中山大学学报自然科学版 ›› 2019, Vol. 58 ›› Issue (5): 119-127.doi: 10.13471/j.cnki.acta.snus.2019.05.015

• 论文 • 上一篇    下一篇

水环境下羟自由基致布洛芬分子损伤的机理

姜春旭1,2,王佐成1,3,高峰1,3,佟华1,3,杨晓翠1,3,丛建民4   

  1. . 白城师范学院理论计算中心,吉林 白城137000; 
    2. 白城师范学院传媒学院,吉林 白城 137000;
    3. 白城师范学院物理学院,吉林 白城 137000;
    4. 白城师范学院生命科学学院,吉林 白城 137000
  • 收稿日期:2018-06-01 出版日期:2019-09-25 发布日期:2019-09-25
  • 通讯作者: 王佐成(1963年生),男;研究方向:化学反应机理;E-mail: wangzc188@163.com 丛建民 (1974年生),男;研究方向:生物物理化学;E-mail: congjianmin@126.com

Mechanism of ibuprofen molecule damage induced by hydroxyl radical in water environment

JIANG Chunxv1,2, WANG Zuocheng1,3, GAO Feng1,3, TONG Hua1,3, YANG Xiaocui1,3,CONG Jianmin4   

  1. 1.Theoretical Computing Center, Baicheng Normal University, Baicheng 137000, China;
    2.Communication College, Baicheng Normal University, Baicheng 137000, China;
     3.College of Physics, Baicheng Normal University, Baicheng 137000, China;
    4. College of Life Science,Baicheng Normal University, Baicheng 137000, China
  • Received:2018-06-01 Online:2019-09-25 Published:2019-09-25

摘要:

采用基于密度泛函理论的B3LYP方法和从头算的MP2方法,结合自洽反应场理论的SMD模型方法,研究了水汽环境下羟自由基致2种构象的布洛芬分子损伤及水溶剂化效应。研究发现:羟自由基致布洛芬损伤有羟自由基(水分子簇)抽α氢和羟自由基加成到苯环两种机理。势能面计算表明:对于布洛芬分子构象1,水分子辅助羟自由基抽α氢的反应通道具有优势,抽氢反应能垒是34.68 kJ/mol;对于布洛芬分子构象2,羟自由基抽α氢的反应通道具有优势,抽氢反应能垒是34.81 kJ/mol ;羟自由基加成到苯环的能垒大约是26.00 kJ/mol ;损伤的布洛芬分子难以修复。水溶剂化效应对羟自由基(水分子簇)抽α氢和羟自由基加成到苯环致布洛芬损伤反应的影响很小。

关键词: 布洛芬, 损伤, 羟自由基, 过渡态, 能垒

Abstract:

The studyinvestigated the damage of ibuprofen molecules with two conformations induced by hydroxyl radical and the effect of water solvation in water vapor environment. The methods were density functional theory using the B3LYP functional, ab initio MP2 and Slovation Model Density (SMD) model method based on self consistent reaction field theory. The study showed that ibuprofen molecule damage had two mechanisms: α-H abstraction of hydroxyl radicals(water clusters) and hydroxyl radicals addition to benzene ring. The calculation of potential energy surface showed that, for ibuprofen conformation-1, the reaction channel of αH abstraction of hydroxyl radicals assisted by water molecular had an advantage, where the energy barrier of α-H abstraction was 34.68 kJ·mol-1. For ibuprofen conformation-2, the reaction channel of α-H abstraction of hydroxyl radicals had an advantage, where the energy barrier of α-H abstraction was 34.81 kJ·mol-1. In addition, the energy barrier of hydroxyl radicals addition to benzene ring was about 26.00 kJ·mol-1, and damaged ibuprofen molecules were difficult to repair. The effect of water solvation had little effect on the ibuprofen molecules damage induced by αH abstraction of hydroxyl radicals(water clusters) and hydroxyl radicals addition to benzene ring.

 

Key words: ibuprofen, damage, hydroxyl radicals, transient state, energy barrier

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