光谱法研究普萘洛尔与ctDNA相互作用及手性识别
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摘要
第一章:简要综述了小分子与DNA相互作用的模式和研究方法,同时简述了手性识别研究的进展。
第二章:考察了普萘洛尔的紫外可见吸收光谱、荧光光谱和室温磷光光谱等光谱特性。普萘洛尔本身有很强的紫外吸收和荧光发射,但其本身不易观察到室温磷光发射。加入重原子微扰剂KI和除氧剂Na_2SO_3后,诱导普萘洛尔产生了强的室温磷光信号,并对影响其室温磷光的发光条件如:重原子和除氧剂的浓度及稳定性进行了详细探索。普萘洛尔磷光强度可稳定达1 h,可以满足实际分析要求。
第三章:采用光谱法研究了普萘洛尔与小牛胸腺DNA的相互作用。实验表明:小牛胸腺DNA能够猝灭普萘洛尔的荧光,并通过盐效应、阴离子猝灭、荧光偏振、热变性等实验方法推断出普萘洛尔与ctDNA的作用方式可能为沟槽键合,并根据McGheeand von Hippel提出的修正了的Scatchard方程计算了二者的结合常数和结合位点数。普萘洛尔与牛胸腺DNA的结合常数为9.67×10~5 L/mol,说明普萘洛尔与小牛胸腺DNA具有较强的结合能力。
第四章:非除氧条件下,加入少量溴代环己烷后,可以诱导普萘洛尔外消旋体在γ-环糊精溶液中产生室温磷光信号。并详细考察了影响普萘洛尔磷光强度及其磷光寿命的不同因素,包括酸度、γ-环糊精和溴代环己烷的浓度等。在最佳实验条件下测定了普萘洛尔对映异构体的室温磷光寿命。实验结果表明:普萘洛尔对映体的室温磷光衰减曲线符合一级指数方程,利用origin 7.5进行拟合,得出R-PPL的寿命为4.60ms、S-PPL的寿命为5.74 ms,二者的磷光寿命差异达22.05%。基于此,可以实现时间分辨磷光技术对普萘洛尔对映异构体的手性识别。
第五章:利用荧光光谱法研究了胆酸盐脱氧胆酸钠(NaDC)对联二萘胺对映异构体的手性识别。以A(R)与A(S)的比值(A=F_(250)/F_(282))和R和S的荧光增强率的比值(ΔF和ΔC的比值)作为衡量NaDC对联二萘胺对映异构体识别能力的标准。考察了不同介质中(包括有无一价或二价无机盐离子存在下)NaDC胶束的手性识别能力。通过比较,实验结果表明:脱氧胆酸钠胶束在一价无机盐NaCl存在下,对联二萘胺对映体分子的手性识别能力最强
Chapter 1:The binding mode of small molecule probes to DNA and study methods of their interactions are reviewed briefly.Posteriorly,the recent development of the research on chiral recognition is outlined tersely.
Chapter 2:The UV-visible absorption spectroscopy,fluorescence and room temperature phosphorescence(RTP) spectra of propranolol are investigated. Propranolol has strong absorption and fluorescence emission,but it's not easy to be observed its RTP emission.Upon addition of KI as a heavy atom perturber and Na_2SO_3 as a chemical deoxygenator,RTP signals of propranolol can be directly induced in aqueous solutions.Besides,the influencing factors including the concentrations of heavy atom and deoxidant and the stability of RTP intensity are studied in detail.And the RTP intensity can be stable for an hour,which can meet the actual analysis demand.
Chapter 3:The interactions of propranolol with ctDNA are studied by spectrometry.The experimental results show that the fluorescence of propranolol can be quenched by ctDNA.Furthermore,we can conclude that the binding mode of propranolol to ctDNA may be grooving binding by experiments of salt effect,anionic quenching,fluorescence polarization, ctDNA denaturalization and so on.According to the modified Scatchard equation proposed by McGhee and von Hippel,we can estimate the intrinsic binding constant and the binding site number.The intrinsic binding constant is 9.67×10~5L/mol,which bears out that propranolol have intense affinity to ctDNA.
Chapter 4:Upon addition of small amount of bromocyclohexane(BrCH), propranolol displays room temperature phosphorescence(RTP) inγ-CD solution without deoxygenation.Simultaneity,the factors including pH,the concentration ofγ-CD and BrCH,which affect the RTP intensity and RTP lifetime of propranolol are studied detailedly.Under optimal conditions,the RTP lifetimes of propranolol enantiomers are measured.The experimental results show that the associated phosphorescence decay curves can be best fitted to single-exponetial patterns and RTP lifetimes of R and S-PPL are 4.60ms and 5.74ms,respectively,acoording to the fitting results by origin7.5 software.The difference of the RTP lifetimes of R and S-PPL is 22.05%.Based on that,chiral discrimination of propranolol enantiomers is carried out successfully by time-resolved phosphorescence.
Chapter 5:The chiral discrimination of bile salt sodium deoxycholate (NaDC) micelles to 1,1'-binaphthyl-2,2'-diamine enantiomers is studied by fluorescence spectroscopy.Take the ratio of A(R) to A(S)(A=F_(250)/F_(282)) and the ratio of fluorescence increase rate(the ratio of△F to△C) as the standard of the chiral discrimination ability of NaDC to 1,1'-binaphthyl-2, 2'-diamine enantiomers.The chiral discrimination ability of NaDC micelles in different media including in the presence or absence of monovalent or bivalent inorganic salt are investigated.By comparison,the experimental results show that in the presence of monovalent inorganic salt NaCl,the chiral discrimination ability of NaDC micelles to 1,1'-binaphthyl-2,2'-diamine enantiomers is strongest.
第二章:考察了普萘洛尔的紫外可见吸收光谱、荧光光谱和室温磷光光谱等光谱特性。普萘洛尔本身有很强的紫外吸收和荧光发射,但其本身不易观察到室温磷光发射。加入重原子微扰剂KI和除氧剂Na_2SO_3后,诱导普萘洛尔产生了强的室温磷光信号,并对影响其室温磷光的发光条件如:重原子和除氧剂的浓度及稳定性进行了详细探索。普萘洛尔磷光强度可稳定达1 h,可以满足实际分析要求。
第三章:采用光谱法研究了普萘洛尔与小牛胸腺DNA的相互作用。实验表明:小牛胸腺DNA能够猝灭普萘洛尔的荧光,并通过盐效应、阴离子猝灭、荧光偏振、热变性等实验方法推断出普萘洛尔与ctDNA的作用方式可能为沟槽键合,并根据McGheeand von Hippel提出的修正了的Scatchard方程计算了二者的结合常数和结合位点数。普萘洛尔与牛胸腺DNA的结合常数为9.67×10~5 L/mol,说明普萘洛尔与小牛胸腺DNA具有较强的结合能力。
第四章:非除氧条件下,加入少量溴代环己烷后,可以诱导普萘洛尔外消旋体在γ-环糊精溶液中产生室温磷光信号。并详细考察了影响普萘洛尔磷光强度及其磷光寿命的不同因素,包括酸度、γ-环糊精和溴代环己烷的浓度等。在最佳实验条件下测定了普萘洛尔对映异构体的室温磷光寿命。实验结果表明:普萘洛尔对映体的室温磷光衰减曲线符合一级指数方程,利用origin 7.5进行拟合,得出R-PPL的寿命为4.60ms、S-PPL的寿命为5.74 ms,二者的磷光寿命差异达22.05%。基于此,可以实现时间分辨磷光技术对普萘洛尔对映异构体的手性识别。
第五章:利用荧光光谱法研究了胆酸盐脱氧胆酸钠(NaDC)对联二萘胺对映异构体的手性识别。以A(R)与A(S)的比值(A=F_(250)/F_(282))和R和S的荧光增强率的比值(ΔF和ΔC的比值)作为衡量NaDC对联二萘胺对映异构体识别能力的标准。考察了不同介质中(包括有无一价或二价无机盐离子存在下)NaDC胶束的手性识别能力。通过比较,实验结果表明:脱氧胆酸钠胶束在一价无机盐NaCl存在下,对联二萘胺对映体分子的手性识别能力最强
Chapter 1:The binding mode of small molecule probes to DNA and study methods of their interactions are reviewed briefly.Posteriorly,the recent development of the research on chiral recognition is outlined tersely.
Chapter 2:The UV-visible absorption spectroscopy,fluorescence and room temperature phosphorescence(RTP) spectra of propranolol are investigated. Propranolol has strong absorption and fluorescence emission,but it's not easy to be observed its RTP emission.Upon addition of KI as a heavy atom perturber and Na_2SO_3 as a chemical deoxygenator,RTP signals of propranolol can be directly induced in aqueous solutions.Besides,the influencing factors including the concentrations of heavy atom and deoxidant and the stability of RTP intensity are studied in detail.And the RTP intensity can be stable for an hour,which can meet the actual analysis demand.
Chapter 3:The interactions of propranolol with ctDNA are studied by spectrometry.The experimental results show that the fluorescence of propranolol can be quenched by ctDNA.Furthermore,we can conclude that the binding mode of propranolol to ctDNA may be grooving binding by experiments of salt effect,anionic quenching,fluorescence polarization, ctDNA denaturalization and so on.According to the modified Scatchard equation proposed by McGhee and von Hippel,we can estimate the intrinsic binding constant and the binding site number.The intrinsic binding constant is 9.67×10~5L/mol,which bears out that propranolol have intense affinity to ctDNA.
Chapter 4:Upon addition of small amount of bromocyclohexane(BrCH), propranolol displays room temperature phosphorescence(RTP) inγ-CD solution without deoxygenation.Simultaneity,the factors including pH,the concentration ofγ-CD and BrCH,which affect the RTP intensity and RTP lifetime of propranolol are studied detailedly.Under optimal conditions,the RTP lifetimes of propranolol enantiomers are measured.The experimental results show that the associated phosphorescence decay curves can be best fitted to single-exponetial patterns and RTP lifetimes of R and S-PPL are 4.60ms and 5.74ms,respectively,acoording to the fitting results by origin7.5 software.The difference of the RTP lifetimes of R and S-PPL is 22.05%.Based on that,chiral discrimination of propranolol enantiomers is carried out successfully by time-resolved phosphorescence.
Chapter 5:The chiral discrimination of bile salt sodium deoxycholate (NaDC) micelles to 1,1'-binaphthyl-2,2'-diamine enantiomers is studied by fluorescence spectroscopy.Take the ratio of A(R) to A(S)(A=F_(250)/F_(282)) and the ratio of fluorescence increase rate(the ratio of△F to△C) as the standard of the chiral discrimination ability of NaDC to 1,1'-binaphthyl-2, 2'-diamine enantiomers.The chiral discrimination ability of NaDC micelles in different media including in the presence or absence of monovalent or bivalent inorganic salt are investigated.By comparison,the experimental results show that in the presence of monovalent inorganic salt NaCl,the chiral discrimination ability of NaDC micelles to 1,1'-binaphthyl-2,2'-diamine enantiomers is strongest.
引文
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