Citation: ZHONG Yu-Jun, CHEN Zhen-Feng, LIANG Hong. Synthesis, Structural Characterization and Antitumor Activity of Copper(Ⅱ) Complex of 4-(2-Hydroxy-3-chlorine)phenyl-2, 2': 6', 2'-terpyridine[J]. Chinese Journal of Inorganic Chemistry, ;2019, 35(11): 2089-2094. doi: 10.11862/CJIC.2019.253 shu

Synthesis, Structural Characterization and Antitumor Activity of Copper(Ⅱ) Complex of 4-(2-Hydroxy-3-chlorine)phenyl-2, 2': 6', 2'-terpyridine

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, Guilin, Guangxi 541004, China

Corresponding author: CHEN Zhen-Feng, chenzf@gxnu.edu.cn LIANG Hong, hliang@gxnu.edu.cn
Received Date: 15 September 2019
Revised Date: 17 October 2019

Figures(6)

A new copper(Ⅱ) complex [Cu₂(μ-L-κO, O)₂Cl₂] (1) with 4-(2-hydroxy-3-chloro)phenyl-2, 2':6', 2'-tribi-pyridine(HL) as ligand was synthesized and characterized by elemental analysis, NMR, ESI-MS as well as single crystal X-ray diffraction analysis. Complex 1 is a binuclear structure, and the central copper(Ⅱ) is coordinated by one Cl^- anion, two N atoms and two hydroxyl O atoms from L^- to form five-coordination distorted square-pyramid geometric configurations; two copper centers are bridged by two hydroxyl O atoms. MTT assay was employed to test the inhibitory activities of complex 1 against five selected cancer cell lines. The results showed that inhibition rate of MGC80-3 cells was the highest, reaching(84.30±1.28)%, and its IC₅₀ value was(3.36±0.43) μmol·L^-1. Flow cytometry analytical results indicated that complex 1 could induce apoptosis of MGC80-3 cells. Under the complex 1 concentration of 4.5 μmol·L^-1, the MGC80-3 cell apoptosis percentage was 42.2%. Complex 1 arrested MGC80-3 cells in G1 phase, thereby inhibiting the growth of tumor cells.
- tribipyridine,
- copper(Ⅱ) complex,
- antitumor activity,
- cell apoptosis,
- cell cycle
1. [1]
  Wilson J J, Lippard S J. Chem. Rev., 2014, 45(24):4470-4495
2. [2]
  Duan X, He C, Kron S J, et al. Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol., 2016, 8(5):776-791 doi: 10.1002/wnan.1390
3. [3]
  Olszewski U, Hamilton G. Anti-Cancer Agents in Med. Chem., 2010, 10(4):293-301 doi: 10.2174/187152010791162306
4. [4]
  Hartmann J T, Lipp H P. Expert Opin. Pharmacother., 2003, 4(6):889-901 doi: 10.1517/14656566.4.6.889
5. [5]
  Kumar A, Chinta J P, Ajay A K, et al. Dalton Trans., 2011, 40(41):10865-10872 doi: 10.1039/c1dt10201j
6. [6]
  Santini C, Pellei M, Gandin V, et al. Chem. Rev., 2013, 114(1):815-862
7. [7]
  Yang P, Zheng W, Hua Z. Inorg. Chem., 2000, 39(24):5454-5463 doi: 10.1021/ic0000146
8. [8]
  Mahendiran D, Kumar R S, Viswanathan V, et al. Dalton Trans., 2016, 45(18):7794-7814 doi: 10.1039/C5DT03831F
9. [9]
  Gama S, Rodrigues I, Marques F, et al. RSC Adv., 2014, 4(106):61363-61377 doi: 10.1039/C4RA12085J
10. [10]
  Zhao L X, Kim T S, Ahn S H, et al. Bioorg. Med. Chem. Lett., 2001, 11(19):2659-2662 doi: 10.1016/S0960-894X(01)00531-5
11. [11]
  Fik M A, Gorczyński A, Kubicki M, et al. Polyhedron, 2015, 97:83-93 doi: 10.1016/j.poly.2015.05.021
12. [12]
  Ghosh S, Mendoza O, Cubo L, et al. Chemistry, 2014, 20(16):4772-4779 doi: 10.1002/chem.201304905
13. [13]
  Qin Q P, Wang Z F, Wang S L, et al. Eur. J. Med. Chem., 2019, 170:195-202 doi: 10.1016/j.ejmech.2019.03.014
14. [14]
  Roy S, Saha S, Majumdar R, et al. Polyhedron, 2010, 29(14):2787-2794 doi: 10.1016/j.poly.2010.06.028
15. [15]
  Czerwinska K, Golec M, Skonieczna M, et al. Dalton Trans., 2017, 46(10):3381-3392 doi: 10.1039/C6DT04584G
16. [16]
  Sheldrick G M. Acta Crystallogr. Sect. C:Cryst. Struct. Commun., 2015, C71:3-8
17. [17]
  Chen Z F, Gu Y Q, Song X Y, et al. Eur. J. Med. Chem., 2013, 59:168-175 doi: 10.1016/j.ejmech.2012.11.001
18. [18]
  Heidary D K, Howerton B S, Glazer E C. J. Med. Chem., 2014, 57(21):8936-8946 doi: 10.1021/jm501043s
19. [19]
  Jacques A, Kirsch-De Mesmaeker A, Elias B. Inorg. Chem., 2014, 53(3):1507-1512 doi: 10.1021/ic402476b
20. [20]
  Milutinovi M M, Rilak A, Bratsos I, et al. J. Inorg. Biochem., 2017, 169:1-12 doi: 10.1016/j.jinorgbio.2016.10.001
21. [21]
  Ma Z, Cao Y, Li Q, et al. J. Inorg. Biochem., 2010, 104(7):704-711 doi: 10.1016/j.jinorgbio.2010.03.002
22. [22]
  Karidi K, Garoufis A, Tsipis A, et al. Dalton Trans., 2005(7):1176-1187 doi: 10.1039/b418838a
23. [23]
  Wang Z, Ma L M, Su M Q, et al. Cell Death Dis., 2018, 9(2):217 doi: 10.1038/s41419-017-0223-0
24. [24]
  Wu S G, Huang Y J, Bao B, et al. Neoplasma, 2017, 64(1):40-47 doi: 10.4149/neo_2017_105
25. [25]
  Banerjee S, Kitchen J A, Bright S A, et al. Chem. Commun., 2013, 49(76):8522-8524 doi: 10.1039/c3cc44962a
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