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

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

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 K_b=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.
- phenanthroline,
- 1, 2, 4-triazine,
- calf thymus DNA,
- fluorescence probe,
- Co-complexes
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
1. [1]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
2. [2]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
3. [3]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
4. [4]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
5. [5]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
6. [6]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
7. [7]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
8. [8]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
9. [9]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
10. [10]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
11. [11]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
12. [12]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
13. [13]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
14. [14]
  Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105
15. [15]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
16. [16]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
17. [17]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
18. [18]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
19. [19]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
20. [20]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(679)
HTML views(163)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142