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. 2018 Jul 5:2018:8478152.
doi: 10.1155/2018/8478152. eCollection 2018.

Synthesis, Structure, DNA Interaction, and SOD Activity of Three Nickel(II) Complexes Containing L-Phenylalanine Schiff Base and 1,10-Phenanthroline

Peiran Zhao  1 , Shanshan Zhai  1 , Jianfang Dong  1 , Lei Gao  2 , Xinru Liu  1 , Lei Wang  1 , Jinming Kong  3 , Lianzhi Li  1
Affiliations

Synthesis, Structure, DNA Interaction, and SOD Activity of Three Nickel(II) Complexes Containing L-Phenylalanine Schiff Base and 1,10-Phenanthroline

Peiran Zhao et al. Bioinorg Chem Appl. .

Abstract

Three hexacoordinated octahedral nickel(II) complexes, [Ni(sal-L-phe)(phen)(CH3OH)]·CH3OH (1), [Ni(naph-L-phe)(phen)(CH3OH)] (2), and [Ni(o-van-L-phe)(phen)(CH3OH)]·5CH3OH (3) (sal-L-phe = a Schiff base derived from salicylaldehyde and L-phenylalanine, naph-L-phe = a Schiff base derived from 2-hydroxy-1-naphthaldehyde and L-phenylalanine, o-van-L-phe = a Schiff base derived from o-vanillin and L-phenylalanine, and phen = 1,10-phenanthroline), have been synthesized and characterized by elemental analysis, IR spectra, and single-crystal X-ray diffraction. The interactions of these complexes with CT-DNA were studied by UV-Vis absorption spectroscopy, fluorescence spectroscopy, circular dichroism spectroscopy, and viscosity measurements. The binding constant (Kb) values of 1.82 × 104 M-1 for 1, 1.96 × 104 M-1 for 2, and 2.02 × 104 M-1 for 3 suggest that each of these complexes could bind with DNA in a moderate intercalative mode. Complex 3 exhibited a stronger interaction with CT-DNA than complexes 1 and 2. In addition, the superoxide scavenging activity of these complexes was investigated by the nitrotetrazolium blue chloride (NBT) light reduction method, and the results showed that they exhibited a significant superoxide scavenging activity with the IC50 values of 4.4 × 10-5 M for complex 1, 5.6 × 10-5 M for complex 2, and 3.1 × 10-5 M for complex 3, respectively.

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Figures

Scheme 1
Scheme 1
Synthetic routes for the preparation of complexes 1, 2, and 3.
Figure 1
Figure 1
FTIR spectra of the title complexes 1 (a), 2 (b), and 3 (c).
Figure 2
Figure 2
Molecular structures of complexes 1 (a), 2 (b), and 3 (c).
Figure 3
Figure 3
2D supramolecular network in complexes 1 (a), 2 (b), and 3 (c) formed by intermolecular hydrogen-bonding interactions. Some H atoms and C atoms were omitted for clarity.
Figure 4
Figure 4
UV-Vis spectra of complexes 1 (a), 2 (b), and 3 (c) in the absence and presence of CT-DNA; the complex concentration was 1.5 × 10−5 M, and DNA concentrations were 0, 0.5 × 10−5, 1.5 × 10−5, 3.0 × 10−5, 6.0 × 10−5, and 9.0 × 10−5 M corresponding to the curves from 1 to 6, respectively. The arrow shows the intensity change on increasing the DNA concentration.
Figure 5
Figure 5
Fluorescence quenching spectra of EB bound to CT-DNA by complexes 1 (a), 2 (b), and 3 (c). λex = 510 nm; DNA and EB concentrations were 1.0 × 10−5 and 1.0 × 10−5 M, and the complex concentrations were 0, 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, and 7.0 × 10−5 M corresponding to the curves from 1 to 8, respectively. The arrow shows the intensity change on increasing the complex concentration.
Figure 6
Figure 6
The Stern–Volmer fluorescence quenching curves.
Figure 7
Figure 7
Effect of complexes 1, 2, and 3 on CD spectra of CT-DNA. DNA concentration was 1.0 × 10−4 M, and the complex concentration was 4.0 × 10−5 M.
Figure 8
Figure 8
Effect of increasing amounts of complexes 1, 2, and 3, EB, and methyl green on the relative viscosity of CT-DNA (1.0 × 10−4 M at pH = 7.4).
Figure 9
Figure 9
Effect of the concentrations of complexes 1 (a), 2 (b), and 3 (c) on the absorbance (A 560) of the reaction system with time. [NBT] = 1.0 × 10−4 mol·L−1, [VB2] = 6.2 × 10−6 mol·L−1, [TMEDA] = 8.3 × 10−4 mol·L−1, [complex] = 0, 0.8 × 10−5, 1.6 × 10−5, 2.4 × 10−5, 3.2 × 10−5, 4.0 × 10−5, 4.8 × 10−5, and 5.6 × 10−5 mol·L−1.
Figure 10
Figure 10
The inhibitory rates of complexes 1, 2, and 3 varying with concentration.
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References

    1. Liu Y. J., Zeng C. H. Synthesis and DNA interaction studies of ruthenium(II) complexes with isatino[1,2-b]-1,4,8,9-tetraazatriphenylene as an intercalative ligand. Transition Metal Chemistry. 2009;34(4):455–462. doi: 10.1007/s11243-009-9216-x. - DOI
    1. Liu H., Li L., Guo Q., Dong J., Li J. Synthesis, crystal structure, DNA and BSA binding properties of a chromium(III) complex with L-glycine Schiff base and 1,10-phenanthroline. Transition Metal Chemistry. 2013;38(4):441–448. doi: 10.1007/s11243-013-9709-5. - DOI
    1. Li L., Guo Q., Dong J., Xu T., Li J. DNA binding, DNA cleavage and BSA interaction of a mixed-ligand copper(II) complex with taurine Schiff base and 1,10-phenanthroline. Journal of Photochemistry and Photobiology B: Biology. 2013;125:56–62. doi: 10.1016/j.jphotobiol.2013.05.007. - DOI - PubMed
    1. Genin M. J., Biles C., Keiser B. J., et al. Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives. Journal of Medicinal Chemistry. 2011;43(5):1034–1040. doi: 10.1021/jm990383f. - DOI - PubMed
    1. Verma M., Pandeya S. N., Singh K. N., Stables J. P. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica. 2004;54(1):49–56. - PubMed

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