Citation: Jia-Chi XU, Ze-Cheng HU, Ying CUI, Wu-Jiu JIANG, Yu-Xing TAN, Shan-Ji FAN. Syntheses, Crystal Structures and Inhibitory Activity against MCF-7, NCI-H460 and HepG2 Cancer Cells of the Di-2, 4-dichlorobenzyltin Thiophene-2-carbohydrazone Complexes[J]. Chinese Journal of Structural Chemistry, ;2021, 40(6): 827-835. doi: 10.14102/j.cnki.0254–5861.2011–3007 shu

Syntheses, Crystal Structures and Inhibitory Activity against MCF-7, NCI-H460 and HepG2 Cancer Cells of the Di-2, 4-dichlorobenzyltin Thiophene-2-carbohydrazone Complexes

a.
Department of Thyroid Breast Surgery, The First Affiliated Hospital of University South China, Hengyang 421001, China
b.
Hengyang Normal University, Hengyang 421008, China

Corresponding author: Shan-Ji FAN, firear333@hotmail.com
Received Date: 25 October 2020
Accepted Date: 7 January 2021

Fund Project: the Natural Science Foundation of Hunan Province 2020JJ8096

Figures(6)

Di-2, 4-dichlorobenzyltin-2-(2-(thiophen-2-formyl)hydrazono)-propanoic carboxylate complex Ⅰ {[C₄H₃S(O)C=N-N=C(CH₃)COO]₂[(2, 4-Cl₂-C₆H₃CH₂)₂Sn]₂(CH₃OH)₂} and di-2, 4-dichlorobenzyltin-2-(2-(thiophen-2-formyl)hydrazono)-3-phenylpropanoic carboxylate complex Ⅱ {[C₄H₃S(O)C=N-N=C(PhCH₂)COO](2, 4-Cl₂-C₆H₃CH₂)₂Sn}_n were synthesized and characterized by IR, ¹H, ¹³C and ¹¹⁹Sn NMR spectra, HRMS, elemental analysis and thermal stability analysis, and the crystal structures were determined by X-ray diffraction. The crystal of complex Ⅰ belongs to monoclinic system, space group P2₁/n with a = 11.987(3), b = 35.359(9), c = 12.982(3) Å, β = 103.028(5)°, Z = 4, V = 5361(2) Å³, D_c = 1. 688 Mg·m^–3, μ(MoKα) = 1.463 mm^–1, F(000) = 2704, R = 0.0572 and wR = 0.1423. The crystal of complex Ⅱ is of monoclinic system, space group P2₁/n with a = 15.5758(17), b = 9.6020(10), c = 19.599(2) Å, β = 98.886(2)°, Z = 4, V = 2896.0(5) Å³, D_c = 1.663 Mg·m^–3, μ(MoKα) = 1.357 mm^–1, F(000) = 1440, R = 0.0341 and wR = 0.0936. In vitro antitumor activities of both complexes were evaluated by MTT against three human cancer cell lines (MCF7, NCI-H460 and HepG2), and they all exhibited good antitumor activity. The interaction between complexes and calf thymus DNA was studied by UV-vis and fluorescence spectroscopy, it indicated intercalation as probable mode of interaction.
- diorganotin,
- carboxylate,
- synthesis,
- crystal structure,
- biological activity
1. [1]
  Dasari, S.; Bernard, T. P. Cisplatin in cancer therapy: molecular mechanisms of action. Eur. J. Pharmacol. 2014, 740, 364−378. doi: 10.1016/j.ejphar.2014.07.025
2. [2]
  van den Berg, J. H.; Beijnen, J. H.; Balm, A. J. M.; Schellens, J. H. M. Future opportunities in preventing cisplatin induced ototoxicity. Cancer Treat. Rev. 2006, 32, 390−397. doi: 10.1016/j.ctrv.2006.04.011
3. [3]
  Shahid, F.; Farooqui, Z.; Khan, F. Cisplatin-induced gastrointestinal toxicity: an update on possible mechanisms and on available gastroprotective strategies. Eur. J. Pharmacol. 2018, 827, 49−57. doi: 10.1016/j.ejphar.2018.03.009
4. [4]
  Rajeswaran, A.; Trojan, A.; Burnand, B.; Giannelli, M. Efficacy and side effects of cisplatin- and carboplatin-based doublet chemotherapeutic regimens versus non-platinum-based doublet chemotherapeutic regimens as first line treatment of metastatic non-small cell lung carcinoma: a systematic review of randomized controlled trials. Lung Cancer-J. Iaslc 2008, 59, 1−11. doi: 10.1016/j.lungcan.2007.07.012
5. [5]
  Milosavljevic, N.; Duranton, C.; Djerbi, N.; Puech, P. H.; Gounon, P.; Lagadic-Gossmann, D.; Dimanche-Boitrel, M. T.; Rauch, C.; Tauc, M.; Counillon, L.; Poët, M. Nongenomic effects of cisplatin: acute inhibition of mechanosensitive transporters and channels without actin remodeling. Cancer Res. 2010, 70, 7514−7522. doi: 10.1158/0008-5472.CAN-10-1253
6. [6]
  Levi, J. A.; Aroney, R. S.; Dalley, D. N. Haemolytic anaemia after cisplatin treatment. Br. Med. J. 1981, 282, 2003−2004. doi: 10.1136/bmj.282.6281.2003
7. [7]
  Karasawa, T.; Steyger, P. S. An integrated view of cisplatin-induced nephrotoxicity and ototoxicity. Toxicol. Lett. 2015, 237, 219−227. doi: 10.1016/j.toxlet.2015.06.012
8. [8]
  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
9. [9]
  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.
10. [10]
  Jiang, W.; Fan, S.; Zhou, Q.; Zhang, F.; Kuang, D.; Tan, Y. 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, 103402. doi: 10.1016/j.bioorg.2019.103402
11. [11]
  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.
12. [12]
  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.
13. [13]
  Sheldrick, G. M. SHELXL-97, A Program for Crystal Structure Refinement. Germany Geöttingen: University of Geöttingen 1997.
14. [14]
  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
15. [15]
  Wu, Q.; Yin, H.; Yue, C.; Zhang, X.; Hong, M.; Cui, J. Synthesis, crystal structure, and bioactivity of two triphenylantimony derivatives with benzohydroxamic acid and N-phenylbenzohydroxamic acid. J. Coord. Chem. 2012, 65, 2098−2109. doi: 10.1080/00958972.2012.688118
16. [16]
  Yin, H.; Liu, H.; Hong, M. Synthesis, structural characterization and DNA-binding properties of organotin(Ⅳ) complexes based on Schiff base ligands derived from 2-hydroxy-1-naphthaldy and 3- or 4-aminobenzoic acid. J. Organomet. Chem. 2012, 713, 11−19. doi: 10.1016/j.jorganchem.2012.03.027
17. [17]
  Yan, C.; Zhang, J.; Liang, T.; Li, Q. 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
18. [18]
  Tan, Y. X.; Zhang, Z. J.; Feng, Y. L.; Yu, J. X.; Zhu, X. M.; Zhang, F. X.; Kuang, D. Z.; Jiang, W. J. Syntheses, crystal structures and biological activity of the 1D chain benzyltin complexes based on 2-oxo-propionic acid benzoyl hydrazone. J. Inorg. Organomet. P 2017, 27, 342−352. doi: 10.1007/s10904-016-0477-5
19. [19]
  Tan, Y. X.; Zhang, Z. J.; Liu, Y.; Yu, J. X.; Zhu, X. M.; Kuang, D. Z.; Jiang, W. J. Synthesis, crystal structure and biological activity of the Schiff base organotin(Ⅳ) complexes based on salicylaldehyde-o-aminophenol. J. Mol. Struct. 2017, 1149, 874−881. doi: 10.1016/j.molstruc.2017.08.058
20. [20]
  Pretsch, E.; Bühlmann, P.; Badertscher, M. Structure Determination of Organic Compounds. Fourth ed. Berlin Heidelberg: Springer-Verlag 2009, p69−242.
21. [21]
  Basu Baul, T. S.; Addepalli, M. R.; Lyčka, A.; van Terwingen, S.; Englert, U. Synthesis, characterization and structural systematics in diorganotin complexes with O, N, O′-tris-chelating semirigid diaza-scaffolds: mono- vs. di-nuclear compounds. J. Organomet. Chem. 2020, 927, 121522−11. doi: 10.1016/j.jorganchem.2020.121522
22. [22]
  Zhang, Z. J.; Zeng, H. T.; Liu, Y.; Kuang, D. Z.; Zhang, F. X.; Tan, Y. X.; Jiang, W. J. Synthesis, crystal structure and anticancer activity of the dibutyltin(Ⅳ) oxide complexes containing substituted salicylaldehyde-o-aminophenol Schiff base with appended donor functionality. Inorg. Nano-Met. Chem. 2018, 48, 486−494. doi: 10.1080/24701556.2019.1571513
23. [23]
  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.
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