稀土、(稀土—铜)类金属配合物的合成、表征及其相关生物活性研究
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摘要
近年来金属配合物在抗菌、抗肿瘤以及与DNA相互作用等方面的研究一直是生物无机化学研究的热点。本文则以稀土离子和铜离子在这三方面的生物性能为着眼点,合成了10种纳米稀土谷氨酸咪唑三元配合物(简称纳米稀土配合物)和8种稀土-铜甘氨酸咪唑异核金属配合物(简称稀土-铜配合物)。通过元素分析、摩尔电导、红外光谱、紫外光谱、氢谱、碳谱、XRD、差热-热重以及TEM等方法对它们的组成、结构和形貌进行了表征,确定了它们的化学组成为:RE(Glu)_3ImCl_3·3H_2O(RE~(3+)=La~(3+),Ce~(3+),Pr~(3+),Nd~(3+),Sm~(3+),Er~(3+),Eu~(3+),Y~(3+),Gd~(3+),Dy~(3+); L-Glu =C_5H_9NO_4;Im=C_3H_4N_2)和RECu_6(μ-OH)_3(Gly)_6Im_6Cl_6(RE~(3+)=La~(3+),Ce~(3+),Pr~(3+),Nd~(3+), Sm~(3+), Er~(3+),Eu~(3+),Y~(3+);L-Gly=C_2H_5NO_2;Im=C3H_4N_2)。
     采用培养基扩散法和营养肉汤稀释法测定了上述18种金属配合物的抗菌活性,结果表明:所合成的这18种金属配合物对大肠杆菌、金黄色葡萄球菌和白色念珠菌均具有较好的抗菌性,属于广谱抗菌剂,且具有耐久性和长效性。
     采用形态学观察、MTT比色实验和流式细胞仪检测等方法研究了纳米稀土镧配合物、镧-铜配合物对K562白血病肿瘤细胞的凋亡和生长的抑制作用。结果表明:该两种金属配合物均能够诱导K562肿瘤细胞凋亡,抑制其生长,但是有浓度依赖性和时间依赖性;并且它们对K562肿瘤细胞的凋亡率和生长抑制率均高于其相应配体。
     采用紫外吸收光谱、荧光光谱、粘度分析和琼脂糖凝胶电泳分析等方法研究了纳米稀土镧配合物和镧-铜配合物与DNA的相互作用模式。结果表明:该两种金属配合物都是以部分插入模式与DNA相互作用的,其中镧-铜配合物对DNA的插入模式稍强一些,测得其与DNA的结合常数约为3.78×10~4 L·mol~(-1),而且该配合物还能够有效切割pBR322DNA,但是有浓度依赖性。
In recent years, the development of metal complexes have been the active field of bioinorganic chemistry in the study of antibacterial, antitumor and with DNA interaction. On the biological properties of RE~(3+) and Cu2+, ten new nano-rare earth complexes with L-glutamic acid and imidazole,and eight rare earth-copper complexes with L-glycine and imidazole were synthesized.Their composition and structure was characterized by elemental analysis,molar conductance, IR, UV, 1HNMR, 13CNMR, X-RD, TG-DTA and TEM etc.The compositions of the complexes were confirmed to be RE(Glu)_3ImCl_3·3H_2O(RE~(3+)=La~(3+),Ce~(3+),Pr~(3+),Nd~(3+),Sm~(3+),Er~(3+), Eu~(3+),Y~(3+),Gd~(3+),Dy~(3+); L-Glu =C_5Hv9NO_4; Im=C_3H_4N_2)and RECu_6(μ-OH)_3(Gly)_6Im_6Cl_6(RE~(3+)=La~(3+),Ce~(3+),Pr~(3+),Nd~(3+), Sm~(3+),Er~(3+),Eu~(3+),Y~(3+); L-Gly=C_2H_5NO_2; Im= C_3H_4N_2)。
     The antibacterial activities of the complexes were evaluated by the agar diffusion method and nutrition broth dilution method. The results indicated that all the eighteen complexes exhibited excellent antibacterial activities against Escherichia coli, Staphylococcus aureus and Candida albicans,their antimicrobial spectrum were broad and have durable quality.
     The antitumor activity of the nano-rare earth La complex and La-Cu complex in vitro were researched by morphological observation, MTT assay and Flow Cytometry. The results showed that the two complexes all could induced K562 tumor cells apoptosis and inhibited their growth,but the cell apoptosis rate and the inhibition rate both higher than their ligands and have concentration-dependent and time-dependent.
     The interaction of the nano-rare earth La complex and La-Cu complex with DNA were studyed by UV, fluorescence spectrum, viscosity analysis and agarose gel electrophoresis etc.The results indicated that the interaction of the two complexes would bind DNA mainly by partially intercalation and the La-Cu complex could cleave pBR322DNA effectively,but has concentration-dependent.
引文
[1] 杨静,何其庄,郁慧,封婕,孙剑剑.稀土苯丙氨酸邻菲咯啉三元配合物的合成、表征及抗菌活性研究.中国稀土学报[J]. 2006,24(01):103-109.
    [2] 赵国良,张萍华,冯云龙.金刚烷胺邻香兰素 Schiff 碱稀土配合物的合成、表征及抗菌活性研究.无机化学学报[J].2005,21(3):421-424.
    [3] 曹锦荣,王则民,杨海峰.稀土苯甲酸 8-羟基喹啉配合物的研究.上海师范大学学报(自然科学版) [J].1997,26(1):50-56.
    [4] 王则民.稀土水杨酸8-羟基喹啉配合物的表征和抑菌效应.自然杂志[J].1995, 17(1):54-55.
    [5] 张仲生,吴集贵.硼合山梨醇稀土化合物的制备和抑菌作用.兰州大学学报[J].1989,25(3):157-158.
    [6] 宋之刚,曲建强,王流芳.间羟基苯甲酸邻菲罗琳稀土三元配合物的合成、表征和抗菌活性研究.化学研究与应用[J].1999, 11(1):41-45.
    [7] 王流芳,吴集贵,高竹青等.高竹青等对羟基苯甲酸 8-羟基喹啉稀土三元配合物的合成与性质. 兰州大学学报(自然科学版) [J].1995, 31(2):165-167. [ 8 ] 夏金虹 , 刘峥 , 冯小珍 .β- 氨基酸 Schiff 碱铜 (Ⅱ) 配合物的合成及表征 . 化学世界[J].2007,(6):321-325.
    [9] 唐定兴,冯丽霞.配合物[Cu2(C4H2O6)(Phen)2(H2O)]·8H2O 的合成、晶体结构和抗菌活性.无机化学学报[J].2007,23(4):635-639.
    [10] 蒋毅民,张淑华,徐庆,肖瑜.双核Cu(Ⅱ)-牛磺酸缩水杨醛席夫碱配合物的合成、晶体结构及生物活性.化学学报[J].2007,61(4):573-577.
    [11] Rosenberg B,et al.Cancer Res.Nature(London) [J].1970,30(30):1799.
    [12] Chu G.Cellular responses to cisplatin.The roles of DNA-binding proteins and DNA repair.J Biol Chem. [J].1994,269(2):787-790.
    [13] Keppler B.K.,Friesen C.,Moritz H.G.,et al.Tumor-inhibiting bis(β-Diketonato) metal complexes. Budotitane,cis-diethoxybis(1-phenylbutane-1,3-dionato)titanium(IV).Struct.Bonding.[J].1991,78(7):97-127.
    [14] H. Bischoff, M. R. Berger, Keppler B.K., et al.Efficacy of β-diketonato complexes of titanium, zirconium, and hafnium against chemically induced autochthonous colonic tumors in rats.Journal of Cancer Research and Clinical Oncology. [J].1987, 113(5):446-450.
    [ 15 ] Harstrick A.,Schmol H.J.,Sass G., et al.Titanocendichloride activity in cisplatin and doxorubicin-resistant human ovarian carcinoma cell lines. Eur.J.Cancer[J].1993, 29(7):1000-1002.
    [16] Korfel A.,Scheulen M.E.,Schmoll H.J,et al. Phase I clinical and pharmacokinetic study of titanocene dichloride in adults with advanced solid tumors.Clin Cancer Res.[J].1998,4(11): 2701-2708.
    [ 17 ] Christian M.Kurbacher and Ian A. Cree,In vitro activity and chemomodulation of titanocenedichloride versus doxorubicin and cis platin in human breast cancer cells. Journal of Cancer Research and Clinical Oncology[J].1995,121(1):A49.
    [18] Gianni S., Sabrina P., Giovanni M.,et al.Na[trans-RuCl4(DMSO)Im], a metal complex of ruthenium with antimetastatic properties.Clinical and Experimental Metastasis.[J].1992, 10(4):273-280.
    [19] Alessio E.,Balducci G.,Lutman A., et al. Synthesis and characterization of two new classes of ruthenium(III)-sulfoxide complexes with nitrogen donor ligands (L): Na[trans-RuCl4(R2SO)(L)] and mer, cis-RuCl3(R2SO)(R2SO)(L).Inorg. Chim.Acta. [J].1993,203(2):205-217.
    [20] Kratz F.,keppler B.K.,Hartmann M., et al. Comparison of the antiproliferative activity of two antitumour ruthenium(III) complexes with their apotransferrin and transferrin-bound forms in a human colon cancer cell line.Metal-based drugs[J]. 1996,3(1):15-24.
    [21] Frasca D.,Ciampa J.,Emerson J.,et al.Effects of hypoxia and transferrin on toxicity and DNA binding of Ruthenium antitumor agents in hela cells. Metal-Based Drugs[J].1996,3(1):197-210.
    [22] Easmon J.,Purstinger G.,Heinisch G., et al. Synthesis, Cytotoxicity, and Antitumor Activity of Copper(II) and Iron(II) Complexes of 4N-Azabicyclononane Thiosemicarbazones Derived from Acyl Diazines.J.Med.Chem[J].2001,44(13):2164-2171.
    [23] Ferrari M.B.,Bisceglie F.,Pelosi G., et al. Synthesis, characterization and biological activity of copper complexes with pyridoxal thiosemicarbazone derivatives. X-ray crystal structure of three dimeric complexes.J.Inorg.Biochem[J].2004,98(2):301-312.
    [24] De Vizcaya-Ruiz A.,Rivero-Muller A.,Ruiz-Ramirez L.,et al. Induction of apoptosis by a novel copper-based anticancer compound, Casiopeina II, in L1210 murine leukaemia and CH1 human ovarian carcinoma cells.Toxicology.In Vitro[J]. 2000,14(1):1-5.
    [25] Gracia-Mora L.,Ruiz-Ramirez L.,Gomez-Ruiz C., et al.Knigth’s move in the periodic table,from copper to platinum,novel antitumor mixed chelate copper compounds,casiopeinas, evaluated by an in vitro human and murine cancer cell line panel.Met.Based.Drug.[J].2001,8(1):19-28.
    [26] Kong D.Y.,Qin C.,Meng L.H.,Xie Y.Y. Synthesis, structural characterization and antitumor activity evaluations of copper complex with tetraazamacrocyclic ligand.Bioorg.Med.Chem.Lett.[J]. 1999,9(8):1087-1092.
    [27] Dovinova L.,Paulikova H.,Rauko P., et al. Main targets of tetraaza macrocyclic copper complex on L1210 murine leukemia cells.Toxicology.In Vitro[J].2002,16(5):491-498.
    [28] 吴振 高国辉. 稀土丙二酸类配合物的合成和体外抗癌活性的初步研究. 黑龙江大学自然科学学报[J].2003,20(4):104-107.
    [29] 黎植昌,任绍光. 谷氨酸硫酸镧固体配合物的合成,性质及抗癌活性.中国药物化学[J].1999, 9 (1) : 13-15.
    [30] 廖子君,南克俊.现代肿瘤治疗药物学[M].西安:世界图书出版社,2002.p3-4.
    [31] 韩锐.抗癌药物研究与实验技术[M], 北京:北京医科大学、中国协和医科大学联合出版社,1997.p389-404.
    [32] Jie Liu,Tixing Zhang,Tongbu Lu et al. DNA-binding and cleavage studies of macrocyclic copper(II) complexes.J.Inorg.Biochem.[J].2002,91(1):269-276. [ 33 ] C.V.Sastri,D.Eswaramoorthy,L.Giribabu et al. DNA interactions of new mixed-ligand complexes of cobalt(III) and nickel(II) that incorporate modified phenanthroline ligands. J.Inorg.Biochem.[J].2003,94(1-2): 138-145. [ 34 ] Per L,Bengt N.DNA Binding Geometries of Ruthenium(II) Complexes with 1,10- Phenanthroline and 2,2'-Bipyridine Ligands Studied with Linear Dichroism Spectroscopy Borderline Cases of Intercalation.J.Phys.Chem.(B). [J].1998,102(47):9583-9594.
    [35] 韩大雄,杨频. 分子模拟手性金属配合物 △ ,∧-[Co(phen)2dppz]3+与B-DNA的作用.中国科学(B辑)[J].2000,(30):392-398.
    [36] 孙雪光,曹恩华.双链,三链,四链 DNA 与溴乙锭相互作用的荧光研究.中国科学(B 辑)[J].1998,28(6):554.
    [37] Kumar C V,Asuncion E H. Sequence dependent energy transfer from DNA to a simple aromatic chromophore.J.Chem.Soc.Chem.Commun.[J].1992,(6):470-472.
    [38] Kumar C V, Asuncion E H. DNA binding studies and site selective fluorescence sensitiza- tion of an anthryl probe. J.Am.Chem.Soc.[J].1993,115(19):8547-8553.
    [39] Satyanara Y S,Dabrowiak J C,Chairs J B. Multiple binding modes of the single-stranded DNA binding protein from Escherichia coli as detected by tryptophan fluorescence and site-directed mutagenesis.Biochemistry[J].1993,32(10):2573-2591.
    [40] Satyanara Y S,Dabrowiak J C,Chairs J B. Neither .DELTA.- nor.LAMBDA.–tris(phen- anthroline) ruthenium(II) binds to DNA by classical intercalation.Biochemistry[J].1992,31 (39):9319-9324.
    [41] Brun A.M.,Harriuman.,et al. Energy- and Electron-Transfer Processes Involving Palladium Porphyrins Bound to DNA.J.Am.Chem.Soc.[J].1994,116(23):10383-10393.
    [42] Pitchumony Tamil Selvi,Mallayan Palaniandavar.Inorg.Chim.Acta.[J].2002, (337): 420.
    [43] Jian-Zhong Wu,Li Yuan. Synthesis and DNA interaction studies of a binuclear ruthenium(II) complex with 2,9-bis(2-imidazo[4,5-f][1,10]phenanthroline)-1,10-phenanthroline as bridging and intercalating ligand.J.Inorg.Biochem.[J].2004,98(1):41-45.
    [44] 何忠效,张树政.电泳[M].北京:科学出版社,1999,p11.
    [45] Dingley A J,Grzesick S. Direct Observation of Hydrogen Bonds in Nucleic Acid Base Pairs by Internucleotide 2JNN Couplings.J.Am.Chem.Soc.[J].1998,120(33):8293-8304.
    [46] Liu A,Majumdar,Hu W,et al.NMR Detection of N-H···O=C Hydrogen Bonds in 13C, 15N-Labeled Nucleic Acids.J.Am.Chem.Soc.[J].2000,122(13):3206-3210.
    [47] Lam S L,IP L N. Low Temperature Solution Structures and Base Pair Stacking of Double Helical d(CGTACG)2.J.Biomol.Struct.Dyn.[J].2002,19(5):907-918.
    [48] Xiangli Meng,Pin Yang,Huili Chen. Study of the coordination of amino acids with metals using [trans-en2Os(η2-H2)L]2+ as a 1H NMR probe.J.Inorg.Biochem.[J].2002,92(1):28-36.
    [49] Marzilli L G,Saad J S,Kukjenyik Z,et al. Relationship of Solution and Protein-Bound Structures of DNA Duplexes with the Major Intrastrand Cross-Link Lesions Formed on Cisplatin Binding to DNA.J. Am.Chem.Soc.[J].2001,123(12):2764-2770.
    [50] Zhou YL,Li Y Z. Studies of the interaction between poly(diallyldimethyl ammonium chloride) and DNA by spectroscopic methods.Colloid Surface A.[J].2004,233(1-3):129-135.
    [51] 王树玲,于俊生.表面增强拉曼光谱研究小檗碱与DNA的相互作用.高等学校化学学报[J].2002,23(9):1676-1679.
    [52] 倪嘉缵. 稀土生物无机化学[M].北京: 科学出版社,2002. p288~307.
    [53] 邓汝温,张仲生.稀土药物和药学性质.稀土[J].1987,8(3):41~43.
    [54] 邸友莹,谭志诚,李彦生. 稀土高氯酸盐-谷氨酸配合物[Pr2(L-α-Glu)2(ClO4)(H20)7] (ClO4)3·4H2O 的低温热容和热化学研究.化学学报[J].2006,64(13):1393~1401.
    [55] Wu Xin-Min, Tan Zhi-Cheng, Xue-Chuan Lv, et al. Synthesis heat capacity and enthalpy of formation of [Ho2(L-Glu)2(H2O)8](ClO4)4·H2O [J]. Thermochimica acta,2006, 441(2): 199~202
    [56] Rao G.N,Li N.C. Preparation and characterization of some binaray and tenary melt complexes of imidazole and amino acids.Canadian Journal of Chemistry[J].1966,34(44):1637~1641.
    [57] 张芳,张前前,李苓,王修林.铜(Ⅱ)-苏氨酸-咪唑混配配合物的合成及其与 DNA 作用的光谱研究.中国海养大学学报[J].2005,35(3):467~470.
    [58] 杨锐,何水样,顾爱萍等.镧三元配合物的合成、热稳定性及生物活性.物理化学学报[J].2003,19(7):610~615.
    [59] 杨一心,王艳,赵天成等.稀土乙酰丙氨酸咪唑配合物的合成及光谱性质.无机化学学报[J].2005,21(4):578~582.
    [60] Li Ping,Li Juan,Wu Qingsheng, et al. Synergistic antibacterial effects of β-lactam antibiotic combined with silver nanoparticles. Nanotechnology[J].2005,16,1912~1917.
    [61] Yu Hui,He Qizhuang,YangJing, et al. Synthesis, Characteriza -tion and Antibacterial Proper- ties of Rare Earth (Ce3+,Pr3+,Nd3+,Sm3+,Er3+) Complexes with L-Aapartic Acid and o-Phenanthro- line. Journal of Rare Earths[J].2006,24 (spec. issue):4~8.
    [62] 中国人民共和国卫生部.消毒技术规范[S].北京:中国人民共和国卫生部,2006.
    [63] 刘绍威,周柞万,李毕忠等. 中华人民共和国化工行业标准HG/T 3794-2005 无机抗菌剂-性能及评价[S].北京:化学工业出版社,2005,
    [64] 王则民,曹锦荣,周德兴等. 稀土水杨酸与 8-羟基喹啉三元配合物的研究.无机化学学报[J].1995,11(3):308~312.
    [65] 陈菊香,冉新权,郭志箴等. 三元体系 LaCl-Am(Am=Gly, Glu,ser)-H2O (25 ℃ )的研究.高等学校化学学报[J].1990,11(6):556~558.
    [66] 中本一雄著,黄德如,汪仁庆译.无机配位化合物的红外和拉曼光谱[M].山东:化学工业出版社,1986.p251.
    [67] 何水样,陈军利,张维平,刘向荣,宋迪生.RE(ClO4)3·nH2O 与丙氨酸、咪唑配合物的合成、表征及生物活性.中国稀土学报[J].2001,19(1):80~84.
    [68] 侯安新,刘义,黄伟国等.钇离子及其阳离子卟啉配合物与金黄色葡萄球菌的相互作用.化学学报[J].2003,61(9):1382~1387.
    [69] Ahmed Hafiz, Abdul G.,A.Chaudhary., DNA methylation - an essential mechanism in plant molecular biology. Acta Physiologiae Plantarum.[J].2001,23(4):491-499.
    [70] Seminara A.,Guiffrida S.,Musumeci A.,Fragala L. Polynuclear complexes of lanthanides with nickel and copper schiff bases as ligands.Inorg.Chim.Acta.[J].1984,95(1):201-205.
    [71] Bencini A., Benelli C., Caneschi A., et al.Crystal and molecular structure of and magnetic coupling in two complexes containing gadolinium(III) and copper(II) ions.J.Am. Chem.Soc. [J].1985,107(26):8128-8136.
    [72] Benelli C., Gatteschi D., Organo Lanthanide Metal Complexes for Electroluminescent Materials.Chem.Rev.[J].2002, 102(6): 2369-2388.
    [73] Jorge A. R. Navarro, Bernhard Lippert. Simple 1:1 and 1:2 complexes of metal ions with heterocycles as building blocks for discrete molecular as well as polymeric assemblies. Coord.Chem.Rev.[J].2001, 222(1): 219-250.
    [74] Wen-Xin Du, Jian-Jun Zhang, Sheng-Min Hu, et al.Synthese and crystal structures of a series of heptanuclear trigonal prismatic clusters {LnCu6}(Ln=La,Sm,Er) with glycine and imidazole as ligands.Journal of Molecular Structure[J].2004, 701, 25030.
    [75] Qin-De Liu, Song Gao, Jun-Ran Li, et al. Structures and Magnetism of Two Novel Heptanuclear Lanthanide-Centered Trigonal Prismatic Clusters: [LnCu6(μ3-OH)3(HL)2(L)4] (ClO4)·25H2O (Ln ) La, Tb; H2L ) Iminodiacetic Acid).Inorg.Chem.[J].2000, 39, 2488-2492.
    [76] Xue-Chuan Lv, Zhi-Cheng Tan, Xiao-Han Gao, et al. Synthesis and thermodynamic properties of a metal-organic framework: [LaCu6(μ-OH)3(Gly)6im6](ClO4)6.Thermochimica Acta[J]. 2006,450, 102-104
    [77] 季君晖,史维明.抗菌材料[M].北京:化学工业出版社,2003,p85.
    [78] 金宗哲.无机抗菌材料及其应用[M].北京:化学工业出版社,2004.p123.
    [ 79 ] 司玉昌 , 王玉 祥 , 郝鹤 等 . 金 属配 合 物抗癌药物研究新进展 . 武警医学院学报[J].2006,15(1):64-68.
    [80] 朱解方,朱国芳.抗癌金属配合物的研究综述.现代食品与药品杂志[J].2007,17(4):22-25.
    [81] 王国平,傅旭春.朱龙观. 双核铜(Ⅱ)-氟喹诺酮-邻菲咯啉混配配合物的合成、晶体结构和抗肿瘤活性.无机化学学报[J].2003,19(9):1001-1005.
    [82] 尹富玲,申佳,邹佳嘉等.2,2’-联吡啶和去甲基斑蝥酸根桥联双核铜(Ⅱ)配合物的合成、结构表征及抗癌活性的研究.化学学报[J].2003,61(4):556-561. [ 83 ] Cheng-Yong Zhou,Jing Zhao,Pin Yang,et al.synthesis,characterization and studies on DNA-binding of a new Cu(Ⅱ ) complex with N1,N8-bis(1-methyl-4-nitropyrrole-2-carbonyl) triethylenetetramine.Journal of InorganicBiochemistry[J].2007, 101,10-18.
    [84] Xu Shen,Yuyuan Xie,Hualiang Jiang. Lanthanide (III) Complexes With a Hydrazone Derived From a Novel Amido Acid and Isonicotinic Acid Hydrazide: Synthesis, Characterization and Antibacterial Activity.Synth React Inorg Met-Org Chem[J].1995, 25(4) :511-519.
    [85] Xu Shen,Quan Li,Hauliang Jiang, et al. Synthesis, Characterization and Antibacterial Activity of Lanthanide (III) Complexes with a Hydrazone Derived from a New Amido Acid and Thiosemicarbazide.Synth React Inorg Met-Org Chem[J].1995, 25 (8): 1239-1247.
    [86] 刘颖梅,王流芳,赵红等.维甲酸稀土金属配合物对 Vero 细胞的体外作用及其在动物体内毒性的研究.兰州大学学报(自然科学版) [J].1999,35(4):131-132.
    [87] 肖白, 纪云晶, 崔明珍等. 镧、铈对癌细胞恶性增殖及其相关基因表达的影响.中华预防医学杂志[J].1997, 31( 4) : 228 -230.
    [88] 赵卫红编著,细胞凋亡[M].河南:河南医科大学出版社,1997.p223.
    [89] 卢圣东,马清钧,刘德培等编著.现代分子生物学实验技术(第三版)[M].北京:中国协和医科大学出版社,2004.p443
    [90] 程宝鸾编著.动物细胞培养技术[M].广东:华南理工大学出版社,2000.p131.
    [91] 姜泊编著.细胞凋亡基础与临床[M].北京:人民军医出版社,1999.p281.
    [92] Li H.D.,Fedorova o.s., Grachev A.N., et al. A series of meso-tris(N-methyl-pyridiniumyl) -(4-alkylamidophenyl) porphyrins: Synthesis, interaction with DNA and antibacterial activity. Biochimia. Biophysica.Acta-Gene Structure and Expression.,.1997, 1354(3):252-260.
    [93] Chaviara,A.T.; Cox,P.J.; Repana,K.H.; et al. The unexpected formation of biologically active Cu(II)Schiff mono-base complexes with 2-thiophene-carboxaldehyde and dipropyle- netriamine: crystal and molecular structure of CudptaSCl2. J.Biol.Inorg.Chem.[J].2005, 99(2):467-476.
    [94] A.-E.F.Nassar, J.F.Rusling, N.Nakashima. Electron Transfer between Electrodes and Heme Proteins in Protein-DNA Films.J.Am.Chem.Soc.[J].1996,118(12):3043-3044.
    [95] M.Maeda, K.Nakano, S.Uchida et al. Mg2+-Selective Electrode Comprising Double-HelicalDNA as Receptive Entity.Chem.Lett.[J].1994,23(10):1805-1809.
    [96] 汪中明,计亮年.钌配合物的抗肿瘤活性研究进展.化学进展[J].2002,14(4): 296-304.
    [97] 宋宇飞,杨频.对 DNA 具有识别和断裂功能的金属插入剂的研究.化学进展[J].2001, 13(5):368-375.
    [98] Tu,C.; Wu,X.F.; Liu,Q.; Wang,X.Y.; Xu,Q.; Guo,Z.J. Crystal structure, DNA-binding ability and cytotoxic activity of platinum(II) 2,2′-dipyridylamine complexes.Inorg.Chim.Acta[J].2004, 357(1):95~102.
    [99] 靳兰,杨频,李青山.荧光法研究手性金属配合物与 DNA 的作用机理.高等化学学报[J].1996,17(9):1345-1348.
    [100] 曹瑛,何锡文. DNA 与邻苯二胺—过氧化氢—过氧化物酶体系相互作用的光谱研究.分析化学[J].1998,26(10):1165-1168.
    [101] Satyanara Y S,Dabrowiak J C,Chairs J B. Neither .DELTA.- nor.LAMBDA.–tris (phenan- throline)ruthenium(II) binds to DNA by classical intercalation.Biochemistry[J].1992,31 (39):9319 -9324.

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