平面型大环共轭配合物的制备及其光学生物敏感特性研究
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摘要
光纤生物传感器对于生命科学的发展起到了非常重要的作用,其性能的好坏主要取决于敏感材料性能的优劣。高性能敏感材料的研制是获得高性能光纤生物传感器的关键技术之一,通过对敏感材料的结构调控和性能优化可以达到优化其生物敏感性能的目的。由于其特殊的物理、化学性质,平面型大环共轭配合物已被广泛用于各种生物敏感材料。平面型大环共轭配合物是指由平面型多环芳香配体所形成的金属配合物,一般都具有稳定的结构。大部分平面型大环共轭配合物都具有发光性质,通常在一定波长光的激发下会发出相应频率的荧光和磷光。它们不仅结构特殊而且性质优异,在物理、化学、材料学、生物学和医学等众多领域都有着重要的应用。本学位论文针对光纤生物传感器和临床医学检测现存的主要问题,制备并优化了生物敏感材料,构建了荧光猝灭型光纤肾上腺素(AD)传感器和荧光型光纤DNA传感器,采用锁相放大技术,实现了AD和小牛胸腺DNA(ctDNA)浓度的检测。
本学位论文在以下几个方面进行了系统的研究:1、合成了5种金属酞菁作仿生酶用于儿茶酚胺(CAs)的催化氧化,研究了催化时间、催化温度、溶液pH值和仿生酶用量等对催化效率的影响;2、以FePc为催化剂构建了基于仿生酶催化的光纤AD传感器,研究了传感器的性能;3、合成并表征了3种平面型大环共轭配合物,采用电子吸收光谱法、荧光法和粘度法等手段研究了配合物与ctDNA的相互作用;4、以钌(Ⅱ)多吡啶配合物为指示剂,制备了光学DNA敏感膜,采用锁相放大技术构建了荧光型光纤DNA传感器,研究了传感器的性能。主要研究结论如下:
1、金属酞菁仿生酶催化CAs氧化的性质研究
(1)以二甲苯作溶剂合成了5种金属酞菁(MPc,M=Mn~(2+),Fe~(2+),Co~(2+),Ni~(2+),Cu~(2+))仿生酶,采用电子吸收光谱法研究了其催化儿茶酚胺氧化的性质。在磷酸缓冲溶液(PBS)中,5种仿生酶均能有效地催化CAs的氧化,AD的氧化过程与去甲肾上腺素(NA)的氧化过程相同,而与多巴胺(DA)的氧化过程不同,其相应的氧化产物分别为肾上腺素红、去甲肾上腺素红和黑色素。
5种仿生酶催化AD和NA氧化的最佳条件为:pH=8.0,T=55℃,[MPc]=1.00 mg/mL,[AD]/[NA]=5.0×10~(-4) mol/L;其催化效率有如下顺序ηMnPc＞ηFePc＞ηNiPc＞ηCuPc＞ηCoPc。在最佳pH 8.0的条件下,虽然MnPc的催化活性最好,但在低pH值下,FePc的催化活性都好于MnPc。探讨了其催化机理,以配体场理论为依据,从配合物结构的角度解释了催化效率的顺序。
仿生酶催化DA氧化的最佳催化反应条件为pH=8.0,[MPc]=1.00 mg/mL,[AD]=5.6×10~(-4)mol/L,最佳温度因仿生酶种类不同而不同。在55℃,催化效率为:ηMnPc＞ηFePc＞ηCoPc≈ηCuPc＞ηNiPc。
(2)以FePc为催化剂采用锁相放大技术构建了基于MPc催化的荧光猝灭型光纤AD传感器,研究了传感器的性能。以pH 7.4 PBS缓冲溶液为介质,在2.0×10~(-6)～9.0×10~(-5)mol/L范围,AD的浓度与光学氧敏感膜的相对滞后相移△φ有较好的线性关系;检测下限为4.0×10~(-7)mol/L;响应时间为10 min,该传感器具有良好的重复性和稳定性。
2、有机磺酸配合物与ctDNA键合性质的研究
(1)以金属盐、双齿螯合配体与氨基萘磺酸盐为原料合成了两个新型有机磺酸配合物{一水合[二(1,10-邻菲啰啉)二(4-氨基萘磺酸根)合镉(Ⅱ)],[Cd(phen)_2(ans)_2]·H_2O 1}和{一水合[二(1,10-邻菲啰啉)二(4-氨基萘磺酸根)合铅(Ⅱ)],[Pb(phen)_2(ans)_2]·H_2O 2},对其结构进行了表征:两配合物分属不同的晶系,但其不对称独立单元的构成却是相同的,都是包含一个中性配合物分子和一个结晶水分子,中心离子Cd(Ⅱ)和Pb(Ⅱ)的配位环境相同,均为六配位变形八面体构型MN_4O_2。
(2)采用电子吸收光谱法、荧光法和粘度法等研究了配合物1和2与ctDNA的相互作用。实验结果表明两配合物与DNA之间都存在较强的作用,作用模式均为静电结合和插入方式,静电作用为N-H…O氢键,插入配体为phen,与DNA的相互作用,1大于2,其键合常数K_b为分别为1.82×10~5和4.96×10~4 L/mol。
3、钌(Ⅱ)多吡啶配合物与ctDNA键合性质的研究
(1)以1,10-邻菲啰啉和对硝基苯肼为原料合成了一个新的席夫碱4,5-二氮杂芴-9-对硝基苯腙(DAFND)作主配体,以2,2′-联吡啶(bipy)为辅助配体,与RuCl_3反应合成得到一种新型钌(Ⅱ)多吡啶配合物{高氯酸[二(2,2′-联吡啶)(4,5-二氮杂芴-9-对硝基苯腙)]合钌(Ⅱ),[Ru(bipy)_2DAFND](ClO_4)_2},采用红外、核磁、质谱和X-射线单晶衍射等手段对所合成的配体和配合物进行了表征。
(2)通过研究配合物与ctDNA的相互作用,发现配合物以插入模式与ctDNA发生作用,插入配体为DAFND,其键合常数K_b为8.91×10~5L/mol。
(3)以钌(Ⅱ)多吡啶配合物[Ru(bipy)_2DAFND](ClO_4)_2为荧光指示剂,制备了光学DNA敏感材料,采用锁相放大技术构建了荧光型光纤DNA传感器,研究了传感器的性能。以pH 7.1 Tris缓冲溶液为介质,在3.6×10~(-7)～1.56×10~(-6)mol/L范围,ctDNA浓度与光学DNA敏感膜的相对滞后相移△φ有较好的线性关系,检测下限为8.4×10~(-8)mol/L;响应时间为70 s,该传感系统具有较好的重复性和稳定性。
The fiber optic biosensor plays an important role in the development of life science. As a key technique,the preparation of the opitc sensing material is vital to the fiber optic biosensor with high performance.The biosensitivity can be optimized by the structural adjusting and performance optimizing of the sensing material.Due to their characteristic structure and perporties,the planar ring-conjugated complexes are extensively applied to the sensitive materials.The planar ring-conjugated complex is referred to the complex constructed by the planar ligands with some aromatic rings. Generally,these complexes have stable structures and excellent physical and chemical properties especially luminescence,and have been extensively applied to chemistry,physics,material science,biology,medicine,etc.
In order to solve the existing problems in clinical medicine detection and the fiber optic biosensor,in this thesis,the optimized sensing materials are used to the fiber optic biosensors based on fluorescence change.Two biosensors were designed and constructed,and have successfully been used to detect the concentrations of adrenalin (AD)and calf thymus DNA(ctDNA).
In this thesis,the systematic studies have been done as following:Firstly, metallophthalocyanines(MPc,M=Mn~(2+),Fe~(2+),Co~(2+),Ni~(2+),Cu~(2+))were synthesized and used to catalyze the oxidation of catecholamines(CAs).The influence factors of catalytic efficiency,such as catalytic time and temperature,the pH value of solution and the amount of MPc,have been investigated,and the catalytic mechanism was proposed.Secondly,a novel fiber optic AD biosensor was designed and constructed using FePc as catalyzer.Thirdly,three novel planar ring-conjugated complexes were synthesized and characterized.Interactions of the complexes with ctDNA were explored by UV-Vis spectra,luminescence spectra and viscosity measurements. Fourthly,a fiber optic biosensor for DNA detection based on fluorescence change of [Ru(bipy)_2DAFND]~(2+)was fabricated and studied.
The main conclusions of this thesis include the following three parts:
1.The oxidation of catecholamines catalyzed by MPc
(1)MPc were synthesized using dimethylbenzene as solvent.In phosphate buffer solution(PBS),MPc could effectively catalyze three kinds of CAs,namely AD, noradrenalin(NA)and dopamine(DA),to the corresponding oxidation products of adrenochrome,noradrenchrome and melanin.The reaction processes of AD and NA oxidized by MPc were similar,which was different from the oxidation of DA.The catalytic mechanism was proposed,and the order of catalytic efficiency was interpreted based on the electronic structure of the complexes.
For the oxidation reaction of AD and NA,the optimal catalytic conditions were determined:pH=8.0,T=55℃,[MPc]=1.00 mg/mL and[AD]/[NA]=5.0×10~(-4) mol/L.MPc had the catalytic activity order ofη_(MnPc)＞η_(FePc)＞η_(nipc)>η_(CuPc)＞η_(CoPc)at the optimal catalytic conditions,while MnPc showed worse activity than FePc in low pH environment,indicating that FePc could be used in larger pH range. cAs for the oxidation of DA,the product was melanin,which is different from the oxidation of AD and NA.The optimal conditions are pH 8.0,[MPc]=1.00 mg/mL [DA]=5.6×10~(-4)mol/L,the temperatures are different for different MPc.At 55℃,the order of catalytic efficiency isη_(MnPc)>η_(FePc)＞η_(CoPc)≈η_(CuPc)＞ηf_(NiPc).
(2)A novel fiber optic AD biosensor based on the oxidation of AD by O_2 was designed and fabricated using FePc as catalyzer.The performance of the biosensor was investigated.The dissolved oxygen and AD content were evaluated by relative phase delay△(?).In PBS with pH 7.4,a linear relationship between△(?)and AD concentration was observed in the range of 2.0×10~(-6)～9.0×10~(-5)mol/L,and the detection limit is 4.0×10~(-7)mol/L.The biosensor has good stability and repeatability, and its response time is 10 min.
2.DNA-binding properties of two complexes containing organosulfonate ligand (1)Two novel organosulfonate complexes,[M(phen)_2(ans)_2]·H_2O(M=Cd 1,M= Pb 2),were obtained from the reaction of 1,10-phenanthroline(phen),sodium 4-aminonaphthalene-1-sulfonate(Naans)and Cd(OAc)_2·2H_2O or Pb(NO_3)_2 in a mixed solvent of water and methanol at room temperature.The compounds were characterized by elemental analysis,IR,and single crystal X-ray diffraction method. In spite of the different cell systems,the asymmetric units of the complexes were identical,namely one neutral compound and one water molecule.The coordination geometries of the central atom were the same within two complexes,showing a distorted octahedral environment with MN_4O_2.
(2)Interactions of the complexes with ctDNA were studied by UV/Vis spectra, luminescence titrations,steady-state emission quenching by[Fe(CN)_6]~(4-),DNA competitive binding with ethidium bromide(EB)and viscosity measurements.The results indicated that there were two interactions between the complexes and DNA, namely the electrostatic interaction and intercalation,with the binding constants of 1.82×l0~5 L/mol for 1 and 4.96×10~4 L/mol for 2 in buffer of 50 mmol/L NaCl and 5 mmol/L Tris-HCl(pH 7.1,Tris buffer).
3.DNA-binding properties of the polypyridyl Ru(Ⅱ)complex
(1)A new Schiff base of 4,5-diazafluorene-9-p-nitrophenylhydrazone(DAFND) was synthesized using 1,10-phenanthroline and p-nitrophenylhydrazine as raw materials.DAFND and 2,2'-bipyridyl(bipy)acting as the main and auxiliary ligands, a polypyridyl complex of[Ru(bipy)_2DAFND](ClO_4)_2 was obtained.The synthesized compounds were characterized by IR,~1H NMR,elemental analysis,ES-MS and single crystal X-ray diffraction method.
(2)Interaction of the complex with ctDNA was explored by UV/Vis absorption spectra,luminescence spectra and viscosity measurements,illustrating that the complex interacted with ctDNA via intercalation,with the binding constant of 8.91×10~5 L/mol in Tris buffer.
(3)A fiber optic biosensor for DNA detection based on fluorescence change was fabricated,using[Ru(bipy)_2DAFND]~(2+)embedded in CA as indicator for the optic sensing membrane.The performance of the biosensor was studied and it has the analytical range of 3.6×10~(-7)～1.56×10~(-6)mol/L,response time of 70 s and detection limit of 8.4xl0~(-8)mol/L in Tris buffer(pH 7.1).The biosensor showed excellent reproducibility and stability and its working temperature was below 40℃.
本学位论文在以下几个方面进行了系统的研究:1、合成了5种金属酞菁作仿生酶用于儿茶酚胺(CAs)的催化氧化,研究了催化时间、催化温度、溶液pH值和仿生酶用量等对催化效率的影响;2、以FePc为催化剂构建了基于仿生酶催化的光纤AD传感器,研究了传感器的性能;3、合成并表征了3种平面型大环共轭配合物,采用电子吸收光谱法、荧光法和粘度法等手段研究了配合物与ctDNA的相互作用;4、以钌(Ⅱ)多吡啶配合物为指示剂,制备了光学DNA敏感膜,采用锁相放大技术构建了荧光型光纤DNA传感器,研究了传感器的性能。主要研究结论如下:
1、金属酞菁仿生酶催化CAs氧化的性质研究
(1)以二甲苯作溶剂合成了5种金属酞菁(MPc,M=Mn~(2+),Fe~(2+),Co~(2+),Ni~(2+),Cu~(2+))仿生酶,采用电子吸收光谱法研究了其催化儿茶酚胺氧化的性质。在磷酸缓冲溶液(PBS)中,5种仿生酶均能有效地催化CAs的氧化,AD的氧化过程与去甲肾上腺素(NA)的氧化过程相同,而与多巴胺(DA)的氧化过程不同,其相应的氧化产物分别为肾上腺素红、去甲肾上腺素红和黑色素。
5种仿生酶催化AD和NA氧化的最佳条件为:pH=8.0,T=55℃,[MPc]=1.00 mg/mL,[AD]/[NA]=5.0×10~(-4) mol/L;其催化效率有如下顺序ηMnPc＞ηFePc＞ηNiPc＞ηCuPc＞ηCoPc。在最佳pH 8.0的条件下,虽然MnPc的催化活性最好,但在低pH值下,FePc的催化活性都好于MnPc。探讨了其催化机理,以配体场理论为依据,从配合物结构的角度解释了催化效率的顺序。
仿生酶催化DA氧化的最佳催化反应条件为pH=8.0,[MPc]=1.00 mg/mL,[AD]=5.6×10~(-4)mol/L,最佳温度因仿生酶种类不同而不同。在55℃,催化效率为:ηMnPc＞ηFePc＞ηCoPc≈ηCuPc＞ηNiPc。
(2)以FePc为催化剂采用锁相放大技术构建了基于MPc催化的荧光猝灭型光纤AD传感器,研究了传感器的性能。以pH 7.4 PBS缓冲溶液为介质,在2.0×10~(-6)～9.0×10~(-5)mol/L范围,AD的浓度与光学氧敏感膜的相对滞后相移△φ有较好的线性关系;检测下限为4.0×10~(-7)mol/L;响应时间为10 min,该传感器具有良好的重复性和稳定性。
2、有机磺酸配合物与ctDNA键合性质的研究
(1)以金属盐、双齿螯合配体与氨基萘磺酸盐为原料合成了两个新型有机磺酸配合物{一水合[二(1,10-邻菲啰啉)二(4-氨基萘磺酸根)合镉(Ⅱ)],[Cd(phen)_2(ans)_2]·H_2O 1}和{一水合[二(1,10-邻菲啰啉)二(4-氨基萘磺酸根)合铅(Ⅱ)],[Pb(phen)_2(ans)_2]·H_2O 2},对其结构进行了表征:两配合物分属不同的晶系,但其不对称独立单元的构成却是相同的,都是包含一个中性配合物分子和一个结晶水分子,中心离子Cd(Ⅱ)和Pb(Ⅱ)的配位环境相同,均为六配位变形八面体构型MN_4O_2。
(2)采用电子吸收光谱法、荧光法和粘度法等研究了配合物1和2与ctDNA的相互作用。实验结果表明两配合物与DNA之间都存在较强的作用,作用模式均为静电结合和插入方式,静电作用为N-H…O氢键,插入配体为phen,与DNA的相互作用,1大于2,其键合常数K_b为分别为1.82×10~5和4.96×10~4 L/mol。
3、钌(Ⅱ)多吡啶配合物与ctDNA键合性质的研究
(1)以1,10-邻菲啰啉和对硝基苯肼为原料合成了一个新的席夫碱4,5-二氮杂芴-9-对硝基苯腙(DAFND)作主配体,以2,2′-联吡啶(bipy)为辅助配体,与RuCl_3反应合成得到一种新型钌(Ⅱ)多吡啶配合物{高氯酸[二(2,2′-联吡啶)(4,5-二氮杂芴-9-对硝基苯腙)]合钌(Ⅱ),[Ru(bipy)_2DAFND](ClO_4)_2},采用红外、核磁、质谱和X-射线单晶衍射等手段对所合成的配体和配合物进行了表征。
(2)通过研究配合物与ctDNA的相互作用,发现配合物以插入模式与ctDNA发生作用,插入配体为DAFND,其键合常数K_b为8.91×10~5L/mol。
(3)以钌(Ⅱ)多吡啶配合物[Ru(bipy)_2DAFND](ClO_4)_2为荧光指示剂,制备了光学DNA敏感材料,采用锁相放大技术构建了荧光型光纤DNA传感器,研究了传感器的性能。以pH 7.1 Tris缓冲溶液为介质,在3.6×10~(-7)～1.56×10~(-6)mol/L范围,ctDNA浓度与光学DNA敏感膜的相对滞后相移△φ有较好的线性关系,检测下限为8.4×10~(-8)mol/L;响应时间为70 s,该传感系统具有较好的重复性和稳定性。
The fiber optic biosensor plays an important role in the development of life science. As a key technique,the preparation of the opitc sensing material is vital to the fiber optic biosensor with high performance.The biosensitivity can be optimized by the structural adjusting and performance optimizing of the sensing material.Due to their characteristic structure and perporties,the planar ring-conjugated complexes are extensively applied to the sensitive materials.The planar ring-conjugated complex is referred to the complex constructed by the planar ligands with some aromatic rings. Generally,these complexes have stable structures and excellent physical and chemical properties especially luminescence,and have been extensively applied to chemistry,physics,material science,biology,medicine,etc.
In order to solve the existing problems in clinical medicine detection and the fiber optic biosensor,in this thesis,the optimized sensing materials are used to the fiber optic biosensors based on fluorescence change.Two biosensors were designed and constructed,and have successfully been used to detect the concentrations of adrenalin (AD)and calf thymus DNA(ctDNA).
In this thesis,the systematic studies have been done as following:Firstly, metallophthalocyanines(MPc,M=Mn~(2+),Fe~(2+),Co~(2+),Ni~(2+),Cu~(2+))were synthesized and used to catalyze the oxidation of catecholamines(CAs).The influence factors of catalytic efficiency,such as catalytic time and temperature,the pH value of solution and the amount of MPc,have been investigated,and the catalytic mechanism was proposed.Secondly,a novel fiber optic AD biosensor was designed and constructed using FePc as catalyzer.Thirdly,three novel planar ring-conjugated complexes were synthesized and characterized.Interactions of the complexes with ctDNA were explored by UV-Vis spectra,luminescence spectra and viscosity measurements. Fourthly,a fiber optic biosensor for DNA detection based on fluorescence change of [Ru(bipy)_2DAFND]~(2+)was fabricated and studied.
The main conclusions of this thesis include the following three parts:
1.The oxidation of catecholamines catalyzed by MPc
(1)MPc were synthesized using dimethylbenzene as solvent.In phosphate buffer solution(PBS),MPc could effectively catalyze three kinds of CAs,namely AD, noradrenalin(NA)and dopamine(DA),to the corresponding oxidation products of adrenochrome,noradrenchrome and melanin.The reaction processes of AD and NA oxidized by MPc were similar,which was different from the oxidation of DA.The catalytic mechanism was proposed,and the order of catalytic efficiency was interpreted based on the electronic structure of the complexes.
For the oxidation reaction of AD and NA,the optimal catalytic conditions were determined:pH=8.0,T=55℃,[MPc]=1.00 mg/mL and[AD]/[NA]=5.0×10~(-4) mol/L.MPc had the catalytic activity order ofη_(MnPc)＞η_(FePc)＞η_(nipc)>η_(CuPc)＞η_(CoPc)at the optimal catalytic conditions,while MnPc showed worse activity than FePc in low pH environment,indicating that FePc could be used in larger pH range. cAs for the oxidation of DA,the product was melanin,which is different from the oxidation of AD and NA.The optimal conditions are pH 8.0,[MPc]=1.00 mg/mL [DA]=5.6×10~(-4)mol/L,the temperatures are different for different MPc.At 55℃,the order of catalytic efficiency isη_(MnPc)>η_(FePc)＞η_(CoPc)≈η_(CuPc)＞ηf_(NiPc).
(2)A novel fiber optic AD biosensor based on the oxidation of AD by O_2 was designed and fabricated using FePc as catalyzer.The performance of the biosensor was investigated.The dissolved oxygen and AD content were evaluated by relative phase delay△(?).In PBS with pH 7.4,a linear relationship between△(?)and AD concentration was observed in the range of 2.0×10~(-6)～9.0×10~(-5)mol/L,and the detection limit is 4.0×10~(-7)mol/L.The biosensor has good stability and repeatability, and its response time is 10 min.
2.DNA-binding properties of two complexes containing organosulfonate ligand (1)Two novel organosulfonate complexes,[M(phen)_2(ans)_2]·H_2O(M=Cd 1,M= Pb 2),were obtained from the reaction of 1,10-phenanthroline(phen),sodium 4-aminonaphthalene-1-sulfonate(Naans)and Cd(OAc)_2·2H_2O or Pb(NO_3)_2 in a mixed solvent of water and methanol at room temperature.The compounds were characterized by elemental analysis,IR,and single crystal X-ray diffraction method. In spite of the different cell systems,the asymmetric units of the complexes were identical,namely one neutral compound and one water molecule.The coordination geometries of the central atom were the same within two complexes,showing a distorted octahedral environment with MN_4O_2.
(2)Interactions of the complexes with ctDNA were studied by UV/Vis spectra, luminescence titrations,steady-state emission quenching by[Fe(CN)_6]~(4-),DNA competitive binding with ethidium bromide(EB)and viscosity measurements.The results indicated that there were two interactions between the complexes and DNA, namely the electrostatic interaction and intercalation,with the binding constants of 1.82×l0~5 L/mol for 1 and 4.96×10~4 L/mol for 2 in buffer of 50 mmol/L NaCl and 5 mmol/L Tris-HCl(pH 7.1,Tris buffer).
3.DNA-binding properties of the polypyridyl Ru(Ⅱ)complex
(1)A new Schiff base of 4,5-diazafluorene-9-p-nitrophenylhydrazone(DAFND) was synthesized using 1,10-phenanthroline and p-nitrophenylhydrazine as raw materials.DAFND and 2,2'-bipyridyl(bipy)acting as the main and auxiliary ligands, a polypyridyl complex of[Ru(bipy)_2DAFND](ClO_4)_2 was obtained.The synthesized compounds were characterized by IR,~1H NMR,elemental analysis,ES-MS and single crystal X-ray diffraction method.
(2)Interaction of the complex with ctDNA was explored by UV/Vis absorption spectra,luminescence spectra and viscosity measurements,illustrating that the complex interacted with ctDNA via intercalation,with the binding constant of 8.91×10~5 L/mol in Tris buffer.
(3)A fiber optic biosensor for DNA detection based on fluorescence change was fabricated,using[Ru(bipy)_2DAFND]~(2+)embedded in CA as indicator for the optic sensing membrane.The performance of the biosensor was studied and it has the analytical range of 3.6×10~(-7)～1.56×10~(-6)mol/L,response time of 70 s and detection limit of 8.4xl0~(-8)mol/L in Tris buffer(pH 7.1).The biosensor showed excellent reproducibility and stability and its working temperature was below 40℃.
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