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学科主题: 基础医学
题名:
Synthesis, Characterization, Biological Activity and Interaction with Bovine Serum Albumin of 8-or 6-(3-Chlorobenzoyl)coumarin Derivatives
作者: Yang Shu-Ping1; Han Li-Jun2; Pan Yan3,4; Wang Da-Qi5; Wang Nan-Nan1; Wang Ting1
关键词: 4-Methyl-7-hydroxy-8-or 6-(3-chlorobenzoyl)coumarin ; Crystal structure ; Antibacterial activity ; Antioxidation activity ; Bovine serum albumin
刊名: CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE
发表日期: 2013-02-10
DOI: 10.7503/cjcu20120666
卷: 34, 期:2, 页:364-374
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
关键词[WOS]: INHIBITORY-ACTIVITY ; CELL LINES ; COUMARINS ; FLUORESCENCE ; BINDING ; ANTIOXIDANTS ; INDUCTION ; MECHANISM
英文摘要:

Two new compounds, 4-methyl-7-hydroxy-8-(3-chlorobenzoyl) coumarin (1) and 4-methyl-7-hydroxy-6-(3-chlorobenzoyl) coumarin (2), were synthesized and characterized by elemental analysis, infrared spectra, H-1 NMR and single crystal X-ray diffraction methods. The crystals of compounds 1 and 2 belong to monoclinic system with space group P2(1)/c, compound 1: alpha=1.21527 (14) nm, b=1.01550 (12) nm, c= 1.5045(2) nm, beta=112.377 (2)degrees, V=1.7169 (4) nm(3), D-c = 1.396 g/cm(3), Z = 4, F (000)= 752, R-1 = 0.0415, wR(2) = 0.0981 [I>2 sigma (I)], S=1.063; compound 2: alpha = 2.0168(2) nm, b =0.76229(12) nm, c= 2.25497 (17) nm, beta=123. 987 (6)degrees, V=0.8745 (6) nm(3), D-c=1.454 g/cm(3), Z = 8, F(000) = 1296, R-1= 0.0604, wR2 = 0.1384 [I>2 sigma (I)], S = 0.948. The results of antibacterial experiment showed that the title compounds had the activity for inhibiting growth of E. coli, B. subtilis and S. aureus. The antioxidation activity of the title compounds were investigated by the O-2(-)center dot, DPPH center dot and center dot OH methods. The results showed that the title compounds had strong antioxidation activity. The interactions of title compounds and bovine serum albumin(BSA) were investigated by fluorescence spectroscopy at different temperatures. The results indicated that the title compounds caused the fluorescence quenching of BSA through a static quenching procedure. The corresponding thermodynamic parameters enthalpy change (Delta H), entropy change (Delta S), Gibbs free energy change(Delta G), between the title compounds and BSA were calculated. The interaction between the compound 1 (Delta H>0, Delta S>0, Delta G<0) and BSA was driven mainly by hydrophobic force, whereas the interaction between compound 2(Delta H<0, Delta S<0, Delta G<0) and BSA was driven mainly by hydrogen bond force or van der Waals force. The binding average distance r between the donor(BSA) and acceptors(compounds 1 and 2) were obtained to be 2.59 and 2.38 urn, respectively, based on the Foster′s theory, which indicate the energy transfer can occur from BSA to title compounds with high probability.

语种: 中文
WOS记录号: WOS:000317085400017
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/66547
Appears in Collections:基础医学院_药理学系_期刊论文

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作者单位: 1.Huaihai Inst Technol, Sch Chem Engn, Lianyungang 222005, Peoples R China
2.Huaihai Inst Technol, Sch Math & Sci, Lianyungang 222005, Peoples R China
3.Peking Univ, Sch Basic Med Sci, Dept Pharmacol, Beijing 100191, Peoples R China
4.State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
5.Liaocheng Univ, Sch Chem & Chem Engn, Liaocheng 252059, Peoples R China

Recommended Citation:
Yang Shu-Ping,Han Li-Jun,Pan Yan,et al. Synthesis, Characterization, Biological Activity and Interaction with Bovine Serum Albumin of 8-or 6-(3-Chlorobenzoyl)coumarin Derivatives[J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,2013,34(2):364-374.
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