Citation: YANG Lining, HEI Jiahui, CHENG Zhao, Li li, YU Lili. Synthesis, Crystal Structures and DNA Interaction of Nickel and Cadmium Complexes Involving Biimidazole[J]. Chinese Journal of Applied Chemistry, ;2016, 33(6): 710-718. doi: 10.11944/j.issn.1000-0518.2016.06.150350 shu

Synthesis, Crystal Structures and DNA Interaction of Nickel and Cadmium Complexes Involving Biimidazole

YANG Lining ^a,, ,
HEI Jiahui ^b ,
CHENG Zhao ^a ,
Li li ^a ,
YU Lili ^a

1.
a Department of Pharmacy, Medical University of Xi'an, Xi'an 710021, China;
2.
b Shaanxi Aerospace Staffs & Vocation University, Xi'an 710100, China

Corresponding author: YANG Lining,
Received Date: 28 September 2015
Available Online: 2 February 2016
Fund Project:

Two complexes {[Ni(H₂biim)₃](phth)}(H₂biim=2,2'-biimidazole, phth=phthalate)(1) and[Cd(H₃biim)₂Cl₄](2) were synthesized under hydrothermal and common solution conditions, and characterized by elemental analysis, IR spectroscopy and single crystal X-ray diffraction analysis. Complex 1 consists of[Ni(H₂biim)₃]²⁺ cations hydrogen bonds with phthalate dianions. Each Ni atom coordinates six N atoms of three chelating biimidazole ligands in a pseudo-octahedral geometry. Complex 2 is a neutral compound. One N atom in H₂biim is protonated, forming a H₃biim⁺ cation. The central metal Cd is coordinated by two unidentate H₃biim⁺ ligands and four Cl atoms. The binding of the complexes with calf thymus DNA has been investigated by UV and fluorescence spectroscopy and viscosity measurement. All of the results indicate that the complexes 1 and 2 bind to DNA base pairs in intercalation and partial intercalation modes, respectively.
- biimidazole,
- the nickel and cadmium complexes,
- crystal structure,
- DNA
1. [1]
  [1] LI Guanying,ZOU Shanshan,CHAO Hui,et al.Recent Advances in DNA Interactions with Ruthenium (Ⅱ) Polypyridyl Complexes[J].Sci Sin Chim,2014,44(4):448-459(in Chinese).李观营,邹姗珊,巢晖,等.钌多吡啶配合物与DNA相互作用研究新进展[J].中国科学:化学,2014,44(4):448-459.
2. [2]
  [2] Liu L,Zhang H,Meng X G,et al.Dinuclear Metal (Ⅱ) Complexes of Polybenzimidazole Ligands as Carriers for DNA Delivery[J].Biomaterials,2010,31(6):1380-1391.
3. [3]
  [3] Yin J,Meng X G,Zhang S B,et al.The Effect of a Nuclear Localization Sequence on Transfection Efficacy of Genes Delivered by Cobalt (Ⅱ)-polybenzimidazole Complexes[J].Biomaterials,2012,33(31):7884-7894.
4. [4]
  [4] Jiang R,Yin J,Hu S,et al.Cobalt (Ⅱ)-polybenzimidazole Complexes as a Nonviral Gene carrier:Effects of Charges and Benzimidazolyl Groups[J].Curr Drug Deliv,2013,10(1):122-133.
5. [5]
  [5] Yang X,Chen L,Liu Y,et al.Ruthenium Methylimidazole Complexes Induced Apoptosis in Lung Cancer A549cells Through Intrinsic Mitochondrial Pathway[J].Biochimie,2012,94(2):345-353.
6. [6]
  [6] Tadokoro M,Nakasuji K.Hydrogen Bonded 2,2'-Biimidazolate Transition Metal Complexes as a Tool of Crystal Engineering[J].Coord Chem Rev,2000,198(1):205-218.
7. [7]
  [7] Yu K,Wan B,Yu Y,et al.Assembly of Organic-inorganic Hybrid Supramolecular Materials Based on Basketlike{McP₆Mo₁₂O₇₃}(M=Ca,Sr,Ba) Cage and Transition-metal Complex[J].Inorg Chem,2013,52(1):485-498.
8. [8]
  [8] Meng C L,Zhang P P,Peng J,et al.Keggin-type Polyoxometalate Cluster Functionalized with Dinuclear M-H₂biim (M=Cu,Ag) Metal-organic Segments[J].J Clust Sci,2012,23(2):567-576.
9. [9]
  [9] Yang C Y,Zhang L C,Wang Z J,et al.Three New Extended Preyssler-type Polyoxometalates Modified by Transition metal-2,2'-Biimidazole Complexes[J].J Solid State Chem,2012,194:270-276.
10. [10]
  [10] Tan C P,Hu S,Liu J,et al.Synthesis,Characterization,Antiproliferative and Anti-metadtatic Properties of Two Ruthenium-DMSO Complexes Containing 2,2'-Biimidazole[J].Eur J Med Chem,2011,46(5):1555-1563.
11. [11]
  [11] Sowwan M,Haj M A,Faroun M,et al.Growth of 2,2'-Biimidazole-based Nanorods on Mica Substrate[J].J Nanomater,2010,2010:706920.
12. [12]
  [12] Borel C,Larsson K,Hakansson M,et al.Oxalate-and Squarate-biimidazole Supramolecular Synthons:Hydrogen-bonded Networks Based on[Co (H₂biimidazole)₃]³⁺[J].Cryst Growth Des,2009,9(6):2821-2827.
13. [13]
  [13] Jin H J,Zhou B B,Yu Y,et al.Inorganic-organic Hybirds Constructed from Heteropolymolyb Date Anions and Copper-organic Fragments:Syntheses,Structures and Properties[J].Cryst Eng Comm,2011,13(2):585-590.
14. [14]
  [14] Buist D,Williams N J,Reibenspies J H,et al.Control of Metal Ion Size-based Selectivity Through Chelate Ring Geometry.Metal ion Complexing Properties of 2,2'-Biimidazole[J].Inorg Chem,2010,49(11):5033-5039.
15. [15]
  [15] Mo H J,Niu Y L,Zhang M,et al.Photophysical,Electrochemical and Anion Sensing Properties of Ru (Ⅱ) Bipyridine Complexes with 2,2'-Biimidazole-like Ligand[J].Dalton Trans,2011,40(32):8218-8225.
16. [16]
  [16] Phan H V,Chakraborty P,Chen M,et al.Heteroleptic FeⅡ Complexes of 2,2'-Biimidazole and its Alkylated Derivatives:Spin-crossover and Photomagnetic Behavior[J].Chem-Eur J,2012,18(49):15805-15815.
17. [17]
  [17] Casas J S,Castineiras A,Parajo Y,et al.Pd (Ⅱ) and Pt (Ⅱ) Complexes of 2,2'-Biimidazole and Its N,N'-Dimethyl Derivative.The Crystal Structure of[{PtBr (DMSO)}₂(Me₂bim)](Me₂bim=N,N'-dimethyl-2,2'-biimida-zole)[J].Polyhedron,2003,22(8):1113-1121.
18. [18]
  [18] Ramirez K,Reyes J A,Briceno A,et al.Supramolecular Building Blocks from Modular Self-assembly of Biimidazolium Species.Crystal Structure of 2-(2-1H-imidazolyl)-1H-Imidazolium Chloride Monohydrate[J].Cryst Eng Comm,2002,4(38),208-212.
19. [19]
  [19] Fieselmann B F,Hendrickson D N,Stucky G D.Synthesis,Electron Paramagnetic Resonance,and Magnetic Studies of Binuclear bis (.eta.5-cyclopentadienyl) titanium (Ⅲ) Compounds with Bridging Pyrazolate,Biimidazolate,and Bibenzimidazolate Anions[J].Inorg Chem,1978,17(8),2078-2084.
20. [20]
  [20] Wu S S,Yuan W B,Wang H Y,et al.Synthesis,Crystal Structure and Interaction with DNA and HAS of (N,N'-dibenzylethane-1,2-diamine) Transition Metal Complexes[J].J Inorg Biochem,2008,102(11):2026-2034.
21. [21]
  [21] Liu M,Yuan W B,Zhang Q,et al.Synthesis,Characterization and DNA Interaction Studies of Complexes of Lanthanide Nitrates with tris{2-[(3,4-Dihydroxybenzylidene) imino]ethyl}amine[J].Spectrochim Acta Part A,2008,70(5):1114-1119.
22. [22]
  [22] Sheldrick G M.SHELXL97,Program for the Refinement of Crystal Structure[M].University of Gottingen Germany,1997.
23. [23]
  [23] Tadokoro M,Isobe K,Uekusa H,et al.Cation-Dependent Formation of Superstructures by One-Pot SelfOrganization of Hydrogen-Bonded Nickel Complexes[J].Angew Chem Int Ed,1999,38(1/2):95-98.
24. [24]
  [24] Yang L N,Zhi Y X,Hei J H,et al.Two Coordination Polymers Based on 2,2'-Biimidazoles and d¹⁰ Metal ions:Syntheses,Structures,and Luminescence[J].J Coord Chem,2011,64(16):2912-2922.
25. [25]
  [25] Sang R,Xu L.A Series of Single,Double,and Triple Me₂biim-bridged Dinuclear,Trinuclear,and Polymeric Complexes:Syntheses,Crystal Structures,and Luminescent Properties[J].Inorg Chem,2005,44(10):3731-3737.
26. [26]
  [26] Friedman A E,Chambron J C,Sauvage J P,et al.A Molecular Light Switch for DNA:Ru (bpy)₂(dppz)²⁺[J].J Am Chem Soc,1990,112(12):4960-4962.
27. [27]
  [27] Ramakrishnan S,Suresh E,Riyasdeen A,et al.Interaction of rac-[M (diimine)₃]²⁺(M=Co,Ni) Complexes with CT DNA:Role of 5,6-dmp Ligand on DNA Binding and Cleavage and Cytotoxicity[J].Dalton Trans,2011,40(13):3245-3256.
28. [28]
  [28] Li Y,Yang P.Synthesis,Crystal Structure,and DNA-Binding Properties of a New Cd (Ⅱ) Complex Involving 2-(2-1H-Imidazolyl)-1H-Imdazolium Ligand[J].Chinese J Chem,2010,28(5):759-765.
29. [29]
  [29] Abdi K,Hadadzadeh H,Weil M,et al.Mononuclear Copper (Ⅱ) Complex with Terpyridine and an Extended Phenanthroline Base,[Cu (tpy)(dppz)]²⁺:Synthesis,Crystal Structure,DNA Binding and Cytotoxicity Activity[J].Polyhedron,2012,31(1):638-648.
30. [30]
  [30] Efink M R,Ghiron C A.Fluorescence Quenching Studies with Proteins[J].Anal Biochem,1981,114(2):199-206.
31. [31]
  [31] Pyle A M,Rehmann J P,Meshoyrer R,et al.Mixed-ligand Complexes of Ruthenium (Ⅱ):Factors Governing Binding to DNA[J].J Am Chem Soc,1989,111(8):3051-3058.
32. [32]
  [32] Satyanarayana S,Dabrowiak J C,Chaires J B.Neither △-nor Λ-Tris (Phenan-throline) ruthenium (Ⅱ) Binds to DNA by Classical Intercalation[J].Biochem,1992,31(39):9319-9324.
33. [33]
  [33] Liu J G,Zhang Q L,Shi X F,et al.Interaction of[Ru (dmp)₂(dppz)]²⁺and[Ru (dmb)₂(dppz)]²⁺ with DNA:Effects of the Ancillary Ligands on the DNA-binding Behaviors[J].Inorg Chem,2001,40(19):5045-5050.
34. [34]
  [34] Satyanarayana S,Dabrowiak J C,Chaires J B.Tris (phenanthroline) Ruthenium (Ⅱ) Enantiomer Interactions with DNA:Mode and Specificity of Binding[J].Biochemistry,1993,32(10):2573-2584.
1. [1]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
2. [2]
  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
3. [3]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
4. [4]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
5. [5]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
6. [6]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
7. [7]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
8. [8]
  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
9. [9]
  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
10. [10]
  Yan Liu , Yuexiang Zhu , Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084
11. [11]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
12. [12]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
13. [13]
  Junqiao Zhuo , Xinchen Huang , Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100
14. [14]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
15. [15]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016
16. [16]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
17. [17]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
18. [18]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
19. [19]
  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
20. [20]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(254)
HTML views(36)

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