用于识别、检测细胞内阴离子（CI~-、OCI~-）的新型荧光探针的设计、合成与应用
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摘要
动植物体内存在许多微量或痕量的活性物种(自由基和阴、阳离子等),它们对各种生理、病理过程具有重要的影响,对生命活动起着至关重要的作用,在多种致病过程中都是重要的介导因素,与癌症、机体炎症、组织过氧化、蛋白质交联变性、DNA损伤和细胞信号转导等都有着直接的关系。要进一步了解这些活性小分子物种与上述生理、病理过程中的密切关联,就必须对它们进行准确、实时的检测。但是,由于生物体内大多数活性物种浓度极低,加之生物环境的多样性与复杂性,目前真正能够用于高选择性检测生物活体内活性物种的方法还比较少。荧光法结合共聚焦显微成像技术和微区光谱检测技术,是一种能够实现活细胞和组织内活性物种“实时、可视、定量”检测的有效方法。综上,发展选择性好、灵敏度高、用于检测生物体内痕量物种的分子荧光探针,对动、植物活体细胞中的活性物种动态、原位可视化成像分析是目前生命科学研究的重要热点领域之一。
氯是人体内的宏量元素,约占体重的0.15%,主要以氯离子的形式存在于细胞内外,参与维持生物体内的酸碱平衡和细胞外液的渗透压,调节细胞凋亡、免疫应答,此外,在酶催化反应等生理过程中也起着至关重要的作用。细胞中氯离子水平的非正常波动会引发各种疾病,例如:囊肿性纤维化、肌强直症、心律不齐以及心肌缺血等。为了更好地探究氯离子参与的众多生理和病理过程,就要求广大生物学家和化学工作者开发出具有高选择性,高灵敏度的荧光分子探针,并将其用于监测细胞内氯离子的含量及其变化情况。
作为人体内重要的活性氧之一,次氯酸根在人体的生理和病理过程中起着举足轻重的作用。其在生物体内的产生过程如下:在髓过氧化物酶(MPO)的催化作用下,过氧化氢和氯离子发生化学反应,随之产生次氯酸根。作为一种具有强亲核特性的活性物种,次氯酸根最突出的作用就是其具有抗菌性。然而,过多或过少水平的次氯酸根也会引发一系列的疾病,例如:动脉硬化、关节炎以及癌症等。因此,近年来关于次氯酸根的生理功能的探索和研究引起越来越多的关注。
综上所述,由于阴离子在各种生理、病理过程中的重要作用,对各种阴离子的识别和检测已经成为生命化学学科发展中具有挑战性的前沿课题之一。就目前所报道的阴离子识别方法中,阴离子与受体之间的相互作用过程会受到各种因素的干扰,因而,设计、合成一种具有特异性识别阴离子的荧光受体显得尤为重要。
针对阴离子的研究和发展现状,本论文以提高探针的响应速度、灵敏度以及选择性为主要出发点,进而发挥探针在实际生物样品和临床疾病诊断等方面的应用,以荧光检测和共聚焦显微成像技术为研究手段。开展了以下两方面的工作:
(一)设计合成了一种用于检测氯离子的荧光比率探针。该探针的结构由两部分组成:一部分是对氯离子有特异性反应的六甲氧基喹啉衍生物;另一部分是对氯离子不敏感的5-氨基荧光素基团。探针的合成路线简单、快捷,并且通过1H NMR和13C NMR对探针的结构进行了表征,研究了其相关光谱性质。实验表明,该探针能够在瞬间实现对氯离子高灵敏度、高选择性的检测。此外,激光共聚焦荧光比率成像的实验结果表明该探针能够成功监测正常和缺血时心肌细胞中氯离子的浓度波动。
(二)设计了连接有盐酸羟胺基团的花菁结构的近红外荧光分子探针,用于检测生物体内的ClO-进一步实现在线粒体中的定位。推测探针的检测机理可能是:盐酸羟胺能够被次氯酸根氧化。初步实验结果表明,探针具有较宽的激发波长和发射波长范围,并且对次氯酸根具有较高的灵敏度和较好的选择性,能够实现在近红外区域对次氯酸根的检测。
There were various micro or trace amounts of active species (free radicals, anions and cations) in living systems. They hold a unique position in life processes and are of central importance for many physiological functions. These active species are important mediators for the pathological conditions of various diseases, such as carcinogenesis, inflammation, ischemia-reperfusion injury, and signal transduction. In order to further explore the close relation between these small biological molecules and various physiological or pathological processes, there is an exigent need for researchers to develop fast-respond probes to realize the accurate detection of these important species. However, as a result of the low concentrations of these active species, and the diversities and complexity of the biological environment, methods that can detect the bio-relative species with high selectivity are few. Take full advantage of benefits provided by confocal laser scanning microscopy (CLSM), spectrofluorimetry can serve as a powerful method due to its high sensitivity, simplicity in data collection, and high spatial resolution in imaging techniques. They are considered as the unique method that can realize the“real-time, dynamic, visualized”analysis of fluctuations of various bio-relative species in cells and in tissue. In a word, it is of great value for the researchers to explore fast and convenient probes to investigate the levels of the trace molecules in bio-system, and furthermore realize the real-time imaging in living cells.
As one important element, chlorine distributes widely in cells in forms of chloride (Cl-). It holds a unique position in a wide range of many cellular functions, including regulation of cells volume and pH, apoptosis and immune response, intracellular trafficand enzyme catalysis reactions. Exceptional fluctuation in concentration of Cl- can result in some diseases, such as cystic fibrosis, myotonia, arrhythmia and myocardial ischemia. Thus, there is exigent challenge for researchers to develop fast-respond probes to trap Cl- for investigation of the mechanisms of the physiological and pathological processes that the chloride anions participate.
As one of the biologically important ROS, which is produced in living organisms from hydrogen peroxide and chloride ions in a chemical reaction catalyzed by the enzyme myeloperoxidase (MPO) in activated neurophils, hypochlorite anion ( OCl- ) is known to be essential to several biological functions , for example, because OCl- can behave as a strong nucleophilic nonradical oxidant, it is regarded as an important agent with strong antibacterial properties that is used for natural defense; its efficacy lies in the fact that neither bacteria nor mammalian cells can neutralize its toxic effects-they lack the enzymes required for its catalytic detoxification. However, excessive or misplacedprod uction of OCl- can lead to tissue damage and diseases, such as atherosclerosis, arthritis, and cancers. Therefore, more and more attention has been paid to the studies of the biological functions.
All in all, based on the crucial function of various anions during the physiological and pathological processes, researches about recognition and detection of the bio-relative anions have attracted drastic attention. Up to now, considering the external influence factors that will disturb the recognition process between the anion and the acceptor, it is of vital importance to develop and synthesis probes that are exclusive to specific anions.
Considering the development status of anions and the excellent rate, sensitivity and selectivity, spectrofluorimetry combined with CLSM was applied successfully. It realized the application both in vivo and in clinic. The following are the main content of dissertation:
First, we chose the low-toxic 5-Aminofluorescein as the chloride insensitive group. Simultaneously, 6-Methoxyquinoline was chosen as the chloride reactive group, whose fluorescence was quenched linearly with the increased chloride concentration. It was synthesized conveniently by only two steps. Structure of the MQAF was characterized by 1H NMR and 13C NMR, and fluorescence properties of the reaction between MQAF and Cl- were optimized in chemical system. It showed that the probe possessed potent selectivity to Cl- and could respond instantaneously to changes of chloride concentration. During experiments, MQAF was proved to exhibit potent selectivity toward Cl- and respond to changes in chloride concentration instantaneously. Owing to the outstanding performance of the MQAF presented here, we successfully applied it to monitor chloride concentration fluctuations between normal and ischemic conditions.
Second, in this paper, we design a NIR OCl- fluorescent probe based on tricarbocyanine (Cy), whose maximum emission wavelength is within near-infrared region and choosing hydroxylamine hydrochloride as the reactive group. After addition of the OCl- anion, there undergoes an obvious fluorescence enhancement. Experiment results showed that the probe exhibited wide excitation and emission spectrum, besides, it could detect the hypochlorite anion sensitively and selectively in the near-infrared region.
氯是人体内的宏量元素,约占体重的0.15%,主要以氯离子的形式存在于细胞内外,参与维持生物体内的酸碱平衡和细胞外液的渗透压,调节细胞凋亡、免疫应答,此外,在酶催化反应等生理过程中也起着至关重要的作用。细胞中氯离子水平的非正常波动会引发各种疾病,例如:囊肿性纤维化、肌强直症、心律不齐以及心肌缺血等。为了更好地探究氯离子参与的众多生理和病理过程,就要求广大生物学家和化学工作者开发出具有高选择性,高灵敏度的荧光分子探针,并将其用于监测细胞内氯离子的含量及其变化情况。
作为人体内重要的活性氧之一,次氯酸根在人体的生理和病理过程中起着举足轻重的作用。其在生物体内的产生过程如下:在髓过氧化物酶(MPO)的催化作用下,过氧化氢和氯离子发生化学反应,随之产生次氯酸根。作为一种具有强亲核特性的活性物种,次氯酸根最突出的作用就是其具有抗菌性。然而,过多或过少水平的次氯酸根也会引发一系列的疾病,例如:动脉硬化、关节炎以及癌症等。因此,近年来关于次氯酸根的生理功能的探索和研究引起越来越多的关注。
综上所述,由于阴离子在各种生理、病理过程中的重要作用,对各种阴离子的识别和检测已经成为生命化学学科发展中具有挑战性的前沿课题之一。就目前所报道的阴离子识别方法中,阴离子与受体之间的相互作用过程会受到各种因素的干扰,因而,设计、合成一种具有特异性识别阴离子的荧光受体显得尤为重要。
针对阴离子的研究和发展现状,本论文以提高探针的响应速度、灵敏度以及选择性为主要出发点,进而发挥探针在实际生物样品和临床疾病诊断等方面的应用,以荧光检测和共聚焦显微成像技术为研究手段。开展了以下两方面的工作:
(一)设计合成了一种用于检测氯离子的荧光比率探针。该探针的结构由两部分组成:一部分是对氯离子有特异性反应的六甲氧基喹啉衍生物;另一部分是对氯离子不敏感的5-氨基荧光素基团。探针的合成路线简单、快捷,并且通过1H NMR和13C NMR对探针的结构进行了表征,研究了其相关光谱性质。实验表明,该探针能够在瞬间实现对氯离子高灵敏度、高选择性的检测。此外,激光共聚焦荧光比率成像的实验结果表明该探针能够成功监测正常和缺血时心肌细胞中氯离子的浓度波动。
(二)设计了连接有盐酸羟胺基团的花菁结构的近红外荧光分子探针,用于检测生物体内的ClO-进一步实现在线粒体中的定位。推测探针的检测机理可能是:盐酸羟胺能够被次氯酸根氧化。初步实验结果表明,探针具有较宽的激发波长和发射波长范围,并且对次氯酸根具有较高的灵敏度和较好的选择性,能够实现在近红外区域对次氯酸根的检测。
There were various micro or trace amounts of active species (free radicals, anions and cations) in living systems. They hold a unique position in life processes and are of central importance for many physiological functions. These active species are important mediators for the pathological conditions of various diseases, such as carcinogenesis, inflammation, ischemia-reperfusion injury, and signal transduction. In order to further explore the close relation between these small biological molecules and various physiological or pathological processes, there is an exigent need for researchers to develop fast-respond probes to realize the accurate detection of these important species. However, as a result of the low concentrations of these active species, and the diversities and complexity of the biological environment, methods that can detect the bio-relative species with high selectivity are few. Take full advantage of benefits provided by confocal laser scanning microscopy (CLSM), spectrofluorimetry can serve as a powerful method due to its high sensitivity, simplicity in data collection, and high spatial resolution in imaging techniques. They are considered as the unique method that can realize the“real-time, dynamic, visualized”analysis of fluctuations of various bio-relative species in cells and in tissue. In a word, it is of great value for the researchers to explore fast and convenient probes to investigate the levels of the trace molecules in bio-system, and furthermore realize the real-time imaging in living cells.
As one important element, chlorine distributes widely in cells in forms of chloride (Cl-). It holds a unique position in a wide range of many cellular functions, including regulation of cells volume and pH, apoptosis and immune response, intracellular trafficand enzyme catalysis reactions. Exceptional fluctuation in concentration of Cl- can result in some diseases, such as cystic fibrosis, myotonia, arrhythmia and myocardial ischemia. Thus, there is exigent challenge for researchers to develop fast-respond probes to trap Cl- for investigation of the mechanisms of the physiological and pathological processes that the chloride anions participate.
As one of the biologically important ROS, which is produced in living organisms from hydrogen peroxide and chloride ions in a chemical reaction catalyzed by the enzyme myeloperoxidase (MPO) in activated neurophils, hypochlorite anion ( OCl- ) is known to be essential to several biological functions , for example, because OCl- can behave as a strong nucleophilic nonradical oxidant, it is regarded as an important agent with strong antibacterial properties that is used for natural defense; its efficacy lies in the fact that neither bacteria nor mammalian cells can neutralize its toxic effects-they lack the enzymes required for its catalytic detoxification. However, excessive or misplacedprod uction of OCl- can lead to tissue damage and diseases, such as atherosclerosis, arthritis, and cancers. Therefore, more and more attention has been paid to the studies of the biological functions.
All in all, based on the crucial function of various anions during the physiological and pathological processes, researches about recognition and detection of the bio-relative anions have attracted drastic attention. Up to now, considering the external influence factors that will disturb the recognition process between the anion and the acceptor, it is of vital importance to develop and synthesis probes that are exclusive to specific anions.
Considering the development status of anions and the excellent rate, sensitivity and selectivity, spectrofluorimetry combined with CLSM was applied successfully. It realized the application both in vivo and in clinic. The following are the main content of dissertation:
First, we chose the low-toxic 5-Aminofluorescein as the chloride insensitive group. Simultaneously, 6-Methoxyquinoline was chosen as the chloride reactive group, whose fluorescence was quenched linearly with the increased chloride concentration. It was synthesized conveniently by only two steps. Structure of the MQAF was characterized by 1H NMR and 13C NMR, and fluorescence properties of the reaction between MQAF and Cl- were optimized in chemical system. It showed that the probe possessed potent selectivity to Cl- and could respond instantaneously to changes of chloride concentration. During experiments, MQAF was proved to exhibit potent selectivity toward Cl- and respond to changes in chloride concentration instantaneously. Owing to the outstanding performance of the MQAF presented here, we successfully applied it to monitor chloride concentration fluctuations between normal and ischemic conditions.
Second, in this paper, we design a NIR OCl- fluorescent probe based on tricarbocyanine (Cy), whose maximum emission wavelength is within near-infrared region and choosing hydroxylamine hydrochloride as the reactive group. After addition of the OCl- anion, there undergoes an obvious fluorescence enhancement. Experiment results showed that the probe exhibited wide excitation and emission spectrum, besides, it could detect the hypochlorite anion sensitively and selectively in the near-infrared region.
引文
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