桦木酮缩氨基硫脲铜、银、钯、镉金属配合物的合成、表征与生物活性研究
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摘要
运用拼合原理,合成了4种桦木酮缩氨基硫脲配体及其铜、银、镉、钯金属配合物,通过核磁共振氢谱(~1 H NMR)、红外光谱(IR)、元素分析、热重谱(TG)、飞行时间质谱(MALDI-TOF-MS)和元素分析对配体和配合物进行了结构表征.以最小抑菌浓度(MIC)评价了S.aureus 4220、S.mutans 3289、S.mutans 3065、E.coli1924和E.coli 1356的抑菌活性.结果表明:Ag(L_4)_2Cl_2·2H_2O对S.aureus 4220、S.mutans 3065和E.coli1924具有相对较好的抑制作用;Ag(L_1)_2NO_3·2MeOH、Cu(L_3)_2Cl_2·H_2O、Ag(L_3)_2Cl·3H_2O、Cd(L_3)_2Cl_2、Cu(L_4)_2Cl_2和Ag(L_4)_2Cl_2·2H_2O对Hela细胞有显著的抑制作用.
Four betulone thiosemicarbazone ligands and their copper(Ⅱ),silver(I),cadmium(Ⅱ)and palladium(Ⅱ)metal complexes were prepared by combination principle and characterized by ~1 H NMR,IR,TG,MALDI-TOF-MS,elemental analysis.Their antimicrobial activities on S.aureus 4220,S.mutans 3289,S.mutans3065,E.coli 1924 and E.coli 1356 were evaluated by mininum inhibitory concentration(MIC).The results showed that the complex Ag(L_4)_2Cl_2·2H_2O has relatively good inhibitory effects on S.aureus 4220,S.mutans3065 and E.coli 1924.Ag(L_1)_2NO_3 ·2MeOH,Cu(L_3)_2Cl_2 ·H_2O,Ag(L_3)_2Cl·3H_2O,Cd(L_3)_2Cl_2,Cu(L_4)_2Cl_2 and Ag(L_4)_2Cl_2·2H_2O have obvious inhibitory effects on the Hela cell.
Four betulone thiosemicarbazone ligands and their copper(Ⅱ),silver(I),cadmium(Ⅱ)and palladium(Ⅱ)metal complexes were prepared by combination principle and characterized by ~1 H NMR,IR,TG,MALDI-TOF-MS,elemental analysis.Their antimicrobial activities on S.aureus 4220,S.mutans 3289,S.mutans3065,E.coli 1924 and E.coli 1356 were evaluated by mininum inhibitory concentration(MIC).The results showed that the complex Ag(L_4)_2Cl_2·2H_2O has relatively good inhibitory effects on S.aureus 4220,S.mutans3065 and E.coli 1924.Ag(L_1)_2NO_3 ·2MeOH,Cu(L_3)_2Cl_2 ·H_2O,Ag(L_3)_2Cl·3H_2O,Cd(L_3)_2Cl_2,Cu(L_4)_2Cl_2 and Ag(L_4)_2Cl_2·2H_2O have obvious inhibitory effects on the Hela cell.
引文
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[3]Chi W F,Jin L,Piao F Y,et al.Synthesis of betulin derivatives containing triazole fragments[J].Chemistry of Natural Compounds,2013,49(2):484-487.
[4]Shreelekha Adsule,Sanjeev Banerjee,Fakhara Ahmed,et al.Hybrid anticancer agents:Isothiocyanate-progesterone conjugates as chemotherapeutic agents and insights into their cytotoxicities[J].Bioorganic&Medicinal Chemistry Letters,2010,20(3):1247-1251.
[5]敬娟,韩佳.生物电子等排原理在药学设计中的应用[J].黑龙江科技信息,2010(25):23.
[6]Prathimaa B,Raoa Y Subba,Reddyb S Adinarayana,et al.Copper(II)and nickel(II)complexes of benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone:synthesis,character-rization and biological activity[J].Part A:Molecular and Biomolecular Spectroscopy,2010,77(1):248-252.
[7]Shayma A Shaker.Synthesis,spectral and magnetic studies of newly mixed-ligand complexes of 4-formyl-acetanilide thiosemicarbazone and 3,4-dihydrocinnamic acid with some metal Ions[J].E-Journal of Chemistry,2010,7(s1):s594-s600.
[8]Duong Tuan Quang,Nguyen Van Hop,Nguyen Dinh Luyen,et al.A new fluorescent chemosensor for Hg2+in aqueous solution[J].The Journal of Biological and Chemical Luminescence,2013,28(2):222-225.
[9]R M C,F M B.Acenaphthenequinone thiosemicarbazone and its transition metal complexes:synthesis,structure,and biological activity[J].Journal of Inorganic Biochemistry,1997,66(1):7-17.
[10]Sandra S Konstantinovic,Blaga C Radovanovic,Sofija P Sovilj,et al.Antimicrobial activity of some isatin-3-thiosemicarbazone complexes[J].JSerb Chem Soc,2008,73(1):7-13.
[11]Adoracion G Quiroga,Jose M Perez,Isabel LopezSolera,et al.Binuclear chloro-bridged palladated and platinated complexes derived from p-isopropylbenzaldehyde thiosemicarbazone with cytotoxicity against cisplatin resistant tumor cell lines[J].Journal of Inorganic Biochemistry,1998,69(4):275-281.
[12]Vi珘nuelas-Zahínos E,Luna-Giles F,Torres-García P,et al.Co(III),Ni(II),Zn(II)and Cd(II)complexes with 2-acetyl-2-thiazoline thiosemicarbazone:synthesis,characterization,X-ray structuresand antibacterial activity[J].European Journal of Medicinal Chemistry,2011,46(1):150-159.
[13]Tudor Rosu,Aurelian Gulea,Anca Nicolae,et al.Complexes of 3dn metal ions with thiosemicarbazones:synthesis and antimicrobial activity[J].Molecules,2007,12(4):782-796.
[14]Marc-Andre Leblanc,Antonio Gonzalez-Sarrias,Floyd A Beckford,et al.Coordination chemistry of polyaromatic thiosemicarbazones 2:synthesis and biological activity of zinc,cobalt,and copper complexes of 1-(naphthalene-2-yl)ethanone thiosemicarbazone[J].International Journal of Inorganic Chemistry,2011(4-6),Article ID:624756,8.
[15]Sun Qiaozhen,Chai Liyuan.Structure and luminescence property of a hexanuclear silver(I)cluster containing pyridine-3-carboxaldehyde thiosemicarbazone[J].Chinese J Struct Chem,2012,31(3):408-414.
[16]Tamara R Todorovic,Alessia Bacchi,Nenad O Juranic,et al.Synthesis and characterization of novel Cd(II),Zn(II)and Ni(II)complexes with 2-quinolinecarboxaldehyde selenosemicarbazone.Crystal structure of bis(2-quinolinecarboxaldehyde selenosemicarbazonato)nickel(II)[J].Polyhedron,2007,26(13):3428-3436.
[17]邓汉琴,王明雄.胡椒醛缩氨基硫脲与钴、镍、铜和镉配合物的合成与性质研究[J].湖北大学学报(自然科学版),1992,14(2):155-160.
[18]Li Wenzhi,Wang Zhanyu,Wang Longmei,et al.Effectiveness of inhibitor rapamycin,saracatinib,linsitinib and JNJ-38877605against human prostate cancer cells[J].Int J Clin Exp Med,2015,8(4):6563-6567.
[19]Wayne.Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically[M].CLSI Approved Standard-Ninth Edition,Clinical and Laboratory Standards Institute PA.USA,2012:1-63.