Citation: JIANG Wu-Jiu, WU Xu-Meng, LIU Chao, YU Jiang-Xi, ZHU Xiao-Ming, FENG Yong-Lan, ZHANG Fu-Xing, KUANG Dai-Zhi. Syntheses, Crystal Structures and Biological Activity of Schiff Base Organotin Complexes Based on o-Vanillin and 2-Amino-4-nitrophenol[J]. Chinese Journal of Inorganic Chemistry, ;2015, 31(7): 1321-1328. doi: 10.11862/CJIC.2015.116 shu

Syntheses, Crystal Structures and Biological Activity of Schiff Base Organotin Complexes Based on o-Vanillin and 2-Amino-4-nitrophenol

  • Corresponding author: KUANG Dai-Zhi, 
  • Received Date: 28 December 2014
    Available Online: 26 January 2015

    Fund Project: 湖南省科技计划项目(No.2013TZ2025, 2014NK3086, 2014FJ3060) (No.2013TZ2025, 2014NK3086, 2014FJ3060)自然科学基金(No.13JJ3112) (No.13JJ3112) 湖南省普通高校重点实验室开放基金 项目(No.13K105, 14K014) (No.13K105, 14K014) 湖南省教育厅基金项目(No.14C0171) (No.14C0171) 功能金属有机材料湖南省普通高校重点实验室开放基金项目 (No.13K01, 13K04, GN14K01)资助。 (No.13K01, 13K04, GN14K01)

  • Schiff base organotin complexes 1 and 2 have been synthesized via the reaction of the o-Vanillin-2-amino-4-nitrophenol Schiff base(H2L) with the dibutyltin oxide and the dibenzyltin dichloride, respectively. The complexes have been characterized by IR, 1H NMR, 13C NMR spectra, elemental analysis and the crystal structures have been determined by X-ray diffraction. The anticancer activity of H2L, 1 and 2 against five species of cancer cell which are Hela, MCF7, HepG2, Colo205, NCI-H460 were tested respectively, and the tests showed that complex 1 was more active than carboplatin against tested carcinoma cell lines and has a potential application of drug preparation. The interaction between Schiff base ligand, complex 2 and Herring sperm DNA were studied by EB fluorescent probe, the result shows that fluorescence quenching was really resulted from the synergistic effect of the Schiff base ligand. CCDC: 939077, 1; 939078, 2.
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    1. [1]

      [1] Buck B, Mascioni A, Que L, et al. J. Am. Chem. Soc., 2003, 125(44):13316-13317

    2. [2]

      [2] Carraher J C E, Roner M R. J. Organomet. Chem., 2014, 751: 67-82

    3. [3]

      [3] Gasser G, Ott I, Metzler-Nolte N. J. Med. Chem., 2011, 54(1): 3-25

    4. [4]

      [4] Chandrasekhar V, Mohapatra C, Butcher R J. Cryst. Growth Des., 2012, 12(6):3285-3295

    5. [5]

      [5] Shang X, Ding N, Xiang G. Eur. J. Med. Chem., 2012, 48: 305-312

    6. [6]

      [6] Metsios A, Verginadis I, Simos Y, et al. Eur. J. Pharm. Sci., 2012, 47(2):490-496

    7. [7]

      [7] Yang P, Guo M. Coord. Chem. Rev., 1999, 185-186:189-211

    8. [8]

      [8] Gleeson B, Claffey J, Ertler D, et al. Polyhedron, 2008, 27(18): 3619-3624

    9. [9]

      [9] YANG Pin(杨频), GAO Fei(高飞). Principle of Biological Inorganic Chemistry(生物无机化学原理). Beijing: Science Press, 2002.

    10. [10]

      [10] Mohapatra C, Tripathi S, Anantharaman G, et al. Cryst. Growth Des., 2014, 14(7):3182-3185

    11. [11]

      [11] Shariatinia Z, Mirhosseini M H S, Bereciartua P J, et al. J. Organomet. Chem., 2013, 745-746:432-438

    12. [12]

      [12] Sirajuddin M, Ali S, McKee V, et al. Eur. J. Med. Chem., 2014, 84:343-363

    13. [13]

      [13] García-López M C, Muoz-Flores B M, Jiménez-Pérez V M, et al. Dyes Pigm., 2014, 106:188-196

    14. [14]

      [14] Hong M, Geng H, Niu M, et al. Eur. J. Med. Chem., 2014, 86:550-561

    15. [15]

      [15] Yin H, Liu H, Hong M. J. Organomet. Chem., 2012, 713:11-19

    16. [16]

      [16] Arjmand F, Yousuf I. J. Organomet. Chem., 2013, 743:55-62

    17. [17]

      [17] Dubey R K, Singh A P, Patil S A. Inorg. Chim. Acta, 2014, 410:39-45

    18. [18]

      [18] Prasad K S, Kumar L S, Chandan S, et al. Spectrochim. Acta A, 2011, 81(1):276-282

    19. [19]

      [19] Sisido K, Takeda Y, Dinugawa Z, et al. J. Am. Chem. Soc., 1961, 83(3):538-541

    20. [20]

      [20] Sheldrick G M. SHELXL-97, Program for Crystal Structure Analysis, University of Göttingen, Germany, 1998.

    21. [21]

      [21] JIANG Wu-Jiu(蒋伍玖), YANG Nian-Fa(阳年发), KUANG Dai-Zhi(邝代治), et al. Chinese J. Struct. Chem.(结构化学), 2011, 30(9):1327-1331

    22. [22]

      [22] YU Jiang-Xi(庾江喜), FENG Yong-Lan(冯泳兰), KUANG Dai-Zhi(邝代治), et al. Chinese J. Inorg. Chem.(无机化学学报), 2012, 28(2):279-284

    23. [23]

      [23] Nikoloz K, Norberto F, Margarita R, et al. J. Organomet. Chem., 2010, 695(8):1189-1199

    24. [24]

      [24] JIANG Wu-Jiu(蒋伍玖), KUANG Dai-Zhi(邝代治), YU Jiang-Xi(庾江喜), et al. Chinese J. Inorg. Chem.(无机化学学报), 2012, 28(11):2363-2368

    25. [25]

      [25] Yin H D, Hong M, Li G, et al. J. Organomet. Chem., 2005, 690(16):3714-3719

    26. [26]

      [26] KUANG Dai-Zhi(邝代治), FENG Yong-Lan(冯泳兰), ZHANG Fu-Xing(张复兴), et al. Chinese J. Inorg. Chem.(无机化学学报), 2010, 26(12):2160-2164

    27. [27]

      [27] Pretsch E, Bühlmann P, Badertscher M. Structure Determin-ation of Organic Compounds: Tables of Spectral Data. 4th Ed. Berlin and Heidelberg: Springer-Verlag, 2009.

    28. [28]

      [28] Clark H C, Jian V K, Mehrotra R C, et al. J. Organomet. Chem., 1985, 279(3):385-394

    29. [29]

      [29] Fulmer G R, Miller A J M, Sherden N H, et al. Organometallics, 2010, 29(9):2176-2179

    30. [30]

      [30] ZHANG Fu-Xing(张复兴), WANG Jian-Qiu(王剑秋), KUANG Dai-Zhi(邝代治), et al. Chinese J. Inorg. Chem.(无机化学学报), 2013, 29(3):537-543

    31. [31]

      [31] Chuprunov E V, Tarkhova T N, Korallova T Y, et al. Dokl. Akad. Nauk. SSSR, 1978, 242(3):606-608

    32. [32]

      [32] KUANG Dai-Zhi(邝代治), JIANG Wu-Jiu(蒋伍玖), FENG Yong-Lan(冯泳兰), et al. Chinese J. Inorg. Chem.(无机化学学报), 2013, 29(2):413-418

    33. [33]

      [33] Chuprunov E V, Stolyarova N E, Shcherbakov V I, et al. Zh. Strukt. Khim., 1987, 28(5):797-799

    34. [34]

      [34] KUANG Dai-Zhi(邝代治), JIANG Wu-Jiu(蒋伍玖), FENG Yong-Lan(冯泳兰), et al. Chinese J. Inorg. Chem.(无机化学学报), 2011, 27(10):1981-1987

    35. [35]

      [35] Hong M, Yin H D, Chen S W, et al. J. Organomet. Chem., 2010, 695(5):653-662

    36. [36]

      [36] Yin H, Cui J, Qiao Y. Polyhedron, 2008, 27(9/10):2157-2166

    37. [37]

      [37] Yin H D, Chen S W. J. Organomet. Chem., 2006, 691(13): 3103-3108

    38. [38]

      [38] Chandrasekhar V, Gopal K, Sasikumar P, et al. Coord. Chem. Rev., 2005, 249(17/18):1745-1765

    39. [39]

      [39] Jímenez-Pérez V M, Camacho-Camacho C, Güizado-Rodríguez M, et al. J. Organomet. Chem., 2000, 614-615:283-293

    40. [40]

      [40] Labib L, Khalil T E, Iskander M F, et al. Polyhedron, 1996, 15(21):3697-3707

    41. [41]

      [41] FENG Yong-Lan(冯泳兰), ZHENG Jian-Hua(郑建华), JIANG Wu-Jiu(蒋伍玖), et al. Chinese J. Inorg. Chem.(无机化学学报), 2014, 30(12):2767-2774

    42. [42]

      [42] JIANG Wu-Jiu(蒋伍玖), KUANG Dai-Zhi(邝代治), FENG Yong-Lan(冯泳兰), et al. Chin. J. Org. Chem.(有机化学), 2014, 34(11):2288-2295

    43. [43]

      [43] ZHAO Guo-Liang(赵国良), SHI Xia(施霞), ZHANG Jun-Ping(张均平), et al. Scientia Sinica Chimica(中国科学:化学), 2010, 40(10):1525-1535

    44. [44]

      [44] Wolfe A, George H S J, Thomas M. Biochemistry, 1987, 26 (20):6392-6396

    45. [45]

      [45] ZHAO Guo-Liang(赵国良), SHEN Jin-Bei(沈金杯), SHI Xia (施霞), et al. Chinese J. Inorg. Chem.(无机化学学报), 2012, 28(5):959-964

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