吡唑衍生物合成、生物活性及罗丹明B类pH荧光探针
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摘要
第一部分：
吡唑衍生物是一类非常重要的含氮杂环化合物,该类化合物具有广泛的生物活性,比如抗癌、抗炎、杀菌、抗氧化、抗抑郁、抗血管生成和抗感冒等。另外,已有多个吡唑类化合物被当作药物来使用,如塞来昔布、西地那非、扎来普隆和瑞司瓜特。
自顺铂的抗癌活性被报道以来,金属复合物在药物化学领域一直发挥着重要的作用。过去的几年里,大量具有抗癌活性的金属复合物被报道,例如金类、铑类、钌类、二茂铁衍生物等。由于二茂铁基团具有独特的氧化还原性以及形态学上与苯环相似的芳香性和亲油性,在有机分子中引入二茂铁基团往往能够提高小分子的生物活性。
在这一部分里,我们设计合成了多个系列新型吡唑衍生物,通过红外、核磁共振、高分辨质谱及X射线衍射对化合物的结构进行了表征,并进一步研究了化合物的抗癌活性和光谱性质。
第一章,对吡唑衍生物和二茂铁衍生物在生物活性方面的应用,及吡唑并杂环的化合物的合成进行了简要总结。同时还简要综述了微波辐射在有机合成中的应用和旋光活性对药物活性的影响。
第二章,通过微波辐射法合成了一系列含有手性氨基醇结构的二茂铁基吡唑衍生物。通过红外、核磁共振、高分辨质谱及X射线衍射对化合物的结构进行了表征。初步的生物活性评价表明,该系列化合物能够抑制肺癌A549和H322细胞的增殖。
第三章,通过微波辐射法合成了一系列手性二茂铁基吡唑并[1,5-a][1,4]二氮杂卓-4-酮衍生物。通过红外、核磁共振、高分辨质谱及X射线衍射对化合物的结构进行了表征。初步的生物活性评价结果显示,部分化合物能够抑制肺癌A549、H322和H1299的增殖。
第四章,合成了一系列新型的手性3-二茂铁基-1-(2-羟基-3-(苯胺基)丙基)-1H-吡唑-5-甲酰肼衍生物,通过红外、核磁共振及高分辨质谱对化合物的结构进行了表征。部分化合物可以抑制肺癌A549细胞的增殖。
第五章,合成了一系列(E)-1-苄基-N□-(3-香豆素亚甲基)-3-芳基-1H-吡唑-5-碳酰腙衍生物。化合物的结构得到了红外、核磁共振、高分辨质谱和X射线衍射实验的确认,同时还考察了部分化合物在四氢呋喃、甲苯和乙醇溶剂中的紫外吸收和荧光性质。
第二部分：
细胞内pH值在许多细胞行为中发挥重要作用,如细胞生长、凋亡、自噬、离子运输与平衡和酶活性保持等。细胞内环境有不同的pH值,如细胞质是弱碱性的(pH-7.2),而溶酶体和核内体的内环境为酸性(pH4.0-6.0)。细胞内pH异常往往导致细胞功能障碍,从而导致很多疾病的发生,如阿尔茨海默症、中风和癌症,因此监测细胞内pH值的变化对研究细胞新陈代谢、生理和病理过程具有重要意义。
由于荧光探针具有高的灵敏性和选择性、响应快、操作简单、对细胞无损伤等优点,利用荧光探针来检测细胞内pH值的方法引起了人们的关注。其中,由于罗丹明类染料具有优异的生物相容性及光学性质,它们已被广泛地应用于金属离子检测和细胞成像。基于此,我们设计合成了三个罗丹明B类pH荧光探针RML, RC1和RC2。
第一章,简要综述了荧光探针的识别机理和pH荧光探针的研究进展。
第二章,合成了一个含有溶酶体靶向基团4-(2-氨乙基)吗啉的pH探针RML。该探针具有长的激发和发射波长、高的灵敏性和选择性及膜透性。RML的pKa为5.16,适合于酸性细胞器中pH的测定,该探针被成功地用于溶酶体标记及细胞内pH的测定。
第三章,以香豆素为能量供体、罗丹明B为能量受体,通过改变连接基团,合成了两个FRET类pH比率荧光探针RC1和RC2。探针RC1可以比率测定pH2.20-4.20范围内的pH变化,而探针RC2适用于pH4.20-6.00范围内pH变化的比率测定。
本论文的创新点：
1.将二茂铁基团和毗唑基团拼接,合成了三个系列手性二茂铁基吡唑衍生物,生物活性评价表明,这些化合物均能抑制肺癌A549细胞的增殖。
2.将荧光基团(香豆素结构)引入到吡唑衍生物中,合成了一系列可以发荧光的吡唑酰腙衍生物,为以后研究其活性机理提供了便利。
3.首次将溶酶体靶向基团—4-(2-氨乙基)吗啉引入到罗丹明B类pH探针中,合成了探针RML。探针RML具有高的灵敏性。
4.合成了两个FRET类pH比率荧光探针RC1和RC2。探针RC1可以比率测定pH2.20-4.20范围内的变化。探针RC2具有高的灵敏性,可以比率测定pH4.20-6.00范围内的变化。
Part I:
Pyrazole derivatives represent an important category of nitrogen-containing heterocycles. Compound with pyrazole framework displays diverse biological activities such as anti-cancer, anti-inflammatory, anti-microbial, anti-oxidant, anti-depressant, anti-angiogenesis and anti-influenza activities. Moreover, some of the derivatives have been applied in the field of medicine, such as Celecoxib, Sildenafil, Zaleplon and Riociguat.
Metal-based complexes have been playing a prominent role in the medicinal chemistry area since the discovery of cisplatin. During the past years, numerous new promising organometallic complexes were reported to exhibit high anti-cancer activity, including Au complexes, Rh complexes, Ru complexes and ferrocene derivatives. Incorporation of the ferrocene fragment into an organic molecule often results in excellent biological activities due to its similarities in aromaticity and lipophilicity of morphology to the benzene ring, along with the particular redox property.
In this part, we designed and synthesized several series of novel pyrazole derivatives. Their structures were characterized by means of IR,1H NMR, HRMS and X-ray diffraction. The biological activities and, optical properties of the compounds were also investigated.
Chapter1, we reviewed the applications of pyrazole and ferrocene derivatives in the biological activity and the synthetic methods of pyrazole fused heterocyclic derivatives. We also summarized the influence of microwave irradiation on chemical reaction and the chirality on drugs.
Chapter2, a series of novel ferrocenyl pyrazole-containing chiral aminoethanol derivatives were synthesized by microwave-assisted reaction. Structural features were confirmed by IR,1H NMR, X-ray diffraction and mass spectroscopy. Preliminary biological evaluation showed that all the compounds could suppress the growth of A549and H322lung cells.
Chapter3, a series of novel chiral ferrocenylpyrazolo[1,5-a][1,4]diazepin-4-one derivatives were synthesized under the microwave-assisted condition. Their structures were determined by IR,1H NMR, HRMS and X-ray analysis. As was indicated in the preliminary biological evaluation, some compounds were able to suppress the growth of A549, H322and H1299lung cancer cells.
Chapter4, a series of novel chiral3-ferrocenyl-l-(2-hydroxy-3-(arylamino) propyl)-1H-pyrazole-5-carbohydrazide derivatives were successfully synthesized and their structural features were confirmed by virtue of IR,1HNMR, HRMS. Preliminary biological evaluation showed that some compounds could suppress A549lung cancer cells growth.
Chapter5, a series of novel1-arylmethyl-3-aryl-H'-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)-1H-pyrazole-5-carbohydrazide derivatives were synthesized. Their structures were determined by IR,1H NMR, HRMS and X-ray diffraction analysis. The absorption and fluorescence characteristics were investigated in tetrahydrofuran, toluene and ethanol.
Part II:
Intracellular pH plays a pivotal role in many biological behaviors, such as cell growth, apoptosis, autophagy, ion transport, homeostasis and enzymatic activity. The intracellular microenvironment has various pH values, for instance, the cytosol has slightly basic pH values (pH～7.2), whereas the interior of lysosome and endosome is slightly acidic (pH4.0-6.0). Aberrations of the intracellular pH homeostasis in organelles can lead to cellular dysfunctions and affect human physiology, causing serious diseases such as Alzheimer's disease, stroke and cancer. Therefore, monitoring pH changes inside living cells is of great importance for gaining insights into cellular metabolisms, physiological and pathological process.
Fluorescent sensors have attracted much attention for assessing intact and subcellular pH due to their high sensitivity and selectivity, unrivaled spatiotemporal resolution, simple operation and nondestructive use in cells. Rhodamine dyes have been widely used for metal ion detection and intracellular imaging on account of their excellent biocompatibility and photophysical properties. In this part, we reported three rhodamine-based pH fluorescent probes RML, RC1and RC2.
Chapter1, we reviewed the recognition mechanisms of fluorescent probes and the research on the application of pH fluorescent probes in recent years.
Chapter2, we synthesized a rhodamine-based pH fluorescent sensor RML, in which a lysosome-targetable group,4-(2-aminoethyl)morpholine, is introduced. The probe has long absorption and emission wavelengths, high sensitivity and selectivity. It is also membrane permeable. The probe with pKa5.16is suitable for monitoring pH in acidic organelles. It has been successfully applied in monitoring pH changes inside living cells and can selectively stain lysosomes.
Chapter3, novel ratiometric pH probes RC1and RC2were successfully designed and synthesized. These two ratiometric pH probes were constructed by integrating a coumarin fluorophore as an FRET donor into the rhodamine B fluorophore as an FRET acceptor. Probe RC1and RC2could be used for the ratiometric measurement of pH values in range2.20-4.20(RC1) and4.20-6.00(RC2) with high selectivity.
吡唑衍生物是一类非常重要的含氮杂环化合物,该类化合物具有广泛的生物活性,比如抗癌、抗炎、杀菌、抗氧化、抗抑郁、抗血管生成和抗感冒等。另外,已有多个吡唑类化合物被当作药物来使用,如塞来昔布、西地那非、扎来普隆和瑞司瓜特。
自顺铂的抗癌活性被报道以来,金属复合物在药物化学领域一直发挥着重要的作用。过去的几年里,大量具有抗癌活性的金属复合物被报道,例如金类、铑类、钌类、二茂铁衍生物等。由于二茂铁基团具有独特的氧化还原性以及形态学上与苯环相似的芳香性和亲油性,在有机分子中引入二茂铁基团往往能够提高小分子的生物活性。
在这一部分里,我们设计合成了多个系列新型吡唑衍生物,通过红外、核磁共振、高分辨质谱及X射线衍射对化合物的结构进行了表征,并进一步研究了化合物的抗癌活性和光谱性质。
第一章,对吡唑衍生物和二茂铁衍生物在生物活性方面的应用,及吡唑并杂环的化合物的合成进行了简要总结。同时还简要综述了微波辐射在有机合成中的应用和旋光活性对药物活性的影响。
第二章,通过微波辐射法合成了一系列含有手性氨基醇结构的二茂铁基吡唑衍生物。通过红外、核磁共振、高分辨质谱及X射线衍射对化合物的结构进行了表征。初步的生物活性评价表明,该系列化合物能够抑制肺癌A549和H322细胞的增殖。
第三章,通过微波辐射法合成了一系列手性二茂铁基吡唑并[1,5-a][1,4]二氮杂卓-4-酮衍生物。通过红外、核磁共振、高分辨质谱及X射线衍射对化合物的结构进行了表征。初步的生物活性评价结果显示,部分化合物能够抑制肺癌A549、H322和H1299的增殖。
第四章,合成了一系列新型的手性3-二茂铁基-1-(2-羟基-3-(苯胺基)丙基)-1H-吡唑-5-甲酰肼衍生物,通过红外、核磁共振及高分辨质谱对化合物的结构进行了表征。部分化合物可以抑制肺癌A549细胞的增殖。
第五章,合成了一系列(E)-1-苄基-N□-(3-香豆素亚甲基)-3-芳基-1H-吡唑-5-碳酰腙衍生物。化合物的结构得到了红外、核磁共振、高分辨质谱和X射线衍射实验的确认,同时还考察了部分化合物在四氢呋喃、甲苯和乙醇溶剂中的紫外吸收和荧光性质。
第二部分：
细胞内pH值在许多细胞行为中发挥重要作用,如细胞生长、凋亡、自噬、离子运输与平衡和酶活性保持等。细胞内环境有不同的pH值,如细胞质是弱碱性的(pH-7.2),而溶酶体和核内体的内环境为酸性(pH4.0-6.0)。细胞内pH异常往往导致细胞功能障碍,从而导致很多疾病的发生,如阿尔茨海默症、中风和癌症,因此监测细胞内pH值的变化对研究细胞新陈代谢、生理和病理过程具有重要意义。
由于荧光探针具有高的灵敏性和选择性、响应快、操作简单、对细胞无损伤等优点,利用荧光探针来检测细胞内pH值的方法引起了人们的关注。其中,由于罗丹明类染料具有优异的生物相容性及光学性质,它们已被广泛地应用于金属离子检测和细胞成像。基于此,我们设计合成了三个罗丹明B类pH荧光探针RML, RC1和RC2。
第一章,简要综述了荧光探针的识别机理和pH荧光探针的研究进展。
第二章,合成了一个含有溶酶体靶向基团4-(2-氨乙基)吗啉的pH探针RML。该探针具有长的激发和发射波长、高的灵敏性和选择性及膜透性。RML的pKa为5.16,适合于酸性细胞器中pH的测定,该探针被成功地用于溶酶体标记及细胞内pH的测定。
第三章,以香豆素为能量供体、罗丹明B为能量受体,通过改变连接基团,合成了两个FRET类pH比率荧光探针RC1和RC2。探针RC1可以比率测定pH2.20-4.20范围内的pH变化,而探针RC2适用于pH4.20-6.00范围内pH变化的比率测定。
本论文的创新点：
1.将二茂铁基团和毗唑基团拼接,合成了三个系列手性二茂铁基吡唑衍生物,生物活性评价表明,这些化合物均能抑制肺癌A549细胞的增殖。
2.将荧光基团(香豆素结构)引入到吡唑衍生物中,合成了一系列可以发荧光的吡唑酰腙衍生物,为以后研究其活性机理提供了便利。
3.首次将溶酶体靶向基团—4-(2-氨乙基)吗啉引入到罗丹明B类pH探针中,合成了探针RML。探针RML具有高的灵敏性。
4.合成了两个FRET类pH比率荧光探针RC1和RC2。探针RC1可以比率测定pH2.20-4.20范围内的变化。探针RC2具有高的灵敏性,可以比率测定pH4.20-6.00范围内的变化。
Part I:
Pyrazole derivatives represent an important category of nitrogen-containing heterocycles. Compound with pyrazole framework displays diverse biological activities such as anti-cancer, anti-inflammatory, anti-microbial, anti-oxidant, anti-depressant, anti-angiogenesis and anti-influenza activities. Moreover, some of the derivatives have been applied in the field of medicine, such as Celecoxib, Sildenafil, Zaleplon and Riociguat.
Metal-based complexes have been playing a prominent role in the medicinal chemistry area since the discovery of cisplatin. During the past years, numerous new promising organometallic complexes were reported to exhibit high anti-cancer activity, including Au complexes, Rh complexes, Ru complexes and ferrocene derivatives. Incorporation of the ferrocene fragment into an organic molecule often results in excellent biological activities due to its similarities in aromaticity and lipophilicity of morphology to the benzene ring, along with the particular redox property.
In this part, we designed and synthesized several series of novel pyrazole derivatives. Their structures were characterized by means of IR,1H NMR, HRMS and X-ray diffraction. The biological activities and, optical properties of the compounds were also investigated.
Chapter1, we reviewed the applications of pyrazole and ferrocene derivatives in the biological activity and the synthetic methods of pyrazole fused heterocyclic derivatives. We also summarized the influence of microwave irradiation on chemical reaction and the chirality on drugs.
Chapter2, a series of novel ferrocenyl pyrazole-containing chiral aminoethanol derivatives were synthesized by microwave-assisted reaction. Structural features were confirmed by IR,1H NMR, X-ray diffraction and mass spectroscopy. Preliminary biological evaluation showed that all the compounds could suppress the growth of A549and H322lung cells.
Chapter3, a series of novel chiral ferrocenylpyrazolo[1,5-a][1,4]diazepin-4-one derivatives were synthesized under the microwave-assisted condition. Their structures were determined by IR,1H NMR, HRMS and X-ray analysis. As was indicated in the preliminary biological evaluation, some compounds were able to suppress the growth of A549, H322and H1299lung cancer cells.
Chapter4, a series of novel chiral3-ferrocenyl-l-(2-hydroxy-3-(arylamino) propyl)-1H-pyrazole-5-carbohydrazide derivatives were successfully synthesized and their structural features were confirmed by virtue of IR,1HNMR, HRMS. Preliminary biological evaluation showed that some compounds could suppress A549lung cancer cells growth.
Chapter5, a series of novel1-arylmethyl-3-aryl-H'-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)-1H-pyrazole-5-carbohydrazide derivatives were synthesized. Their structures were determined by IR,1H NMR, HRMS and X-ray diffraction analysis. The absorption and fluorescence characteristics were investigated in tetrahydrofuran, toluene and ethanol.
Part II:
Intracellular pH plays a pivotal role in many biological behaviors, such as cell growth, apoptosis, autophagy, ion transport, homeostasis and enzymatic activity. The intracellular microenvironment has various pH values, for instance, the cytosol has slightly basic pH values (pH～7.2), whereas the interior of lysosome and endosome is slightly acidic (pH4.0-6.0). Aberrations of the intracellular pH homeostasis in organelles can lead to cellular dysfunctions and affect human physiology, causing serious diseases such as Alzheimer's disease, stroke and cancer. Therefore, monitoring pH changes inside living cells is of great importance for gaining insights into cellular metabolisms, physiological and pathological process.
Fluorescent sensors have attracted much attention for assessing intact and subcellular pH due to their high sensitivity and selectivity, unrivaled spatiotemporal resolution, simple operation and nondestructive use in cells. Rhodamine dyes have been widely used for metal ion detection and intracellular imaging on account of their excellent biocompatibility and photophysical properties. In this part, we reported three rhodamine-based pH fluorescent probes RML, RC1and RC2.
Chapter1, we reviewed the recognition mechanisms of fluorescent probes and the research on the application of pH fluorescent probes in recent years.
Chapter2, we synthesized a rhodamine-based pH fluorescent sensor RML, in which a lysosome-targetable group,4-(2-aminoethyl)morpholine, is introduced. The probe has long absorption and emission wavelengths, high sensitivity and selectivity. It is also membrane permeable. The probe with pKa5.16is suitable for monitoring pH in acidic organelles. It has been successfully applied in monitoring pH changes inside living cells and can selectively stain lysosomes.
Chapter3, novel ratiometric pH probes RC1and RC2were successfully designed and synthesized. These two ratiometric pH probes were constructed by integrating a coumarin fluorophore as an FRET donor into the rhodamine B fluorophore as an FRET acceptor. Probe RC1and RC2could be used for the ratiometric measurement of pH values in range2.20-4.20(RC1) and4.20-6.00(RC2) with high selectivity.
引文
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