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高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (4): 671-677.doi: 10.1007/s40242-013-3059-x

• Articles • 上一篇    下一篇

Effects of Micelle on Pyrazoles as Antioxidants in Radical-induced Oxidation of DNA

LI Yan-feng, LIU Zai-qun   

  1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, P. R. China
  • 收稿日期:2013-02-04 修回日期:2013-04-03 出版日期:2013-08-01 发布日期:2013-07-15
  • 通讯作者: LIU Zai-qun E-mail:zaiqun-liu@jlu.edu.cn
  • 基金资助:

    Support by the Project of the Jilin Provincial Science and Technology Department, China(No.20130206075GX).

Effects of Micelle on Pyrazoles as Antioxidants in Radical-induced Oxidation of DNA

LI Yan-feng, LIU Zai-qun   

  1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, P. R. China
  • Received:2013-02-04 Revised:2013-04-03 Online:2013-08-01 Published:2013-07-15
  • Contact: LIU Zai-qun E-mail:zaiqun-liu@jlu.edu.cn
  • Supported by:

    Support by the Project of the Jilin Provincial Science and Technology Department, China(No.20130206075GX).

被引次数

2

摘要：

Effects of 4-(1,3-diphenyl-1H-pyrazol-5-yl)phenol(APP), 4-(1,5-diphenyl-1H-pyrazol-3-yl)phenol(BPP) and 4-(3,5-diphenyl-1H-pyrazol-1-yl)phenol(CPP) on 2,2'-azobis-(2-amidinopropane hydrochloride)(AAPH)-induced oxidation of DNA were measured in the presence of various concentrations of Triton X-100, cetyltrimethylammonium bromide(CTAB), or sodium dodecyl sulfate(SDS) in order to clarify the influence of neutral, cationic and anionic microenvironments on antioxidant capacities of APP, BPP and CPP. Although these surfactants can protect DNA against AAPH-induced oxidation, the pyrazoles in the presence of these surfactants functioned as prooxidants when the concentrations of Triton X-100 and CTAB increased. However, CPP exhibited antioxidant property with the increase of the concentration of CTAB. On the contrary, APP, BPP and CPP were antioxidants in the presence of various concentrations of SDS. The added surfactants resulted in the complication of the microenvironments around DNA, pyrazoles and peroxyl radical(ROO·) derived from AAPH. The anionic charge of SDS was beneficial to enhancing the antioxidant effectiveness of these pyrazoles. It can be concluded that the charge property of surfactants markedly influenced the behavior of an antioxidant in AAPH-induced oxidation of DNA.

关键词: Pyrazole, Surfactant, Oxidation, DNA, Free radical, Microenvironment effect

Abstract:

Effects of 4-(1,3-diphenyl-1H-pyrazol-5-yl)phenol(APP), 4-(1,5-diphenyl-1H-pyrazol-3-yl)phenol(BPP) and 4-(3,5-diphenyl-1H-pyrazol-1-yl)phenol(CPP) on 2,2'-azobis-(2-amidinopropane hydrochloride)(AAPH)-induced oxidation of DNA were measured in the presence of various concentrations of Triton X-100, cetyltrimethylammonium bromide(CTAB), or sodium dodecyl sulfate(SDS) in order to clarify the influence of neutral, cationic and anionic microenvironments on antioxidant capacities of APP, BPP and CPP. Although these surfactants can protect DNA against AAPH-induced oxidation, the pyrazoles in the presence of these surfactants functioned as prooxidants when the concentrations of Triton X-100 and CTAB increased. However, CPP exhibited antioxidant property with the increase of the concentration of CTAB. On the contrary, APP, BPP and CPP were antioxidants in the presence of various concentrations of SDS. The added surfactants resulted in the complication of the microenvironments around DNA, pyrazoles and peroxyl radical(ROO·) derived from AAPH. The anionic charge of SDS was beneficial to enhancing the antioxidant effectiveness of these pyrazoles. It can be concluded that the charge property of surfactants markedly influenced the behavior of an antioxidant in AAPH-induced oxidation of DNA.

Key words: Pyrazole, Surfactant, Oxidation, DNA, Free radical, Microenvironment effect