Citation: Li-Ning YANG, Chun-Ye LIU, Zhao CHENG, Ling-Ling LIANG, Jian ZHANG. Synthesis, Crystal Structure and Biological Activity of Cu(Ⅱ) and Ag(Ⅰ) Complexes Involving Nitroimidazole Derivative[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(9): 1547-1554. doi: 10.11862/CJIC.2021.186 shu

Synthesis, Crystal Structure and Biological Activity of Cu(Ⅱ) and Ag(Ⅰ) Complexes Involving Nitroimidazole Derivative

Department of Pharmacy, Medical University of Xi'an, Xi'an 710021, China

Corresponding author: Li-Ning YANG, zyfyln828@163.com
Received Date: 27 January 2021
Revised Date: 25 May 2021

Figures(11)

The copper(Ⅱ) and silver(Ⅰ) complexes[Cu(L)(Ac)₂]₂ (1), [Ag(L)(NO₃)]·H₂O (2) (L=N, N'-dimethyl-5-nitro-2, 2'-biimidazole) has been synthesized. X-ray crystallographic study was used to determine the crystallographic structure of complex 1, which exhibits a five-coordinated dimeric copper-acetato paddle-wheel geometry. Complex 2 was characterized by elemental analysis, UV-Vis, FT-IR, solid fluorescence spectra, thermogravimetric analysis, ESI-MS and conductivity analysis. The structure of complex 2 probably was a two-coordinated mononuclear structural unit of linear configuration. The binding property of L and complexes toward calf thymus DNA (ct-DNA) was figured out via electronic absorption, fluorescence spectra and viscosity measurements. Complex 1 revealed slightly stronger DNA binding capability than 2 and ligand. The antianaerobe activities of L and its complexes were tested by two-fold agar dilution method. The results showed that L displayed favorable activity of anti-anaerobic bacteria against Actinobacillus actinomycetem (ATCC 29523) selectively with minimum inhibitory concentrations of 0.625~1.25 μg·mL^-1, even better than the classical anti-anaerobic drug metronidazole.
- nitroimidazole derivative,
- metal complex,
- crystal structure,
- DNA interaction,
- anti-anaerobic activity
1. [1]
  Oberhausen K J, Richardson J F, Buchanan R M, Mccusker J K, Hendrickson D N, Latour J M. Inorg. Chem., 1991, 30(6): 1357-1365 doi: 10.1021/ic00006a036
2. [2]
  Al-Said N H, Lown J W. Tetrahedron Lett., 1994, 35(41): 7577-7580 doi: 10.1016/S0040-4039(00)78347-X
3. [3]
  Mallik S, Johnson R D, Arnold F H. J. Am. Chem. Soc., 1993, 115(6): 2518-2520 doi: 10.1021/ja00059a063
4. [4]
  Sackton K L, Dimova N, Zeng X, Tian W, Zhang M, Sackton T B, Meaders J, Pfaff K L, Sigoillot F, Yu H T, Luo X L, King R W. Nature, 2014, 514(7524): 646-649 doi: 10.1038/nature13660
5. [5]
  Edgar L J, Vellanki R N, Halupa A, Hedley D, Wouters B D, Nitz M. Angew. Chem. Int. Ed., 2014, 53(43): 11473-11477 doi: 10.1002/anie.201405233
6. [6]
  Dey C, Banerjee R. Chem. Commun., 2013, 49(59): 6617-6619 doi: 10.1039/c3cc42904k
7. [7]
  Ang C W, Jarrad A M, Cooper M A, Blaskovich M A T. J. Med. Chem., 2017, 60(18): 7636-765
8. [8]
  Rowan R, Tallon T, Sheahan A M, Curran R, Mccann M, Kavanagh K, Devereux M, Mckee V. Polyhedron, 2006, 25(8): 1771-1778 doi: 10.1016/j.poly.2005.11.021
9. [9]
  Baird I R, Skov K A, James B R. Inorg. Chim. Acta, 2019, 489(4): 100-107
10. [10]
  Ali A E, Elasala G S, Ibrahim R S. J. Mol. Struct., 2019, 1176(1): 673-684
11. [11]
  Mushtaque M, Avecilla F, Haque A, Yab Z, Rizvi M M A, Khan M S. J. Mol. Struct., 2019, 1185(6): 440-449
12. [12]
  Wang Y Y, Shi Q Z, Gao Y C, Zhou Z Y. Polyhedron, 1999, 18(15): 2009-2015 doi: 10.1016/S0277-5387(99)00092-3
13. [13]
  Török I, Surdy P, Rockenbauer A, Jr L K, Koolhaas G J A A, Gajda T. J. Inorg. Biochem., 1998, 71(1/2): 7-14
14. [14]
  Nomiya K, Tsuda K, Sudoh T, Oda M. J. Inorg. Biochem., 1997, 68(1): 39-44 doi: 10.1016/S0162-0134(97)00006-8
15. [15]
  Mao F, Mano N, Heller A. J. Am. Chem. Soc., 2003, 125(16): 4951-4957 doi: 10.1021/ja029510e
16. [16]
  Piero M, Emanuele D, Willy L. J. Med. Chem., 1972, 15(9): 926-930 doi: 10.1021/jm00279a012
17. [17]
  Wu S S, Yuan W B, Wang H Y, Zhang Q, Liu M, Yu K B. J. Inorg. Biochem., 2008, 102(11): 2026-2034 doi: 10.1016/j.jinorgbio.2008.08.005
18. [18]
  Liu M, Yuan W B, Zhang Q, Yan L, Yang R D. Spectrochimica Acta Part A, 2008, 70(5): 1114-1119 doi: 10.1016/j.saa.2007.10.023
19. [19]
  (a) Sheldrick G M. SADABS, University of Göttingen, Germany, 1996. (b)Sheldrick G M. SHELXL-97, Program for the Refinement of Crystal Structure, University of Göttingen, Germany, 1997.
20. [20]
  Tong Z C, Dong L P, Zhou L, Tao R, Ni L X. Peptides, 2010, 31(11): 2003-2008 doi: 10.1016/j.peptides.2010.07.016
21. [21]
  LI J. Comprehensive Chemical Experiment. Xi'an: Northwest University Press, 2003: 208-209
22. [22]
  Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds: Parts A and B. 5th ed. New York: John Wiley and Sons, Inc., 1997.
23. [23]
  CHANG J H, DONG Q G. Principle and Analysis of Spectrum. Beijing: Science Press, 2001: 96-98
24. [24]
  WANG D Q, CHEN Y, LIU X Q, BIAN J J, YI X Y, TENG M Y, RONG M Z, WANG Z L. Chinese J. Inorg. Chem., 2021, 37(1): 33-38
25. [25]
  Kazi S A A. J. Chem., 2011, 8(s1): S127-S136
26. [26]
  Du Q Y, Ma L, Qin J H. Chin. J. Struct. Chem., 2007, 26(3): 347-351
27. [27]
  CAI D H, MO H W, HE L, LE X Y. Chinese J. Inorg. Chem., 2021, 37(1): 74-84
28. [28]
  Tu C, Wu X F, Liu Q, Wang X Y, Xu Q, Guo Z J. Inorg. Chim. Acta, 2004, 357(1): 95-102 doi: 10.1016/S0020-1693(03)00389-X
29. [29]
  ZHOU Q H, YANG P. Acta Chim. Sinica, 2006, 64(8): 793-798 doi: 10.3321/j.issn:0567-7351.2006.08.016
30. [30]
  Liu F, Meadows K A, McMillin D R. J. Am. Chem. Soc., 1993, 115(15): 6699-6704 doi: 10.1021/ja00068a029
31. [31]
  Carter M T, Rodriguez M, Bard A J. J. Am. Chem. Soc., 1989, 111(24): 8901-8911 doi: 10.1021/ja00206a020
32. [32]
  Satyanaryana S, Dabrowial J C, Chaires J B. Biochemistry, 1992, 31(39): 9319-9324 doi: 10.1021/bi00154a001
33. [33]
  ZHAO Z C, LU Y, XU Z. World Notes on Antibiotics, 2019, 40(6): 544-553 doi: 10.3969/j.issn.1001-8751.2019.06.006
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