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Research Articles

In vitro DNA binding, pBR322 cleavage and molecular docking studies of 1,2-diaminobenzene, dichloro glycyl glycinate tin(IV) and zirconium(IV) complexes

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Pages 11484-11494 | Received 14 Nov 2020, Accepted 19 Jul 2021, Published online: 05 Aug 2021

References

  • Al-Asbahy, W. M., & Manal, S. (2021). Synthesis and characterization of copper-based anticancer compound; in vitro interaction studies with DNA/HSA, SOD mimetic, cytotoxic activity and molecular docking investigation. Journal of Biomolecular Structure and Dynamics, 39(4), 1431–1446. https://doi.org/10.1080/07391102.2020.1733663
  • Al-Asbahy, W. M., Usman, M., Arjmand, F., Manal, S., & Tabassum, S. (2016). A dinuclear copper (II) complex with piperazine bridge ligand as a potential anticancer agent: DFT computation and biological evaluation. Inorganica Chimica Acta, 445, 167–178. https://doi.org/10.1016/j.ica.2016.02.046
  • Arjmand, F., & Jamsheera, A. (2011). Synthesis, characterization and in vitro DNA binding studies of tin(IV) complexes of tert-butyl 1-(2-hydroxy-1-phenylethylamino)-3-methyl-1-oxobutan-2-yl carbamate. Journal of Organometallic Chemistry, 696(22), 3572–3579. https://doi.org/10.1016/j.jorganchem.2011.08.009
  • Arno, L., & Jessica, L. B. (2014). Viscosity measurements of DNA solution with and without condensing agents. Biorheology, 51(1), 15–28. https://doi.org/10.3233/BIR–140649
  • Barton, J. K., Danishefsky, A. T., & Goldberg, J. M. (1984). Tris(phenanthroline)ruthenium(II): Stereoselectivity in binding to DNA. Journal of the American Chemical Society, 106(7), 2172–2176. https://doi.org/10.1021/ja00319a043
  • Blackburn, G. M., & Gait, M. J. (1996). Nucleic Acids in chemistry and biology (2nd ed., pp. 329). Oxford University Press.
  • Blower, P. J. (2004). Inorganic pharmaceuticals. Annual Report Sect. A, 100, 633–658. https://doi.org/10.1039/B312109G
  • Chauhan, M., Banerjee, K., & Arjmand, F. (2007). DNA binding studies of novel copper(II) complexes containing L-tryptophan as chiral auxiliary: In vitro antitumor activity of Cu–Sn2 complex in human neuroblastoma cells. Inorganic Chemistry, 46(8), 3072–3082. https://doi.org/10.1021/ic061753a
  • Chikira, M. (2008). DNA–fiber EPR spectroscopy as a tool to study DNA–metal complex interactions: DNA binding of hydrated Cu(II) ions and Cu(II) complexes of amino acids and peptides. Journal of Inorganic Biochemistry, 102(5–6), 1016–1024. https://doi.org/10.1016/j.jinorgbio.2008.01.019
  • Crowe, A. J. (1989). The antitumour activity of tin compounds. In M. Gielen (Ed.), Metal-based antitumour drugs (Vol. 1, pp. 103). Freund.
  • Crowe, A. J., & Fricker, S. P. (Eds.). (1994). Metal compounds in cancer therapy (pp. 147). Chapman and Hall.
  • De Castro, L. F. P., & Zacharias, M. (2002). DAPI binding to the DNA minor groove: A continuum solvent analysis. Journal of Molecular Recognition: JMR, 15(4), 209–220. https://doi.org/10.1002/jmr.581
  • Dehand, J., Jordanov, J., Keck, F., Mosset, A., Bonnet, J. J., & Galy, J. (1979). Synthesis, crystal structure, and electronic properties of (L-methionylglycinato)copper(II). Inorganic Chemistry, 18(6), 1543–1549. https://doi.org/10.1021/ic50196a031
  • de Sousa, G. F., Deflon, V. M., Gambardella, M. T. d P., Francisco, R. H. P., Ardisson, J. D., & Niquet, E. (2006). X-ray crystallographic and Mössbauer spectroscopic applications in dependence of partial quadrupole splitting, [R], on the C–Sn–C angle in seven-coordinated diorganotin(IV) complexes . Inorganic Chemistry, 45(11), 4518–4525. https://doi.org/10.1021/ic0516360
  • Gielen, M. (1995). Tin-based antitumour drugs: new developments. Metal-Based Drugs, 2(2), 99–103. https://doi.org/10.1007/978-94-011-5780-3˗27 https://doi.org/10.1155/MBD.1995.99
  • Grover, N., Gupta, N., Singh, P., & Thorp, H. H. (1992). Studies of electrocatalytic DNA cleavage by oxoruthenium(IV). X-ray crystal structure of [Ru(tpy)(tmen)OH2](ClO4)2 (tmen = N,N,N′,N′-tetramethylethylenediamine, tpy = 2,2′,2″-–terpyridine. Inorganic Chemistry, 31(11), 2014–2020. https://doi.org/10.1021/ic00037a008
  • Farukh, A., Iymtiaz, Y., Yusra, Z., & Loic, T. (2015). Crystal structure determination, spectroscopic characterization and biological profile of a tailored ionic molecular entity, Sn(iv) iminodiacetic acid–piperazinediium conjugate: In vitro DNA/RNA binding studies, Topo I inhibition activity, cytotoxic and systemic toxicity studies. (2015). RSC Advance, 5, 16250–16264. https://doi.org/10.1039/C4RA13718C
  • Healy, E. F. (2007). Quantitative determination of DNA–ligand binding using fluorescence spectroscopy. Journal of Chemical Education, 84(8), 1304–1307. https://doi.org/10.1021/ed084p1304
  • Hong, M., Yin, H., Zhang, X., Li, C., Yue, C., & Cheng, S. (2013). Di- and tri-organotin(IV) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone: Synthesis, characterization and in vitro antitumor activities. Journal of Organometallic Chemistry, 724, 23–31. https://doi.org/10.1016/j.jorganchem.2012.10.031
  • Indumathy, R., Radhika, S., Kanthimathi, M., Weyhermuller, T., & Nair, B. U. (2007). Cobalt complexes of terpyridine ligand: Crystal structure and photocleavage of DNA. Journal of Inorganic Biochemistry, 101(3), 434–443. https://doi.org/10.1016/j.jinorgbio.2006.11.002
  • Karidi, K., Garoufis, A., Hadjiliadis, N., Lutz, M., Spek, A. L., & Reedijk, J. (2006). Synthesis, characterization, and DNA-binding studies of nitro(oligopyridine)ruthenium(II) complexes. Inorganic Chemistry, 45(25), 10282–10292. https://doi.org/10.1021/ic0608039
  • Kelland, L. (2007). The resurgence of platinum-based cancer chemotherapy. Nature Reviews. Cancer, 7(8), 573–584. https://doi.org/10.1038/nrc2167
  • Kostova, I., & Momekov, G. (2006). New zirconium (IV) complexes of coumarins with cytotoxic activity. European Journal of Medicinal Chemistry, 41(6), 717–726. https://doi.org/10.1016/j.ejmech.2006.03.020
  • Krishna, P. M., Reddy, K. H., Krishna, P. G., & Phillip, G. H. (2007). DNA interactions of mixed ligand copper(II) complexes with sulphur containing ligands. Indian Journal of Chemistry, 46, 904–908.
  • Lepecq, J.-B., & Paoletti, C. (1967). A fluorescent complex between ethidium bromide and nucleic acids. Physical–chemical characterization. Journal of Molecular Biology, 27(1), 87–106. https://doi.org/10.1016/0022-2836(67)90353-1
  • Manessi-Zoupa, E., Perlepes, S. P., Hondrellis, V., & Tsangaris, J. M. (1994). Transition metal complexes of N-(2-benzamide)pyridine-2′-carboxamide, a potentially tridentate ligand containing one secondary and one primary amide group: Preparation and characterization in the solid state. Journal of Inorganic Biochemistry, 55(3), 217–233. https://doi.org/10.1016/0162-0134(94)85022-4
  • Nebojša, Đ. P., Bojana, B. Z., Bojan, B., Biljana, D., Nebojša, R. B., Ludger, A. W., & Goran, N. K. (2020). Synthesis, characterization and in vitro biological evaluation of novel organotin(IV) compounds with derivatives of 2-(5-arylidene-2,4-dioxothiazolidin-3-yl)propanoic acid. Journal of Inorganic Biochemistry, 211, 111207. https://doi.org/10.1016/j.jinorgbio.2020.111207
  • Pettinari, C., Caruso, F., Zaffaroni, N., Villa, R., Marchetti, F., Pettinari, R., Phillips, C., Tanski, J., & Rossi, M. J. (2006). Synthesis, spectroscopy (IR, multinuclear NMR, ESI–MS), diffraction, density functional study and in vitro antiproliferative activity of pyrazole-beta-diketone dihalotin(IV) compounds on 5 melanoma cell lines. Journal of Inorganic Biochemistry, 100(1), 58–69. https://doi.org/10.1016/j.jinorgbio.2005.10.002
  • Pettinari, C., Marchetti, F., Pettinari, R., Martini, D., Drozdov, A., & Troyanov, S. (2001). Synthesis and characterisation of tin(IV) and organotin(IV) derivatives 2-{[(2-hydroxyphenyl)imino]methyl}phenol. Inorganica Chimica Acta, 325(1–2), 103–114. https://doi.org/10.1016/S0020-1693(01)00654-5
  • Reedijk, J. (1996). Improved understanding in platinum antitumor chemistry. Chemical Communications, 7, 801–806. https://doi.org/10.1039/cc9960000801
  • Reinhardt, C. G., & Krugh, T. R. (1978). A comparative study of ethidium bromide complexes with dinucleotides and DNA: Direct evidence for intercalation and nucleic acid sequence preferences. Biochemistry, 17(23), 4845–4854. https://doi.org/10.1021/bi00616a001
  • Rosser, C. J. (2013). Targeting prostatic tumor microenvironment to address therapy resistance. Translation Cancer Research, 2, 62–63. https://doi.org/10.3978/j.issn.2218-676X.2013.04.07
  • Roy, B., Tang, C., Alam, M. P., & Hecht, S. M. (2014). DNA methylation reduces binding and cleavage by bleomycin. Biochemistry, 53(38), 6103–6112. https://doi.org/10.1021/bi5010848
  • Sangeetha, G. K. R., Mathew, B. B., Sudhamani, C. N., & Naik, B. H. S. (2014). Mechanism of DNA binding and cleavage. Biomedicine and Biotechnology, 2(1), 1–9. https://doi.org/10.12691/bb-2-1-1.
  • Soliman, A. A. (2006). Spectral and thermal study of the ternary complexes of nickel with sulfasalazine and some amino acids. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 65(5), 1180–1185. https://doi.org/10.1016/j.saa.2006.01.035
  • Tabassum, S., Al-Asbahy, W. M., Afzal, M., Arjmand, F., & Bagchi, V. (2012). Molecular drug design, synthesis and structure elucidation of a new specific target peptide based metallo drug for cancer chemotherapy as topoisomerase I inhibitor. Dalton Transactions (Cambridge, England: 2003), 41(16), 4955–4965. https://doi.org/10.1039/c2dt12044e
  • Tabassum, S., Al-Asbahy, W. M., Arjmand, F., & Afzal, M. (2012). Synthesis, characterization and interaction studies of copper based drug with human serum albumin (HSA): Spectroscopic and molecular docking investigations . Journal of Photochemistry and Photobiology. B, Biology, 114, 132–139. https://doi.org/10.1016/j.jphotobiol.2012.05.021
  • Tan, L.-F., Chao, H., Zhen, K.-C., Fei, J.-J., Wang, F., Zhou, Y.-F., & Ji, L.-N. (2007). Effects of the ancillary ligands of polypyridyl ruthenium(II) complexes on the DNA-binding and photocleavage behaviors. Polyhedron, 26(18), 5458–5468. https://doi.org/10.1016/j.poly.2007.08.025
  • Tiliakos, M., Katsoulakou, E., Nastopoulos, V., Terzis, A., Raptopoulou, C., Cordopatis, P., & Manessi-Zoupa, E. (2003). Dipeptides containing the α-aminoisobutyric residue (Aib) as ligands: Preparation, spectroscopic studies and crystal structures of copper(II) complexes with H–Aib–X–OH (X = Gly, l-Leu, l-Phe). Journal of Inorganic Biochemistry, 93(3–4), 109–118. https://doi.org/10.1016/S0162-0134(02)00560-3
  • Trotta, E., Del Grosso, N., Erba, M., & Paci, M. (2000). The ATT strand of AAT.ATT trinucleotide repeats adopts stable hairpin structures induced by minor groove binding ligands. Biochemistry, 39(23), 6799–6808. https://doi.org/10.1021/bi0001473
  • van Rijt, S. H., & Sadler, P. J. (2009). Current applications and future potential for bioinorganic chemistry in the development of anticancer drugs. Drug Discovery Today, 14(23–24), 1089–1097. https://doi.org/10.1016/j.drudis.2009.09.003
  • Waddhaah, M. A., Sabah, A. A. E., & Manal, S. (2018). Design, synthesis andcharacterizationof tin-based cancer chemotherapy drug entity: In vitro DNA binding, cleavage, induction ofcancer cell apoptosis by triggering DNA damage-mediated p53 phosphorylation andmolecular docking. Applied Organometallic Chemistry, e4651, 1–14. https://doi.org/10.1002/aoc.4651
  • Wilson, W. D., Ratmeyer, L., Zhao, M., Strekowski, L., & Boykin, D. (1993). The search for structure-specific nucleic acid-interactive drugs: Effects of compound structure on RNA versus DNA interaction strength. Biochemistry, 32 (15), 4098–4104. https://doi.org/10.1021/bi00066a035
  • Wittung, P., Nielsen, P., & Norden, B. (1996). Direct observation of strand invasion by peptide nucleic acid (PNA) into double-stranded DNA. Journal of the American Chemical Society, 118(30), 7049–7054. https://doi.org/10.1021/ja960521f
  • Wolfe, A., Shimer, G. H., & Meehan, T. (1987). Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry, 26(20), 6392–6396. https://doi.org/10.1021/bi00394a013
  • Xu, H., Zheng, K., Chen, Y., Li, Y. Z., Lin, L. J., Li, H., Zhang, P. X., & Ji, L. N. (2003). Effects of ligand planarity on the interaction of polypyridyl Ru(II) complexes with DNA. Dalton Transactions, 11, 2260–2268. https://doi.org/10.1039/b300353a
  • Yang, C. T., Moubaraki, B., Murray, K. S., & Vittal, J. J. (2003). Synthesis, characterization and properties of ternary copper(ii) complexes containing reduced Schiff base N-(2-hydroxybenzyl)-α-amino acids and 1,10-phenanthroline. Dalton Transactions, 5(5), 880–889. https://doi.org/10.1039/b211496h
  • Yin, H. D., Wang, Q. B., & Xue, S. C. (2004). Synthesis and structural characterization of diorganotin(IV) esters of salicylidene-amino acids. Journal of Organometallic Chemistry, 689(15), 2480–2485. https://doi.org/10.1016/j.jorganchem.2004.05.004
  • Yousuf, I., Usman, M., Ahmad, M., Tabassum, S., & Arjmand, F. (2018). Single X-ray crystal structure, DFT studies and topoisomerase I inhibition activity of a tailored ionic Ag(I) nalidixic acid-piperazinium drug entity specific for pancreatic cancer cells. New Journal of Chemistry, 42(1), 506–519. https://doi.org/10.1039/C7NJ03602G

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