Syntheses, Crystal Structures, Anticancer Activities and DNA-Binding Properties of the Dibutyltin Complexes Based on Benzoin Aroyl Hydrazone
- Corresponding author: Yu-Xing TAN, tanyuxing@hynu.edu.cn
Citation:
Wu-Jiu JIANG, Yu-Jun TAN, Jia-Tai MAN, Yu-Xing TAN. Syntheses, Crystal Structures, Anticancer Activities and DNA-Binding Properties of the Dibutyltin Complexes Based on Benzoin Aroyl Hydrazone[J]. Chinese Journal of Structural Chemistry,
;2022, 41(2): 220210.
doi:
10.14102/j.cnki.0254-5861.2011-3246
Rosenberg, B.; Vancamp, L.; Trosko, J. E.; Mansour, V. H. Platinum compounds: a new class of potent antitumour agents. Nature 1969, 222, 385−386.
doi: 10.1038/222385a0
Banti, C. N.; Hadjikakou, S. K.; Sismanoglu, T.; Hadjiliadis, N. Anti-proliferative and antitumor activity of organotin(IV) compounds. An overview of the last decade and future perspectives. J. Inorg. Biochem. 2019, 194, 114−152.
doi: 10.1016/j.jinorgbio.2019.02.003
Wang, H.; Hu, L.; Du, W.; Tian, X.; Zhang, Q.; Hu, Z.; Luo, L.; Zhou, H.; Wu, J.; Tian, Y. Two-photon active organotin(IV) carboxylate complexes for visualization of anticancer action. ACS Biomater. Sci. Eng. 2017, 3, 836−842.
doi: 10.1021/acsbiomaterials.6b00786
Caruso, F.; Bol-Schoenmakers, M.; Penninks, A. H. Crystal and molecular structure and in vitro antiproliferative and antitumor activity of two organotin(IV) carbohydrate compounds. J. Med. Chem. 1993, 36, 1168−1174.
doi: 10.1021/jm00061a007
Nath, M.; Saini, P. K. Chemistry and applications of organotin(IV) complexes of Schiff bases. Dalton. Trans. 2011, 40, 7077−7121.
doi: 10.1039/c0dt01426e
Diulus, J. T.; Frederick, R. T.; Li, M.; Hutchison, D. C.; Olsen, M. R.; Lyubinetsky, I.; Árnadóttir, L.; Garfunkel, E. L.; Nyman, M.; Ogasawara, H.; Herman, G. S. Ambient-pressure X-ray photoelectron spectroscopy characterization of radiation-induced chemistries of organotin clusters. Acs Appl. Mater. Interfaces 2019, 11, 2526−2534.
doi: 10.1021/acsami.8b19302
Sharps, M. C.; Frederick, R. T.; Javitz, M. L.; Herman, G. S.; Johnson, D. W.; Hutchison, J. E. Organotin carboxylate reagents for nanopatterning: chemical transformations during direct-write electron beam processes. Chem. Mater. 2019, 31, 4840−4850.
doi: 10.1021/acs.chemmater.9b01440
Chrétien, J. M.; Zammattio, F.; Le Grognec, E.; Paris, M.; Cahingt, B.; Montavon, G.; Quintard, J. P. Polymer-supported organotin reagents for regioselective halogenation of aromatic amines. J. Org. Chem. 2005, 70, 2870−2873.
doi: 10.1021/jo0480141
Jiang, W. J.; Mo, T. Z.; Zhang, F. X.; Kuang, D. Z.; Tan, Y. X. Syntheses, crystal structures and in vitro anticancer activities of dibenzyltin compounds based on the N-(2-phenylacetic acid)-aroyl hydrazone. Chin. J. Struct. Chem. 2020, 39, 673−681.
Jiang, W. J.; Fan, S. J.; Zhou, Q.; Zhang, F. X.; Kuang, D. Z.; Tan, Y. X. Diversity of complexes based on p-nitrobenzoylhydrazide, benzoylformic acid and diorganotin halides or oxides self-assemble: cytotoxicity, the induction of apoptosis in cancer cells and DNA-binding properties. Bioorg. Chem. 2020, 94, 1−12.
Li, Y. X.; Yu, H. T.; Zeng, H. T.; Liu, M. Q.; Kuang, D. Z.; Tan, Y. X.; Jiang, W. J. Two new dibenzyltin complexes based on the 2-oxo-3-phenylpropionic acid arylformylhydrazone: syntheses, crystal structures and biological activity. Chin. J. Struct. Chem. 2019, 38, 1947−1955.
Jiang, W. J.; Tan, Y. X.; Yu, J. X.; Zhu, X. M.; Zhang, F. X.; Kuang, D. Z. Syntheses, crystal structures and biological activity of 2-oxo-3-phenylpropionic acid aroyl hydrazone di-2, 4-dichlorobenzyltin complexes. Chin. J. Inorg. Chem. 2016, 32, 1383−1390.
Sheldrick, G. M. SHELXL-97, A Program for Crystal Structure Refinement. Germany Geöttingen: University of Geöttingen 1997.
Kong, C. F.; Hao, M.; Chen, X.; Zhao, X. M.; Wang, Y. Q.; Li, J.; Gao, Y. Y.; Zhang, H.; Yang, B.; Jiang, J. L. NF-κB inhibition promotes apoptosis in androgen-independent prostate cancer cells by the photothermal effect via the IκBα/AR signaling pathway. Biomater. Sci-uk. 2019, 7, 2559−2570.
doi: 10.1039/C8BM01007B
Li, G.; Wang, Y. X.; Li, L.; Ren, Y. C.; Deng, X.; Liu, J.; Wang, W.; Luo, M. H.; Liu, S. W.; Chen, J. J. Design, synthesis, and bioevaluation of pyrazolo[1, 5-a]pyrimidine derivatives as tubulin polymerization inhibitors targeting the colchicine binding site with potent anticancer activities. Eur. J. Med. Chem. 2020, 202, 1−15.
Luo, G. L.; Ma, Y. X.; Liang, X. T.; Xie, G. Q.; Luo, Y. Q.; Zha, D. L.; Wang, S.; Yu, L. H.; Zheng, X. H.; Wu, W. H.; Zhang, C. Design, synthesis and antitumor evaluation of novel 5-methylpyrazolo[1, 5-a]pyrimidine derivatives as potential c-met inhibitors. Bioorg. Chem. 2020, 104, 1−11.
Baguley, B. C.; Le Bret, M. Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect. Biochemistry-us. 1984, 23, 937−943.
doi: 10.1021/bi00300a022
Pyle, A. M.; Rehmann, J. P.; Meshoyrer, R.; Kumar, C. V.; Turro, N. J.; Barton, J. K. Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA. J. Am. Chem. Soc. 1989, 111, 3051−3058.
doi: 10.1021/ja00190a046
Tan, C. P.; Liu, J.; Chen, L. M.; Shi, S.; Ji, L. N. Synthesis, structural characteristics, DNA binding properties and cytotoxicity studies of a series of Ru(III) complexes. J. Inorg. Biochem. 2008, 102, 1644−1653.
doi: 10.1016/j.jinorgbio.2008.03.005
Jiang, W. J.; Zhou, Q.; Liu, M. Q.; Zhang, F. X.; Kuang, D. Z.; Tan, Y. X. Microwave assisted synthesis of disubstituted benzyltin arylformylhydrazone complexes: anticancer activity and DNA-binding properties. Appl. Organomet. Chem. 2019, 33, e5092.
Pretsch, E.; Bühlmann, P.; Badertscher, M. Structure Determination of Organic Compounds. Fourth ed. Berlin Heidelberg: Springer-Verlag 2009, p69−242.
Yan, C. Q.; Zhang, J. L.; Liang, T. G.; Li, Q. S. Diorganotin (IV) complexes with 4-nitro-N-phthaloyl-glycine: synthesis, characterization, antitumor activity and DNA-binding studies. Biomed. Pharmacother. 2015, 71, 119−127.
doi: 10.1016/j.biopha.2015.02.027
Nath, M.; Kumari, M. R. Microwave-assisted synthesis of mixed ligands organotin(IV) complexes of 1, 10-phenanthroline and l-proline: physicochemical characterization, DFT calculations, chemotherapeutic potential validation by in vitro DNA binding and nuclease activity. J. Photoch. Photobio. B 2017, 174, 182−194.
doi: 10.1016/j.jphotobiol.2017.07.017
Gao, T.; Zhang, W. J.; Wang, F.; Zhang, H. B.; Zhang, W. Application of UV spectra in the interaction of DNA and metal complexes. Guangzhou Chemical Industry 2010, 38, 23−25.
Pu, X. W.; Li, L. Z.; Dong, J. F.; Huang, L.; Bian, L. Synthesis, crystal structure and DNA interaction of a copper(II) complex with ligands of L-phenylalanine Schiff base and 1, 10-phenanthroline. Acta Chim Sinica 2011, 69, 647−652.
Tariq, M.; Ali, S.; Shah, N. A.; Muhammad, N.; Tahir, M. N.; Khalid, N. Catalytic, biological and DNA interaction studies of 3-(4-cyanophenyl)-2-methylacrylate organotin(IV) carboxylates derivatives: synthesis, spectroscopic characterization and X-ray structures. Inorg. Chim. Acta 2013, 405, 444−454.
Iqbal, M.; Karim, A.; Ali, S.; Tahir, M. N.; Sohail, M. Synthesis, characterization, structural elucidation, electrochemistry, DNA binding study, micellization behaviour and antioxidant activity of the Cu(II) carboxylate complexes. Polyhedron 2020, 178, 1−8.
Zhao, Y.; Li, Z.; Li, H. H.; Wang, S.; Niu, M. J. Synthesis, crystal structure, DNA binding and in vitro cytotoxicity studies of Zn(II) complexes derived from amino-alcohol Schiff-bases. Inorg. Chim. Acta 2018, 482, 136−143.
Cai, D. H.; Mo, H. W.; He, L.; Le, X. Y. Crystal structure, DNA binding properties and biological activities of a ternary mixed-ligand copper(II) complex. Chin. J. Inorg. Chem. 2021, 37, 74−84.
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