Synthesis of 1,2,4-Triazine-PhenanthrolineCo(Ⅲ) Complexes and Their FluorescenceRecognition on Calf Thymus DNA

doi:10.11944/j.issn.1000-0518.2019.02.180161

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (2): 212-222.DOI: 10.11944/j.issn.1000-0518.2019.02.180161

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Synthesis of 1,2,4-Triazine-PhenanthrolineCo(Ⅲ) Complexes and Their FluorescenceRecognition on Calf Thymus DNA

ZHANG　Chenglu(),WANG　Jing,LI Jingyi,YU Xiangkun,YANG Jingyi,CAI Jinhua,LI Yizhen,WANG Huayu,GONG Rongqing

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

Received:2018-05-08 Published:2019-02-01 Online:2019-01-31
Contact: ZHANG　Chenglu
Supported by:
Supported by Technology Research Program of Liaoning Provincial Department of Education(No.2009A426)

Abstract

Abstract:

Four 1,2,4-triazine-phenanthroling derivatives(ARTP1ARTP4) were designed and synthesized successfully. ARTP1ARTP4 were selected to coordinate with Co³⁺ to afford four novel complexes(Co-ARTP1Co-ARTP4). The structures and properties of ARTP1ARTP4 and Co-ARTP1Co-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.

Key words: phenanthroline, 1,2,4-triazine, calf thymus DNA, fluorescence probe, Co-complexes

ZHANG　Chenglu, WANG　Jing, LI Jingyi, YU Xiangkun, YANG Jingyi, CAI Jinhua, LI Yizhen, WANG Huayu, GONG Rongqing. Synthesis of 1,2,4-Triazine-PhenanthrolineCo(Ⅲ) Complexes and Their FluorescenceRecognition on Calf Thymus DNA[J]. Chinese Journal of Applied Chemistry, 2019, 36(2): 212-222.

References

[1]	Masato K,Ramesh G,Yang J H,et al. Stereocoutroiled Synthesis of Syn- and Anti-diol Epoxide Metabolites of Triphenylene[J]. Tetrahedron Lett,1996,46:8267-8270.
[2]	Pascal D,Rafika J,Johanne L,et al. 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.
[3]	Irannejad H,Amini M,Khodagholi F,et al. Synthesis and in Vitro Evaluation of Novel 1,2,4-Triazine Derivatives as Neuroprotective Agents[J]. Bioorg Med Chem,2010,18(12):4224-4230.
[4]	Congreve M,Andrews S P,Dore A S,et al. 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.
[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.
[6]	Sigman D S.Nuclease Activity of 1,10-Phenanthroline-Copper Ion[J]. J Org Chem,1986,19(6):180-186.
[7]	GAO Yunhua,LI Haifeng,LI Jianxin,et al. Quantitative Analysis of High-resolution Inductively Coupled Plasma Mass Spectrometry with Fluorescent Labeled DNA[J]. Chem J Chinese Univ,2010,31(12):2360-2365(in Chinese). 高运华,李海峰,李建新,等. 荧光标记DNA高分辨电感耦合等离子质谱定量分析[J]. 高等学校化学学报,2010,31(12):2360-2365.
[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 (in Chinese). 李玉荣,陈长宝,周杰. 聚环氧乙烷无胶筛分毛细管电泳分离宽分子量范围DNA片段[J]. 高等学校化学学报,2011,32(4):844-850.
[9]	LIU Tao,ZHANG Conglei,CHEN Ping,et al. Time-Resolved Spectroscopy Study of the Interaction Between Methylene Blue and Calf Thymus DNA[J]. Chem J Chinese Univ,2011,32(8):1854-1859(in Chinese). 刘涛,张崇磊,陈平,等. 时间分辨光谱技术研究亚甲基蓝与小牛胸腺DNA的相互作用[J]. 高等学校化学学报,2011,32(8):1854-1859.
[10]	ZENG Guopin,XIANG Dongshan,CAI Jinzhang,et al. 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(in Chinese). 曾国平,向东山,蔡金杖,等. 荧光探针Ru(phen)2(dppx)2+测定H1N1禽流感病毒DNA[J]. 高等学校化学学报,2011,32(8):1737-1743.
[11]	Peng X J,Wu T,Fan J L,et al. 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.
[12]	Gill M R,Garcia L J,Foster S J,et al. A Ruthenium(Ⅱ) Polypyridyl Complex for Direct Imaging of DNA Structure in Living Cells[J]. Nat Chem,2009,1:662-667.
[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]	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,(6):665-670(in Chinese). 张莺,孙向英,刘斌. 罗丹明B自组装膜对单、双链脱氧核糖核酸的荧光识别[J]. 分析化学,2009,(5):665-670.
[15]	Andreea P,Vickie M,Orla H,et al. Regulating Bioactivity of Cu2+ Bis-1,10-Phenanthroline Artificial Metallonucleases with Sterically Functionalized Pendant Carboxylates[J]. J Med Chem,2013,56(21):8599-8615.
[16]	Pitie M,Pratviel G.Activation of DNA Carbon Hydrogen Bonds by Metal Complexes[J]. Chem Rev,2010,110(2):1018-1059.
[17]	SHUI Yonghong.Cobalt and Social life[J]. J Chengdu Text College,2000,17:61-62(in Chinese). 税永红. 钴与社会生活[J]. 成都纺织高等专科学校学报,2000,17:61-62.
[18]	WANG Genzhi,WANG Qiuxia.Trace Elements and Human Health[J]. Stud Trace Elem Health,2004,21(2):54-56(in Chinese). 王根志,王秋霞. 微量元素与人体健康[J]. 微量元素与健康研究,2004,21(2):54-56.
[19]	Battaglia V,Compagnone A,Bandino A,et al. 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.
[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.
[21]	CAI Jinhua,WANG Yue,XU Deqing,et al. 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(in Chinese). 柴金华,王越,徐德青,等. 具有生物活性的芳基咪唑并邻菲啰啉衍生物的合成及用作pH荧光传感探针[J]. 高等学校化学学报,2014,35(4):750-754.
[22]	Ziad M,Ahmed S A,ElDouhaibi A S,et al. 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.
[23]	Swapnil S D,Sameerana N H,Ravindra R J,et al. Oxidative Fragmentation of Oxiranes to Nitriles with Hypervalent Iodine(Ⅴ) Reagents in Aqueous Ammonia[J]. Tetrahedron Lett,2011,52(35):4533-4536.
[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.
[25]	Heinrich W,Milena T.Novel 6-Azapteridines from Bifunctional 1,2,4-Triazines[J]. Collect Czech Chem Commun,2003,68(5):965-974.
[26]	Irini A Z,Wang Y,Zhao H Y,et al. 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.
[27]	Zou X H,Ye B H,Li H,et al. 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]	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.
[29]	Chao H,Qiu Z R,Cai L R,et al. 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.
[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]	WANG Qiang.Synthesis, Characterization and Biological Activity of Methionine Schiff Base Complexes[D]. Ocean University of China,2011(in Chinese) 王强. 氨基酸类希夫碱配合物的合成、表征及生物活性研究[D]. 中国海洋大学,2011.
[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(in Chinese). 胡亚敏,王兴明,张欢. 金属配合物与DNA相互作用的研究进展[J]. 化学与生物工程,2007,24(8):1-4.
[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(in Chinese). 项朋志,刘丽梅. 金属配合物与DNA相互作用研究手段和进展[J]. 衡水学院学报,2011,13(1):33-35.
[34]	GAO Ting,ZHANG Wanju,WANG Fang,et al. Application of UV Spectroscopy in the Study of Interaction Between Metal Complexes and DNA[J]. Guangzhou Chem Ind,2010,38(5):23-25(in Chinese). 高婷,张万举,王芳,等. 紫外光谱在研究金属配合物与DNA相互作用中的应用[J]. 广州化工,2010,38(5):23-25.
[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(in Chinese). 蒋才武. 新型不对称三齿多吡啶配体及其混配钌(Ⅱ)配合物的合成、表征及与DNA相互作用研究[J]. 化学学报,2004,62(7):692-696.
[36]	ZHEN Qixiong,YE Baohui,LIU Jingang,et al. Syntheses and Insertion of Ligand Complexes Effect of Steric Hindrance on DNA Binding[J]. Chem J Chinese Univ,1999,20(11):1661-1666(in Chinese). 甄启雄,叶保辉,刘劲刚,等. 钌多吡啶配合物的合成及插入配体的位阻效应对键合DNA的影响[J]. 高等学校化学学,1999,20(11):1661-1666.
[37]	KANG Yong,AI Shi.Interaction Between Inorganic Metal Complexes and DNA[J]. Biomed Eng Prog,2011,31(1):24-28(in Chinese). 康永,艾昰. 无机金属配合物与DNA的相互作用问题[J]. 生物医学工程学进展,2011,31(1): 24-28.
[38]	Ekmekci Z.Highly Selective Fluorescence‘Turn-Off’Sensors for Cu2+ in Aqueous Environments[J]. Tetrahedron Lett,2015,56(14):1878-1881.

Synthesis of 1,2,4-Triazine-PhenanthrolineCo(Ⅲ) Complexes and Their FluorescenceRecognition on Calf Thymus DNA

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