桦木醛缩氨基硫脲铜、银、镉、钯金属配合物的合成及其生物活性研究
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摘要
运用拼合原理,合成了2种桦木醛缩氨基硫脲配体以及它们的铜、银、镉、钯金属配合物,运用红外光谱、核磁共振氢谱、热重分析、飞行质谱和元素分析方法对其进行了结构表征,并测试了配体和配合物的抑菌活性和细胞毒性.结果表明:配合物Ag(L_1)_2NO_3·3H_2O对S.aureus 4220、S.mutans 3065和E.coli 1924有较好的抑制作用;配合物Ag(L_1)_2NO_3·3H_2O和Cu(L_1)_2Cl_2能够显著抑制Hela细胞的生存能力.
Using combination principle,two betulinal thiosemicarbazone ligands and their Cu(II),Ag(I),Cd(II)and Pd(II)metal complexes were synthesized,which were characterized by IR,~1H NMR,TGA,MALDI-TOF and elemental analysis.The ligands and their metal complexes were evaluated for their antimicrobial activity and cytotoxicity.The results showed that the complex Ag(L_1)_2NO_3·3H_2O has relatively good inhibitory effects on S.aureus 4220,S.mutans 3065 and E.coli 1924.Complexes Ag(L_1)_2NO_3·3H_2O and Cu(L_1)_2Cl_2 can significantly inhibit the viability of Hela cell.
Using combination principle,two betulinal thiosemicarbazone ligands and their Cu(II),Ag(I),Cd(II)and Pd(II)metal complexes were synthesized,which were characterized by IR,~1H NMR,TGA,MALDI-TOF and elemental analysis.The ligands and their metal complexes were evaluated for their antimicrobial activity and cytotoxicity.The results showed that the complex Ag(L_1)_2NO_3·3H_2O has relatively good inhibitory effects on S.aureus 4220,S.mutans 3065 and E.coli 1924.Complexes Ag(L_1)_2NO_3·3H_2O and Cu(L_1)_2Cl_2 can significantly inhibit the viability of Hela cell.
引文
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[2]Pettit G R,Melody N,Hempenstall F,et al.Antineoplastic agents.595.structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer[J].Natural Products,2014,77(4):863-872.
[3]Sinha D,Tiwari A K,Singh S,et al.Synthesis,characterization and biological activity of Schiff base analogues of indole-3-carboxald ehyde[J].Eur J Med Chem,2008,43(1):160-165.
[4]Karthikeyan M S,Prasad D J,Poojary B,et al.Synthesis and biological activity of schiff and mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety[J].Bioorg Med Chem,2006,14(22):7482-7489.
[5]Adsule S,Barve V,Chen D,et al.Novel schiff base copper complexes of quinoline-2 carboxaldehyde as proteasome inhibitors in human prostate cancer cells[J].J Med Chem,2006,49(24):7242-7246.
[6]Samus N M,Tsapkov V I,Gulya A P,et al.Coordination compounds of copper(II),nickel(II),and cobalt(II)withβ-thiosemicarbazones of isatin and N-methylisatin[J].Russian Journal of General Chemistry,2004,74(9):1428-1432.
[7]Petering H G,Buskirk H H,Underwood G E E,et al.Antitumor action of 2-oxo-3-ethoxybutyraldehyde bis(thiosemicarbazone)and similar compounds[J].Cancer Res,1964,64(3):367-372.
[8]West D X,Padhye S B,Sonawane P B.Structural and physical correlations in the biological properties of transition metal heterocyclic thiosemicarbazone and S-alkyldithiocarbazate complexes[J].Structure and Bonding:Complex Chemistry,1991,76:1-50.
[9]张夺.桦木醛缩氨基硫脲铜、银、镉金属配合物的合成[D].延吉:延边大学,2015.
[10]Prathimaa B,Yakkate S R,Somala A R,et al.Copper(II)and nickel(II)complexes of benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone:synthesis,character rization and biological activity[J].Spectrochimica Acta Part A,2010,77(1):248-252.
[11]Shaker S A.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.
[12]Quang D T,Hop N V,Luyen N D,et al.A new fluorescent chemosensor for Hg2+in aqueous solution[J].Luminescence:the Journal of Biological and Chemical Luminescence,2013,28(2):222-225.
[13]Rodriguez-Argüelles M C,Ferrari M B,Fava G G,et al.Acenaphthenequinone thiosemicarbazone and its transition metal complexes:synthesis,structure,and biological activity[J].Journal of Inorganic Biochemistry,1997,66(1):7-17.
[14]Konstantinovic S S,Radovanovic B C,Sovili S P,et al.Antimicrobial activity of some isatin-3-thiosemicarbazone complexes[J].J Serb Chem Soc,2008,73(1):7-13.
[15]Quiroga A G,Pérez J M,López-Solera I,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.
[16]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 structures and antibacterial activity[J].European Journal of Medicinal Chemistry,2011,46(1):150-159.
[17]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.
[18]SUN Qiao-Zhen,CHAI Li-Yuan.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.
[19]Todorovic T R,Bacchi A,Juranic N O.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.
[20]Wayne.Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically[M].PA,USA:Clinical and Laboratory Standards Institute,2012:22-41.
[21]邓汉芹,王明雄.胡椒醛缩氨基硫脲与钻(Ⅱ)、镍(Ⅱ)、铜(Ⅱ)和镉(Ⅱ)配合物的合成与性质研究[J].湖北大学学报,1992,14(2):155-160.