荧光成像技术对部分抗血吸虫药物与日本血吸虫尾蚴的作用机理研究
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摘要
氯硝柳胺和吡喹酮对血吸虫尾蚴具有良好的杀灭效果,但其与日本血吸虫尾蚴的作用机理尚不清楚,本论文通过分子改性手段在氯硝柳胺和吡喹酮分子上引入荧光基团,并采用荧光成像法研究了氯硝柳胺、吡喹酮与日本血吸虫尾蚴之间的相互作用。
针对日本血吸虫尾蚴在水面的静态生活习性,我们设计合成了两个氯硝柳胺衍生物NI-2a和NI-2b。NI-2b具有水面自扩散和水面漂浮的性质,并有很好的灭尾蚴活性。采用MTT(噻唑蓝)法测定细胞毒性结果表明NI-2a和NI-2b对HeLa细胞的毒性较低。为了研究NI-2a与日本血吸虫尾蚴的作用机理,我们在NI-2a的基础上连接荧光分子合成荧光衍生物NI-3。尾蚴荧光成像实验结果表明NI-3能够快速地经尾蚴表皮吸收和运输,说明NI-3容易被尾蚴吸收从而影响尾蚴的体内代谢导致尾蚴的死亡。
吡喹酮经过硝化和还原两步反应得到两个吡喹酮衍生物PZQ-2和PZQ-3,MTT法测定细胞毒性结果表明在200μM PZQ-2和PZQ-3的浓度下细胞的存活率分别为86%和80%。为了研究吡喹酮与日本血吸虫尾蚴的相互作用机理,我们在PZQ-3的基础上连接荧光分子合成荧光衍生物PZQ-5。荧光成像实验结果表明PZQ-5的荧光信号主要集中在尾蚴的表皮部位,说明吡喹酮能够对尾蚴的表皮进行影响或破坏,继而影响尾蚴的渗透压、体内Ca~2+的平衡和虫体的生物代谢。
此外还合成了五个含有乙腈配位型的铱配合物Ir-1至Ir-5。配合物Ir-5单晶的结构解析得出产物为单斜晶系结构,磷光光谱表明配合物Ir-5能够发射较强的黄色磷光。其次,我们应用铱配合物用于尾蚴的磷光标记,实验结果表明当配合物的主配体有较大共轭结构时,有利于尾蚴的磷光成像;同时配合物有合适的脂水分配系数也有助于尾蚴的磷光标记。
The niclosamide and praziquantel were efficacious for killing Schistosoma japonicum cercariae, but the action mechanism of niclosamide and praziquantel in Schistosoma japonicum cercariae was unknown. In this thesis, a series of fluorescent derivatives of niclosamide and praziquantel were synthesized, and we elucidated the preliminary interaction of niclosamide and praziquantel with Schistosoma japonicum cercariae by fluorescence imaging technology.
To match water-floating habit of Schistosoma japonicum cercariae, two novel niclosamide derivatives containing compound NI-2a and NI-2b were synthesized. Compound NI-2b possesses properties of self-diffusion and the water-surface floating which was sufficient for killing cercariae. The MTT assay data show that the NI-2a and NI-2b exhibit low cytotoxicity to HeLa cells. To investigate the interaction between the medicine and Schistosoma japonicum cercariae, a fluorescent niclosamide derivative (compound NI-3) based on compound 2a was further designed and synthesized. Confocal fluorescence imaging results show that compound NI-3 could penetrate into cercarial body and it can be transformed by the cercariae. These facts indicate that novel NI-2a can destroy the circulatory system of cercariae leading to the rapid death of cercariae.
Two praziquantel derivatives PZQ-2 and PZQ-3 were synthesized by means of nitration and reduction reaction. The cytotoxicity of PZQ-2 is lower than that of PZQ-3. When incubating HeLa cells with 200μM PZQ-2 and PZQ-3, the cell validity is assigned to 86% and 80%, respectively. To investigate the interaction between the PZQ-3 and Schistosoma japonicum cercariae, a fluorescent derivative (compound PZQ-5) based on PZQ-3 was designed and synthesized. Fluorescence imaging experiments reveal that PZQ-5 is mainly located at cercarial tegument. It is concluded that the praziquantel can influent or demolish the cercariae tegument, which leads to a series of change of osmolality, calcium(Ca~2+) balance and metabolism for cercariae.
Five iridium complexes (Ir-1 to Ir-5) containing acetonitrile ligand (CH_3CN) were synthesized. The structure of Ir-5 was confirmed by X-ray crystal diffraction. Photophysical data show that complex Ir-5 can emit yellow phosphorescence. Some complexes were used for phosphorescence imaging of Schistosoma japonicum cercariae. Interestingly, the iridium complexes having higher conjugation ligands and appropriate partition coefficients could contribute to cercariae phosphorescence labeling.
针对日本血吸虫尾蚴在水面的静态生活习性,我们设计合成了两个氯硝柳胺衍生物NI-2a和NI-2b。NI-2b具有水面自扩散和水面漂浮的性质,并有很好的灭尾蚴活性。采用MTT(噻唑蓝)法测定细胞毒性结果表明NI-2a和NI-2b对HeLa细胞的毒性较低。为了研究NI-2a与日本血吸虫尾蚴的作用机理,我们在NI-2a的基础上连接荧光分子合成荧光衍生物NI-3。尾蚴荧光成像实验结果表明NI-3能够快速地经尾蚴表皮吸收和运输,说明NI-3容易被尾蚴吸收从而影响尾蚴的体内代谢导致尾蚴的死亡。
吡喹酮经过硝化和还原两步反应得到两个吡喹酮衍生物PZQ-2和PZQ-3,MTT法测定细胞毒性结果表明在200μM PZQ-2和PZQ-3的浓度下细胞的存活率分别为86%和80%。为了研究吡喹酮与日本血吸虫尾蚴的相互作用机理,我们在PZQ-3的基础上连接荧光分子合成荧光衍生物PZQ-5。荧光成像实验结果表明PZQ-5的荧光信号主要集中在尾蚴的表皮部位,说明吡喹酮能够对尾蚴的表皮进行影响或破坏,继而影响尾蚴的渗透压、体内Ca~2+的平衡和虫体的生物代谢。
此外还合成了五个含有乙腈配位型的铱配合物Ir-1至Ir-5。配合物Ir-5单晶的结构解析得出产物为单斜晶系结构,磷光光谱表明配合物Ir-5能够发射较强的黄色磷光。其次,我们应用铱配合物用于尾蚴的磷光标记,实验结果表明当配合物的主配体有较大共轭结构时,有利于尾蚴的磷光成像;同时配合物有合适的脂水分配系数也有助于尾蚴的磷光标记。
The niclosamide and praziquantel were efficacious for killing Schistosoma japonicum cercariae, but the action mechanism of niclosamide and praziquantel in Schistosoma japonicum cercariae was unknown. In this thesis, a series of fluorescent derivatives of niclosamide and praziquantel were synthesized, and we elucidated the preliminary interaction of niclosamide and praziquantel with Schistosoma japonicum cercariae by fluorescence imaging technology.
To match water-floating habit of Schistosoma japonicum cercariae, two novel niclosamide derivatives containing compound NI-2a and NI-2b were synthesized. Compound NI-2b possesses properties of self-diffusion and the water-surface floating which was sufficient for killing cercariae. The MTT assay data show that the NI-2a and NI-2b exhibit low cytotoxicity to HeLa cells. To investigate the interaction between the medicine and Schistosoma japonicum cercariae, a fluorescent niclosamide derivative (compound NI-3) based on compound 2a was further designed and synthesized. Confocal fluorescence imaging results show that compound NI-3 could penetrate into cercarial body and it can be transformed by the cercariae. These facts indicate that novel NI-2a can destroy the circulatory system of cercariae leading to the rapid death of cercariae.
Two praziquantel derivatives PZQ-2 and PZQ-3 were synthesized by means of nitration and reduction reaction. The cytotoxicity of PZQ-2 is lower than that of PZQ-3. When incubating HeLa cells with 200μM PZQ-2 and PZQ-3, the cell validity is assigned to 86% and 80%, respectively. To investigate the interaction between the PZQ-3 and Schistosoma japonicum cercariae, a fluorescent derivative (compound PZQ-5) based on PZQ-3 was designed and synthesized. Fluorescence imaging experiments reveal that PZQ-5 is mainly located at cercarial tegument. It is concluded that the praziquantel can influent or demolish the cercariae tegument, which leads to a series of change of osmolality, calcium(Ca~2+) balance and metabolism for cercariae.
Five iridium complexes (Ir-1 to Ir-5) containing acetonitrile ligand (CH_3CN) were synthesized. The structure of Ir-5 was confirmed by X-ray crystal diffraction. Photophysical data show that complex Ir-5 can emit yellow phosphorescence. Some complexes were used for phosphorescence imaging of Schistosoma japonicum cercariae. Interestingly, the iridium complexes having higher conjugation ligands and appropriate partition coefficients could contribute to cercariae phosphorescence labeling.
引文
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