Citation: Shan-ji FAN, Jia-chi XU, Ze-cheng HU, Ying CUI, Yu-xing TAN, Wu-jiu JIANG. Syntheses, Antitumor Activity and DNA Interaction of p-Chlorine-Benzyltin Complexes Based on Acylhydrazone Ligand[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(4): 684-692. doi: 10.11862/CJIC.2021.083 shu

Syntheses, Antitumor Activity and DNA Interaction of p-Chlorine-Benzyltin Complexes Based on Acylhydrazone Ligand

1.
Department of Thyroid Breast Surgery, The First Affiliated Hospital of University of South China
2.
College of Chemistry and Materials Science, Hengyang Normal University

Corresponding author: Shan-ji FAN, Firear333@hotmail.com
Received Date: 29 October 2020
Revised Date: 1 May 2021

Figures(9)

Two p-chlorobenzyltin complexes have been synthesized via the reaction of p-methyl benzoyl hydrazide-benzoyl formic acid or benzoyl hydrazide-benzoyl formic acid with di-p-chlorobenzyltin dichloride. The complexes C1 and C2 have been characterized by IR, ¹H NMR, ¹³C NMR, ¹¹⁹Sn NMR spectra, elemental analysis and HRMS, and the crystal structures have been determined by X-ray diffraction. The thermogravimetric of the complexes C1 and C2 were analyzed, and in vitro antitumor activities of both complexes were evaluated by MTT(3-(4, 5-dimethyl-thiazole-2)-2, 5-diphenyltetrazolium bromide) against three human cancer cell lines(NCI-H460, Hep G2 and MCF7).It was found that complex C2 showed a good inhibitory effect on cancer cells NCI-H460, HepG2, MCF7. The interaction of complex C2 with DNA was investigated using electronic absorption spectroscopy, fluorescence quench, and viscosity measurement. It was found that the complex could bind to DNA through an intercalation mode. CCDC: 2039991, C1; 2039990, C2.
- organotin complex,
- synthesis,
- crystal structure,
- antitumor activities,
- DNA
1. [1]
  Dasari S, Bernard Tchounwou P. Eur. J. Pharmacol. , 2014, 740: 364-378 doi: 10.1016/j.ejphar.2014.07.025
2. [2]
  Amable L. Pharmacol. Res. , 2016, 106: 27-36 doi: 10.1016/j.phrs.2016.01.001
3. [3]
  Köberle B, Tomicic M T, Usanova S, Kaina B. Biochim. Biophys. Acta Rev. Cancer, 2010, 1806(2): 172-182 doi: 10.1016/j.bbcan.2010.07.004
4. [4]
  Shahid F, Farooqui Z, Khan F. Eur. J. Pharmacol. , 2018, 827: 49-57 doi: 10.1016/j.ejphar.2018.03.009
5. [5]
  Karasawa T, Steyger P S. Toxicol. Lett. , 2015, 237(3): 219-227 doi: 10.1016/j.toxlet.2015.06.012
6. [6]
  Jiang W J, Fan S J, Zhou Q, Zhang F X, Kuang D Z, Tan Y X. Bioorg. Chem. , 2020, 94: 103402 doi: 10.1016/j.bioorg.2019.103402
7. [7]
  LUO B, YU H T, LIU M Q, ZHANG F X, KUANG D Z, TAN Y X, JIANG W J. Chinese J. Inorg. Chem. , 2019, 35(7): 1212-1220
8. [8]
  LIU J, LI Z Q, YI Y Y, ZHONG Y X, YU H T, TAN Y X, JIANG W J. Chinese J. Inorg. Chem. , 2019, 35(12): 2200-2208
9. [9]
  JIANG W J, TAN Y X, KUANG D Z, ZHANG F X, LIU M Q. SCIENTIA SINICA Chimica, 2019, 49(8): 1083-1093
10. [10]
  Armarego W L F, Chai C L L. Purification of Laboratory Chemicals. 6th ed. Oxford: Elsevier, 2009.
11. [11]
  Sheldrick G M. SHELXL-97, a Program for Crystal Structure Refinement. University of Göttingen, Germany, 1997.
12. [12]
  Jiang W J, Mo T Z, Zhang F X, Kuang D Z, Tan Y X. Chin. J. Struct. Chem. , 2020, 39(4): 673-681
13. [13]
  Salam M A, Hussein M A, Ramli I, SaifulIslam M. J. Organomet. Chem. , 2016, 813: 71-77 doi: 10.1016/j.jorganchem.2016.04.007
14. [14]
  Jiang W J, Zhou Q, Liu M Q, Zhang F X, Kuang D Z, Tan Y X. Appl. Organomet. Chem. , 2019, 33(9): e5092
15. [15]
  Zhang Z J, Zeng H T, Liu Y, Kuang D Z, Zhang F X, Tan Y X, Jiang W J. Inorg. Nano-Met. Chem. , 2018, 48(10): 486-494 doi: 10.1080/24701556.2019.1571513
16. [16]
  Pretsch E, Bühlmann P, Badertscher M. Structure Determination of Organic Compounds. 4th ed. Berlin Heidelberg: Springer-Verlag, 2009 .
17. [17]
  JIANG W J, TAN Y X, YU J X, ZHU X M, ZHANG F X, KUANG D Z. Chinese J. Inorg. Chem. , 2016, 32(8): 1383-1390
18. [18]
  Tan Y X, Zhang Z J, Tan Y H, Kuang D Z, Yu J X, Zhu X M, Jiang W J. J. Coord. Chem. , 2017, 70(15): 2606-2624 doi: 10.1080/00958972.2017.1355460
19. [19]
  Nath M, Saini P K. Dalton Trans. , 2011, 40(27): 7077-7121 doi: 10.1039/c0dt01426e
20. [20]
  Pyle A M, Rehmann J P, Meshoyrer R, Kumar C V, Turro N J, Barton J K. J. Am. Chem. Soc. , 1989, 111(8): 3051-3058 doi: 10.1021/ja00190a046
21. [21]
  Yao G Y, Ye M Y, Huang R Z, Li Y J, Pan Y M, Xu Q, Liao Z X, Wang H S. Bioorg. Med. Chem. Lett. , 2014, 24(2): 501-507 doi: 10.1016/j.bmcl.2013.12.030
22. [22]
  Liu K, Yan H, Chang G L, Li Z, Niu M J, Hong M. Inorg. Chim. Acta, 2017, 464: 137-146 doi: 10.1016/j.ica.2017.05.017
23. [23]
  Yan C Q, Zhang J L, Liang T G, Li Q S. Biomed. Pharmacother. , 2015, 71: 119-127 doi: 10.1016/j.biopha.2015.02.027
24. [24]
  Ganji N, Rambabu A, Vamsikrishna N, Daravath S, Shivaraj. J. Mol. Struct. , 2018, 1173: 173-182
25. [25]
  Tan C P, Liu J, Chen L M, Shi S, Ji L N. J. Inorg. Biochem. , 2008, 102(8): 1644-1653
26. [26]
  Zhao Y, Li Z, Li H H, Wang S N, Niu M J. Inorg. Chim. Acta, 2018, 482: 136-143
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沈阳化工大学材料科学与工程学院沈阳 110142