Citation: YAN Hui, YANG Lei, CHANG Guo-Liang, LI Xiao, NIU Mei-Ju. DNA Interaction and Cytotoxic Activity of a Chiral Amino-alcohol Schiff Base Derived Cu(II) Complex[J]. Chinese Journal of Structural Chemistry, ;2016, 35(3): 465-471. doi: 10.14102/j.cnki.0254-5861.2011-0989 shu

DNA Interaction and Cytotoxic Activity of a Chiral Amino-alcohol Schiff Base Derived Cu(II) Complex

  • Corresponding author: NIU Mei-Ju, 
  • Received Date: 28 September 2015
    Available Online: 12 January 2016

    Fund Project: the Natural Science Foundation of China (No. 21105042) (No. ZR2013BM017)

  • A novel copper(II) complex based on chiral amino-alcohol derived Schiff base ligand, [Cu4(R-L)4(H2O)2]·(CH3COOH)2·(H2O) (1, (R)-H2L = (R)-3-phenyl-2-(2-hydroxy-3-methoxybenzylideneamino) propane-1-ol), was synthesized and characterized by EA, IR, UV-Vis, ESI-MS, circular dichroism spectra and single-crystal X-ray diffraction. Complex 1 crystallizes in orthorhombic, space group R21212 with a = 15.7660(14), b = 49.526(3), c = 10.4213(9) Å, V = 8137.2(12) Å3, Z = 4, C72H81Cu4N4O19, Mr = 1560.57, m = 1.096 mm-1, F(000) = 3244, Flack = 0.06(3), the final R = 0.0924 and wR = 0.2451 (I > 2s(I)) for 41108 observed reflections. The interactions of the complex with calf thymus DNA (CT-DNA) were investigated by some spectroscopic technique methods. The results show the complex exhibits strong binding with CT-DNA. In addition, in vitro cytotoxicity test of 1 towards four kinds of human cancerous cell lines (HeLa, HL-60, Caco-2 and A549) showed substantial cytotoxic activity. The experimental investigations indicated that the chirality of complex 1 play an important role in cytotoxicity and interactions with DNA.
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    1. [1]

      (1) Annaraj, B.; Neelakantan, M. A. Synthesis, crystal structure, spectral characterization and biological exploration of water soluble Cu(II) complexes of vitamin B6 derivative european. Eur. J. Med. Chem. 2015, 102, 1-8.

    2. [2]

      (2) Liu, W. Q.; Zhou, S. L.; Fan, M. Z.; Pan, Z. Q.; Chen, Y. F. Synthesis and crystal structure of a dinuclear Cu(II) complex based on a carboxyl-substituted 1H-1, 2, 3-triazole and its DNA cleavage activity. Chin. J. Struct. Chem. 2015, 6, 917-924.

    3. [3]

      (3) Seth, B. K.; Ray, A.; Saha, A.; Saha, P.; Basu, S. Potency of photoinduced electron transfer and antioxidant efficacy of pyrrole and pyridine based Cu(II)-Schiff complexes while binding with CT-DNA. J. Photochem. Photobiol. B 2014, 132, 72-84.

    4. [4]

      (4) Jayamani, A.; Thamilarasan, V.; Sengottuvelan, N.; Manisankar, P.; Kang, S. K.; Kim, Y. I.; Ganesan, V. Synthesis of mononuclear copper(II) complexes of acyclic Schiff's base ligands: spectral, structural, electrochemical, antibacterial, DNA binding and cleavage activity. Spectrochim. Acta A 2014, 122, 365-374.

    5. [5]

      (5) Raja, D. S.; Bhuvanesh, N. S. P.; Natarajan, K. Effect of N(4)-phenyl substitution in 2-oxo-1, 2-dihydroquinoline-3-carbaldehyde semicarbazones on the structure, DNA/protein interaction, and antioxidative and cytotoxic activity of Cu(II) complexes. Inorg. Chem. 2011, 24, 12852-12866.

    6. [6]

      (6) Chauhan, M.; Banerjee, K.; Arjmand, F. DNA binding studies of novel copper(II) complexes containing L-tryptophan as chiral auxiliary: in vitro antitumor activity of Cu-Sn2 complex in human neuroblastoma cells. Inorg. Chem. 2007, 8, 3072-3082.

    7. [7]

      (7) Fei, B. L.; Xu, W. S.; Tao, H. W.; Li, W.; Zhang, Y.; Long, J. Y.; Liu, Q. B.; Xia, B.; Sun, W. Y. Effects of copper ions on DNA binding and cytotoxic activity of a chiral salicylidene Schiff base. J. Photochem. Photobiol. B 2014, 132, 36-44.

    8. [8]

      (8) Xiang, H.; Jiang, L.; Li, H. Y.; Zheng, X. D.; Li, Y. Synthesis and characterization of a tetranuclear copper(II) complex with a chiral Schiff base ligand. Chin. Chem. Lett. 2013, 1, 49-51.

    9. [9]

      (9) Vyas, K. M.; Jadeja, R. N.; Patel, D.; Devkar, R. V.; Gupta, V. K. Effect of ligand substitution in pyrazolone based binary and ternary Cu(II) complexes on DNA binding, protein binding and anti-cancer activity on A549 lung carcinoma cell lines. Polyhedron 2014, 80, 20-33.

    10. [10]

      (10) Niu, M. J.; Hong, M.; Chang, G. L.; Li, X.; Li, Z. A comparative study of cytotoxicity and interaction with DNA/protein of five transition metal complexes with Schiff base ligands. J. Photochem. Photobio. B 2015, 148, 232-241.

    11. [11]

      (11) Li, P.; Niu, M. F.; Niu, M. J.; Hong, M. Effect of structure and composition of copper and cobalt complexes with Schiff base ligands on their DNA/protein interaction and cytotoxicity. Z. Anorg. Allg. Chem. 2014, 11, 2238-2246.

    12. [12]

      (12) Li, P.; Niu, M. J.; Hong, M.; Cheng, S.; Dou, J. M. Effect of structure and composition of nickel(II) complexes with salicylidene Schiff base ligands on their DNA/protein interaction and cytotoxicity. J. Inorg. Biochem. 2014, 137, 101-108.

    13. [13]

      (13) Niu, M. J.; Li, Z.; Li, H. H.; Li, X; Dou, J. M.; Wang, S. N. DNA/protein interaction, cytotoxic activity and magnetic properties of amino-alcohol Schiff base derived Cu(II)/Ni(II) metal complexes: influence of the nuclearity and metal ions RSC. Adv. 2015, 47, 37085-37095.

    14. [14]

      (14) Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Germany 1997.

    15. [15]

      (15) Xiang, H.; Lan, Y. H.; Jiang, L.; Zhang, W. X.; Anson, C. E.; Lu, T. B.; Powell, A. K. A chiral tetranuclear copper(II) complex based on a new Schiff-base ligand: synthesis, structure, magnetic property and CD spectra. Inorg. Chem. Commun. 2012, 16, 51-54.

    16. [16]

      (16) Jin, X.; Zhou, P.; Zheng, C. Y.; Li, H. A new coordination mode of (E)-3-(3-hydroxyl-phenyl)-acrylic acid in copper complex: crystal structure and magnetic properties. J. Solid. State. Chem. 2015, 225, 41-44.

    17. [17]

      (17) Khan, N. H.; Pandya, N.; Kumar, M.; Bera, P. K.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H. C. Influence of chirality using Mn(III) salen complexes on DNA binding and antioxidant activity. Org. Biomol. Chem. 2010, 19, 4297-4307.

    18. [18]

      (18) Khan, N. H.; Pandya, N.; Prathap, K. J.; Kureshy, R. I.; Abdi, S. H. R.; Mishra, S.; Bajaj, H. C. Chiral discrimination asserted by enantiomers of Ni(II), Cu(II) and Zn(II) Schiff base complexes in DNA binding, antioxidant and antibacterial activities. Spectrochim. Acta A 2011, 81, 199-208.

    19. [19]

      (19) Sathyadevi, P.; Krishnamoorthy, P.; Butorac, R. R.; Cowley, A. H.; Bhuvanesh, N. S. P.; Dharmaraj, N. Effect of substitution and planarity of the ligand on DNA/BSA interaction, free radical scavenging and cytotoxicity of diamagnetic Ni(II) complexes: a systematic investigation. Dalton Trans. 2011, 38, 9690-9702.

    20. [20]

      (20) Liu, J.; Zhang, T. X.; Lu, T. B.; Qu, L. H.; Zhou, H.; Zhang, Q. L.; Ji, L. N. DNA-binding and cleavage studies of macrocyclic copper(II) complexes. J. Inorg. Biochem. 2002, 91, 269-276.

    21. [21]

      (21) Mishra, M.; Tiwari, K.; Shukla, S.; Mishra, R.; Singh, V. P. Synthesis, structural investigation, DNA and protein binding study, of some 3d-metal complexes with N'-(phenyl-pyridin-2-yl-methylene)-thiophene-2-carboxylic acid hydrazide. Spectrochim. Acta A 2014, 132, 452-464.

    22. [22]

      (22) Sobha, S.; Mahalakshmi, R.; Raman, N. Studies on DNA binding behaviour of biologically active transition metal complexes of new tetradentate N2O2 donor Schiff bases: inhibitory activity against bacteria. Spectrochimica Acta A 2012, 92, 175-183.

    23. [23]

      (23) Liu, H. Y.; Li, L. Z.; Guo, Q.; Dong, J. F.; Li, J. H. Synthesis, crystal structure, DNA- and albumin-binding properties of a chromium(III) complex with 1, 10-phenanthroline and a Schiff base derived from glycine. Trans. Met. Chem. 2013, 4, 441-448.

    24. [24]

      (24) McMillan, D. R.; McNett, K. M. Photoprocesses of copper complexes that bind to DNA. Chem. Rev. 1998, 3, 1201-1220.

    25. [25]

      (25) Ravichandran, J.; Gurumoorthy, P.; Musthafa, M. A. I.; Rahiman, A. K. Antioxidant, DNA binding and nuclease activities of heteroleptic copper(II) complexes derived from 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-substituted phenols and diimines. Spectrochimica Acta A 2014, 133, 785-793.

    26. [26]

      (26) Wen, J. H.; Li, C. Y.; Geng, Z. R.; Ma, X. Y.; Wang, Z. L. A potent antitumor Zn2+ tetraazamacrocycle complex targeting DNA: the fluorescent recognition, interaction and apoptosis studies. Chem. Commun. 2011, 40, 11330-11332.

    27. [27]

      (27) Li, J. H.; Dong, J. F.; Cui, H.; Xu, T.; Li, L. Z. A copper(II) complex of the Schiff base from l-valine and 2-hydroxy-1-naphthalidene plus 1, 10-phenanthroline: synthesis, crystal structure, and DNA interaction. Transition Met. Chem. 2012, 2, 175-182.

    28. [28]

      (28) Pradeepa, S. M.; Bhojya, N. H. S.; Kumar, B. V.; Priyadarsini, K. I.; Barik, A.; Prabhakara, M. C. DNA binding, photoactivated DNA cleavage and cytotoxic activity of Cu(II) and Co(II) based Schiff-base azo photosensitizers. Spectrochimica Acta A 2015, 141, 34-42.

    29. [29]

      (29) Chen, W. B.; Liu, J. B.; Dou, D. L.; Song, F. B.; Li, L. Y.; Xi, Z. Synthesis and screening of novel inositol phosphonate derivatives for anticancer functions in vitro. Chin. Chem. Lett. 2015, 3, 329-333.

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