蛋白质结合小分子（离子）物质及变构效应
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摘要
小分子(离子)与生物大分子相互作用的研究是探索各类小分子(离子)生物学效应和功能的基本途径之一,此类课题的研究有助于人们从分子层面了解生命过程。
采用荧光光谱(FS)、紫外光谱(UV)研究了中药有效成分盐酸小檗碱(BC)在胃蛋白酶(pepsin)分子上的结合过程,应用核磁共振(1H NMR)技术研究了BC、苯甲酸钠、葡萄糖、维生素C(VC)与牛血清白蛋白(BSA)和胃蛋白酶(pepsin)相互作用的关键结合部位以及咪唑型离子液体与BSA相互作用的关键结合部位。为探讨离子液体的潜在毒性,采用多种光谱手段研究了咪唑型离子液体与BSA的相互作用。考虑到生物体内小分子(离子)在结合蛋白质时相互作用的复杂性,采用光谱手段研究了共存物对中药有效成分七叶内酯-BSA、BC-pepsin相互作用的扰动以及金属离子(Cu2+、Zn2+)、BC与BSA结合过程中的变构效应,并结合圆二色(CD)光谱对其机理进行了探讨。为更准确的获取药物分子-蛋白质相互作用参数,基于同步荧光获得了BC与pepsin分子中色氨酸、酪氨酸相互作用的定量参数;借助SAS软件尝试建立药物小分子-血清白蛋白结合过程构效关系的一般数学规律。在本文实验范围内,主要结论如下:
1. BC对Cu2+猝灭BSA内源荧光呈负变构效应,而对BSA-Cu2+复合物稳定性以及Cu2+在BSA分子上的结合位点呈正变构效应。Cu2+、Zn2+对BC猝灭BSA内源荧光呈正变构效应,而对BSA-BC复合物稳定性以及BC在BSA分子上的结合位点呈负变构效应。
2. BC能够以特定取向方式插入pepsin分子的疏水空腔,且距酪氨酸残基的平均结合距离最近。BC与BSA和pepsin分子的关键结合部位为BC分子中的共轭π体系异喹啉环和苯环结构;苯甲酸钠(SB)、葡萄糖、VC与BSA、pepsin结合的关键部位各有不同,三者在蛋白质分子上的结合部位可能处于临近蛋白质分子表面的亲水区域层。
3.实验所选的共存物对七叶内酯-BSA、BC-pepsin结合过程存在不同程度的扰动,与BSA结合引致BSA分子构象的改变是共存物参与并影响七叶内酯-BSA相互作用过程的共同机制,但各种共存物扰动的具体方式有所不同,如离子架桥(I-),同位取代(SB),对药物结合部位的破坏(SDS),使BSA构象的转变(TW-80、VC、葡萄糖)。
4.咪唑型离子液体与BSA结合的关键部位为其阳离子部分,但阳离子部分不是使BSA内源性荧光产生猝灭的主要基团,且咪唑型离子液体在BSA上的结合部位不深,与BSA的相互作用比较复杂,作用结果使BSA的二级结构发生明显改变。
5. BC猝灭pepsin分子内源性荧光的主要因素为静态猝灭,对色氨酸的猝灭最为显著,BC与色氨酸残基部位的结合最为强烈。
6.药物分子结构参数与药物分子-血清白蛋白结合常数的关系并不严格遵循简单线性关系,单纯从药物分子结构的有限个参数考虑归纳药物分子-蛋白质结合过程的构效关系存在明显的局限性。
Investigation on the interaction between small molecules (ions) and biological macromolecules is a path to explore the biology effects and functions of small molecules (ions), which is helpful to understand life process from molecular level.
To understand the interactions between small molecules (ions) and proteins thoroughly, fluorescence spectrum (FS), ultra-violet spectrum (UV) was used to study the binding site of a traditional Chinese Herb active component, berberine chloride (BC), on the pepsin in this paper, and nuclear magnetic resonance (1H NMR) was used to investigate the key segments of BC, sodium benzoate, glucose, Vitamin C(VC) binding bovine serum albumin (BSA) and pepsin , as well as that of imidazole ionic liquids binding BSA. In order to explore the latent toxicity of ionic liquid, multi-spectrum methods were used to study the interaction between imidazole ionic liquids and BSA. Considering the complexity of the interactions among small molecules (ions) binding proteins, the interference of coexisting substances in esculetin-BSA, BC-BSA binding process and the allosteric effects of Cu2+, Zn2+, BC-BSA binding process were studied, the mechanisms were also discussed combined the results of CD spectra. To make the drug-protein interaction parameters more accurate, the interaction parameters between BC and tryptophan, tyrosine were abtained respectively. Generally mathematics rule in structure-performance relationship of drug molecules-serum albumin interaction was also discussed with the model formed by SAS. In the experimental range of this paper, the main conclusions are listed as follow:
1. The allosteric effect of BC on Cu2+ quenching BSA intrinsic fluorescence is negative, while the allosteric effect of BC on the stability of Cu2+-BSA complex and the binding sites of Cu2+ is positive. The allosteric effects of Cu2+, Zn2+ on BC quenching BSA intrinsic fluorescence is positive, while the allosteric effects of Cu2+, Zn2+ on the stability of BC-BSA complex and the binding sites of BC is positive.
2. BC can insert the hydrophobic cavity of pepsin in special direction, and the average spatial distance between BC and tyrosine is smallest. The key segment of BC binding BSA and pepsin is the group of isoquinoline and benzene ring with conjugateπsystem, its binding orientations existence difference. The key segments of sodium benzoate (SB), glucose, VC binding BSA and the pepsin are different, while their binding site on BSA and pepsin are possibly located in the hydrophilic region on the protein molecular surface.
3. Both esculetin-BSA and BC-pepsin binding process are interfered by each selected coexisting substances more or less. BSA molecular conformational transition due to coexisting substances bound to BSA is the common mechanism of coexisting substances participating in esculetin-BSA binding process. The interference mechanism of the selected coexisting substances is different among each other, such as ionic bridge (I-), appositional replacement (SB), destroying the binding sites (SDS), inducing the conformation of BSA changed (TW-80, VC, glucose).
4. The key segment of imidazole ionic liquids binding BSA is its cationic part, while the cationic part is not the key group that makes BSA intrinsic fluorescence quenching, and the binding site of imidazole ionic liquids on BSA is not deep, the interaction mechanism is quite complex. Imidazole ionic liquids make BSA the secondary structure change obviously.
5. The type of pepsin intrinsic fluorescence being quenched is mainly static quenching but with the dynamic character, the quenching extend of tryptophan is greatest. The BC-pepsin binding is strong, the binding extend of tryptophan is greatest.
6. The mathematic rule in structure-performance relationship of drug molecules-serum albumin interaction is not a strict linear relationship. Thus, liminations consist in simply inducing structure-performance relationship of drug molecules-serum albumin interaction based on several specific parameters characterizing the structure of drug molecules.
采用荧光光谱(FS)、紫外光谱(UV)研究了中药有效成分盐酸小檗碱(BC)在胃蛋白酶(pepsin)分子上的结合过程,应用核磁共振(1H NMR)技术研究了BC、苯甲酸钠、葡萄糖、维生素C(VC)与牛血清白蛋白(BSA)和胃蛋白酶(pepsin)相互作用的关键结合部位以及咪唑型离子液体与BSA相互作用的关键结合部位。为探讨离子液体的潜在毒性,采用多种光谱手段研究了咪唑型离子液体与BSA的相互作用。考虑到生物体内小分子(离子)在结合蛋白质时相互作用的复杂性,采用光谱手段研究了共存物对中药有效成分七叶内酯-BSA、BC-pepsin相互作用的扰动以及金属离子(Cu2+、Zn2+)、BC与BSA结合过程中的变构效应,并结合圆二色(CD)光谱对其机理进行了探讨。为更准确的获取药物分子-蛋白质相互作用参数,基于同步荧光获得了BC与pepsin分子中色氨酸、酪氨酸相互作用的定量参数;借助SAS软件尝试建立药物小分子-血清白蛋白结合过程构效关系的一般数学规律。在本文实验范围内,主要结论如下:
1. BC对Cu2+猝灭BSA内源荧光呈负变构效应,而对BSA-Cu2+复合物稳定性以及Cu2+在BSA分子上的结合位点呈正变构效应。Cu2+、Zn2+对BC猝灭BSA内源荧光呈正变构效应,而对BSA-BC复合物稳定性以及BC在BSA分子上的结合位点呈负变构效应。
2. BC能够以特定取向方式插入pepsin分子的疏水空腔,且距酪氨酸残基的平均结合距离最近。BC与BSA和pepsin分子的关键结合部位为BC分子中的共轭π体系异喹啉环和苯环结构;苯甲酸钠(SB)、葡萄糖、VC与BSA、pepsin结合的关键部位各有不同,三者在蛋白质分子上的结合部位可能处于临近蛋白质分子表面的亲水区域层。
3.实验所选的共存物对七叶内酯-BSA、BC-pepsin结合过程存在不同程度的扰动,与BSA结合引致BSA分子构象的改变是共存物参与并影响七叶内酯-BSA相互作用过程的共同机制,但各种共存物扰动的具体方式有所不同,如离子架桥(I-),同位取代(SB),对药物结合部位的破坏(SDS),使BSA构象的转变(TW-80、VC、葡萄糖)。
4.咪唑型离子液体与BSA结合的关键部位为其阳离子部分,但阳离子部分不是使BSA内源性荧光产生猝灭的主要基团,且咪唑型离子液体在BSA上的结合部位不深,与BSA的相互作用比较复杂,作用结果使BSA的二级结构发生明显改变。
5. BC猝灭pepsin分子内源性荧光的主要因素为静态猝灭,对色氨酸的猝灭最为显著,BC与色氨酸残基部位的结合最为强烈。
6.药物分子结构参数与药物分子-血清白蛋白结合常数的关系并不严格遵循简单线性关系,单纯从药物分子结构的有限个参数考虑归纳药物分子-蛋白质结合过程的构效关系存在明显的局限性。
Investigation on the interaction between small molecules (ions) and biological macromolecules is a path to explore the biology effects and functions of small molecules (ions), which is helpful to understand life process from molecular level.
To understand the interactions between small molecules (ions) and proteins thoroughly, fluorescence spectrum (FS), ultra-violet spectrum (UV) was used to study the binding site of a traditional Chinese Herb active component, berberine chloride (BC), on the pepsin in this paper, and nuclear magnetic resonance (1H NMR) was used to investigate the key segments of BC, sodium benzoate, glucose, Vitamin C(VC) binding bovine serum albumin (BSA) and pepsin , as well as that of imidazole ionic liquids binding BSA. In order to explore the latent toxicity of ionic liquid, multi-spectrum methods were used to study the interaction between imidazole ionic liquids and BSA. Considering the complexity of the interactions among small molecules (ions) binding proteins, the interference of coexisting substances in esculetin-BSA, BC-BSA binding process and the allosteric effects of Cu2+, Zn2+, BC-BSA binding process were studied, the mechanisms were also discussed combined the results of CD spectra. To make the drug-protein interaction parameters more accurate, the interaction parameters between BC and tryptophan, tyrosine were abtained respectively. Generally mathematics rule in structure-performance relationship of drug molecules-serum albumin interaction was also discussed with the model formed by SAS. In the experimental range of this paper, the main conclusions are listed as follow:
1. The allosteric effect of BC on Cu2+ quenching BSA intrinsic fluorescence is negative, while the allosteric effect of BC on the stability of Cu2+-BSA complex and the binding sites of Cu2+ is positive. The allosteric effects of Cu2+, Zn2+ on BC quenching BSA intrinsic fluorescence is positive, while the allosteric effects of Cu2+, Zn2+ on the stability of BC-BSA complex and the binding sites of BC is positive.
2. BC can insert the hydrophobic cavity of pepsin in special direction, and the average spatial distance between BC and tyrosine is smallest. The key segment of BC binding BSA and pepsin is the group of isoquinoline and benzene ring with conjugateπsystem, its binding orientations existence difference. The key segments of sodium benzoate (SB), glucose, VC binding BSA and the pepsin are different, while their binding site on BSA and pepsin are possibly located in the hydrophilic region on the protein molecular surface.
3. Both esculetin-BSA and BC-pepsin binding process are interfered by each selected coexisting substances more or less. BSA molecular conformational transition due to coexisting substances bound to BSA is the common mechanism of coexisting substances participating in esculetin-BSA binding process. The interference mechanism of the selected coexisting substances is different among each other, such as ionic bridge (I-), appositional replacement (SB), destroying the binding sites (SDS), inducing the conformation of BSA changed (TW-80, VC, glucose).
4. The key segment of imidazole ionic liquids binding BSA is its cationic part, while the cationic part is not the key group that makes BSA intrinsic fluorescence quenching, and the binding site of imidazole ionic liquids on BSA is not deep, the interaction mechanism is quite complex. Imidazole ionic liquids make BSA the secondary structure change obviously.
5. The type of pepsin intrinsic fluorescence being quenched is mainly static quenching but with the dynamic character, the quenching extend of tryptophan is greatest. The BC-pepsin binding is strong, the binding extend of tryptophan is greatest.
6. The mathematic rule in structure-performance relationship of drug molecules-serum albumin interaction is not a strict linear relationship. Thus, liminations consist in simply inducing structure-performance relationship of drug molecules-serum albumin interaction based on several specific parameters characterizing the structure of drug molecules.
引文
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