Citation: CAI Dai-Hong, MO Hui-Wen, HE Liang, LE Xue-Yi. Crystal Structure, DNA Binding Properties and Biological Activities of a Ternary Mixed-Ligand Copper(Ⅱ) Complex[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(1): 74-84. doi: 10.11862/CJIC.2021.026 shu

Crystal Structure, DNA Binding Properties and Biological Activities of a Ternary Mixed-Ligand Copper(Ⅱ) Complex

Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China

Corresponding author: HE Liang, heling@scau.edu.cn LE Xue-Yi, lexyfu@163.com
Received Date: 6 July 2020
Revised Date: 28 October 2020

Figures(10)

A new ternary Cu(Ⅱ) complex[Cu(HPBC)(L-Phe)(H₂O)]ClO₄ (1) was synthesized with 5-chloro-2-(2'-pyridyl) benzimidazole (HPBC) as the main ligand and L-phenylalaninate (L-Phe) as the auxiliary ligand. Complex 1 was characterized by elemental analysis, various spectroscopic methods and molar conductivity measurement, and the X-ray crystallographic study was used to determine the crystallographic structure of the complex, which exhibits a five-coordinated distorted square-pyramidal geometry. The binding property of the complex toward calf thymus DNA (CT-DNA) was studied by electronic absorption, competitive fluorescence titration, viscosity measurement and molecular docking technology, revealing that the complex mainly bound to DNA by an intercalative mode. The antibacterial activities (Listeria monocytogenes, Staphylococcus aureus and Escherichia coli) of Cu(ClO₄)₂, HPBC and the complex were tested by Oxford Cup method. In addition, the complex displayed favorable cytotoxic activities toward all the tested cancer cells such as SGC-7901, Bel-7402, HeLa and A549 with IC₅₀ values of 1.69~2.50 μmol·L^-1. Most importantly, the possible anticancer mechanism of the complex was explored by determining the morphological changes of cells (AO/EB double staining method) and cell cycle measurement analyses. The results revealed that the complex could induce apoptosis through the DNA binding pathway. CCDC:2032899.
- copper(Ⅱ) complex,
- 5-chloro-2-(2'-pyridyl)benzimidazole,
- L-phenylalanine,
- DNA interaction,
- antimicrobial,
- anticancer activity
1. [1]
  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
2. [2]
  Liang J X, Zhong H J, Yang G J, Vellaisamy K, Ma D L, Leung C H. J. Inorg. Biochem., 2017, 177:276-286 doi: 10.1016/j.jinorgbio.2017.06.002
3. [3]
  Ndagi U, Mhlongo N, Soliman M E. Drug Des. Dev. Ther., 2017, 11:599-616 doi: 10.2147/DDDT.S119488
4. [4]
  LIU Q Y, CAI D H, QI Y Y, LE X Y. Acta Chim. Sinica, 2020, 78(3):263-270
5. [5]
  Lakshmipraba J, Arunachalam S, Gandi D A, Thirunalasundari T. Eur. J. Med. Chem., 2011, 46(7):3013-3021 doi: 10.1016/j.ejmech.2011.04.033
6. [6]
  Mehta J V, Gajera S B, Patel D D, Patel M N. Appl. Organomet. Chem., 2015, 29(6):357-367
7. [7]
  ZHANG Y, MENG X G, CAI P, CHENG G Z, JIA S F. Chinese J. Inorg. Chem., 2018, 34(10):1864-1874 doi: 10.11862/CJIC.2018.234
8. [8]
  WEN X M, HU H, ZHOU H, PAN Z Q. Chinese J. Inorg. Chem., 2012, 28(9):1985-1996
9. [9]
  HAI S K, LOU S F, CHOU X Y. Chinese J. Inorg. Chem., 2016, 32(5):906-912
10. [10]
  MO H W, LIU Y X, CAI D H, SHEN F, LE X Y. Chinese J. Inorg. Chem., 2019, 35(3):477-484
11. [11]
  LU Y M, LE X Y. Chinese J. Inorg. Chem., 2011, 27(2):199-213
12. [12]
  Haugwitz R D, Maurer B V, Jacobs G A, Narayanan V L, Cruthers L, Szanto J. J. Med. Chem., 1979, 22(9):1113-1118 doi: 10.1021/jm00195a021
13. [13]
  APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, 2009.
14. [14]
  Sheldrick G M. Acta Crystallogr. Sect. A, 2015, A71(1):3-8
15. [15]
  OU Z B, HUANG S H, FU X B, ZHU L, LE X Y. Chinese J. Inorg. Chem., 2014, 30(5):1017-1024
16. [16]
  Zhang C L, Zhang X M, Liu W, Chen S, Mao Z W, Le X Y. Appl. Organomet. Chem., 2018, 32(2):e3994
17. [17]
  Ma T L, Xu J, Wang Y, Yu H, Yang Y, Liu Y, Ding W L, Zhu W J, Chen R H, Ge Z J, Tan Y F, Jia L, Zhu T F. J. Inorg. Biochem., 2015, 144:38-46 doi: 10.1016/j.jinorgbio.2014.12.011
18. [18]
  Patra A K, Roy S, Chakravarty A R. Inorg. Chim. Acta, 2009, 362(5):1591-1599
19. [19]
  Loganathan R, Ganeshpandian M, Bhuvanesh N S P, Palaniandavar M, Muruganantham A, Ghosh S K, Riyasdeen A, Akbarsha M A. J. Inorg. Biochem., 2017, 174:1-13 doi: 10.1016/j.jinorgbio.2017.05.001
20. [20]
  Haribabu J, Jeyalakshmi K, Arun Y, Bhuvanesh N S P, Perumal P T, Karvembu R. RSC Adv., 2015, 5(57):46031-46049 doi: 10.1039/C5RA04498G
21. [21]
  Yi Q Y, Wan D, Tang B, Wang Y J, Zhang W Y, Du F, He M, Liu Y J. Eur. J. Med. Chem., 2018, 145:338-349 doi: 10.1016/j.ejmech.2017.11.091
22. [22]
  Wan D, Tang B, Wang Y J, Guo B H, Yin H, Yi Q Y, Liu Y J. Eur. J. Med. Chem., 2017, 139:180-190 doi: 10.1016/j.ejmech.2017.07.066
23. [23]
  Paul A, Mistri S, Bhunia A, Manna S, Puschmann H, Manna S C. RSC Adv., 2016, 6(65):60487-60501
24. [24]
  Lu J, Sun Q, Li J L, Jiang L, Gu W, Liu X, Tian J L, Yan S P. J. Inorg. Biochem., 2014, 137:46-56
25. [25]
  Gu S S, Yu P, Hu J N, Liu Y N, Li Z W, Qian Y, Wang Y, Gou Y, Yang F. Eur. J. Med. Chem., 2019, 164:654-664
26. [26]
  Deng J G, Yu P, Zhang Z L, Wang J, Cai J H, Wu N, Sun H B, Liang, H, Yang F. Eur. J. Med. Chem., 2018, 158:442-452
27. [27]
  Rehman S U, Sarwar T, Husain M A, Ishqi H M, Tabish M. Arch. Biochem. Biophys., 2015, 576:49-60
28. [28]
  Psomas G. J. Inorg. Biochem., 2008, 102(9):1798-1811
29. [29]
  Chen J W, Wang X Y, Shao Y, Zhu J H, Zhu Y G, Li Y Z, Xu Q, Guo Z J. Inorg. Chem., 2007, 46(8):3306-3312
30. [30]
  DING Y, REN X X, ZHUANG C X, LE X Y. Chinese J. Inorg. Chem., 2009, 25(4):656-662
31. [31]
  Tishchenko K, Beloglazkina E, Proskurnin M, Malinnikov V, Guk D, Muratova M, Krasnovskaya O, Udina A, Skvortsov D, Shafikov R R, Ivanenkov Y, Aladinskiy V, Sorokin I, Gromov O, Majouga A, Zyk N. J. Inorg. Biochem., 2017, 175:190-197
32. [32]
  Qi Y Y, Liu Y X, Gan Q, Xiong Y H, Mao Z W, Le X Y. Appl. Organomet. Chem., 2017, 32(3):e4126
33. [33]
  Zhang C L, Liu Y X, Zhang X M, Chen S, Shen F, Xiong Y H, Liu W, Mao Z W, Le X Y. Mater. Sci. Eng. C, 2018, 91:414-425
34. [34]
  Ganeshpandian M, Ramakrishnan S, Palaniandavar M, Suresh E, Riyasdeen A, Akbarsha M A. J. Inorg. Biochem., 2014, 140:202-212
35. [35]
  Ye X L, Li X G, Yuan L J, Ge L H, Zhang B S, Zhou S B. Colloids Surf. A, 2007, 301(1/2/3):412-418
36. [36]
  Liu X L, Xia W S, Jiang Q X, Xu Y S, Yu P P. J. Biosci. Bioeng., 2015, 120(3):335-339
37. [37]
  Surivet J P, Zumbrunn C, Rueedi G, Bur D, Bruyère T, Locher H, Ritz D, Seiler P, Kohl C, Ertel E A, Hess P, Gauvin J C, Mirre A, Kaegi V, Dos Santos M, Kraemer S, Gaertner M, Delers J, Enderlin-Paput M, Weiss M, Sube R, Hadana H, Keck W, Hubschwerlen C. J. Med. Chem., 2015, 58(2):927-942
38. [38]
  Johansen C, Verheul A, Gram L, Gill T, Abee T. Appl. Environ. Microbiol., 1997, 63(3):1155-1159
39. [39]
  Liu Y X, Mo H W, Lv Z Y, Shen F, Zhang C L, Qi Y Y, Mao Z W, Le X Y. Transition Met. Chem., 2018, 43(3):259-271
40. [40]
  Ford M C, Ho P S. J. Med. Chem., 2016, 59(5):1655-1670
41. [41]
  Gilday L C, Robinson S W, Barendt T A, Langton M J, Mullaney B R, Beer P D. Chem. Rev., 2015, 115(15):7118-7195
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