稀土席夫碱8-羟基喹啉配合物合成及抑菌活性研究
|
摘要
本论文采用液相沉淀法合成了稀土席夫碱8-羟基喹啉配合物并对其抑菌性能进行了详细的研究。首先以水杨醛和5-氨基水杨酸为原料,合成配体席夫碱水杨醛缩5-氨基水杨酸,再以稀土氯化物(分别为轻稀土La、Nd,中稀土Gd、Tb,重稀土Yb)、席夫碱水杨醛缩5-氨基水杨酸和8-羟基喹啉为配体,在无水乙醇溶液中反应,制备出一类稀土新型三元配合物。通过核磁共振、红外光谱、紫外-可见吸收光谱、差热-热重分析等测试分析方法确定了所制备配合物的化学组成、性质和成键特性。配体席夫碱水杨醛缩5-氨基水杨酸以四齿形式参与配位,配体8-羟基喹啉以二齿形式参与配位,配位数分别为7(La和Nd)和9(Gd、Tb和Yb)。通过抗菌实验对所制备的稀土新型三元配合物的抑菌效果进行了研究,结果表明,配合物对大肠杆菌、枯草杆菌和青霉菌均表现出不同程度的抑菌效果,其中对枯草杆菌具有中等的抑菌效果,对大肠杆菌具有强抑菌效果,而对青霉菌的抑菌效果最好。Gd配合物、Tb配合物和Yb配合物的抑菌效果明显好于La配合物和Nd配合物,这说明中、重稀土配合物的抑菌性能好于轻稀土配合物。在室温条件下,5种稀土三元配合物对3种细菌的抑制作用,均可达一周时间以上,说明所合成的稀土三元配合物抑菌效果稳定。
In this dissertation, we have prepared the complex of rare earth Schiff base 8-hxyquinoline via liquid-phase deposition, and studied their antimicrobial performance in detail. The ligand of Schiff base salicylaldehyde 5-aminosalicylic acid was obtained by the synthesis of salicylaldehyde and 5-aminosalicylic acid as the raw material. A class of new ternary rare earth complexes, prepared with in ethanol solution with rare earth (light rare earth La, Nd, middle rare earth Gd, Tb, heavy rare earth Yb) chloride, Schiff base salicylaldehyde 5-aminosalicylic acid and 8-hxyquinoline as ligand. The chemical composition, properties and bonding characteristics of the complex were identified by magnetic resonance spectra, infra-red spectra, UV-visible absorption spectra and DTA-TGA modern analytical techniques. Schiff base salicylaldehyde 5-aminosalicylic acid and 8-hxyquinoline participate in a four-tooth and two-tooth of coordination with the rare earth ion, and the coordinate number are 7 (for La and Nd)and 9 (for Gd、Tb and Yb), respectively. Through the studying of the antimicrobial effects test of the obtained ternary rare earth complexes, the results show that the complexes have different antimicrobial effects on the E.coli, bacillus subtilis and Penicillium, the complexes have a moderate antibacterial activity against bacillus subtilis, better antibacterial effect against E.coli, and best antibacterial effect against Penicillium. The antibacterial effect on the complex of Gd, Tb and Yb are better than the complex of La and Nd, which can be illustrated that the antibacterial of the complex of hight and middle rare earth are better than the complex of light rare earth. In addition, at room temperature, the antimicrobial effects of five kinds of rare earth ternary complexs to the three kinds of bacteria inhibition can keep more than a week, which can be indicated that the synthesized ternary complex have good stability antimicrobial effects.
In this dissertation, we have prepared the complex of rare earth Schiff base 8-hxyquinoline via liquid-phase deposition, and studied their antimicrobial performance in detail. The ligand of Schiff base salicylaldehyde 5-aminosalicylic acid was obtained by the synthesis of salicylaldehyde and 5-aminosalicylic acid as the raw material. A class of new ternary rare earth complexes, prepared with in ethanol solution with rare earth (light rare earth La, Nd, middle rare earth Gd, Tb, heavy rare earth Yb) chloride, Schiff base salicylaldehyde 5-aminosalicylic acid and 8-hxyquinoline as ligand. The chemical composition, properties and bonding characteristics of the complex were identified by magnetic resonance spectra, infra-red spectra, UV-visible absorption spectra and DTA-TGA modern analytical techniques. Schiff base salicylaldehyde 5-aminosalicylic acid and 8-hxyquinoline participate in a four-tooth and two-tooth of coordination with the rare earth ion, and the coordinate number are 7 (for La and Nd)and 9 (for Gd、Tb and Yb), respectively. Through the studying of the antimicrobial effects test of the obtained ternary rare earth complexes, the results show that the complexes have different antimicrobial effects on the E.coli, bacillus subtilis and Penicillium, the complexes have a moderate antibacterial activity against bacillus subtilis, better antibacterial effect against E.coli, and best antibacterial effect against Penicillium. The antibacterial effect on the complex of Gd, Tb and Yb are better than the complex of La and Nd, which can be illustrated that the antibacterial of the complex of hight and middle rare earth are better than the complex of light rare earth. In addition, at room temperature, the antimicrobial effects of five kinds of rare earth ternary complexs to the three kinds of bacteria inhibition can keep more than a week, which can be indicated that the synthesized ternary complex have good stability antimicrobial effects.
引文
[1]李炜罡,吕维平,王海滨等.抗菌材料进展[J].化工新型材料,2003,31(3):7-10
[2]沈萍.微生物学[M].北京:高等教育出版社,2003,27
[3]牛晓东.化工新型材料,1999,27(11):44
[4]吕维平,王海滨等.抗菌材料进展[J].化工新型材料,2003,31(3):7-10
[5]吉向飞,李玉平,杨柳青等.抗菌剂及抗菌材料的发展与应用fJ].太原理工大学学报,2003,34(1):11-15
[6]Ziche M,Morbidelli L,Masini E,et al.Nitric oxide mediates angiogenesis in vivo and endothelial cell growth and migration in vitro promoted by substance p[J].J Chin Invest,1994,94(5):2036-2044
[7]Fukumura D,Jain RK.Role of nitric oxide in angiogenesis and microcirculation in tumors[J].Cancer Metastasis Rev,1998,17(1):77-89
[8]Kolb H,Kolb-Bachofen V.Nitric oxide a pathogenetic factor in autoimmunity[J].Immunol Today,1992,13(5):157-159
[9]Buchholz HW,Elson RA,Heinert K.Antibiotic-loaded acrylic cement:current concepts[J].Clin Orthop Relat Res,1984,190:96-108
[10]Kroncke KD,Kolb-Bachofen V,Berschick B,et al.Activated macrophages kill pancreatic syngeneic islet cells via arginine-dependent nitric oxide generation[J].Biochem Biophys Res Commun,1991,175(3):752-758
[11]李梅,王庆瑞.抗菌材料的发展及其应用[J].化工新型材料,1998,26(5):8-11
[12]Bengtson S,Knutson K.The infected knee arthoplasty:A 6-year follow-up of 357 cases[J].Acta Orthop Scand,1991,62(4):301-311
[13]周轩榕,卢滇楠,邵曼君等.表面接枝季铵盐型高分子材料抗菌过程的特性的研究[J].高等学校化学学报,2003,24(6):1131-1135
[14]Salvati EA,Brause BD.Infection of orthopedic prostheses.In:Schlossberg D,editor.Orthopeadic infection[M].New York:Springer,1988.133-144
[15]Badia J M,Torres J M,Tur C,et al.Saline wound irrigation reduces the postoperative infection rate in guinea pigs[J].J Surg Res,1996,63(2):457-459
[16]王耀明.陶瓷抗菌剂极其应用[J].现代技术陶瓷,1998,(2):19-22
[17]马凤英,王文英.大蒜素的药理学研究进展[J].中草药,1997,28(11):697
[18]马慕英.大蒜抗真菌作用的研究[J].食品科学,1993,157(1):7211
[19]张葵花,林松柏,谭绍早.有机抗菌剂研究现状及发展趋势[J].涂料工业,2005(5):45-49
[20]Hibbs J B,Taintor R R,Vavrin Z,et al.Nitric oxide a cytotoxic activated macrophage effector molecule[J].Biochem Biophys Res Commun,1988,157(1):87-94
[21]Marletta M A,Yoon P S,lyengar R,et al.Macrophage oxidation of 1-arginnine to nitrite and nitrate:nitric oxide is an intermediate[J].Biochemistry,1988,27(24):8706-8711
[22]Stuehr D J,Nathan C F.Nitric oxide a macrophage product responsible for cytostasis and respiratory inhibition in tumor target cells[J].J Exp Med,1989,169(5):1543-1555
[23]Nussler A,Drapier JC,Renia L,et al.L-arginine-dependent destruction of intrahepatic malaria parasites in response to tumor necrosis factor and/or interleukin 6 stimulation[J].Eur J Immunol,1991,21(1):227-230
[24]Liew FY,Millott S,Parkinson C,et al.Macrophage killing of Leishmania parasite in vivo is mediated by nitric oxide from L-arginine[J].J Immunol,1990,144(12):4794-4797
[25]Granger DL,Hibbs JB,Perfect JR,et al.Specific amino acid(L-arginine) requirement for the microbiostatic activity of murine macrophages[J].J Clin Invert,1988,81(4):1129-1136
[26]Shiloh MU,MacMicking JD,Nicholson S,et al.Phenotype of mice and macrophages deficient in both phagocyte oxidase and inducible nitric oxide synthase[J].Immunity,1999,10(1):29-38
[27]McInnes IB,Leung B,Wei XQ,et al.Septic arthritis following Staphylococcus aureus infection in mice lacking inducible nitric oxide synthase[J].J Immunol,1998,160(1):308-315
[28]Kwok CS,Horbett TA,RatnerBD,Design of infection-resistant antibiotic-releasing polymers Ⅱ.Controlled release of antibiotics through a plasma-deposited thin film barrier[J].Journal of Controlled Release,1999,62(3):301-311
[29]张金莲,郑国民.杀菌防霉剂在乳胶漆中的应用研究[J].涂料工业,2001,31(9):1-3
[30]李凤艳,赵天波,汪燮卿等.交联聚苯乙烯树脂固载杀菌活性官能团制备季铵盐类杀菌剂[J].油化工高等学校学报,2001,14(3):22-25
[31]赵天波,李凤艳,汪燮卿等.带长链烷基季铵盐杀菌活性官能团树脂的合成[J].环境污染治理技术与设备,2002,3(10):68-71
[32]萧耀南,曾汉民,张菊梅等.含多官能团功能聚丙烯腈纤维抗菌消臭机理的研究[J].合成纤维工业,2002,25(3):12-16
[33]Li GJ,Shen JR,Zhu YL.Study of pyridinium-type functional polymers.Ⅱ.Antibacterial activity of soluble pyridinium-type polymers[J].J Appl Polym Sci,1998,67(10):1761-1768
[34]Guangji Li,Jiarui Shen,Yinlan Zhu.A study of pyridinium-type functional polymers.Ⅲ.Preparation and characterization of insoluble pyridinium-type polymers[J].J Appl Polym Sci,2000,78(3):668-675
[35]Guangji Li,Jiarui Shen,Yinlan Zhu.A study of pyridinium-type functional polymers.Ⅳ.Behavioral features of the antibacterial activity of insoluble pyridinium-type polymers[J].J Appl Polym Sci,2000,78(3):676-684
[36]J.S.Park,J.H.Kim,et al.Antibacterial activities of acrylic acid-grafted polypropylene fabric and its metallic salt[J].J Appl Polym Sci,1998,69(11):2213-2220
[37]童身毅,吴壁耀编.涂料树脂合成与配方原理[M].武汉:华中理工大学出版社,1990,91
[38]张文钲.载银抗菌剂及其相关产品[J].化工新型材料,2001,29(10):27-29
[39]王永华,杨博.浅谈纳米材料的抗菌实验方法[J].材料开发与应用,2001,16(1):30-32
[40]季君晖,史维明.抗菌材料[M].北京:化学工业出版社,2003,57
[41]王勇.抗菌粉末涂料[J].中国涂料,2001,(1):29
[42]张立德,牟季美.纳米材料和纳米结构[M].北京:科学技术出版社,2001,35
[43]楚珑晟,周祚万.ZnOW/纳米复合抗菌剂的研制[J].材料导报,2003,17(6):84
[44]季君晖,史维民.抗菌材料[M].北京:化学工业出版社,2003,65
[45]李毕忠.抗菌塑料的研究应用和市场现状[J].化工商品科技,1999,22(2):10-12
[46]Sun YY,Sun G.Novel Regenerable N-Halamine Polymeric Biocides.Ⅲ.Grafting Hydantoin-Containing Monomers onto Synthetic Fabrics[J].J Appl Polym Sci,2001,81(6):1517-1525
[47]Takamasa N,Kenji Y,et al.Preparation of superabsorbent polymer hydrogels from trialkyl-4-vinylbenzyl phosphonium chloride-acrylamide-methylenebisacrylamide terpolymers and their properties[J].J Appl Poly Sci,2000,78(10):1833-1844
[48]Nablo BJ,Chen T-Y,Schoenfisch MH.Sol-gel derived nitric-oxide releasing materials that reduce bacterial adhesion[J].J Am Chem Soc,2001,123(39):9712-9713
[49]Nablo BJ,Schoenfisch MH.Antibacterial properties of nitric oxide-releasing sol-gels[J].J Biomed Mater Res,2003,67(4):1276-1283
[50]廖莉玲,刘吉平.新型无机抗菌剂[J].现代化工,2002,21(7):62-64
[51]Marxer SM,Rothrock AR,Nablo BJ,et al.Preparation of nitric oxide(NO)-reteasing sol-gels for biomaterial applications[J].Chem Mater,2003,15(22):4139-4199
[52]张文钲,张羽天.APACIAER抗菌剂及其相关产品[J].化工新型材料,2000,28(6):25-27
[53]张文钲.一种新型无机抗菌剂—钼酸银[J].化工新型材料,2004,32(3):29-30
[54]陈仪本,欧阳友生等.工业杀菌剂[M].北京:化学工业出版社,2001,198
[55]Hu W,Eaton JW,Tang L.Molecular basis of biomaterial mediated foreign body reactions[J].Blood,2001,98(4):1231-1238
[56]赵天波,李凤艳,汪燮卿等.带长链烷基季铵盐杀菌活性官能团树脂的合成[J].环境污染治理技术与设备,2002,3(10):68-71
[57]Park ES,Kim HS,Kim MN,et al.Antibacterial activities of polystyrene-block-poly(4-vinylpyridine) and poly(styrene-random-4-vinyl pyridine)[J].European Polymer Journal,2004,40(12):2819-2822
[58]高胜利,薛鸿福,张万龙等.氯化稀土与丙氨酸配合行为的研究[J].化学学报,1994,52(7):693-698
[59]张若骅.稀土元素化学[M].大津:天津科学技术出版社,1987,26
[60]倪嘉缵.稀土生物无机化学(第二版)[M].北京:科学出版社,2002,298
[61]叶勇,胡继明,曾云鹗.2-氯代苯甲醛丙氨酸席夫碱类抗癌药物对DNA作用的谱学研究[J].无机化学学报,1998,14(1):84
[62]田庆伟,白成江,李裘丽等.活性氯化稀土的研究[J].卫生毒理学杂志,1992,6(1):32-34
[63]邹彤彤,沈华,邹世渠等.5种稀土粉尘的细胞毒性研究[J].工业卫生与职业病,1992,18(2):82
[64]Yanjaneyulu,Swamy R Y,Prabhakra R R,et al.Studies on some mixed ligand complexes of copper(Ⅱ) with 8-hydroxyquinoline and salicylic acids relation between stability constants and antimicrobial activity[J],J Indian Chem.Soc,1985,LⅦ(May):346-351
[65]Yan B,Zhang H,Wang S,et al.Synthesis,Luminescence energy transfer of binary and ternary rare-earth complexes with 5-sulfosalicylic acid and 1,10-phenanthroline[J].Chem.Papers,1998,52(4):199-204
[66]Kolhe V,Dwivedi K.Stability constants of mixed ligand complexes of lanthanide(Ⅲ) and yttrium(Ⅲ)with complexone and substituted salicylic acids[J].Indian Chem Soc,1996,73(6):265-268
[67]庞伦,陈荣莲,张茂东等.稀土磺基水杨酸络合物与抑菌效应[J].暨南大学学报,1990,11(3):102-110
[68]陈淑英,张新怀,王金玉等.具有生物活性的金属配合物研究(Ⅶ)-对氨基水杨酸稀土配合物的合成性质抗结核菌及毒性研究[J].高等学校化学学报,1988,9(8):759-763
[69]王则民,曹锦荣,周德兴等.稀土水杨酸8-羟基喹啉配合物的表征和抑菌效应[J].自然杂志,1995,17(1):54-55
[70]顾尚香,姚卡玲等.硼合水杨酸稀土配合物的合成及抑菌作用[J].应用化学,1996,13(4):45-48
[71]周毓萍,杨正银,于红娟等.3-醛基水杨酸缩氨基硫脲希土配合物的合成、表征及抑菌活性研究[J].无机化学学报,1998,14(2):1-4
[72]张幼珠,黄英.硝酸铈与8-羟基喹啉配合物的合成、表征及抗菌性能[J].印染助剂,2003,20(2):12-14
[73]王学智.稀土氯化物与8-羟基喹啉配合物的合成、表征及抑菌效应研究[J].合成纤维,1997,26(3):21-23
[74]何洪银,朱龙观.稀土8-羟基喹啉四元混合阴离子配合物合成和表征[J].浙江大学学报(理学版),2002,29(4):446-447
[75]吴惠霞,王则民,杨海峰等.稀土烟酸与8-羟基喹啉三元配合物的合成、表征及荧光光谱[J].中国稀土学报,2002,20(4):289-292
[2]沈萍.微生物学[M].北京:高等教育出版社,2003,27
[3]牛晓东.化工新型材料,1999,27(11):44
[4]吕维平,王海滨等.抗菌材料进展[J].化工新型材料,2003,31(3):7-10
[5]吉向飞,李玉平,杨柳青等.抗菌剂及抗菌材料的发展与应用fJ].太原理工大学学报,2003,34(1):11-15
[6]Ziche M,Morbidelli L,Masini E,et al.Nitric oxide mediates angiogenesis in vivo and endothelial cell growth and migration in vitro promoted by substance p[J].J Chin Invest,1994,94(5):2036-2044
[7]Fukumura D,Jain RK.Role of nitric oxide in angiogenesis and microcirculation in tumors[J].Cancer Metastasis Rev,1998,17(1):77-89
[8]Kolb H,Kolb-Bachofen V.Nitric oxide a pathogenetic factor in autoimmunity[J].Immunol Today,1992,13(5):157-159
[9]Buchholz HW,Elson RA,Heinert K.Antibiotic-loaded acrylic cement:current concepts[J].Clin Orthop Relat Res,1984,190:96-108
[10]Kroncke KD,Kolb-Bachofen V,Berschick B,et al.Activated macrophages kill pancreatic syngeneic islet cells via arginine-dependent nitric oxide generation[J].Biochem Biophys Res Commun,1991,175(3):752-758
[11]李梅,王庆瑞.抗菌材料的发展及其应用[J].化工新型材料,1998,26(5):8-11
[12]Bengtson S,Knutson K.The infected knee arthoplasty:A 6-year follow-up of 357 cases[J].Acta Orthop Scand,1991,62(4):301-311
[13]周轩榕,卢滇楠,邵曼君等.表面接枝季铵盐型高分子材料抗菌过程的特性的研究[J].高等学校化学学报,2003,24(6):1131-1135
[14]Salvati EA,Brause BD.Infection of orthopedic prostheses.In:Schlossberg D,editor.Orthopeadic infection[M].New York:Springer,1988.133-144
[15]Badia J M,Torres J M,Tur C,et al.Saline wound irrigation reduces the postoperative infection rate in guinea pigs[J].J Surg Res,1996,63(2):457-459
[16]王耀明.陶瓷抗菌剂极其应用[J].现代技术陶瓷,1998,(2):19-22
[17]马凤英,王文英.大蒜素的药理学研究进展[J].中草药,1997,28(11):697
[18]马慕英.大蒜抗真菌作用的研究[J].食品科学,1993,157(1):7211
[19]张葵花,林松柏,谭绍早.有机抗菌剂研究现状及发展趋势[J].涂料工业,2005(5):45-49
[20]Hibbs J B,Taintor R R,Vavrin Z,et al.Nitric oxide a cytotoxic activated macrophage effector molecule[J].Biochem Biophys Res Commun,1988,157(1):87-94
[21]Marletta M A,Yoon P S,lyengar R,et al.Macrophage oxidation of 1-arginnine to nitrite and nitrate:nitric oxide is an intermediate[J].Biochemistry,1988,27(24):8706-8711
[22]Stuehr D J,Nathan C F.Nitric oxide a macrophage product responsible for cytostasis and respiratory inhibition in tumor target cells[J].J Exp Med,1989,169(5):1543-1555
[23]Nussler A,Drapier JC,Renia L,et al.L-arginine-dependent destruction of intrahepatic malaria parasites in response to tumor necrosis factor and/or interleukin 6 stimulation[J].Eur J Immunol,1991,21(1):227-230
[24]Liew FY,Millott S,Parkinson C,et al.Macrophage killing of Leishmania parasite in vivo is mediated by nitric oxide from L-arginine[J].J Immunol,1990,144(12):4794-4797
[25]Granger DL,Hibbs JB,Perfect JR,et al.Specific amino acid(L-arginine) requirement for the microbiostatic activity of murine macrophages[J].J Clin Invert,1988,81(4):1129-1136
[26]Shiloh MU,MacMicking JD,Nicholson S,et al.Phenotype of mice and macrophages deficient in both phagocyte oxidase and inducible nitric oxide synthase[J].Immunity,1999,10(1):29-38
[27]McInnes IB,Leung B,Wei XQ,et al.Septic arthritis following Staphylococcus aureus infection in mice lacking inducible nitric oxide synthase[J].J Immunol,1998,160(1):308-315
[28]Kwok CS,Horbett TA,RatnerBD,Design of infection-resistant antibiotic-releasing polymers Ⅱ.Controlled release of antibiotics through a plasma-deposited thin film barrier[J].Journal of Controlled Release,1999,62(3):301-311
[29]张金莲,郑国民.杀菌防霉剂在乳胶漆中的应用研究[J].涂料工业,2001,31(9):1-3
[30]李凤艳,赵天波,汪燮卿等.交联聚苯乙烯树脂固载杀菌活性官能团制备季铵盐类杀菌剂[J].油化工高等学校学报,2001,14(3):22-25
[31]赵天波,李凤艳,汪燮卿等.带长链烷基季铵盐杀菌活性官能团树脂的合成[J].环境污染治理技术与设备,2002,3(10):68-71
[32]萧耀南,曾汉民,张菊梅等.含多官能团功能聚丙烯腈纤维抗菌消臭机理的研究[J].合成纤维工业,2002,25(3):12-16
[33]Li GJ,Shen JR,Zhu YL.Study of pyridinium-type functional polymers.Ⅱ.Antibacterial activity of soluble pyridinium-type polymers[J].J Appl Polym Sci,1998,67(10):1761-1768
[34]Guangji Li,Jiarui Shen,Yinlan Zhu.A study of pyridinium-type functional polymers.Ⅲ.Preparation and characterization of insoluble pyridinium-type polymers[J].J Appl Polym Sci,2000,78(3):668-675
[35]Guangji Li,Jiarui Shen,Yinlan Zhu.A study of pyridinium-type functional polymers.Ⅳ.Behavioral features of the antibacterial activity of insoluble pyridinium-type polymers[J].J Appl Polym Sci,2000,78(3):676-684
[36]J.S.Park,J.H.Kim,et al.Antibacterial activities of acrylic acid-grafted polypropylene fabric and its metallic salt[J].J Appl Polym Sci,1998,69(11):2213-2220
[37]童身毅,吴壁耀编.涂料树脂合成与配方原理[M].武汉:华中理工大学出版社,1990,91
[38]张文钲.载银抗菌剂及其相关产品[J].化工新型材料,2001,29(10):27-29
[39]王永华,杨博.浅谈纳米材料的抗菌实验方法[J].材料开发与应用,2001,16(1):30-32
[40]季君晖,史维明.抗菌材料[M].北京:化学工业出版社,2003,57
[41]王勇.抗菌粉末涂料[J].中国涂料,2001,(1):29
[42]张立德,牟季美.纳米材料和纳米结构[M].北京:科学技术出版社,2001,35
[43]楚珑晟,周祚万.ZnOW/纳米复合抗菌剂的研制[J].材料导报,2003,17(6):84
[44]季君晖,史维民.抗菌材料[M].北京:化学工业出版社,2003,65
[45]李毕忠.抗菌塑料的研究应用和市场现状[J].化工商品科技,1999,22(2):10-12
[46]Sun YY,Sun G.Novel Regenerable N-Halamine Polymeric Biocides.Ⅲ.Grafting Hydantoin-Containing Monomers onto Synthetic Fabrics[J].J Appl Polym Sci,2001,81(6):1517-1525
[47]Takamasa N,Kenji Y,et al.Preparation of superabsorbent polymer hydrogels from trialkyl-4-vinylbenzyl phosphonium chloride-acrylamide-methylenebisacrylamide terpolymers and their properties[J].J Appl Poly Sci,2000,78(10):1833-1844
[48]Nablo BJ,Chen T-Y,Schoenfisch MH.Sol-gel derived nitric-oxide releasing materials that reduce bacterial adhesion[J].J Am Chem Soc,2001,123(39):9712-9713
[49]Nablo BJ,Schoenfisch MH.Antibacterial properties of nitric oxide-releasing sol-gels[J].J Biomed Mater Res,2003,67(4):1276-1283
[50]廖莉玲,刘吉平.新型无机抗菌剂[J].现代化工,2002,21(7):62-64
[51]Marxer SM,Rothrock AR,Nablo BJ,et al.Preparation of nitric oxide(NO)-reteasing sol-gels for biomaterial applications[J].Chem Mater,2003,15(22):4139-4199
[52]张文钲,张羽天.APACIAER抗菌剂及其相关产品[J].化工新型材料,2000,28(6):25-27
[53]张文钲.一种新型无机抗菌剂—钼酸银[J].化工新型材料,2004,32(3):29-30
[54]陈仪本,欧阳友生等.工业杀菌剂[M].北京:化学工业出版社,2001,198
[55]Hu W,Eaton JW,Tang L.Molecular basis of biomaterial mediated foreign body reactions[J].Blood,2001,98(4):1231-1238
[56]赵天波,李凤艳,汪燮卿等.带长链烷基季铵盐杀菌活性官能团树脂的合成[J].环境污染治理技术与设备,2002,3(10):68-71
[57]Park ES,Kim HS,Kim MN,et al.Antibacterial activities of polystyrene-block-poly(4-vinylpyridine) and poly(styrene-random-4-vinyl pyridine)[J].European Polymer Journal,2004,40(12):2819-2822
[58]高胜利,薛鸿福,张万龙等.氯化稀土与丙氨酸配合行为的研究[J].化学学报,1994,52(7):693-698
[59]张若骅.稀土元素化学[M].大津:天津科学技术出版社,1987,26
[60]倪嘉缵.稀土生物无机化学(第二版)[M].北京:科学出版社,2002,298
[61]叶勇,胡继明,曾云鹗.2-氯代苯甲醛丙氨酸席夫碱类抗癌药物对DNA作用的谱学研究[J].无机化学学报,1998,14(1):84
[62]田庆伟,白成江,李裘丽等.活性氯化稀土的研究[J].卫生毒理学杂志,1992,6(1):32-34
[63]邹彤彤,沈华,邹世渠等.5种稀土粉尘的细胞毒性研究[J].工业卫生与职业病,1992,18(2):82
[64]Yanjaneyulu,Swamy R Y,Prabhakra R R,et al.Studies on some mixed ligand complexes of copper(Ⅱ) with 8-hydroxyquinoline and salicylic acids relation between stability constants and antimicrobial activity[J],J Indian Chem.Soc,1985,LⅦ(May):346-351
[65]Yan B,Zhang H,Wang S,et al.Synthesis,Luminescence energy transfer of binary and ternary rare-earth complexes with 5-sulfosalicylic acid and 1,10-phenanthroline[J].Chem.Papers,1998,52(4):199-204
[66]Kolhe V,Dwivedi K.Stability constants of mixed ligand complexes of lanthanide(Ⅲ) and yttrium(Ⅲ)with complexone and substituted salicylic acids[J].Indian Chem Soc,1996,73(6):265-268
[67]庞伦,陈荣莲,张茂东等.稀土磺基水杨酸络合物与抑菌效应[J].暨南大学学报,1990,11(3):102-110
[68]陈淑英,张新怀,王金玉等.具有生物活性的金属配合物研究(Ⅶ)-对氨基水杨酸稀土配合物的合成性质抗结核菌及毒性研究[J].高等学校化学学报,1988,9(8):759-763
[69]王则民,曹锦荣,周德兴等.稀土水杨酸8-羟基喹啉配合物的表征和抑菌效应[J].自然杂志,1995,17(1):54-55
[70]顾尚香,姚卡玲等.硼合水杨酸稀土配合物的合成及抑菌作用[J].应用化学,1996,13(4):45-48
[71]周毓萍,杨正银,于红娟等.3-醛基水杨酸缩氨基硫脲希土配合物的合成、表征及抑菌活性研究[J].无机化学学报,1998,14(2):1-4
[72]张幼珠,黄英.硝酸铈与8-羟基喹啉配合物的合成、表征及抗菌性能[J].印染助剂,2003,20(2):12-14
[73]王学智.稀土氯化物与8-羟基喹啉配合物的合成、表征及抑菌效应研究[J].合成纤维,1997,26(3):21-23
[74]何洪银,朱龙观.稀土8-羟基喹啉四元混合阴离子配合物合成和表征[J].浙江大学学报(理学版),2002,29(4):446-447
[75]吴惠霞,王则民,杨海峰等.稀土烟酸与8-羟基喹啉三元配合物的合成、表征及荧光光谱[J].中国稀土学报,2002,20(4):289-292