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
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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.
-
-
[1]
[1] Gajda T, Jancsó A. Met. Ions Life Sci., 2010, 7:111-151
-
[2]
[2] Nath M, Saini P K. Dalton Trans., 2011, 40:7077-7121
-
[3]
[3] Alama A, Tasso B, Novelli F, et al. Drug. Disc. Tod., 2009, 14:500-508
-
[4]
[4] Hadjikakou S K, Hadjiliadis N. Coord. Chem. Rev., 2009, 253:235-249
-
[5]
[5] Sadimenko A P. Adv. Heterocycl. Chem., 2012, 107:133-218
-
[6]
[6] Agarwal R K, Prasad S, Singh U. Int. J. Chem., 2012, 1:264-280
-
[7]
[7] Sreenivasulu B. Supramol. Chem., 2012, 3:826-862
-
[8]
[8] Anand P, Patil V M, Sharma V K, et al. Int. J. Drug Des. Disc., 2012, 3:851-868
-
[9]
[9] Becker E M, Lovejoy D B, Greer J M, et al. J. Pharmacol., 2003, 138:819-830
-
[10]
[10] Bernhardt P V, Caldwell L M, Chaston T B, et al. J. Biol. Inorg. Chem., 2003, 8:866-880
-
[11]
[11] Bernhardt P V, Mattsson J, Richardson D R. Inorg. Chem., 2006, 45:752-760
-
[12]
[12] Bernhardt P V, Wilson G J, Sharpe P C, et al. J. Biol. Inorg. Chem., 2008, 13:107-119
-
[13]
[13] Jeena Pearl A, Abbs F, Reji T F. J. Chem. Pharmac. Res., 2013, 5:115-122
-
[14]
[14] Tabassum S, Amir A, Arjmand F, et al. Eur. J. Med. Chem., 2013, 60:216-232
-
[15]
[15] Sheeja L K L P, Christudhas M, Isac S R C. J. Chem. Pharmac. Res., 2012, 4:4762-4769
-
[16]
[16] Sathiyaraj S, Butcher R J, Jayabalakrishnan C. J. Coord. Chem., 2013, 66:580-591
-
[17]
[17] Yin H D, Liu H, Hong M. J. Organomet. Chem., 2012, 713: 11-19
-
[18]
[18] Rehman W, Baloch M K, Badshah A. Eur. J. Med. Chem., 2008, 43:2380-2385
-
[19]
[19] Hong M, Yin H D, Zhang X Y, et al. J. Organomet. Chem., 2013, 724:23-31
-
[20]
[20] Mun L S, Hapipah M A, Shin S K, et al. Appl. Organomet. Chem., 2012, 26:310-319
-
[21]
[21] Sedaghat T, Naseh M, Khavasi H R, et al. Polyhedron, 2012, 33:435-440
-
[22]
[22] Rehman W, Badshah A, Khan S, et al. Eur. J. Med. Chem., 2009, 44:3981-3985
-
[23]
[23] Ni W X, Li M, Zhan S Z, et al. Inorg. Chem., 2009, 48:1433-1441
-
[24]
[24] Lemmerer A. CrystEngComm, 2012, 14:2465-2478
-
[25]
[25] APEX2 Software Suite (SMART, SAINT, SADABS, etc.), Bruker AXS Inc., Madison, Wisconsin, USA.
-
[26]
[26] Sheldrick G M. SHELXL 2008, Program for the Refinement of Crystal Structure, University of Göttingen, Germany, 2008.
-
[27]
[27] Zhang J Y, Wang X Y, Tu C, et al. J. Med. Chem., 2003, 46: 3502-3507
-
[28]
[28] Elhamzaoui H, Jousseaume B, Toupance T, et al. Chem. Commun., 2006:1304-1306
-
[29]
[29] Švec P, Černošková E, Padělková Z, et al. J. Organomet. Chem., 2010, 695:2475-2485
-
[30]
[30] Li S H, Chen F R, Zhou Y F, et al. Chem. Commun., 2009: 4179-4181
-
[31]
[31] Niu Y F, Han F F, Zhang Q, et al. Angew. Chem. Int. Ed., 2013, 52:1-6
-
[32]
[32] Ni W X, Li M, Zhou X P, et al. Chem. Commun., 2007:3479-3481
-
[33]
[33] Przhonska O V, Webster S, Padilha L A, et al. Fluorescence, 2010, 8:105-148
-
[34]
[34] Hancock R D. Chem. Soc. Rev., 2013, 42:1500-1524
-
[35]
[35] Liu Z P, He W J, Guo Z J. Chem. Soc. Rev., 2013, 42:1568-1600
-
[36]
[36] Terenzi A, Tomasello L, Spinello A, et al. J. Inorg. Biochem., 2012, 117:103-110
-
[37]
[37] Chen X, Gao F, Yang W Y, et al. Chem. Biodivers, 2013, 10:367-384
-
[38]
[38] Kumar C V, Barton J K, Turro N J. J. Am. Chem. Soc., 1985, 107:5518-5523
-
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