Schiff碱铜配合物的制备及生物活性研究
|
摘要
超氧化物歧化酶(SOD)是一种广泛存在于生物体内的金属酶,它能催化超氧阴离子自由基O_2~-·发生歧化反应,在化学、生物学、医药领域及防御生物体免受氧自由基损伤方面具有重要作用,有广泛的应用前景。但天然超氧化物歧化酶普遍存在寿命短、稳定性差、分子量大、不易透过细胞膜等缺点,使其应用受到限制。所以,超氧化物歧化酶模拟物的研究成为近年来的研究热点。
本文设计合成了水杨醛缩二胺、三胺及2,4-二羟基苯甲醛缩乙二胺的Schiff碱配体及其Cu(Ⅱ)配合物,并就其催化超氧阴离子自由基歧化反应的活性进行了研究。
用元素分析、红外光谱、紫外光谱、荧光光谱对配体和配合物进行了结构表征;用EDTA法测定了配合物中金属铜的含量;测定了配合物的摩尔电导率,并用循环伏安法研究了配合物的电化学特性;采用改进的邻苯三酚自氧化法对配合物在不同浓度下的抗超氧阴离子自由基活性进行了测定。研究结果表明:
1.各配合物均表现出一定的SOD活性,且活性大小与配合物的分子构型、空间位阻大小等有关。
2.各配合物的抗O_2~-·活性与浓度成正相关关系。
3.在循环伏安曲线中,各Cu(Ⅱ)配合物的循环伏安曲线都是可逆的,都有一对氧化还原峰。
Superoxide dismutase(SOD),as one kind of metalloenzyme,exists widely in the biological body,which has extensive prospects in the application,it can catalytic superoxide anion racial O_2~-·disproportionation reaction.It is very important that superoxide dismutase(SOD) has been applied in chemistry、biology、medicine and defense against oxygen free radical damage organisms.But the disadvantages of natual superoxide dismutase,such as short life、lower stability、macro molecular weight、lower penetrability and permeability through cell membrane,etc.,restrict its application,So the mimics of SOD is becoming an increasingly hot reseach topic in recent years.
In this papper,four Schiff bases were synthesized by salicylaldehyde and diamine,triamine and 2,4-dihydroxybenzaldehyde and ethylenediamine,and its Cu(Ⅱ) complexes were synthesized.The properties of catalytic activity of the metal complexes in disproportionation of O_2~(-·) were studied.
All compouds were characterized by element analysis,IR,Uv,FR,the copper content of the complexes were determined by EDTA method;the molar conductivity of the complexes were measured,and the electrochemical properties of the complexes were studied by cyclic voltammetry.The tests of catalytic activity of all the complexes, determined by improved pyogallol autoxidation,indicate that:
(1) All the complexes show some inhibitive effects to O_2~(-·),and the activities have close correlation with the molecular structure of complexes,steric size of space and so on.
(2) The activities of all the metal complexes have the direct correction with their concentration.
(3) In the cyclic voltammetry curves,each complex has a pair of reversible curve and redox peaks.
本文设计合成了水杨醛缩二胺、三胺及2,4-二羟基苯甲醛缩乙二胺的Schiff碱配体及其Cu(Ⅱ)配合物,并就其催化超氧阴离子自由基歧化反应的活性进行了研究。
用元素分析、红外光谱、紫外光谱、荧光光谱对配体和配合物进行了结构表征;用EDTA法测定了配合物中金属铜的含量;测定了配合物的摩尔电导率,并用循环伏安法研究了配合物的电化学特性;采用改进的邻苯三酚自氧化法对配合物在不同浓度下的抗超氧阴离子自由基活性进行了测定。研究结果表明:
1.各配合物均表现出一定的SOD活性,且活性大小与配合物的分子构型、空间位阻大小等有关。
2.各配合物的抗O_2~-·活性与浓度成正相关关系。
3.在循环伏安曲线中,各Cu(Ⅱ)配合物的循环伏安曲线都是可逆的,都有一对氧化还原峰。
Superoxide dismutase(SOD),as one kind of metalloenzyme,exists widely in the biological body,which has extensive prospects in the application,it can catalytic superoxide anion racial O_2~-·disproportionation reaction.It is very important that superoxide dismutase(SOD) has been applied in chemistry、biology、medicine and defense against oxygen free radical damage organisms.But the disadvantages of natual superoxide dismutase,such as short life、lower stability、macro molecular weight、lower penetrability and permeability through cell membrane,etc.,restrict its application,So the mimics of SOD is becoming an increasingly hot reseach topic in recent years.
In this papper,four Schiff bases were synthesized by salicylaldehyde and diamine,triamine and 2,4-dihydroxybenzaldehyde and ethylenediamine,and its Cu(Ⅱ) complexes were synthesized.The properties of catalytic activity of the metal complexes in disproportionation of O_2~(-·) were studied.
All compouds were characterized by element analysis,IR,Uv,FR,the copper content of the complexes were determined by EDTA method;the molar conductivity of the complexes were measured,and the electrochemical properties of the complexes were studied by cyclic voltammetry.The tests of catalytic activity of all the complexes, determined by improved pyogallol autoxidation,indicate that:
(1) All the complexes show some inhibitive effects to O_2~(-·),and the activities have close correlation with the molecular structure of complexes,steric size of space and so on.
(2) The activities of all the metal complexes have the direct correction with their concentration.
(3) In the cyclic voltammetry curves,each complex has a pair of reversible curve and redox peaks.
引文
[1]Mann T,Keilin D,Hacmocuprein and hepatocuprein copper protein compounds of blood and liver in mammals[J].Proc R Soc B,1938,126:303-315.
[2].林庆斌,廖升容等.超氧化物歧化酶(SOD)的研究和应用进展[J].化学世界,2006,6:378.
[3]袁勤生.SOD的研究进展[J].中国药学杂志,1988,24(7):45.
[4]Fridvich.I.The Biology of oxygen Radicals[J].Comments,1982,15(7):200-203.
[5]陈忠宁,毛宗万,唐雯霞等.铜锌超氧化物歧化酶的结构机理及其模拟研究进展[J].化学通报,1993,(6):1-7.
[6]田亚平,沈文梅,方允中等.模拟SOD在生命科学中的进展[M].北京:原子能出版社,1994,2:49-52.
[7]张龙泽,马书林.SOD模拟化合物的研究进展[J].药学学报,2002,37(3):235-240
[8]Bannister J V.What is superoxide dismutase[J].Biochemical Education,Inorg Chem,1981,19(2):42.
[9]Lippard S J,Davis W M,Dewan J C.Synthesis and Solid state Properties of a Homodinuclear(Copper-Copper) complex[J].Inorg Chem,1981,20:2928-2830.
[10]Moldovan L,Moldovan N I,Sohn R H et al.Redox chances of cultured endothelialcells and action dynamics[J].Inorg Chem,2000,86:549-557.
[11]廖展如等.超氧化物歧化酶模拟化合物的生物活性研究[J].生物化学与生物物理进展,1996,2:159-163.
[12]Linss M,Weser U.The Di-schiffbase of phridine-2-aldehyde and 1-4-diaminobutane,a flexible Cu(Ⅱ)/Cu(Ⅰ) chelator of significant superoxide,dismutase,mimetic,activity[J].Inorg chim Acta,1986,125(2):117-121.
[13]Luo Q H.Studies on simulation chemistry of Cu-Zn superoxide dismutase[J].Inorg Chem,1997,18(7):1012-1018.
[14]Mueller J,Felix K Maichle C et al.pheyl-substi-tuted copper di-schiff base,a potent Cu-Zn superoxide dismutase mimic survivin competitive biochelation[J].Inorg chim Acta,1995,233(2):1-19.
[15]Ines B H,Stefan I L,Ivan S etal.A potent superoxide dismutase,mimc,man B-octabromo-meso-tetrakis-(N-methylpyridiniurm) porphyrin[J].Arch.Biochem Biophys,1997,338(2):225-233.
[16]孟庆金,戴安邦等.配位化学的创始与现代化[M].无机化学学报,1995,3:219-226.
[17]Desai S B,Desai P B,Desai K R.Synthesis of some Schiff bases thiazolidinones and azetidinones from 2,6 -diaminobonzol bisthiazole and their anticancer activities[J].Inorg Chem,2001,7(1):83-90.
[18]Isse A,Gennaro A,Vianello E.Electrochemical reduction of Schiff bases ligands H_2salen and H_2salophen[J].Electrochemical Acta,1997,42(13):2065-2071.
[19]Bastos M B R,Moreira J C,Farlas P A M.Adsorptive stripping voltammetric behaviour of UO_2 complexed with the Schifff base N,N-prime-rthylenebis in aqueous 4-(2-hydroxyethy)-1-piperazine ethanesulfonic acid medium[J].Analytica Chem,2000,408:83-88.
[20]Ma H,Chen S H,Niu L et al.Studies on electrochemical behavior of copper in aerated NaBr solutions with Schiffbases[J].Journal of Electrochemical Society,2001,148(5):208-216.
[21]赵建章,赵冰,徐蔚青等.Schiff碱N,N'-双水杨醛缩1,6-己二氨的光致变色光谱的研究[J].高等学校化学学报,2001,22(6):971-975.
[22]陈玉红,丁克强,王庆飞等.席夫碱应用研究新进展[J].河北师范大学学报,2003,27(1):71-73.
[23]田君濂,毕思玮,高恩庆.甲酰基甲酸氨基硫脲席夫碱二价金属离子配合物的研究[J].应用化学,1994,11(5):45-47.
[24]李桂芝,毕思玮,刘树祥等.含硫席夫碱配体及其Cu(Ⅱ)配合物的杀菌活性研究[J].曲阜师范大学学报,1996,22(3):91-94.
[25]毕思玮,刘树祥.氨基酸水杨醛席夫碱与Cu(Ⅱ)配合物的合成及其抗菌活性和稳定性、结构间的关系[J].无机化学学报,1996,12(4):423-425.
[26]唐婷,龚钰秋.几个新的席夫碱合铜(Ⅱ)配合物的合成及性质[J].无机化学学报,2001,17(5):745-750.
[27]陈建华,李常胜,季习俊.N-(2-羟基萘甲醛)甘氨酸席夫碱及其铜(Ⅱ)、镍(Ⅱ)配合物的合成、表征和抗癌活性[J].中国药物化学志,1995,5(3):192-194.
[28]李琛,张维萍,姚小泉.一种新型手性席夫碱的合成及其在不对称环丙烷化反应中的催化性能[J].催化学报,2000,21(3):289-291
[29]袁淑军,蔡春,吕春绪.双亲性席夫碱Cu(Ⅱ)配合物的合成及苯甲醇的催化氧化[J].应用化学,2003,20(3):278-280.
[30]仇敏,刘国生,姚小泉.手性Cu(Ⅱ)-席夫碱配合物催化苯乙烯不对称环丙烷化反应[J].催化学报,2001,22(1):77-80.
[31]Z.Y.Sun,R.Yuan et al.Study of a bis-furaldehyde Schiff base copper(Ⅱ)complex as carrier for preparation of highly selective thiocyanate electrodes[J].Anal Bioanal Chem,2004,378:490-494.
[32]Mohammad Reza,Ganjali,Tahereh Poursaberi,Fatemeh Basiripour.Highly selective thiocyanate poly(vinyl chloride) membrane electrode based on cadmium Schiff base complex[J].Fresenius J Anal Chem,2001,370:1091-1095.
[33]陈德余,张义建,张平等.甲硫氨酸席夫碱铜、锌、钴配合物的合成及抗O_2~-·性能[J].应用化学,2000,17(6):607-610.
[34]何秀英,严振寰,吴自慎.邻甲氧基苯甲醛苯丙氨酸席夫碱和配合物的合成、表征及其对超氧离子自由基的作用[J].华中师范大学报,1995,29(4):459-463.
[35]王建华,雷文,王远亮.噻二唑席夫碱配合物的合成及其抗超氧阴离子的活性[J].重庆大学学报,2002,25(7):60-62.
[36]Gartner.A.Weser.U.In Topics in Current Chemistry[J].New York:Springer-Verlag Press,1986,132-140.
[37]王多宁,莫简,孙淑芬等.SOD模拟物PTC对O_2~-·介导的氧化损伤的保护作用[J].第四军医大学学报,1999,22:580-583.
[38]魏丹毅,李宁,鲁桂,姚克敏.双核铜Schiff新配合物的合成及其催化和活性研究[J].中国科学(B辑),2005,35:396-400.
[39]李仲辉,秦圣英,李建章等.冠醚化对双Schiff碱钴(Ⅱ)配合物催化氧化性能的影响[J].应用化学,1998,15(5):43-46.
[40]张邦乐,何炜,王多宁.3,5-二硝基水杨醛缩甘氨酸铜(Ⅱ)配合物的合成、表征、及其抗O_2~-·活性[J].西北药学杂志,2000,15(4),175-176.
[41]雷文.Schiff碱及其金属配合物合成与生物活性研究[D].硕士论文,重庆大学.重庆,2002.
[42]祝心德,李军等.新型硫代磷酰肼希夫碱及其金属配合物的合成与生物活性[J].华中师范大学学报(自然科学版),2003,37(3):343-346.
[43]杨建国,潘富友,李钧敏等.Cu(Ⅱ)-2-(2-噻吩亚甲基)水杨酰腙Schiff碱配合物的合成、表征、晶体结构及抑菌活性研究[J].无机化学学报,2005,10(21):1593-1596.
[44]Cai L S,Mahmoud H,Han Y.Binuclear versusmononuclear copper complexes as catalysts for asymmet-ric cyclopropanation of styrene[J].Tetrahedron Asmmetry,1999,10(3):411-427.
[45]毕思玮,李桂芝等.N-亚水杨基氨基酸及其与铜(Ⅱ)配合物的合成、表征和抗菌活性[J].化学工程,1995,6:13-15.
[46]Hohan.Z.H et al.Structural elucidation and biological significance of 2-hydroxy-1-naphthaldehyde derived sulfonamides and their first row d-transition metal chelates[J].Joural of Enzyme Inhibion and Medicinal Chem,2008,23(3):369-379.
[47]Sun M.Zigman S.An improved spectrophotometric assay for superoxide dismutase based on epinephrine autoxidation[J].Anal.Biochem,1978,90:81-89.
[48]Cohen G.The generation of hydrogen peroxide,superoxide radical and hydroxyl radical by 6-hydroxydopamine,diauric acid and related cytotoxic agents[J].J.Biol.Chem,1974,249:2447-2452.
[49]雷文.Schiff碱及其金属配合物合成与生物活性研究[D].硕士论文,重庆大学.重庆,2002.
[50]Guerriero P,Casellato U,Tamburini S.L anthanide complexes with compartmental Schiff bases[J].Inorg Chem Acta,1987,1(129):127-138.
[51]姚克敏,李冬成,沈联芳.镧系与邻氨基苯甲酸型Schiff碱配合物的合成、表征及催化活性[J].化学学报,1993,51(7):677-682.
[52]华中师范大学等编.分析化学实验(第三版).北京:高等教育出版社,2001:68-69.
[53]任成忠,毛丽芬.加标回收实验[J].工业安全与环保,2006,32(2):9-10.
[54]李必斌等.标准加标回收实验方案探讨[J].中国卫生检验杂志,2000,10(5):618-619.
[55]Geary W J.The use of conductivity measurements in organic solvents for characterisation of coordination compounds[J].Coord.Chem.Rev,1971,7:110-111.
[56]Gerald Cohen,Richard E.Heikkila.The generation of Hydrogen Peroxide,Superoxide Radical,and Hydroxyl Radical by 6-Hydroxydopamine,Dialuric Acid,and Related Cytotoxic Agents[J].Biol.Chem,1974,249(4):2447-2452.
[57]S.Marklund.Spectrophotometric study of spontaneous disproportionation of superoxide anion radical and sensitive direct assay for superoxide dismutase[J].Biol.Chem,1976;(12) 251:7504-7507.
[58]邹果林,桂姓芬,钟晓凌等.一种SOD的测活方法—邻苯三酚自氧化法的改进[J].生物化学生物物理进展,1989,21(1):31-54.
[59]Marklund S,Marklund G.Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase[J].Eur.J.Biochem,1974,47:469-474.
[60]袁勤生,王志友,翁清清等.邻苯三酚自氧化法测定超氧化物歧化酶的活性[J].医药工业,1983,1:16-19.
[61]邹国林,桂兴芬,钟晓凌等.一种SOD的测活方法—邻苯三酚自氧化法的改进[J].生物化学与生物物理进展,1986,(4):71-74.
[62]常建华,董绮功.波谱原理及解析.北京:科学出版社,2001,16-19.
[63]宁永成.有机化合物结构鉴定与有机波谱学(第二版).北京:科学出版社,2000,374.
[64]常建华,董绮功.波谱原理及解析.北京:科学出版社,2001,32-33.
[65]王建华,雷文等.SOD酶模型配合物的合成及催化岐化作用-1,3,4-噻二唑类Schifff碱配合物的合成、表征及对超氧离子的抑制作用合成化学[J].重庆大学学报,2002,4(10):314-317.
[66]中本一雄著,黄德如,汪仁庆译.无机和配位化合物的红外和拉曼光谱.北京:化学工业出版社,1986,237-239.
[67]李思良,水杨醛缩二胺三胺类西佛碱锰配合物的制备及生物活性研究[D].硕士研究生论文,贵州大学,贵州,2004年.
[2].林庆斌,廖升容等.超氧化物歧化酶(SOD)的研究和应用进展[J].化学世界,2006,6:378.
[3]袁勤生.SOD的研究进展[J].中国药学杂志,1988,24(7):45.
[4]Fridvich.I.The Biology of oxygen Radicals[J].Comments,1982,15(7):200-203.
[5]陈忠宁,毛宗万,唐雯霞等.铜锌超氧化物歧化酶的结构机理及其模拟研究进展[J].化学通报,1993,(6):1-7.
[6]田亚平,沈文梅,方允中等.模拟SOD在生命科学中的进展[M].北京:原子能出版社,1994,2:49-52.
[7]张龙泽,马书林.SOD模拟化合物的研究进展[J].药学学报,2002,37(3):235-240
[8]Bannister J V.What is superoxide dismutase[J].Biochemical Education,Inorg Chem,1981,19(2):42.
[9]Lippard S J,Davis W M,Dewan J C.Synthesis and Solid state Properties of a Homodinuclear(Copper-Copper) complex[J].Inorg Chem,1981,20:2928-2830.
[10]Moldovan L,Moldovan N I,Sohn R H et al.Redox chances of cultured endothelialcells and action dynamics[J].Inorg Chem,2000,86:549-557.
[11]廖展如等.超氧化物歧化酶模拟化合物的生物活性研究[J].生物化学与生物物理进展,1996,2:159-163.
[12]Linss M,Weser U.The Di-schiffbase of phridine-2-aldehyde and 1-4-diaminobutane,a flexible Cu(Ⅱ)/Cu(Ⅰ) chelator of significant superoxide,dismutase,mimetic,activity[J].Inorg chim Acta,1986,125(2):117-121.
[13]Luo Q H.Studies on simulation chemistry of Cu-Zn superoxide dismutase[J].Inorg Chem,1997,18(7):1012-1018.
[14]Mueller J,Felix K Maichle C et al.pheyl-substi-tuted copper di-schiff base,a potent Cu-Zn superoxide dismutase mimic survivin competitive biochelation[J].Inorg chim Acta,1995,233(2):1-19.
[15]Ines B H,Stefan I L,Ivan S etal.A potent superoxide dismutase,mimc,man B-octabromo-meso-tetrakis-(N-methylpyridiniurm) porphyrin[J].Arch.Biochem Biophys,1997,338(2):225-233.
[16]孟庆金,戴安邦等.配位化学的创始与现代化[M].无机化学学报,1995,3:219-226.
[17]Desai S B,Desai P B,Desai K R.Synthesis of some Schiff bases thiazolidinones and azetidinones from 2,6 -diaminobonzol bisthiazole and their anticancer activities[J].Inorg Chem,2001,7(1):83-90.
[18]Isse A,Gennaro A,Vianello E.Electrochemical reduction of Schiff bases ligands H_2salen and H_2salophen[J].Electrochemical Acta,1997,42(13):2065-2071.
[19]Bastos M B R,Moreira J C,Farlas P A M.Adsorptive stripping voltammetric behaviour of UO_2 complexed with the Schifff base N,N-prime-rthylenebis in aqueous 4-(2-hydroxyethy)-1-piperazine ethanesulfonic acid medium[J].Analytica Chem,2000,408:83-88.
[20]Ma H,Chen S H,Niu L et al.Studies on electrochemical behavior of copper in aerated NaBr solutions with Schiffbases[J].Journal of Electrochemical Society,2001,148(5):208-216.
[21]赵建章,赵冰,徐蔚青等.Schiff碱N,N'-双水杨醛缩1,6-己二氨的光致变色光谱的研究[J].高等学校化学学报,2001,22(6):971-975.
[22]陈玉红,丁克强,王庆飞等.席夫碱应用研究新进展[J].河北师范大学学报,2003,27(1):71-73.
[23]田君濂,毕思玮,高恩庆.甲酰基甲酸氨基硫脲席夫碱二价金属离子配合物的研究[J].应用化学,1994,11(5):45-47.
[24]李桂芝,毕思玮,刘树祥等.含硫席夫碱配体及其Cu(Ⅱ)配合物的杀菌活性研究[J].曲阜师范大学学报,1996,22(3):91-94.
[25]毕思玮,刘树祥.氨基酸水杨醛席夫碱与Cu(Ⅱ)配合物的合成及其抗菌活性和稳定性、结构间的关系[J].无机化学学报,1996,12(4):423-425.
[26]唐婷,龚钰秋.几个新的席夫碱合铜(Ⅱ)配合物的合成及性质[J].无机化学学报,2001,17(5):745-750.
[27]陈建华,李常胜,季习俊.N-(2-羟基萘甲醛)甘氨酸席夫碱及其铜(Ⅱ)、镍(Ⅱ)配合物的合成、表征和抗癌活性[J].中国药物化学志,1995,5(3):192-194.
[28]李琛,张维萍,姚小泉.一种新型手性席夫碱的合成及其在不对称环丙烷化反应中的催化性能[J].催化学报,2000,21(3):289-291
[29]袁淑军,蔡春,吕春绪.双亲性席夫碱Cu(Ⅱ)配合物的合成及苯甲醇的催化氧化[J].应用化学,2003,20(3):278-280.
[30]仇敏,刘国生,姚小泉.手性Cu(Ⅱ)-席夫碱配合物催化苯乙烯不对称环丙烷化反应[J].催化学报,2001,22(1):77-80.
[31]Z.Y.Sun,R.Yuan et al.Study of a bis-furaldehyde Schiff base copper(Ⅱ)complex as carrier for preparation of highly selective thiocyanate electrodes[J].Anal Bioanal Chem,2004,378:490-494.
[32]Mohammad Reza,Ganjali,Tahereh Poursaberi,Fatemeh Basiripour.Highly selective thiocyanate poly(vinyl chloride) membrane electrode based on cadmium Schiff base complex[J].Fresenius J Anal Chem,2001,370:1091-1095.
[33]陈德余,张义建,张平等.甲硫氨酸席夫碱铜、锌、钴配合物的合成及抗O_2~-·性能[J].应用化学,2000,17(6):607-610.
[34]何秀英,严振寰,吴自慎.邻甲氧基苯甲醛苯丙氨酸席夫碱和配合物的合成、表征及其对超氧离子自由基的作用[J].华中师范大学报,1995,29(4):459-463.
[35]王建华,雷文,王远亮.噻二唑席夫碱配合物的合成及其抗超氧阴离子的活性[J].重庆大学学报,2002,25(7):60-62.
[36]Gartner.A.Weser.U.In Topics in Current Chemistry[J].New York:Springer-Verlag Press,1986,132-140.
[37]王多宁,莫简,孙淑芬等.SOD模拟物PTC对O_2~-·介导的氧化损伤的保护作用[J].第四军医大学学报,1999,22:580-583.
[38]魏丹毅,李宁,鲁桂,姚克敏.双核铜Schiff新配合物的合成及其催化和活性研究[J].中国科学(B辑),2005,35:396-400.
[39]李仲辉,秦圣英,李建章等.冠醚化对双Schiff碱钴(Ⅱ)配合物催化氧化性能的影响[J].应用化学,1998,15(5):43-46.
[40]张邦乐,何炜,王多宁.3,5-二硝基水杨醛缩甘氨酸铜(Ⅱ)配合物的合成、表征、及其抗O_2~-·活性[J].西北药学杂志,2000,15(4),175-176.
[41]雷文.Schiff碱及其金属配合物合成与生物活性研究[D].硕士论文,重庆大学.重庆,2002.
[42]祝心德,李军等.新型硫代磷酰肼希夫碱及其金属配合物的合成与生物活性[J].华中师范大学学报(自然科学版),2003,37(3):343-346.
[43]杨建国,潘富友,李钧敏等.Cu(Ⅱ)-2-(2-噻吩亚甲基)水杨酰腙Schiff碱配合物的合成、表征、晶体结构及抑菌活性研究[J].无机化学学报,2005,10(21):1593-1596.
[44]Cai L S,Mahmoud H,Han Y.Binuclear versusmononuclear copper complexes as catalysts for asymmet-ric cyclopropanation of styrene[J].Tetrahedron Asmmetry,1999,10(3):411-427.
[45]毕思玮,李桂芝等.N-亚水杨基氨基酸及其与铜(Ⅱ)配合物的合成、表征和抗菌活性[J].化学工程,1995,6:13-15.
[46]Hohan.Z.H et al.Structural elucidation and biological significance of 2-hydroxy-1-naphthaldehyde derived sulfonamides and their first row d-transition metal chelates[J].Joural of Enzyme Inhibion and Medicinal Chem,2008,23(3):369-379.
[47]Sun M.Zigman S.An improved spectrophotometric assay for superoxide dismutase based on epinephrine autoxidation[J].Anal.Biochem,1978,90:81-89.
[48]Cohen G.The generation of hydrogen peroxide,superoxide radical and hydroxyl radical by 6-hydroxydopamine,diauric acid and related cytotoxic agents[J].J.Biol.Chem,1974,249:2447-2452.
[49]雷文.Schiff碱及其金属配合物合成与生物活性研究[D].硕士论文,重庆大学.重庆,2002.
[50]Guerriero P,Casellato U,Tamburini S.L anthanide complexes with compartmental Schiff bases[J].Inorg Chem Acta,1987,1(129):127-138.
[51]姚克敏,李冬成,沈联芳.镧系与邻氨基苯甲酸型Schiff碱配合物的合成、表征及催化活性[J].化学学报,1993,51(7):677-682.
[52]华中师范大学等编.分析化学实验(第三版).北京:高等教育出版社,2001:68-69.
[53]任成忠,毛丽芬.加标回收实验[J].工业安全与环保,2006,32(2):9-10.
[54]李必斌等.标准加标回收实验方案探讨[J].中国卫生检验杂志,2000,10(5):618-619.
[55]Geary W J.The use of conductivity measurements in organic solvents for characterisation of coordination compounds[J].Coord.Chem.Rev,1971,7:110-111.
[56]Gerald Cohen,Richard E.Heikkila.The generation of Hydrogen Peroxide,Superoxide Radical,and Hydroxyl Radical by 6-Hydroxydopamine,Dialuric Acid,and Related Cytotoxic Agents[J].Biol.Chem,1974,249(4):2447-2452.
[57]S.Marklund.Spectrophotometric study of spontaneous disproportionation of superoxide anion radical and sensitive direct assay for superoxide dismutase[J].Biol.Chem,1976;(12) 251:7504-7507.
[58]邹果林,桂姓芬,钟晓凌等.一种SOD的测活方法—邻苯三酚自氧化法的改进[J].生物化学生物物理进展,1989,21(1):31-54.
[59]Marklund S,Marklund G.Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase[J].Eur.J.Biochem,1974,47:469-474.
[60]袁勤生,王志友,翁清清等.邻苯三酚自氧化法测定超氧化物歧化酶的活性[J].医药工业,1983,1:16-19.
[61]邹国林,桂兴芬,钟晓凌等.一种SOD的测活方法—邻苯三酚自氧化法的改进[J].生物化学与生物物理进展,1986,(4):71-74.
[62]常建华,董绮功.波谱原理及解析.北京:科学出版社,2001,16-19.
[63]宁永成.有机化合物结构鉴定与有机波谱学(第二版).北京:科学出版社,2000,374.
[64]常建华,董绮功.波谱原理及解析.北京:科学出版社,2001,32-33.
[65]王建华,雷文等.SOD酶模型配合物的合成及催化岐化作用-1,3,4-噻二唑类Schifff碱配合物的合成、表征及对超氧离子的抑制作用合成化学[J].重庆大学学报,2002,4(10):314-317.
[66]中本一雄著,黄德如,汪仁庆译.无机和配位化合物的红外和拉曼光谱.北京:化学工业出版社,1986,237-239.
[67]李思良,水杨醛缩二胺三胺类西佛碱锰配合物的制备及生物活性研究[D].硕士研究生论文,贵州大学,贵州,2004年.