Citation: SHI Peng-Fei, JIANG Qin, DUAN Hai-Chao, TIAN Yu-Peng. Synthesis, Crystal Structure and Antitumor Ability of a Fluorescent Organotin Compound[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(5): 984-992. doi: 10.11862/CJIC.2014.158 shu

Synthesis, Crystal Structure and Antitumor Ability of a Fluorescent Organotin Compound

1.
1 Department of Chemistry, Huaihai Institute of Technology, Lianyungang, Jiangsu 222005, China;

Received Date: 20 June 2013
Available Online: 5 December 2013
Fund Project: 国家自然科学基金(No.21101069)资助项目。 (No.21101069)

A Schiff base derivate from isonicotinohydrazide and p-N,N-di(2-hydroxyethyl)amino benzaldehyde, together with its organotin complex, have been synthesized and characterized by ¹H NMR spectroscopy, elemental analyses and X-ray crystallography. The planar Schiff base compound coordinated to the tin center in a bidentate mode, with the trans-C=N-conformation changed to be cis in the complex. The crystal data of the complex and the large red shift in the fluorescence spectra demonstrated an extension of the π-conjunction due to the coordination. In vitro cytotoxicity data showed that both compounds were more cytotoxic than cisplatin against A-549, MCF-7 and Hela tumor cell lines. The interactions of both compounds with CT-DNA were preliminarily studied by UV-Vis and fluorescence spectroscopy, which suggested that the organotin complex likely induces the distortion of DNA double helix through covalent bonding, while the hydrogen bonds and the large planar structure of the molecule hindered the Schiff base compound from intercalating into the DNA double helix.
- isonicotinohydrazide;fluorescent organotin;antitumor;crystal structure
1. [1]
  [1] Gajda T, Jancsó A. Met. Ions Life Sci., 2010, 7:111-151
2. [2]
  [2] Nath M, Saini P K. Dalton Trans., 2011, 40:7077-7121
3. [3]
  [3] Alama A, Tasso B, Novelli F, et al. Drug. Disc. Tod., 2009, 14:500-508
4. [4]
  [4] Hadjikakou S K, Hadjiliadis N. Coord. Chem. Rev., 2009, 253:235-249
5. [5]
  [5] Sadimenko A P. Adv. Heterocycl. Chem., 2012, 107:133-218
6. [6]
  [6] Agarwal R K, Prasad S, Singh U. Int. J. Chem., 2012, 1:264-280
7. [7]
  [7] Sreenivasulu B. Supramol. Chem., 2012, 3:826-862
8. [8]
  [8] Anand P, Patil V M, Sharma V K, et al. Int. J. Drug Des. Disc., 2012, 3:851-868
9. [9]
  [9] Becker E M, Lovejoy D B, Greer J M, et al. J. Pharmacol., 2003, 138:819-830
10. [10]
  [10] Bernhardt P V, Caldwell L M, Chaston T B, et al. J. Biol. Inorg. Chem., 2003, 8:866-880
11. [11]
  [11] Bernhardt P V, Mattsson J, Richardson D R. Inorg. Chem., 2006, 45:752-760
12. [12]
  [12] Bernhardt P V, Wilson G J, Sharpe P C, et al. J. Biol. Inorg. Chem., 2008, 13:107-119
13. [13]
  [13] Jeena Pearl A, Abbs F, Reji T F. J. Chem. Pharmac. Res., 2013, 5:115-122
14. [14]
  [14] Tabassum S, Amir A, Arjmand F, et al. Eur. J. Med. Chem., 2013, 60:216-232
15. [15]
  [15] Sheeja L K L P, Christudhas M, Isac S R C. J. Chem. Pharmac. Res., 2012, 4:4762-4769
16. [16]
  [16] Sathiyaraj S, Butcher R J, Jayabalakrishnan C. J. Coord. Chem., 2013, 66:580-591
17. [17]
  [17] Yin H D, Liu H, Hong M. J. Organomet. Chem., 2012, 713: 11-19
18. [18]
  [18] Rehman W, Baloch M K, Badshah A. Eur. J. Med. Chem., 2008, 43:2380-2385
19. [19]
  [19] Hong M, Yin H D, Zhang X Y, et al. J. Organomet. Chem., 2013, 724:23-31
20. [20]
  [20] Mun L S, Hapipah M A, Shin S K, et al. Appl. Organomet. Chem., 2012, 26:310-319
21. [21]
  [21] Sedaghat T, Naseh M, Khavasi H R, et al. Polyhedron, 2012, 33:435-440
22. [22]
  [22] Rehman W, Badshah A, Khan S, et al. Eur. J. Med. Chem., 2009, 44:3981-3985
23. [23]
  [23] Ni W X, Li M, Zhan S Z, et al. Inorg. Chem., 2009, 48:1433-1441
24. [24]
  [24] Lemmerer A. CrystEngComm, 2012, 14:2465-2478
25. [25]
  [25] APEX2 Software Suite (SMART, SAINT, SADABS, etc.), Bruker AXS Inc., Madison, Wisconsin, USA.
26. [26]
  [26] Sheldrick G M. SHELXL 2008, Program for the Refinement of Crystal Structure, University of Göttingen, Germany, 2008.
27. [27]
  [27] Zhang J Y, Wang X Y, Tu C, et al. J. Med. Chem., 2003, 46: 3502-3507
28. [28]
  [28] Elhamzaoui H, Jousseaume B, Toupance T, et al. Chem. Commun., 2006:1304-1306
29. [29]
  [29] Švec P, Černošková E, Padělková Z, et al. J. Organomet. Chem., 2010, 695:2475-2485
30. [30]
  [30] Li S H, Chen F R, Zhou Y F, et al. Chem. Commun., 2009: 4179-4181
31. [31]
  [31] Niu Y F, Han F F, Zhang Q, et al. Angew. Chem. Int. Ed., 2013, 52:1-6
32. [32]
  [32] Ni W X, Li M, Zhou X P, et al. Chem. Commun., 2007:3479-3481
33. [33]
  [33] Przhonska O V, Webster S, Padilha L A, et al. Fluorescence, 2010, 8:105-148
34. [34]
  [34] Hancock R D. Chem. Soc. Rev., 2013, 42:1500-1524
35. [35]
  [35] Liu Z P, He W J, Guo Z J. Chem. Soc. Rev., 2013, 42:1568-1600
36. [36]
  [36] Terenzi A, Tomasello L, Spinello A, et al. J. Inorg. Biochem., 2012, 117:103-110
37. [37]
  [37] Chen X, Gao F, Yang W Y, et al. Chem. Biodivers, 2013, 10:367-384
38. [38]
  [38] Kumar C V, Barton J K, Turro N J. J. Am. Chem. Soc., 1985, 107:5518-5523
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沈阳化工大学材料科学与工程学院沈阳 110142