黄酮类希夫碱配体识别Al~(3+)、Zn~(2+)探针的设计合成和表征
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摘要
黄酮类化合物具有低毒和广谱的药理活性,已经成为国内外开发研究自然界药物的热点,具有广阔的前景。Schiff碱一直都备受关注,其原因在于在C=N基团中N原子有一对孤对电子,赋予其重要的化学和生物学方面的意义。Schiff碱是一类非常重要的配体,它的合成相对容易,改变连接的取代基,便可得到从单齿到多齿,性格迥异、结构多变的Schiff碱配体。
铝是自然界中含量最多的金属元素,过多的铝离子会对生物体造成危害。锌离子在自然界和生物体系中都起着至关重要的作用。锌离子在人体内的含量仅次于铁离子,其正常范围在sub-nM～0.3Mm。在不同的生物系统,例如基因表达、蛋白质相互转换和神经传递中扮演着重要的角色。细胞内锌离子浓度的破坏,会导致一系列疾病的发生,例如老年痴呆、癫痫和婴儿腹泻等。因此,设计检测铝离子和锌离子的荧光探针在最近几十年内备受研究者的关注。
在本文中,设计合成了两种铝离子探针,一种锌离子探针。三个探针分别是7-甲氧基色酮-3-醛(3’,4’-二甲基吡咯-2’-甲酰基)腙、7-甲氧基色酮-3-醛((2’-苯并噻唑硫代)乙酰基)腙、7-甲氧基色酮-3-醛(荧光素)腙。这几个探针检测限低、选择性好,因此相信对研究铝、锌离子探针的研究会有一定的作用。
Flavonoids have low toxicity and broad spectrum of pharmacological activity, have become the hotspot of the nature of drug research and development at home and abroad, and have broad prospects. Schiff-base have been of concern, because N atoms in the C=N group have one lone pair electron, given the significance of its chemical and biological. The Schiff-base is a very important class of ligands, and its synthesis is relatively easy. It can be obtained different structure of the Schiff-base ligands from single tooth to polydentate.
Aluminum is the most abundant metal element in nature. As the existence of aluminum is in the form of free aluminum ions, the excessive aluminum ion accumulated in organisms can cause various diseases. Zinc ions play a vital role in nature and biological systems. The content of zinc ions in the human body is second only to iron ions, and their normal concentration range from the sub-nM to0.3Mm. In a variety of biological systems such as gene expression, protein conversion and neurotransmission, zinc ions play an important role. The destruction of the intracellular concentration of zinc ions, will lead to the occurrence of a range of diseases, such as Alzheimer's, epilepsy and infantile diarrhea. Therefore, the design of the fluorescent probes to detect the aluminum ions and zinc ions has attracted much attention from researchers in recent decades.
In this paper, we design and synthesis two aluminum ion probes and one zinc ion probe. The three probes are7-methoxychromone-3-carbaldehyde-(3',4'-dimethyl)pyrrole hydrazone (MCPH)7-methoxychromone-3-carbaldehyde-(2'-benzothiazolylthio) acetic acid hydrazone (MCAH),7-methoxychromone-3-carbaldehyde fluorescein hydrazone (MCFH) respectively. These three probes have low detection limit and good selectivity. We believe they can provide a new direction of the studies on aluminum and zinc ion probe.
铝是自然界中含量最多的金属元素,过多的铝离子会对生物体造成危害。锌离子在自然界和生物体系中都起着至关重要的作用。锌离子在人体内的含量仅次于铁离子,其正常范围在sub-nM～0.3Mm。在不同的生物系统,例如基因表达、蛋白质相互转换和神经传递中扮演着重要的角色。细胞内锌离子浓度的破坏,会导致一系列疾病的发生,例如老年痴呆、癫痫和婴儿腹泻等。因此,设计检测铝离子和锌离子的荧光探针在最近几十年内备受研究者的关注。
在本文中,设计合成了两种铝离子探针,一种锌离子探针。三个探针分别是7-甲氧基色酮-3-醛(3’,4’-二甲基吡咯-2’-甲酰基)腙、7-甲氧基色酮-3-醛((2’-苯并噻唑硫代)乙酰基)腙、7-甲氧基色酮-3-醛(荧光素)腙。这几个探针检测限低、选择性好,因此相信对研究铝、锌离子探针的研究会有一定的作用。
Flavonoids have low toxicity and broad spectrum of pharmacological activity, have become the hotspot of the nature of drug research and development at home and abroad, and have broad prospects. Schiff-base have been of concern, because N atoms in the C=N group have one lone pair electron, given the significance of its chemical and biological. The Schiff-base is a very important class of ligands, and its synthesis is relatively easy. It can be obtained different structure of the Schiff-base ligands from single tooth to polydentate.
Aluminum is the most abundant metal element in nature. As the existence of aluminum is in the form of free aluminum ions, the excessive aluminum ion accumulated in organisms can cause various diseases. Zinc ions play a vital role in nature and biological systems. The content of zinc ions in the human body is second only to iron ions, and their normal concentration range from the sub-nM to0.3Mm. In a variety of biological systems such as gene expression, protein conversion and neurotransmission, zinc ions play an important role. The destruction of the intracellular concentration of zinc ions, will lead to the occurrence of a range of diseases, such as Alzheimer's, epilepsy and infantile diarrhea. Therefore, the design of the fluorescent probes to detect the aluminum ions and zinc ions has attracted much attention from researchers in recent decades.
In this paper, we design and synthesis two aluminum ion probes and one zinc ion probe. The three probes are7-methoxychromone-3-carbaldehyde-(3',4'-dimethyl)pyrrole hydrazone (MCPH)7-methoxychromone-3-carbaldehyde-(2'-benzothiazolylthio) acetic acid hydrazone (MCAH),7-methoxychromone-3-carbaldehyde fluorescein hydrazone (MCFH) respectively. These three probes have low detection limit and good selectivity. We believe they can provide a new direction of the studies on aluminum and zinc ion probe.
引文
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