. M., Fu, P. K.-L., Wicke, S. E., Bacsa, J., Dunbar, K. R., & Turro, C. (2004). DNA binding and photocleavage in vitro by new dirhodium (II) dppz complexes: Correlation to cytotoxicity and photocytotoxicity. Inorganic Chemistry, 43(26), 8510–8519.10.1021/ic049091h
  • Arman, P., & Wain, R. L. (1958). Studies upon the copper fungicides. Annals of Applied Biology, 46(3), 366–374.10.1111/aab.1958.46.issue-3
  • Beck, W. M., Calabrese, J. C., & Kottmair, N. D. (1979). Palladium (II) and platinum (II) complexes with nucleobases and nucleosides. Crystal structure of trans-bis (adeninato) bis (tri-n-butylphosphine) palladium (II). Inorganic Chemistry, 18(1), 176–182.10.1021/ic50191a037
  • Bincoletto, C., Tersariol, I. L. S., Oliveira, C. R., Dreher, S., Fausto, D. M., Soufen, M. A., & … Caires, A. C. F. (2005). Chiral cyclopalladated complexes derived from N, N-dimethyl-1-phenethylamine with bridging bis (diphenylphosphine) ferrocene ligand as inhibitors of the cathepsin B activity and as antitumoral agents. Bioorganic & Medicinal Chemistry, 13(8), 3047–3055.10.1016/j.bmc.2005.01.057
  • Boulikas, T., & Vougiouka, M. (2003). Cisplatin and platinum drugs at the molecular level (Review). Oncology Reports, 10(6), 1663–1682.
  • Bruijnincx, P. C. A., & Sadler, P. J. (2008). New trends for metal complexes with anticancer activity. Current Opinion in Chemical Biology, 12(2), 197–206.10.1016/j.cbpa.2007.11.013
  • Burin, A. L., Armbruster, M. E., Hariharan, M., & Lewis, F. D. (2009). Sum rules and determination of exciton coupling using absorption and circular dichroism spectra of biological polymers. Proceedings of the National Academy of Sciences, 106(4), 989–994.10.1073/pnas.0808513106
  • Chan, H.-L., Liu, H.-Q., Tzeng, B.-C., You, Y.-S., Peng, S.-M., Yang, M., & Che, C.-M. (2002). Syntheses of ruthenium (II) quinonediimine complexes of cyclam and characterization of their DNA-binding activities and cytotoxicity. Inorganic Chemistry, 41(12), 3161–3171.10.1021/ic0112802
  • Chang, Y.-M., Chen, C. K.-M., & Hou, M.-H. (2012). Conformational changes in DNA upon ligand binding monitored by circular dichroism. International Journal of Molecular Sciences, 13(3), 3394–3413.10.3390/ijms13033394
  • Chen, L.-M., Liu, J., Chen, J.-C., Shi, S., Tan, C.-P., Zheng, K.-C., & Ji, L.-N. (2008). Experimental and theoretical studies on the DNA-binding and spectral properties of water-soluble complex [Ru (MeIm) 4 (dpq)] 2+. Journal of Molecular Structure, 881(1), 156–166.10.1016/j.molstruc.2007.09.010
  • Darwish, S. M., Teir, M. M. A., Makharza, S. A., & Abu-hadid, M. M. (2010). Spectroscopic investigations of pentobarbital interaction with human serum albumin. Journal of Molecular Structure, 963(2), 122–129.10.1016/j.molstruc.2009.10.023
  • Das, N. K., Pawar, L., Kumar, N., & Mukherjee, S. (2015). Quenching interaction of BSA with DTAB is dynamic in nature: A spectroscopic insight. Chemical Physics Letters, 635, 50–55.10.1016/j.cplett.2015.06.033
  • Dash, S. P., Panda, A. K., Pasayat, S., Majumder, S., Biswas, A., Kaminsky, W., & … Dinda, R. (2015). Evaluation of the cell cytotoxicity and DNA/BSA binding and cleavage activity of some dioxidovanadium (V) complexes containing aroylhydrazones. Journal of Inorganic Biochemistry, 144, 1–12.
  • de Souza, R. F. V., Sussuchi, E. M., & De Giovani, W. F. (2003). Synthesis, electrochemical, spectral, and antioxidant properties of complexes of flavonoids with metal ions. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33(7), 1125–1144.10.1081/SIM-120023482
  • Dehghan, G., & Khoshkam, Z. (2012). Tin (II)–quercetin complex: Synthesis, spectral characterisation and antioxidant activity. Food Chemistry, 131(2), 422–426.10.1016/j.foodchem.2011.08.074
  • Dekermendjian, K., Kahnberg, P., Witt, M.-R., Sterner, O., Nielsen, M., & Liljefors, T. (1999). Structure − Activity relationships and molecular modeling analysis of flavonoids binding to the benzodiazepine site of the rat brain GABAA receptor complex. Journal of Medicinal Chemistry, 42(21), 4343–4350.10.1021/jm991010 h
  • Efthimiadou, E. K., Katsaros, N., Karaliota, A., & Psomas, G. (2007). Mononuclear copper (II) complexes with quinolones and nitrogen-donor heterocyclic ligands: Synthesis, characterization, biological activity and interaction with DNA. Inorganica Chimica Acta, 360(15), 4093–4102.10.1016/j.ica.2007.05.042
  • Erdem, A., Kerman, K., Meric, B., & Ozsoz, M. (2001). Methylene blue as a novel electrochemical hybridization indicator. Electroanalysis, 13(3), 219–223.10.1002/(ISSN)1521-4109
  • Felsenfeld, G., & Hirschman, S. Z. (1965). Determination of DNA composition and concentration by spectral analysis. Journal of Molecular Biology, 13, 409–419.
  • Ferguson, P. J., Kurowska, E. M., Freeman, D. J., Chambers, A. F., & Koropatnick, J. (2006). In vivo inhibition of growth of human tumor lines by flavonoid fractions from cranberry extract. Nutrition and Cancer, 56(1), 86–94.10.1207/s15327914nc5601_12
  • Fernandez, M. T., Mira, M. L., Florencio, M. H., & Jennings, K. R. (2002). Iron and copper chelation by flavonoids: An electrospray mass spectrometry study. Journal of Inorganic Biochemistry, 92(2), 105–111.10.1016/S0162-0134(02)00511-1
  • Ferrer, E. G., Salinas, M. V., Correa, M. J., Naso, L., Barrio, D. A., Etcheverry, S. B., & … Williams, P. A. M. (2006). Synthesis, characterization, antitumoral and osteogenic activities of quercetin vanadyl (IV) complexes. JBIC Journal of Biological Inorganic Chemistry, 11(6), 791–801.10.1007/s00775-006-0122-9
  • Friebolin, W., Schilling, G., Zöller, M., & Amtmann, E. (2005). Antitumoral activity of non-platinum xanthate complexes. Journal of Medicinal Chemistry, 48(25), 7925–7931.10.1021/jm040899 l
  • Friedmann, T., & Brown, D. M. (1978). Base-specific reactions useful for DNA sequencing: Methylene blue–sensitized photooxidation of guanine and osmium tetraoxide modification of thymine. Nucleic Acids Research, 5(2), 615–622.10.1093/nar/5.2.615
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., … Petersson, G. A. (2009). The molecular orbital calculation was carried out using the Gaussian 09, Revision B. 01. Wallingford CT: Gaussian.
  • Gonzalez, J. M., & Saiz-Jimenez, C. (2005). A simple fluorimetric method for the estimation of DNA–DNA relatedness between closely related microorganisms by thermal denaturation temperatures. Extremophiles, 9(1), 75–79.10.1007/s00792-004-0417-0
  • Gonzalez, M. L., Tercero, J. M., Matilla, A., Niclós-Gutiérrez, J., Fernández, M. T., López, M. C., & … González, S. (1997). Cis-dichloro (α, ω-diamino carboxylate ethyl ester) palladium (II) as palladium (II) versus platinum (II) model anticancer drugs: Synthesis, solution equilibria of their aqua, hydroxo, and/or chloro species, and in vitro/in vivo DNA-binding properties. Inorganic Chemistry, 36(9), 1806–1812.10.1021/ic961226z
  • Hartinger, C. G., & Dyson, P. J. (2009). Bioorganometallic chemistry – From teaching paradigms to medicinal applications. Chemical Society Reviews, 38(2), 391–401.10.1039/B707077 M
  • Havsteen, B. (1983). Flavonoids, a class of natural products of high pharmacological potency. Biochemical Pharmacology, 32(7), 1141–1148.10.1016/0006-2952(83)90262-9
  • He, Y., Wang, Y., Tang, L., Liu, H., Chen, W., Zheng, Z., & Zou, G. (2008). Binding of puerarin to human serum albumin: A spectroscopic analysis and molecular docking. Journal of Fluorescence, 18(2), 433–442.10.1007/s10895-007-0283-0
  • Heng, M. P., Sinniah, S. K., Teoh, W. Y., Sim, K. S., Ng, S. W., Cheah, Y. K., & Tan, K. W. (2015). Synthesis of a DNA-targeting nickel (II) complex with testosterone thiosemicarbazone which exhibits selective cytotoxicity towards human prostate cancer cells (LNCaP). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 150, 360–372.10.1016/j.saa.2015.05.095
  • Hetényi, C., & van der Spoel, D. (2002). Efficient docking of peptides to proteins without prior knowledge of the binding site. Protein Science, 11(7), 1729–1737.
  • Hetényi, C., & van der Spoel, D. (2006). Blind docking of drug-sized compounds to proteins with up to a thousand residues. FEBS Letters, 580(5), 1447–1450.10.1016/j.febslet.2006.01.074
  • Hickey, J. L., Ruhayel, R. A., Barnard, P. J., Baker, M. V., Berners-Price, S. J., & Filipovska, A. (2008). Mitochondria-targeted chemotherapeutics: The rational design of gold (I) N-heterocyclic carbene complexes that are selectively toxic to cancer cells and target protein selenols in preference to thiols. Journal of the American Chemical Society, 130(38), 12570–12571.10.1021/ja804027j
  • Huq, F., Tayyem, H., Beale, P., & Yu, J. Q. (2007). Studies on the activity of three palladium (II) compounds of the form: Trans-PdL 2 Cl 2 where L=2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine. Journal of Inorganic Biochemistry, 101(1), 30–35.10.1016/j.jinorgbio.2006.08.001
  • Ji, L.-N., Zou, X.-H., & Liu, J.-G. (2001). Shape-and enantioselective interaction of Ru (II)/Co (III) polypyridyl complexes with DNA. Coordination Chemistry Reviews, 216, 513–536.10.1016/S0010-8545(01)00338-1
  • Joyeux, M., & Buyukdagli, S. (2005). Dynamical model based on finite stacking enthalpies for homogeneous and inhomogeneous DNA thermal denaturation. Physical Review E, 72(5), 51902.10.1103/PhysRevE.72.051902
  • Kaluđerović, G. N., Hernández-Corroto, E., Brandt, W., Zmejkovski, B. B., & Gómez-Ruiz, S. (2016). Palladium (II) complexes with R2edda-derived ligands. Journal of Coordination Chemistry, 69(8), 1337–1345.
  • Kamal, A., Ramu, R., Tekumalla, V., Khanna, G. B. R., Barkume, M. S., Juvekar, A. S., & Zingde, S. M. (2007). Synthesis, DNA binding, and cytotoxicity studies of pyrrolo [2, 1-c][1, 4] benzodiazepine-anthraquinone conjugates. Bioorganic & Medicinal Chemistry, 15(22), 6868–6875.10.1016/j.bmc.2007.08.026
  • Kapdi, A. R., & Fairlamb, I. J. S. (2014). Anti-cancer palladium complexes: A focus on PdX 2 L 2, palladacycles and related complexes. Chemical Society Reviews, 43(13), 4751–4777.10.1039/C4CS00063C
  • Karami, K., & Salah, M. M. (2010). Highly efficient orthopalladated complexes of second and third benzyl amine for catalyzing the Suzuki cross-coupling reaction. Applied Organometallic Chemistry, 24(11), 828–832.10.1002/aoc.1713
  • Karami, K., Sadeghi-Aliabadi, H., Lipkowski, J., & Mirian, M. (2013). Dinuclear bridged biphosphinic and mononuclear cyclopalladated complexes of benzylamines: Synthesis, structural characterization and antitumor activity. Polyhedron, 50(1), 187–192.10.1016/j.poly.2012.11.002
  • Karami, K., Hosseini-Kharat, M., Sadeghi-Aliabadi, H., Lipkowski, J., & Mirian, M. (2014). In vitro cytotoxicity studies of palladacyclic complexes containing the symmetric diphosphine bridging ligand. Studies of their interactions with DNA and BSA. European Journal of Medicinal Chemistry, 73, 8–17.10.1016/j.ejmech.2013.11.042
  • Karami, K., Lighvan, Z. M., Barzani, S. A., Faal, A. Y., Poshteh-Shirani, M., Khayamian, T., & … Dušek, M. (2015). Design and synthesis of a novel trinuclear palladium (ii) complex containing an oxime chelate ligand: Determining the interaction mechanism with the DNA groove and BSA site I by spectroscopic and molecular dynamics simulation approaches. New Journal of Chemistry, 39(11), 8708–8719.10.1039/C5NJ01280E
  • Karami, K., Shirani-Sarmazeh, Z., Hosseini-Kharat, M., Lipkowski, J., & Saeidifar, M. (2015). Synthesis, spectral characterization, crystal structure and in vitro DNA/protein binding studies of phosphorous ylide palladacyclic complexes containing azide group. Journal of Photochemistry and Photobiology B: Biology, 144, 11–19.10.1016/j.jphotobiol.2015.01.012
  • Karami, K., Lighvan, Z. M., Alizadeh, A. M., Poshteh-Shirani, M., Khayamian, T., & Lipkowski, J. (2016). Synthesis of a novel trinuclear palladium complex: The influence of an oxime chelate ligand on biological evaluation towards double-strand DNA, BSA protein and molecular modeling studies. RSC Advances, 6(82), 78424–78435.10.1039/C6RA08744B
  • Karami, K., Lighvan, Z. M., Jahromi, M. D., Lipkowski, J., & Momtazi-borojeni, A. A. (2017). Synthesis, electronic structure and molecular docking of new organometallic palladium (II) complexes with intercalator ligands: The influence of bridged ligands on enhanced DNA/serum protein binding and in vitro antitumoral activity. Journal of Organometallic Chemistry, 827, 1–14.10.1016/j.jorganchem.2016.10.001
  • Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S., & Kumari, N. S. (2006). Synthesis and biological activity of Schiff and Mannich bases bearing 2, 4-dichloro-5-fluorophenyl moiety. Bioorganic & Medicinal Chemistry, 14(22), 7482–7489.10.1016/j.bmc.2006.07.015
  • Koch, A., Tamez, P., Pezzuto, J., & Soejarto, D. (2005). Evaluation of plants used for antimalarial treatment by the Maasai of Kenya. Journal of Ethnopharmacology, 101(1), 95–99.10.1016/j.jep.2005.03.011
  • Kragh-Hansen, U. (1981). Molecular aspects of ligand binding to serum albumin. Pharmacological Reviews, 33(1), 17–53.
  • Lehrer, S. (1971). Solute perturbation of protein fluorescence. Quenching of the tryptophyl fluorescence of model compounds and of lysozyme by iodide ion. Biochemistry, 10(17), 3254–3263.10.1021/bi00793a015
  • Loganathan, R., Ramakrishnan, S., Suresh, E., Riyasdeen, A., Akbarsha, M. A., & Palaniandavar, M. (2012). Mixed ligand copper (II) complexes of N, N-bis (benzimidazol-2-ylmethyl) amine (BBA) with diimine co-ligands: Efficient chemical nuclease and protease activities and cytotoxicity. Inorganic Chemistry, 51(10), 5512–5532.10.1021/ic2017177
  • Mendiguchia, B. S., Aiello, I., & Crispini, A. (2015). Zn (II) and Cu (II) complexes containing bioactive O, O-chelated ligands: Homoleptic and heteroleptic metal-based biomolecules. Dalton Transactions, 44(20), 9321–9334.10.1039/C5DT00817D
  • Middleton, E. Jr. (1998). Effect of plant flavonoids on immune and inflammatory cell function. In John A. Manthey, & Béla S. Buslig (Eds.) Flavonoids in the Living System (pp. 175–182). Berlin: Springer.10.1007/978-1-4615-5335-9
  • Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19(14), 1639–1662.10.1002/(ISSN)1096-987X
  • Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791.10.1002/jcc.v30:16
  • Neyhart, G. A., Grover, N., Smith, S. R., Kalsbeck, W. A., Fairley, T. A., Cory, M., & Thorp, H. H. (1993). Binding and kinetics studies of oxidation of DNA by oxoruthenium (IV). Journal of the American Chemical Society, 115(11), 4423–4428.10.1021/ja00064a001
  • Nori, A., & Kopeček, J. (2005). Intracellular targeting of polymer-bound drugs for cancer chemotherapy. Advanced Drug Delivery Reviews, 57(4), 609–636.10.1016/j.addr.2004.10.006
  • Park, Y. C., Rimbach, G., Saliou, C., Valacchi, G., & Packer, L. (2000). Activity of monomeric, dimeric, and trimeric flavonoids on NO production, TNF-α secretion, and NF-κB-dependent gene expression in RAW 264.7 macrophages. FEBS Letters, 465(2–3), 93–97.10.1016/S0014-5793(99)01735-4
  • Pereira, R., Andrades, N. E. D., Paulino, N., Sawaya, A. C. H. F., Eberlin, M. N., Marcucci, M. C., … Bydlowski, S. P. (2007). Synthesis and characterization of a metal complex containing naringin and Cu, and its antioxidant, antimicrobial, antiinflammatory and tumor cell cytotoxicity. Molecules, 12(7), 1352–1366.10.3390/12071352
  • Peters, T. (1985). Serum albumin. Advances in protein chemistry (Vol. 37). New York: Elsevier.
  • Rajendiran, V., Murali, M., Suresh, E., Palaniandavar, M., Periasamy, V. S., & Akbarsha, M. A. (2008). Non-covalent DNA binding and cytotoxicity of certain mixed-ligand ruthenium (II) complexes of 2, 2′-dipyridylamine and diimines. Dalton Transactions, 16, 2157–2170.10.1039/b715077f
  • Rakad, M., & Jumaily, A. (2010). Evaluation of anticancer activities of crude extracts of Apium graveolens L. Seeds in two cell lines, RD and L20B in vitro. Iraqi Journal of Cancer and Medical Genetics, 3(2), 20–23.
  • Sebastian, M., Ninan, N., & Elias, E. (2012). Nanomedicine and Cancer therapies. Boca Raton, FL: CRC Press.
  • Senthil Raja, D., Bhuvanesh, N. S. P., & Natarajan, K. (2011). Effect of N (4)-phenyl substitution in 2-oxo-1, 2-dihydroquinoline-3-carbaldehyde semicarbazones on the structure, DNA/protein interaction, and antioxidative and cytotoxic activity of Cu (II) complexes. Inorganic Chemistry, 50(24), 12852–12866.10.1021/ic2020308
  • Serment-Guerrero, J., Cano-Sanchez, P., Reyes-Perez, E., Velazquez-Garcia, F., Bravo-Gomez, M. E., & Ruiz-Azuara, L. (2011). Genotoxicity of the copper antineoplastic coordination complexes casiopeinas®. Toxicology in Vitro, 25(7), 1376–1384.10.1016/j.tiv.2011.05.008
  • Shahabadi, N., Kashanian, S., & Purfoulad, M. (2009). DNA interaction studies of a platinum (II) complex, PtCl 2 (NN)(NN=4, 7-dimethyl-1, 10-phenanthroline), using different instrumental methods. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 72(4), 757–761.10.1016/j.saa.2008.11.022
  • Sim, G.-S., Lee, B.-C., Cho, H. S., Lee, J. W., Kim, J.-H., Lee, D.-H., … Oh, K.-W. (2007). Structure activity relationship of antioxidative property of flavonoids and inhibitory effect on matrix metalloproteinase activity in UVA-irradiated human dermal fibroblast. Archives of Pharmacal Research, 30(3), 290–298.10.1007/BF02977608
  • 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), 6726–6735.10.1021/jf070905x
  • Sudlow, G., Birkett, D. J., & Wade, D. N. (1975). The characterization of two specific drug binding sites on human serum albumin. Molecular Pharmacology, 11(6), 824–832.
  • Thompson, M., Williams, C. R., & Elliot, G. E. P. (1976). Stability of flavonoid complexes of copper (II) and flavonoid antioxidant activity. Analytica Chimica Acta, 85(2), 375–381.10.1016/S0003-2670(01)84703-6
  • Tian, Z., Zang, F., Luo, W., Zhao, Z., Wang, Y., Xu, X., & Wang, C. (2015). Spectroscopic study on the interaction between mononaphthalimide spermidine (MINS) and bovine serum albumin (BSA). Journal of Photochemistry and Photobiology B: Biology, 142, 103–109.10.1016/j.jphotobiol.2014.10.013
  • Tolosa, L., Gryczynski, I., Eichhorn, L. R., Dattelbaum, J. D., Castellano, F. N., Rao, G., & Lakowicz, J. R. (1999). Glucose sensor for low-cost lifetime-based sensing using a genetically engineered protein. Analytical Biochemistry, 267(1), 114–120.10.1006/abio.1998.2974
  • Tuite, E. M., & Kelly, J. M. (1993). New trends in photobiology: Photochemical interactions of methylene blue and analogues with DNA and other biological substrates. Journal of Photochemistry and Photobiology B: Biology, 21(2–3), 103–124.10.1016/1011-1344(93)80173-7
  • Ulukaya, E., Ari, F., Dimas, K., Ikitimur, E. I., Guney, E., & Yilmaz, V. T. (2011). Anti-cancer activity of a novel palladium (II) complex on human breast cancer cells in vitro and in vivo. European Journal of Medicinal Chemistry, 46(10), 4957–4963.10.1016/j.ejmech.2011.07.055
  • Vaden, R. M., Gligorich, K. M., Jana, R., Sigman, M. S., & Welm, B. E. (2014). The small molecule C-6 is selectively cytotoxic against breast cancer cells and its biological action is characterized by mitochondrial defects and endoplasmic reticulum stress. Breast Cancer Research, 16, 472.
  • Valentini, A., Conforti, F., Crispini, A., De Martino, A., Condello, R., Stellitano, C., … Bernardini, S. (2009). Synthesis, oxidant properties, and antitumoral effects of a heteroleptic palladium (II) complex of curcumin on human prostate cancer cells. Journal of Medicinal Chemistry, 52(2), 484–491.10.1021/jm801276a
  • Wang, H., Jiang, X., Zhou, L., Cheng, Z., Yin, W., Duan, M., … Jiang, X. (2013). Interaction of NAEn-sn gemini surfactants with bovine serum albumin: A structure–activity probe. Journal of Luminescence, 134, 138–147.10.1016/j.jlumin.2012.08.058
  • Wang, Q., Liu, X., Su, M., Shi, Z., & Sun, H. (2014). Study on the interaction characteristics of dexamethasone sodium phosphate with bovine serum albumin by spectroscopic technique. New Journal of Chemistry, 38(9), 4092–4098.10.1039/C4NJ00327F
  • Wani, W. A., Prashar, S., Shreaz, S., & Gómez-Ruiz, S. (2016). Nanostructured materials functionalized with metal complexes: In search of alternatives for administering anticancer metallodrugs. Coordination Chemistry Reviews, 312, 67–98.10.1016/j.ccr.2016.01.001
  • Wolfe, A., Shimer, G. H., Jr, & Meehan, T. (1987). Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry, 26(20), 6392–6396.10.1021/bi00394a013
  • Xue, F., Xie, C.-Z., Zhang, Y.-W., Qiao, Z., Qiao, X., Xu, J.-Y., & Yan, S.-P. (2012). Two new dicopper (II) complexes with oxamido-bridged ligand: Synthesis, crystal structures, DNA binding/cleavage and BSA binding activity. Journal of Inorganic Biochemistry, 115, 78–86.10.1016/j.jinorgbio.2012.05.018
  • Zhao, Y., & Truhlar, D. G. (2006). A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions. The Journal of Chemical Physics, 125(19), 194101.10.1063/1.2370993
  • Zhou, J., Wang, L., Wang, J., & Tang, N. (2001). Antioxidative and anti-tumour activities of solid quercetin metal (II) complexes. Transition Metal Chemistry, 26(1), 57–63.10.1023/A:1007152927167
  • Zhou, C.-Y., Xi, X.-L., & Yang, P. (2007). Studies on DNA binding to metal complexes of Sal2trien. Biochemistry (Moscow), 72(1), 37–43.10.1134/S000629790701004X
  • Zhu, X., Sun, J., & Hu, Y. (2007). Determination of protein by hydroxypropyl-β-cyclodextrin sensitized fluorescence quenching method with erythrosine sodium as a fluorescence probe. Analytica Chimica Acta, 596(2), 298–302.10.1016/j.aca.2007.06.008
  • Zuco, V., Supino, R., Righetti, S. C., Cleris, L., Marchesi, E., Gambacorti-Passerini, C., & Formelli, F. (2002). Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells. Cancer Letters, 175(1), 17–25.10.1016/S0304-3835(01)00718-2

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