Citation: ZHANG Chenglu, WANG Jing, LI Jingyi, YU Xiangkun, YANG Jingyi, CAI Jinhua, LI Yizheng, WANG Huayu, GONG Rongqing. Synthesis of 1, 2, 4-Triazine-Phenanthroline Co(Ⅲ) Complexes and Their Fluorescence Recognition on Calf Thymus DNA[J]. Chinese Journal of Applied Chemistry, ;2019, 36(2): 212-222. doi: 10.11944/j.issn.1000-0518.2019.02.180161 shu

Synthesis of 1, 2, 4-Triazine-Phenanthroline Co(Ⅲ) Complexes and Their Fluorescence Recognition on Calf Thymus DNA

  • Corresponding author: ZHANG Chenglu, zhangchenglu@lnnu.edu.cn
  • Received Date: 8 May 2018
    Revised Date: 27 September 2018
    Accepted Date: 15 October 2018

    Fund Project: Supported by Technology Research Program of Liaoning Provincial Department of Education(No.2009A426)Technology Research Program of Liaoning Provincial Department of Education 2009A426

Figures(8)

  • Four 1, 2, 4-triazine-phenanthroling derivatives(ARTP1~ARTP4) were designed and synthesized successfully. ARTP1~ARTP4 were selected to coordinate with Co3+ to afford four novel complexes(Co-ARTP1~Co-ARTP4). The structures and properties of ARTP1~ARTP4 and Co-ARTP1~Co-ARTP4 were studied by means of Fourier transform infrared spectrometer(FT-IR), nuclear magnetic resonance(NMR), high resolution mass spectrometry(HRMS) and ultraviolet-visible spectroscopy(UV-Vis). As a result, the excitation peaks of the complexes are weakened and show red shift. The complexes interact with calf thymus DNA(CT-DNA) through the insert mode and the binding constants are Kb=4.78×105, 6.52×105, 5.97×105 and 6.01×105 L/mol, respectively, which indicates that the complexes are expected to be the DNA fluorescence probes. It provides the important theory references for further study on the interaction between small organic molecules with DNA.
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    1. [1]

      Masato K, Ramesh G, Yang J H. Stereocoutroiled Synthesis of Syn- and Anti-diol Epoxide Metabolites of Triphenylene[J]. Tetrahedron Lett, 1996,46:8267-8270.

    2. [2]

      Pascal D, Rafika J, Johanne L. Synthesis of Novel Diarylamino-1, 3, 5-Triazine Derivatives as FAK Inhibitors with Anti-angiogenic Activity[J]. Bioorg Med Chem, 2013,23(16):4552-4556. doi: 10.1016/j.bmcl.2013.06.038

    3. [3]

      Irannejad H, Amini M, Khodagholi F. Synthesis and in Vitro Evaluation of Novel 1, 2, 4-Triazine Derivatives as Neuroprotective Agents[J]. Bioorg Med Chem, 2010,18(12):4224-4230. doi: 10.1016/j.bmc.2010.04.097

    4. [4]

      Congreve M, Andrews S P, Dore A S. Discovery of 1, 2, 4-Triazine Derivatives as Adenosine A2A Antagonists Using Structure Based Drug Design[J]. J Med Chem, 2012,55(5):1898-1903. doi: 10.1021/jm201376w

    5. [5]

      Shaul M, Cohen Y. Novel Phenanthroline-Containing Trinuclear Double-Stranded Helicates:Self-recognition Between Helicates with Phenanthroline and Bipyridine Binding Sites[J]. J Org Chem, 1999,64(26):9358-936. doi: 10.1021/jo9908905

    6. [6]

      Sigman D S. Nuclease Activity of 1, 10-Phenanthroline-Copper Ion[J]. J Org Chem, 1986,19(6):180-186.  

    7. [7]

      GAO Yunhua, LI Haifeng, LI Jianxin. Quantitative Analysis of High-resolution Inductively Coupled Plasma Mass Spectrometry with Fluorescent Labeled DNA[J]. Chem J Chinese Univ, 2010,31(12):2360-2365.  

    8. [8]

      LI Yurong, CHEN Changbao, ZHOU Jie. Polyethylene Oxide Non-gel Sieving Capillary Electrophoresis Separation of Wide Molecular Weight Range DNA Fragments[J]. Chem J Chinese Univ, 2011,32(4):844-850.  

    9. [9]

      LIU Tao, ZHANG Conglei, CHEN Ping. Time-Resolved Spectroscopy Study of the Interaction Between Methylene Blue and Calf Thymus DNA[J]. Chem J Chinese Univ, 2011,32(8):1854-1859.  

    10. [10]

      ZENG Guopin, XIANG Dongshan, CAI Jinzhang. Determination of H1N1 Avian Influenza Virus DNA with Fluorescent Probe Ru(phen)2(dppx)2+[J]. Chem J Chinese Univ, 2011,32(8):1737-1743.  

    11. [11]

      Peng X J, Wu T, Fan J L. An Effective Minor Groove Binder as a Red Fluorescent Marker for Live-Cell DNA Imaging and Quantification[J]. Angew Chem Int Ed, 2011,50(18):4180-4183. doi: 10.1002/anie.v50.18

    12. [12]

      Gill M R, Garcia L J, Foster S J. A Ruthenium(Ⅱ) Polypyridyl Complex for Direct Imaging of DNA Structure in Living Cells[J]. Nat Chem, 2009,1:662-667. doi: 10.1038/nchem.406

    13. [13]

      Wojcik K, Dobrucki J W. Interaction of a DNA Intercalator DRAQ5, and a Minor Groove Binder SYTO17, with Chromatin in Live Cells-Influence on Chromatin Organization and Histone-DNA Interactions[J]. Cytometry Part A, 2008,73(6):555-562.

    14. [14]

      ZHANG Ying, SUN Xiangying, LIU Bin. Fluorescent Recognition of Single- and Double-Stranded Deoxyribonucleic Acid by Rhodamine B Self-assembled Monolayer[J]. Chinese J Anal Chem, 2009(5):665-670. doi: 10.3321/j.issn:0253-3820.2009.05.007

    15. [15]

      Andreea P, Vickie M, Orla H. Regulating Bioactivity of Cu2+ Bis-1, 10-Phenanthroline Artificial Metallonucleases with Sterically Functionalized Pendant Carboxylates[J]. J Med Chem, 2013,56(21):8599-8615. doi: 10.1021/jm401465m

    16. [16]

      Pitie M, Pratviel G. Activation of DNA Carbon Hydrogen Bonds by Metal Complexes[J]. Chem Rev, 2010,110(2):1018-1059. doi: 10.1021/cr900247m

    17. [17]

      SHUI Yonghong. Cobalt and Social life[J]. J Chengdu Text College, 2000,17:61-62.  

    18. [18]

      WANG Genzhi, WANG Qiuxia. Trace Elements and Human Health[J]. Stud Trace Elem Health, 2004,21(2):54-56. doi: 10.3969/j.issn.1005-5320.2004.02.028

    19. [19]

      Battaglia V, Compagnone A, Bandino A. Cobalt Induces Oxidative Stress in Isolated Liver Mitochondria Responsible for Permeability Transition and Intrinsic Apoptosis in Hepatocyte Primary Cultures[J]. Int J Biochem Cell Biol, 2009,41(3):586-594. doi: 10.1016/j.biocel.2008.07.012

    20. [20]

      Kiran S, Manject S B, Parikshit T. Synthesis and Characterization of Cobalt(Ⅱ), Nickel(Ⅱ), Copper(Ⅱ) and Zinc(Ⅱ) Complexes with Schiff Base Derived from 4-Amino-3-Mercapto-6-Methyl-5-oxo-1, 2, 4-Triazine[J]. Eur J Med Chem, 2007,42(3):394-402. doi: 10.1016/j.ejmech.2006.10.016

    21. [21]

      CAI Jinhua, WANG Yue, XU Deqing. Synthesis of Bioactive Aryl Imidazole Derivatives and Their Applicationsfor the pH-Induced Luminescence Sensing Probe Chem[J]. Chem J Chinese Univ, 2014,35(4):750-754.  

    22. [22]

      Ziad M, Ahmed S A, ElDouhaibi A S. NMR Studies and Electrophilic Properties of Triphenyl Phosphine-Trifluoromethanesulfonic Anhydride; A Remarkable Dehydrating Reagent System for the Conversion of Aldoximes into Nitriles[J]. Tetrahedron Lett, 2010,51(14):1826-1831. doi: 10.1016/j.tetlet.2010.01.119

    23. [23]

      Swapnil S D, Sameerana N H, Ravindra R J. Oxidative Fragmentation of Oxiranes to Nitriles with Hypervalent Iodine(Ⅴ) Reagents in Aqueous Ammonia[J]. Tetrahedron Lett, 2011,52(35):4533-4536. doi: 10.1016/j.tetlet.2011.06.068

    24. [24]

      Suzanne F, Stephen J E, Anthony F H. Nitrile Ylide Dimerization:Investigation of the Carbene Reactivity of Nitrile Ylides[J]. J Org Chem, 2004,69(14):4663-4669. doi: 10.1021/jo049748g

    25. [25]

      Heinrich W, Milena T. Novel 6-Azapteridines from Bifunctional 1, 2, 4-Triazines[J]. Collect Czech Chem Commun, 2003,68(5):965-974. doi: 10.1135/cccc20030965

    26. [26]

      Irini A Z, Wang Y, Zhao H Y. Synthesis of Substituted Fused Pyridines, Pyrazines and Pyrimidines by Sequential Ugi/Inverse Electron Demand Diels-Alder Transformations[J]. Tetrahedron Lett, 2009,50(42):5773-5776. doi: 10.1016/j.tetlet.2009.07.036

    27. [27]

      Zou X H, Ye B H, Li H. Mono- and bi-Nuclear Ruthenium(Ⅱ) Complexes Containing a New Asymmetric Ligand 3-(Pyrazin-2-yl)-as-Triazino[5, 6-f]1, 10-Phenanthroline:Synthesis, Characterization and DNA-Binding Properties[J]. J Chem Soc Dalton Trans, 1999,9:1423-1428.

    28. [28]

      Pabst G R, Pfüller O C, Sauer J. The New and Simple LEGO' System:Its Application for the Synthesis of 6-Oligopyridyl-1, 5, 12-Triazatriphenylenes[J]. Tetrahedron Lett, 1998,39(48):8825-8828. doi: 10.1016/S0040-4039(98)02044-9

    29. [29]

      Chao H, Qiu Z R, Cai L R. Mono-, Di-, and Tetranuclear Ruthenium(Ⅱ) Complexes Containing 3-(Pyridin-2-yl)-as-Triazino[5, 6-f]1, 10-Phenanthroline:Synthesis, Characterization, and Electrochemical and Photophysical Properties[J]. Inorg Chem, 2003,42(26):8823-8830. doi: 10.1021/ic034769z

    30. [30]

      Vlcek A A. Preparation of Co(dipy)2X2+ Complexes(X-=C1-, Br-, I-, NO2-) by Controlled Oxidative Processes[J]. Inorg Chem, 1967,7(6):1425-1427.

    31. [31]

      WANG Qiang. Synthesis, Characterization and Biological Activity of Methionine Schiff Base Complexes[D]. Ocean University of China, 2011(in Chinese) 

    32. [32]

      HU Yamin, WANG Xingming, ZHANG Huan. Research Progress of the Interactions Between Metal Complexes and DNA[J]. Chem Bioeng, 2007,24(8):1-4. doi: 10.3969/j.issn.1672-5425.2007.08.001

    33. [33]

      XIANG Pengzhi, LIU Limei. Research Methods and Progress of Interaction Between Metal Complexes and DNA[J]. J Hengshui Univ, 2011,13(1):33-35. doi: 10.3969/j.issn.1673-2065.2011.01.013

    34. [34]

      GAO Ting, ZHANG Wanju, WANG Fang. Application of UV Spectroscopy in the Study of Interaction Between Metal Complexes and DNA[J]. Guangzhou Chem Ind, 2010,38(5):23-25. doi: 10.3969/j.issn.1001-9677.2010.05.009

    35. [35]

      JIANG Caiwu. Novel Asymmetric Tridentate Polypyridine Ligands and Their Mixtures of Ruthenium(Ⅱ) Complexes Synthesis, Characterization, and Interaction with DNA[J]. Acta Chim Sin, 2004,62(7):692-696. doi: 10.3321/j.issn:0567-7351.2004.07.009

    36. [36]

      ZHEN Qixiong, YE Baohui, LIU Jingang. Syntheses and Insertion of Ligand Complexes Effect of Steric Hindrance on DNA Binding[J]. Chem J Chinese Univ, 1999,20(11):1661-1666. doi: 10.3321/j.issn:0251-0790.1999.11.001

    37. [37]

      KANG Yong, AI Shi. Interaction Between Inorganic Metal Complexes and DNA[J]. Biomed Eng Prog, 2011,31(1):24-28. doi: 10.3969/j.issn.1674-1242.2011.01.006

    38. [38]

      Ekmekci Z. Highly Selective Fluorescence'Turn-Off'Sensors for Cu2+ in Aqueous Environments[J]. Tetrahedron Lett, 2015,56(14):1878-1881. doi: 10.1016/j.tetlet.2015.02.099

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