金属—有机八面体和大环的构筑及性能研究
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摘要
金属-有机多面体和大环结构是一类人工合成的旨在模拟和学习酶催化过程和生物分子识别的重要模型。由于其内部具有高度限域空间,使得这一类化合物在进行主-客体化学及模拟酶催化研究时,显示出高度的立体选择性和特殊的微反应环境。但由于引入光响应、特定的弱作用识别位点以及催化位点等功能基团比较困难,金属-有机大环化合物在生物分子的识别传感以及特定的催化研究中的报道尚未得到充分拓展。在本论文的研究工作中,利用组装策略,将以上这些功能基团引入到金属-有机多面体和大环结构中,构筑了具有相对封闭的金属-有机八面体以及相对开放的金属-有机大环结构,并以这两类结构体系为载体,开展其在生物分子识别与模拟酶催化中的性能研究。
1.金属-有机八面体性能研究
(1)生物小分子识别：将荧光响应单元-喹啉基团以及生物分子识别位点-酰胺基团引入到配体PT1(1,3,5-三(2-喹啉基)苯甲酰腙)中,与过渡金属离子Co2+、Zn2+自组装得到晶体同构的八面体过渡金属笼状化合物。化合物配体中的酰胺基团只与胞苷形成双重氢键相互作用,对胞苷的紫外、荧光响应信号明显优于其他三种核糖核苷。
(2)磁共振成像：将高自旋的稀土离子Gd3+与PT2(1,3,5-三(2-吡啶基)苯甲酰腙)自组装形成八面体稀土金属笼状化合物Gd-PT2。Gd-PT2具有很高的纵向弛豫率(r1=388.5mM-1s-1),可以应用于活体小鼠皮下组织成像。在葡萄糖、氨基葡萄糖及四种核糖核苷生物小分子中,实现了对氨基葡萄糖的专一选择性磁共振成像(MRI)。氨基葡萄糖的加入取代了配位的水分子,与Gd3+发生相互作用直接诱导磁共振响应信号的减弱。
(3)非均相催化：将Lewis酸活化位点-Tb3+离子及弱碱单元-酰胺基团同时引入到具有一维孔道的多孔固态分子材料Tb-PT2中,实现了尺寸选择性非均相催化氰基硅烷化反应和Aldol反应。氰基硅烷化反应发生在催化剂的一维孔道并且活化单元为Tb3+离子；Aldol反应发生在八面体内部洞穴并且酰胺基团与环己酮之间存在氢键相互作用。
2.金属-有机大环结构性能研究
(1)手性催化：
A.将L-脯氨酸作为手性催化中心引入到含有酰胺基团的配体PT3(1,3-二(2-毗啶基)-5-((S)-2-吡咯烷甲酰基)苯甲酰腙)中,分别与Co2+离子、Ni2+离子自组装,形成金属可调的具有单一手性的大环结构。由于该类大环化合物同时含有多个单一手性催化中心和丰富的氢键作用位点,可作为酶模拟反应器,实现了尺寸选择性均相不对称催化Aldol反应。基于其疏水性空腔强烈的空间可塑性,进一步提高了反应的非对映异构选择性(anti:syn最高为10.3：1)
B.设计合成了基于L-脯氨酸和D-脯氨酸的两种对映体配体L-PT4和D-PT4[L-PT4(1,3-二(2-羟基-1-萘基)-5-((S)-2-吡咯烷甲酰基)苯甲酰腙)；D-PT4(1,3-二(2-羟基-1-萘基)-5-((R)-2-吡咯烷甲酰基)苯甲酰腙)],与Ce3+离子自组装,形成两种中性对映体灯笼型化合物,实现了高对映选择性均相催化氰基硅烷化反应(ee值>99%)。
(2)生物分子识别：将具有良好荧光响应基团-蒽单元和双重氢键作用位点-酰胺基团引入到配体PT7(9,10-二(2-乙酰吡啶基)蒽甲酰腙)中,与Co2+离子自组装,形成结构类似于正方形的大环化合物。该正电荷化合物含有丰富的共轭基团、多重氢键作用位点以及具有强烈的空间可塑性的亲/疏水性空腔,实现了专一选择性识别ATP。
Metal-organic polyhedra and macrocycles are important models to realize the process of enzyme catalysis and recognition. These structures discussed exhibit well-defined cavities with gated pores providing specific inner environments for selective uptaking and binding of guest molecules. Yet only a few "artificial systems" achieved the detection and imaging techniques in biological systems and the magnificent catalysis of natural enzymes. The major challenge at stake here goes beyond the introducing of an optical measurable output, the active sites and specific weak effect response sites. On the basis of this context, by combining these functional groups into metal-organic polyhedra/macrocycles with considerable stabilities, we constructed relatively enclosing metal-organic octahedra and relatively open metal-organic macrocycles for biological molecules recognition and simulating enzyme catalysis researches.
1. Metal-organic octahedra research
(1) Biological molecules recognition:By combining three quinoline groups as fluorophores, constituting amide groups as guest binding sites and communicators, we created metal-tunable octahedral nanocages Co-PT1/Zn-PTl [PT1(N',N",N"'-tris(quinolin-2-yl-methylene)benzene-1,3,5-tricarbohydrazide)]. Such a special two-fold hydrogen bonding pattern which only occurs between the cytidine and PT1is important for compounds Co-PT1/Zn-PTl to selectively recognize cytidine over others by both Uv-vis and luminescent responses.
(2) MRI Contrast Agent: By combining high-spin Gd3+ions with PT2(N',N",N"'-tris(pyridin-2-yl-methylene)-benzene-1,3,5-tricarbohydrazide) to form octahedral nanocages Gd-PT2. Gd-PT2exhibited quite high longitudinal relaxivity (r1=388.5mM-1a-1), and could apply images of a living mouse hypodermis, could be described as the glucosamine-specific probes in the MR responses. The glucosamine molecules in the solution substitute the coordinated water molecules, and interact with Gd3+ions directly to induce the decreasing of MR responses.
(3) Heterogeneous catalysis:Through incorporating having characteristic green luminescence Tb3+ions as Lewis acid sites and amide groups as guest-accessible functional weak base sites, we constructed porous molecular materials having one-dimensional channels, for size-selectively heterogeneous catalyzing the cyanosilylation and aldol reactions. The cyanosilylation reactions mostly took part in the channel of the catalysts and the aldehydes substrates were activated by the Tb3+ions, while the aldol reactions mainly occurred in the octahedral cavities and the cyclohexanone substrates possibly interacted with the amide groups through a hydrogen bond, respectively.
2. Metal-organic macrocycles research
(1) Chiral catalysis:
A. Through incorporation of a L-proline moiety within ligand PT3(N',N",N"'-bis(pyridin-2-ylmethylene)-5-((S)-pyrrolidine-2-carboxamido)isophthalohydrazide) containing amide groups, we have developed a new approach to create metal-tunable homochiral triangles Co-PT3/Ni-PT3. With the asymmetric catalytic active sites to stabilize the potential transition state and the helical cavity to increase the local concentration of the substrates, triangles work as asymmetric enzyme-like catalysts prompting the well-known aldol reactions with size-and stereoselectivity [(anti:syn)max=10.3:1].
B. By using L-/D-proline as a chiral adduct, we performed the homochiral lanterns of the two enantiomorphs L-CePT4/D-CePT4[L-PT4(N',N",N"'-bis((2-hydroxynaphthalen-1-y1)-methylene)-5-((S)-pyrrolidine-2-carboxamido)isophthalohydrazide); D-PT4(N',N",N"'-bis((2-hydroxynaphthalen-1-y1)methylene)-5-((R)-pyrrolidine-2-carboxamido)isophthalohydrazide)], having coordinatively unsaturated metal sites Ce3+. Asymmetric cyanosilylations of aromatic aldehydes were dispalyed to validate the excellent enantioselectively catalytic performance of the lanterns (eemax>99%).
(3) Biological molecules recognition:By combining anthracene groups as fluorophores, constituting amide groups as guest binding sites and communicators, we created metal-organic squares Co-PT7[PT7(N',N",N"'-bis(1-(pyridin-2-yl)ethylidene)anthracene-9,10-dicarbohydrazide)]. These squares can be ATP-specific probes in luminescence responses as compared to other nucleotides, by utilizing the synergistic effects of electrostatic.π-stacking. hydrogen-bonding and coordinative interactions inside the cavity.
1.金属-有机八面体性能研究
(1)生物小分子识别：将荧光响应单元-喹啉基团以及生物分子识别位点-酰胺基团引入到配体PT1(1,3,5-三(2-喹啉基)苯甲酰腙)中,与过渡金属离子Co2+、Zn2+自组装得到晶体同构的八面体过渡金属笼状化合物。化合物配体中的酰胺基团只与胞苷形成双重氢键相互作用,对胞苷的紫外、荧光响应信号明显优于其他三种核糖核苷。
(2)磁共振成像：将高自旋的稀土离子Gd3+与PT2(1,3,5-三(2-吡啶基)苯甲酰腙)自组装形成八面体稀土金属笼状化合物Gd-PT2。Gd-PT2具有很高的纵向弛豫率(r1=388.5mM-1s-1),可以应用于活体小鼠皮下组织成像。在葡萄糖、氨基葡萄糖及四种核糖核苷生物小分子中,实现了对氨基葡萄糖的专一选择性磁共振成像(MRI)。氨基葡萄糖的加入取代了配位的水分子,与Gd3+发生相互作用直接诱导磁共振响应信号的减弱。
(3)非均相催化：将Lewis酸活化位点-Tb3+离子及弱碱单元-酰胺基团同时引入到具有一维孔道的多孔固态分子材料Tb-PT2中,实现了尺寸选择性非均相催化氰基硅烷化反应和Aldol反应。氰基硅烷化反应发生在催化剂的一维孔道并且活化单元为Tb3+离子；Aldol反应发生在八面体内部洞穴并且酰胺基团与环己酮之间存在氢键相互作用。
2.金属-有机大环结构性能研究
(1)手性催化：
A.将L-脯氨酸作为手性催化中心引入到含有酰胺基团的配体PT3(1,3-二(2-毗啶基)-5-((S)-2-吡咯烷甲酰基)苯甲酰腙)中,分别与Co2+离子、Ni2+离子自组装,形成金属可调的具有单一手性的大环结构。由于该类大环化合物同时含有多个单一手性催化中心和丰富的氢键作用位点,可作为酶模拟反应器,实现了尺寸选择性均相不对称催化Aldol反应。基于其疏水性空腔强烈的空间可塑性,进一步提高了反应的非对映异构选择性(anti:syn最高为10.3：1)
B.设计合成了基于L-脯氨酸和D-脯氨酸的两种对映体配体L-PT4和D-PT4[L-PT4(1,3-二(2-羟基-1-萘基)-5-((S)-2-吡咯烷甲酰基)苯甲酰腙)；D-PT4(1,3-二(2-羟基-1-萘基)-5-((R)-2-吡咯烷甲酰基)苯甲酰腙)],与Ce3+离子自组装,形成两种中性对映体灯笼型化合物,实现了高对映选择性均相催化氰基硅烷化反应(ee值>99%)。
(2)生物分子识别：将具有良好荧光响应基团-蒽单元和双重氢键作用位点-酰胺基团引入到配体PT7(9,10-二(2-乙酰吡啶基)蒽甲酰腙)中,与Co2+离子自组装,形成结构类似于正方形的大环化合物。该正电荷化合物含有丰富的共轭基团、多重氢键作用位点以及具有强烈的空间可塑性的亲/疏水性空腔,实现了专一选择性识别ATP。
Metal-organic polyhedra and macrocycles are important models to realize the process of enzyme catalysis and recognition. These structures discussed exhibit well-defined cavities with gated pores providing specific inner environments for selective uptaking and binding of guest molecules. Yet only a few "artificial systems" achieved the detection and imaging techniques in biological systems and the magnificent catalysis of natural enzymes. The major challenge at stake here goes beyond the introducing of an optical measurable output, the active sites and specific weak effect response sites. On the basis of this context, by combining these functional groups into metal-organic polyhedra/macrocycles with considerable stabilities, we constructed relatively enclosing metal-organic octahedra and relatively open metal-organic macrocycles for biological molecules recognition and simulating enzyme catalysis researches.
1. Metal-organic octahedra research
(1) Biological molecules recognition:By combining three quinoline groups as fluorophores, constituting amide groups as guest binding sites and communicators, we created metal-tunable octahedral nanocages Co-PT1/Zn-PTl [PT1(N',N",N"'-tris(quinolin-2-yl-methylene)benzene-1,3,5-tricarbohydrazide)]. Such a special two-fold hydrogen bonding pattern which only occurs between the cytidine and PT1is important for compounds Co-PT1/Zn-PTl to selectively recognize cytidine over others by both Uv-vis and luminescent responses.
(2) MRI Contrast Agent: By combining high-spin Gd3+ions with PT2(N',N",N"'-tris(pyridin-2-yl-methylene)-benzene-1,3,5-tricarbohydrazide) to form octahedral nanocages Gd-PT2. Gd-PT2exhibited quite high longitudinal relaxivity (r1=388.5mM-1a-1), and could apply images of a living mouse hypodermis, could be described as the glucosamine-specific probes in the MR responses. The glucosamine molecules in the solution substitute the coordinated water molecules, and interact with Gd3+ions directly to induce the decreasing of MR responses.
(3) Heterogeneous catalysis:Through incorporating having characteristic green luminescence Tb3+ions as Lewis acid sites and amide groups as guest-accessible functional weak base sites, we constructed porous molecular materials having one-dimensional channels, for size-selectively heterogeneous catalyzing the cyanosilylation and aldol reactions. The cyanosilylation reactions mostly took part in the channel of the catalysts and the aldehydes substrates were activated by the Tb3+ions, while the aldol reactions mainly occurred in the octahedral cavities and the cyclohexanone substrates possibly interacted with the amide groups through a hydrogen bond, respectively.
2. Metal-organic macrocycles research
(1) Chiral catalysis:
A. Through incorporation of a L-proline moiety within ligand PT3(N',N",N"'-bis(pyridin-2-ylmethylene)-5-((S)-pyrrolidine-2-carboxamido)isophthalohydrazide) containing amide groups, we have developed a new approach to create metal-tunable homochiral triangles Co-PT3/Ni-PT3. With the asymmetric catalytic active sites to stabilize the potential transition state and the helical cavity to increase the local concentration of the substrates, triangles work as asymmetric enzyme-like catalysts prompting the well-known aldol reactions with size-and stereoselectivity [(anti:syn)max=10.3:1].
B. By using L-/D-proline as a chiral adduct, we performed the homochiral lanterns of the two enantiomorphs L-CePT4/D-CePT4[L-PT4(N',N",N"'-bis((2-hydroxynaphthalen-1-y1)-methylene)-5-((S)-pyrrolidine-2-carboxamido)isophthalohydrazide); D-PT4(N',N",N"'-bis((2-hydroxynaphthalen-1-y1)methylene)-5-((R)-pyrrolidine-2-carboxamido)isophthalohydrazide)], having coordinatively unsaturated metal sites Ce3+. Asymmetric cyanosilylations of aromatic aldehydes were dispalyed to validate the excellent enantioselectively catalytic performance of the lanterns (eemax>99%).
(3) Biological molecules recognition:By combining anthracene groups as fluorophores, constituting amide groups as guest binding sites and communicators, we created metal-organic squares Co-PT7[PT7(N',N",N"'-bis(1-(pyridin-2-yl)ethylidene)anthracene-9,10-dicarbohydrazide)]. These squares can be ATP-specific probes in luminescence responses as compared to other nucleotides, by utilizing the synergistic effects of electrostatic.π-stacking. hydrogen-bonding and coordinative interactions inside the cavity.
引文
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