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5-氯甲基水杨醛缩L-酪氨酸锰(Ⅱ)配合物的合成及生物活性的研究

熊亚红, 黄显才, 何金锋, 钟志伟, 王子芫, 黄嘉琪, 郑嘉雯

熊亚红, 黄显才, 何金锋, 钟志伟, 王子芫, 黄嘉琪, 郑嘉雯. 5-氯甲基水杨醛缩L-酪氨酸锰(Ⅱ)配合物的合成及生物活性的研究[J]. 华南农业大学学报, 2015, 36(4): 129-136. DOI: 10.7671/j.issn.1001-411X.2015.04.023
引用本文: 熊亚红, 黄显才, 何金锋, 钟志伟, 王子芫, 黄嘉琪, 郑嘉雯. 5-氯甲基水杨醛缩L-酪氨酸锰(Ⅱ)配合物的合成及生物活性的研究[J]. 华南农业大学学报, 2015, 36(4): 129-136. DOI: 10.7671/j.issn.1001-411X.2015.04.023
XIONG Yahong, HUANG Xiancai, HE Jinfeng, ZHONG Zhiwei, WANG Ziyuan, HUANG Jiaqi, ZHENG Jiawen. Synthesis and biological activities of maganesium (Ⅱ) complex with 5-(chloromethyl) salicylaldehyde-tyrosine[J]. Journal of South China Agricultural University, 2015, 36(4): 129-136. DOI: 10.7671/j.issn.1001-411X.2015.04.023
Citation: XIONG Yahong, HUANG Xiancai, HE Jinfeng, ZHONG Zhiwei, WANG Ziyuan, HUANG Jiaqi, ZHENG Jiawen. Synthesis and biological activities of maganesium (Ⅱ) complex with 5-(chloromethyl) salicylaldehyde-tyrosine[J]. Journal of South China Agricultural University, 2015, 36(4): 129-136. DOI: 10.7671/j.issn.1001-411X.2015.04.023

5-氯甲基水杨醛缩L-酪氨酸锰(Ⅱ)配合物的合成及生物活性的研究

基金项目: 

国家自然科学基金(青年科学基金) 21207041

广东省自然科学基金团队项目 S2013030012842

详细信息
    作者简介:

    熊亚红(1976-),女,副教授,博士,xiongyahong@scau.edu.cn

  • 中图分类号: O641.4;O644.17

Synthesis and biological activities of maganesium (Ⅱ) complex with 5-(chloromethyl) salicylaldehyde-tyrosine

  • 摘要:
    目的 

    在甲醇溶剂体系中合成5-氯甲基水杨醛缩L-酪氨酸Schiff碱配体及其Mn(Ⅱ)配合物.

    方法 

    通过元素分析、摩尔电导、红外光谱、紫外光谱及差热-热重方法确定它们的分子组成; 采用滤纸片法、光还原NBT法及荧光猝灭法测定该配合物的抗菌活性、SOD活性及其与牛血清白蛋白(BSA)的相互作用.

    结果和结论 

    5-氯甲基水杨醛缩L-酪氨酸Schiff碱配体及其Mn(Ⅱ)配合物的分子组成分别为K2L·3H2O(L = C17H14NO4Cl2-)和K[MnL(CH3COO)]·2H2O,配合物中Schiff碱配体上的亚胺基N、羧基O及酚羟基O均与Mn(Ⅱ)配位.该配合物的抗菌活性高于配体,且对革兰阴性菌大肠埃希菌的抗菌活性高于对革兰阳性菌金黄色葡萄球菌的; 该配合物具有较高的SOD活性,其IC50为1.616 μmol·L-1; 基于静态猝灭机理,该配合物能有效猝灭BSA的内源荧光,并与BSA结合形成1种基态复合物,25 ℃条件下与BSA的结合位点数n约为1,结合常数KA为1.62 × 106 L·mol-1,且分子内可能发生非辐射能量转移.

    Abstract:
    Objective 

    To synthesize a novel Schiff base, 5-(chloromethyl) salicylaldehyde-tyrosine and its maganesium(Ⅱ) complex with methanol solvent.

    Method 

    The ligand and complex were characterized by elemental analysis, molar conductance, IR, UV and TG-DTA.Antibacterial activity, SOD activity of the complex and its interaction with bovine serum albumin (BSA) were examined by filter paper method, photoreduction of nitro-blue tetrazolium (NBT) and fluorescence quenching technique, respectively.

    Result and conclusion 

    The ligand and complex formula were K2L·3H2O (L = C17H14NO4Cl2-) and K[MnL(CH3COO)]·2H2O, respectively.The nitrogen atom of imino group and the oxygen atoms of phenol group and carboxyl group in the ligand and one acetate ion were coordinated with the central metal Mn(Ⅱ). The antibacterial experiments in vitro showed that the complex had higher antibacterial activity than the Schiff base.The antibacterial activity against Escherichia coli as a gramnegative bacterium was higher than Staphylococcus aureus as a gram-positive bacterium. The complex had high SOD activity and its IC50 value was 1.616 μmol·L-1.The complex effectively quenches the intrinsic fluorescence of BSA via static quenching mechanism, and forming a ground-state complex with BSA. The number of binding sites (n) and the binding constant (KA) at 25 ℃ are about 1 and 1.62 × 106 L·mol-1 respectively, and non-radiation energy is transferred red from BSA to the complex possibly.

  • 图  1   配体Cmsatyr和配合物MnCmsatyr的差热-热重图

    Figure  1.   TG-DTA plots of Cmsatyr and MnCmsatyr

    图  2   配体Cmsatyr和配合物MnCmsatyr的FT-IR图

    Figure  2.   FT-IR spectra of Cmsatyr and MnCmsatyr

    图  3   25 ℃下配体Cmsatyr和配合物MnCmsatyr的紫外-可见谱图

    Figure  3.   Ultra-vis spectra of Cmsatyr and MnCmsatyr at 25 ℃

    图  4   配体Cmsatyr和配合物MnCmsatyr对大肠埃希菌和金黄色葡萄球菌的抑菌圈图

    Figure  4.   Bacteriostasis circles of Cmsatyr and MnCmsatyr against Escherichia coli and Staphylococcus aureus

    1: DMSO; 2: Mn(CH3 COO) 2; 3: Cmsatyr; 4: MnCmsatyr.

    图  5   来自人体和大肠埃希菌的天然Mn-SOD的活性中心结构

    Figure  5.   Active-site structure of native Mn-SOD from human and Escherichia coli

    图  6   25 ℃下配合物MnCmsatyr的D560 nm受时间影响图

    Figure  6.   Plot of D560 nm for the complex along with the time at 25 ℃

    图  7   25 ℃下配合物MnCmsatyr抑制率与浓度关系

    Figure  7.   Relationship between the inhibition rate (η) and concentration of the complex at 25 ℃

    图  8   25 ℃ MnCmsatyr-BSA体系的荧光猝灭曲线

    Figure  8.   Fluorescence quenching spectra of MnCmsatyr-BSA system at 25 ℃

    图  9   25 ℃下MnCmsatyr-BSA体系的Stern-Volmer关系图

    Figure  9.   Stern-Volmer plot of MnCmsatyr-BSA system at 25 ℃

    图  10   25 ℃下MnCmsatyr-BSA体系的lg((F0-F)/F)与lg([Q]t-n[P]t(F0-F)/F0)关系图

    Figure  10.   The relationship graph of lg((F0-F)/F) and lg([Q]t-n[P]t(F0-F)/F0) plot in MnCmsatyrBSA system at 25 ℃

    图  11   25 ℃条件下MnCmsatyr紫外光谱与BSA荧光光谱重叠图

    Figure  11.   Overlapping between the UV-vis absorption spectrum of MnCmsatyr and fluorescence emission spectrum of BSA at 25 ℃

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出版历程
  • 收稿日期:  2014-05-20
  • 网络出版日期:  2023-05-17
  • 刊出日期:  2015-07-09

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