Citation: ZHU Qingwen, YU Haotian, LIU Mengqin, ZHANG Fuxing, KUANG Daizhi, TAN Yuxing, JIANG Wujiu. Syntheses, Crystal Structures and Biological Activity of Binuclear Di-2, 4-dichlorobenzyltin Complexes Based on Arylformylhydrazone Ligand[J]. Chinese Journal of Applied Chemistry, ;2019, 36(12): 1387-1396. doi: 10.11944/j.issn.1000-0518.2019.12.190100 shu

Syntheses, Crystal Structures and Biological Activity of Binuclear Di-2, 4-dichlorobenzyltin Complexes Based on Arylformylhydrazone Ligand

Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Functional Organometallic Materials, University of Hunan Province, College of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: JIANG Wujiu, jwj_china@163.com
Received Date: 12 April 2019
Revised Date: 13 June 2019
Accepted Date: 12 July 2019

Fund Project: Supported by Hunan Provincial College Student Researchful Study and Innovative Experiment Project(No.cx1813), Hunan Provincial Natural Science Foundation of China(No.2017JJ3003), and Hengyang Normal University Discipline Group Construction Project(No.18XKQ01)Hunan Provincial Natural Science Foundation of China 2017JJ3003Hunan Provincial College Student Researchful Study and Innovative Experiment Projec cx1813Hengyang Normal University Discipline Group Construction Project 18XKQ01

Figures(7)

Two di-2, 4-dichlorobenzyltin complexes (C1, C2) have been synthesized from p-methoxybenzoyl hydrazide-2-ketobutyric acid or 2-thiophene hydrazide2-ketobutyric acid with di-2, 4-dichlorobenzyltin dichloride, respectively. The properties and the crystal structures of the complexes C1 and C2 were characterized by Fourier transform infrared spectrometer (FTIR), nuclear magnetic resonance spectroscopy (NMR) and single crystal X-ray diffraction (SCXRD). Two complexes are all binuclear molecules containing a Sn₂O₂ four-membered ring. The central tin atom and the coordination atom form a hepta-coordinationed distorted pentagonal bipyramid configuration. The complexes C1 and C2 are stable under 120℃ in air, and exihibit good inhibitory effects on human non-small cell lung cancer (NCI-H460), human liver hepatocellular carcinoma (HepG2) and human breast adenocarcinoma (MCF-7) cancer cells cancer cells, but complex C1 is slightly better than complex C2. The interaction between two complexes and calf thymus DNA is intercalation, and the effect of complex C1 and DNA is slightly stronger than that of complex C2.
- organotin complex,
- hydrazone,
- crystal structure,
- biological activity
1. [1]
  Shahid F, Farooqui Z, Khan F. Cisplatin-induced Gastrointestinal Toxicity:An Update on Possible Mechanisms and on Available Gastroprotective Strategies[J]. Eur J Pharmacol, 2018,827:49-57. doi: 10.1016/j.ejphar.2018.03.009
2. [2]
  Karasawa T, Steyger P S. An Integrated View of Cisplatin-induced Nephrotoxicity and Ototoxicity[J]. Toxicol Lett, 2015,237(3):219-227. doi: 10.1016/j.toxlet.2015.06.012
3. [3]
  Milosavljevic N, Duranton C, Djerbi N. Nongenomic Effects of Cisplatin:Acute Inhibition of Mechanosensitive Transporters and Channels Without Actin Remodeling[J]. Cancer Res, 2010,70(19):7514-7522. doi: 10.1158/0008-5472.CAN-10-1253
4. [4]
  Cao W, Qi J, Qian K. Structure-activity Relationships of 2-Quinolinecarboxaldehyde Thiosemicarbazone Gallium(Ⅲ) Complexes with Potent and Selective Anticancer Activity[J]. J Inorg Biochem, 2019,191:174-182. doi: 10.1016/j.jinorgbio.2018.11.017
5. [5]
  Zaki M, Hairat S, Aazam E S. Scope of Organometallic Compounds Based on Transition Metal-Arene Systems as Anticancer Agents:Starting from the Classical Paradigm to Targeting Multiple Strategies[J]. RSC Adv, 2019,9(6):3239-3278. doi: 10.1039/C8RA07926A
6. [6]
  Kenny R G, Marmion C J. Toward Multi-targeted Platinum and Ruthenium Drugs-A New Paradigm in Cancer Drug Treatment Regimens[J]. Chem Rev, 2019,119(2):1058-1137.
7. [7]
  Crowe A J, Smith P J, Atassi G. Investigations into the Antitumour Activity of Organotin Compounds. I.Diorganotin Dihalide and Di-pseudohalide Complexes[J]. Chem-Biol Interact, 1980,32(1):171-178.
8. [8]
  Attanzio A, Ippolito M, Girasolo M A. Anti-cancer Activity of Di- and Tri-organotin(Ⅳ) Compounds with D-(+)-Galacturonic Acid on Human Tumor Cells[J]. J Inorg Biochem, 2018,188:102-112. doi: 10.1016/j.jinorgbio.2018.04.006
9. [9]
  Shang X, Meng X, Alegria E C B A. Syntheses, Molecular Structures, Electrochemical Behavior, Theoretical Study, and Antitumor Activities of Organotin(Ⅳ) Complexes Containing 1-(4-Chlorophenyl)-1-cyclopentanecarboxylato Ligands[J]. Inorg Chem, 2011,50(17):8158-8167. doi: 10.1021/ic200635g
10. [10]
  Basu Baul T S, Paul A, Pellerito L. Dibutyltin(Ⅳ) Complexes Containing Arylazobenzoate Ligands:Chemistry, in Vitro Cytotoxic Effects on Human Tumor Cell Lines and Mode of Interaction with Some Enzymes[J]. Invest New Drug, 2011,29(2):285-299. doi: 10.1007/s10637-009-9360-3
11. [11]
  Tan Y X, Zhang Z J, Feng Y L. Syntheses, Crystal Structures and Biological Activity of the 1D Chain Benzyltin Complexes Based on 2-Oxo-Propionic Acid Benzoyl Hydrazone[J]. J Inorg Organomet P, 2017,27(1):342-352. doi: 10.1007/s10904-016-0477-5
12. [12]
  Tan Y, Zhang Z, Tan Y. Syntheses, Crystal Structures and Biological Activity of the Dialkytin Complexes Based on 2-Oxo-3-phenylpropionic Acid Salicyloylhydrazone[J]. J Coord Chem, 2017,70(15):2606-2624. doi: 10.1080/00958972.2017.1355460
13. [13]
  ZHENG Jianhua, LIU Jun, XIAO Yao. Synthesis, Crystal Structure, Thermal Stability and DNA Interaction of the Dibutytin Complex Based on Salicylacylhydrazone[J]. Chinese J Appl Chem, 2015,32(5):562-569.
14. [14]
  ZHANG Zhijian, JIANG Wujiu, LIU Yang. Syntheses, Crystal Structures and Biological Activity of N-(2-Propionic acid)-aroyl Hydrazone Di-p-methylbenzytin Complexes[J]. Chinese J Inorg Chem, 2017,33(9):1603-1610.
15. [15]
  HE Shuiyang, CAO Wenkai, CHEN Junli. Synthesis, Crystal Structure and Antibacterial Activity of Copper(Ⅱ) Complexes with 2-Oxo-Propionic Acid Salicyloyl Hydrazone[J]. Chem J Chinese Univ, 2002,23(6):991-995. doi: 10.3321/j.issn:0251-0790.2002.06.002
16. [16]
  Sisido K, Takeda Y, Kinugawa Z. Direct Synthesis of Organotin Compounds. I.Di- and Tribenzyltin Chlorides[J]. J Am Chem Soc, 1961,83(3):538-541. doi: 10.1021/ja01464a008
17. [17]
  Sheldrick G M. SHELXL-97, A Program for Crystal Structure Refinement[M]. Germany:University of Ge ttingen, 1997.
18. [18]
  García-López M C, Muñoz-Flores B M, Chan-Navarro R. Microwave-Assisted Synthesis, Third-Order Nonlinear Pptical Properties, Voltammetry Cyclic and Theoretical Calculations of Organotin Compounds Bearing Push-Pull Schiff Bases[J]. J Organomet Chem, 2016,806:68-76. doi: 10.1016/j.jorganchem.2016.01.030
19. [19]
  Tian L J, Yao Y Z, Liu Q T. Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3, 5-Dibromosalicylidene)valine[J]. Chinese J Struct Chem, 2016,35(6):849-856.
20. [20]
  Yang Y, Hong M, Xu L. Organotin(Ⅳ) Complexes Derived from Schiff Base N'-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-3-carbohydrazone:Synthesis, in Vitro Cytotoxicities and DNA/BSA Interaction[J]. J Organomet Chem, 2016,804:48-58. doi: 10.1016/j.jorganchem.2015.12.041
21. [21]
  Barba V, Zaragoza J, Höpfl H. Use of Bis-aminoalcohol Benzoquinones and Dihydroxybenzoquinones in the Formation of Mono and Polymeric Structures of Diorganotin(Ⅳ) Derivatives[J]. J Organomet Chem, 2011,696:1949-1956. doi: 10.1016/j.jorganchem.2010.10.040
22. [22]
  Pretsch E, Bühlmann P, Badertscher M. Structure Determination of Organic Compounds[M]. Fourth ed, Berlin Heidelberg:Springer-Verlag, 2009.
23. [23]
  Wagner M, Zobel B, Dietz C. Cyclic Dinuclear Organotin Cations Stabilized by Bulky Substituents[J]. Organometallics, 2015,34:5602-5608. doi: 10.1021/acs.organomet.5b00829
24. [24]
  Tan Y X, Zhang Z J, Feng Y L. Syntheses, Crystal Structures and Biological Activities of the 2-Oxo-butyric Acid Salicylacylhydrazone Dibenzyltin Complexes[J]. Chinese J Struct Chem, 2017,36(6):925-936.
25. [25]
  Yan C, Zhang J, Liang T. Diorganotin(Ⅳ) Complexes with 4-Nitro-N-phthaloyl-glycine:Synthesis, Characterization, Antitumor Activity and DNA-Binding Studies[J]. Biomed Pharmacother, 2015,71:119-127. doi: 10.1016/j.biopha.2015.02.027
26. [26]
  Pyle A M, Rehmann J P, Meshoyrer R. Mixed-ligand Complexes of Ruthenium(Ⅱ):Factors Governing Binding to DNA[J]. J Am Chem Soc, 1989,111(8):3051-3058. doi: 10.1021/ja00190a046
27. [27]
  Liu K, Yan H, Chang G. Organotin(Ⅳ) Complexes Derived from Hydrazone Schiff Base:Synthesis, Crystal Structure, in Vitro Cytotoxicity and DNA/BSA Interactions[J]. Inorg Chim Acta, 2017,464:137-146. doi: 10.1016/j.ica.2017.05.017
28. [28]
  Li S T, Ma Z Y, Liu X. Synthesis, Crystal Structures, DNA/bovine Serum Albumin Binding, DNA Cleavage and Cytotoxicity of Five Mononuclear Zinc(Ⅱ) Complexes[J]. Appl Organomet Chem, 2017,31(11)e3802. doi: 10.1002/aoc.3802
29. [29]
  Ganji N, Rambabu A, Vamsikrishna N. Copper(Ⅱ) Complexes with Isoxazole Schiff Bases:Synthesis, Spectroscopic Investigation, DNA Binding and Nuclease Activities, Antioxidant and Antimicrobial Studies[J]. J Mol Struct, 2018,1173:173-182. doi: 10.1016/j.molstruc.2018.06.100
30. [30]
  Rahban M, Divsalar A, Saboury A A. Nanotoxicity and Spectroscopy Studies of Silver Nanoparticle:Calf Thymus DNA and K562 as Targets[J]. J Phys Chem C, 2010,114(13):5798-5803. doi: 10.1021/jp910656g
31. [31]
  Zhao Y, Li Z, Li H. Synthesis, Crystal Structure, DNA Binding and in Vitro Cytotoxicity Studies of Zn(Ⅱ) Complexes Derived From Amino-Alcohol Schiff-Bases[J]. Inorg Chim Acta, 2018,482:136-143. doi: 10.1016/j.ica.2018.06.008
32. [32]
  Chen Z F, Wei J H, Liu Y C. High Antitumor Activity of 5, 7-Dihalo-8-quinolinolato Cerium Complexes[J]. Eur J Med Chem, 2013,68:454-462. doi: 10.1016/j.ejmech.2013.08.007
33. [33]
  Arjmand F, Sayeed F, Parveen S. In Vitro Binding Studies of Organotin(Ⅳ) Complexes of 1, 2-Bis(1H-benzimidazol-2-yl)ethane-1, 2-diol with CT-DNA and Nucleotides (5'-GMP and 5'-TMP):Effect of the Ancillary Ligand on the Binding Propensity[J]. J Organomet Chem, 2011,696(24):3836-3845. doi: 10.1016/j.jorganchem.2011.08.007
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