高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (4): 831-838.doi: 10.7503/cjcu20130797

• 物理化学 • 上一篇    下一篇

2-{[4-氨基-5-(3,4,5-三甲氧基-苄基)-嘧啶-2-亚胺基]-甲基}-6-甲氧基-苯酚与酵母细胞和牛血清白蛋白的相互作用

蒋建宏1, 李旭1, 肖圣雄1, 谷惠文2, 李传华1, 杨平1, 魏得良1, 何笃贵1, 李爱桃1, 李霞1, 姚飞虹1, 李强国1()   

  1. 1. 湘南学院湘南稀贵金属化合物及其应用湖南省重点实验室, 化学与生命科学系, 郴州 423043
    2. 湖南大学化学生物传感与计量学国家重点实验室, 化学化工学院, 长沙 410082
  • 收稿日期:2013-08-16 出版日期:2014-04-10 发布日期:2014-02-27
  • 作者简介:联系人简介: 李强国, 男, 教授, 主要从事热化学和生物热化学研究. E-mail: liqiangguo@163.com
  • 基金资助:
    国家自然科学基金(批准号: 20973145, 21273190)、 湖南省教育厅科研计划基金(批准号: 11A112, 10C1233)和湖南省科技厅计划基金(批准号: 2011TP4016-1, 2012TP4021-5, 2013FJ3033)资助

Interaction of 2-{[4-Amino-5-(3,4,5-trimethoxy-benzyl)-pyrimidin-2-ylimino]-methyl}-6-methoxy-phenol with S. pombe Cells and BSA

JIANG Jianhong1, LI Xu1, XIAO Shengxiong1, GU Huiwen2, LI Chuanhua1, YANG Ping1, WEI Deliang1, HE Dugui1, LI Aitao1, LI Xia1, YAO Feihong1, LI Qiangguo1,*()   

  1. 1. Hunan Provincial Key Laboratory of Xiangnan Rare-Precious Metals Compounds and Applications, Department of Chemistry and Life Science, Xiangnan University, Chenzhou 423043, China
    2. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
  • Received:2013-08-16 Online:2014-04-10 Published:2014-02-27
  • Contact: LI Qiangguo E-mail:liqiangguo@163.com
  • Supported by:
    † Supported by the National Natural Science Foundation of China(No.20973145, 21273190), the Educational Ministry Foundation of Hunan Province, China(No.11A112, 10C1233) and the Science and Technology Ministry Foundation of Hunan Province, China(No.2011TP4016-1, 2012TP4021-5, 2013FJ3033)

摘要:

用等摩尔的邻香草醛(C8H8O3)与甲氧苄胺嘧啶(C14H18N4O3)反应, 合成了一种新的化合物2-{[4-氨基-5-(3,4,5-三甲氧基-苄基)-嘧啶-2-亚胺基]-甲基}-6-甲氧基-苯酚(APYP). 通过元素分析、 核磁共振、 摩尔电导、 红外光谱和紫外光谱等手段对其进行了表征, 其化学式为C22H24N4O5. 采用微量热法测定了APYP在301.15 K时对粟酒裂殖酵母细胞的生长代谢的产热曲线, 计算得到了粟酒裂殖酵母细胞生长速率常数k, 抑制率I 以及半抑制浓度IC50等热动力学参数. 实验结果表明, 随着APYP浓度的增加, 粟酒裂殖酵母细胞的生长代谢速率常数k减小, 抑制率I增加, 半抑制浓度IC50为123.2 mg/L(或2.96×10-4 mol/L), 即APYP对粟酒裂殖酵母细胞有抑制作用. 同时利用荧光光谱和紫外光谱等方法研究了APYP与牛血清白蛋白(BSA)在接近生理条件下的相互作用, 探讨了荧光猝灭机理, 计算了反应的结合常数、 结合位点、 结合距离及热力学参数, 研究了APYP与BSA之间的能量转移情况; 并通过同步荧光光谱考察了APYP对BSA二级结构的影响.

关键词: 邻香草醛, 甲氧苄氨嘧啶, 热动力学参数, 牛血清白蛋白, 粟酒裂殖酵母细胞

Abstract:

A new compound 2-{[4-amino-5-(3,4,5-trimethoxy-benzyl)-pyrimidin-2-ylimino]-methyl}-6-methoxy-phenol(APYP) was synthesized using equivalent moles of o-vanillin(C8H8O3) and trimethoprim(C14H18N4O3). Elemental analysis, molar conductivity, UV-Visual, IR and NMR spectroscopy were employed to characterize the composition and structure of APYP. The analytical results showed that the molecular formula of the compound is C22H24N4O5. The thermokinetic properties of the action of APYP on growth meta-bolism of S. pombe were studied by a TAM air isothermal calorimeter at 301.15 K. The microbial growth rate constant(k), inhibition ratio(I) and half inhibition concentration(IC50) were obtained. Experimental results show that the k values of S. pombe decreased and I values of S. pombe increased with the increase in the concentrations of APYP and the IC50 value of APYP was found to be 123.20 mg/L. The APYP has good inhibition activity on the growth of S. pombe. Besides, fluorescence spectroscopy and UV-Vis absorption spectroscopy were employed to investigate the interactions of APYP with bovine serum albumin(BSA) under the approximatively physiological conditions. The binding constants, binding sites, binding distance, and the thermodynamic parameters were calculated. The energy transfer between the donor(BSA) and acceptor(APYP) was investigated. Furthermore, synchronous fluorescence spectroscopy was used to investigate the structural change of BSA molecules with additions of APYP.

Key words: o-Vanillin, Trimethoprim, Thermokinetic property, Bovine serum albumin, S. pombe cell

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