新型卟啉化合物的设计合成及生物活性研究
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摘要
本文基于卟啉类药物的国内外研究与开发现状,设计合成了新型卟啉类化合物包括水溶性阳离子卟啉和脂溶性不对称卟啉,探索了其合成方法,并初步探讨了其抗微生物活性与抗肿瘤活性。主要内容包括:
(1)以对甲氧基苯甲醛、对羟基苯甲醛和吡咯为原料,设计合成了一系列新型不对称卟啉类化合物,再与临床药物替加氟和具有放射增敏作用的药效团硝基咪唑类化合物反应得到了替加氟和硝基咪唑类卟啉,并探讨了合成路线。通过UV-vis、IR、~1H-NMR、MS、元素分析等表征了其结构,研究了其抗肿瘤活性。
(2)设计合成了一系列新型阳离子卟啉化合物,对其反应条件进行了探索。通过UV-vis、IR、~1H-NMR、MS等确证了其结构;并进行了抗微生物活性研究。
本论文工作共合成得到40个化合物,其中37个化合物未见文献报道,包括9个中间体和28个新的卟啉化合物。
(3)生物活性的测试结果表明:替加氟卟啉衍生物17a～17c和替加氟一样对肝癌细胞SMCC-7721、结肠癌Volo细胞均有一定的抑制作用(p＜0.01),尤其是其金属衍生物(18a～18c)的抑瘤活性得到明显提高(p＜0.01),由于替甲氟是代谢类药物,其对细胞生长抑制的体内实验效果比体外效果更好;卟啉修饰硝基咪唑类放射增敏剂对宫颈癌细胞株Helo也具有较好的增敏效果,尤其是金属络合物33～38当以4 Gy剂量的x射线照射时,对癌细胞的抑制率可达到95%左右。阳离子卟啉的抗微生物活性研究表明:阳离子卟啉化合物40a、40b和41a～41c对金黄色葡萄球菌具有较好的抗菌作用,化合物41a对金黄色葡萄球菌、大肠杆菌均具有显著抗菌作用,并且对白色念珠菌也有一定抗菌作用。实验证实,阳离子型卟啉确实具有良好的光动力抗菌效果。
This thesis focused on the design and synthesis of novel porphyrin derivertives including water-soluble symmetrical cationic porphyrins and lipid-soluble unsymmetrical porphyrins.Antineoplastic and antimicrobial activities were tested.The main contents are as follows:
(1)A series of novel unsymmetrical ftorafur and nitroimidazole porphyrin derivatives were designed and synthesized by three steps starting from pyrrole, 4-methoxyl-benzaldehyde and 4-hydroxylbenzaldehyde,.The synthetic routes of these compounds were investigated.The products obtained were confirmed by UV-vis,IR,~1H NMR and MS analysis.The antineoplastic activities for the new synthetic porphyrin compounds were evaluated.
(2)A series of novel cationic porphyrin derivatives were designed and synthesized and their antimicrobial activities were investigated.The structures of compounds obtained were confirmed by IR,UV-vis,~1H NMR and MS analysis.
In this work,40 compouds were synthesized,among them 9 intermediates and 28 new porphyrins.
(3)Bioactivities showed that the anticancer activities of compounds 17a～17c toward liver cancer cell SMCC-7721 and colon carcinoma cell Volo were similar to that of ftorafur(p＜0.01);however,the anticancer activities of metal compounds 18a～18c were 2.2,2.6 and 2.3 times,comparing with anticancer drug ftorafur in clinic;All new synthetic nitroimidazole porphyrin derivatives as novel radiosensitizers also exhibited good activity to the cancer cell of the cervix,especially,their metallo-complexes 33～38, the value of inhibition rate reaches 95%when they were exposured by x-ray at a dose of 4 Gy;In addition,compounds 40a,40b and 41a～41c showed the strong antibacterial activity against S.aureus and moderate antifungal activity against C.albicans. Compound 41a also showed strong activity against S.aureus and E.coli.It is found that cationic compounds gave better antibacterial activity than neutral compounds.The results in antibacterial activity showed that these compounds as new antibacterial agents are promising for further work in this area.
(1)以对甲氧基苯甲醛、对羟基苯甲醛和吡咯为原料,设计合成了一系列新型不对称卟啉类化合物,再与临床药物替加氟和具有放射增敏作用的药效团硝基咪唑类化合物反应得到了替加氟和硝基咪唑类卟啉,并探讨了合成路线。通过UV-vis、IR、~1H-NMR、MS、元素分析等表征了其结构,研究了其抗肿瘤活性。
(2)设计合成了一系列新型阳离子卟啉化合物,对其反应条件进行了探索。通过UV-vis、IR、~1H-NMR、MS等确证了其结构;并进行了抗微生物活性研究。
本论文工作共合成得到40个化合物,其中37个化合物未见文献报道,包括9个中间体和28个新的卟啉化合物。
(3)生物活性的测试结果表明:替加氟卟啉衍生物17a～17c和替加氟一样对肝癌细胞SMCC-7721、结肠癌Volo细胞均有一定的抑制作用(p＜0.01),尤其是其金属衍生物(18a～18c)的抑瘤活性得到明显提高(p＜0.01),由于替甲氟是代谢类药物,其对细胞生长抑制的体内实验效果比体外效果更好;卟啉修饰硝基咪唑类放射增敏剂对宫颈癌细胞株Helo也具有较好的增敏效果,尤其是金属络合物33～38当以4 Gy剂量的x射线照射时,对癌细胞的抑制率可达到95%左右。阳离子卟啉的抗微生物活性研究表明:阳离子卟啉化合物40a、40b和41a～41c对金黄色葡萄球菌具有较好的抗菌作用,化合物41a对金黄色葡萄球菌、大肠杆菌均具有显著抗菌作用,并且对白色念珠菌也有一定抗菌作用。实验证实,阳离子型卟啉确实具有良好的光动力抗菌效果。
This thesis focused on the design and synthesis of novel porphyrin derivertives including water-soluble symmetrical cationic porphyrins and lipid-soluble unsymmetrical porphyrins.Antineoplastic and antimicrobial activities were tested.The main contents are as follows:
(1)A series of novel unsymmetrical ftorafur and nitroimidazole porphyrin derivatives were designed and synthesized by three steps starting from pyrrole, 4-methoxyl-benzaldehyde and 4-hydroxylbenzaldehyde,.The synthetic routes of these compounds were investigated.The products obtained were confirmed by UV-vis,IR,~1H NMR and MS analysis.The antineoplastic activities for the new synthetic porphyrin compounds were evaluated.
(2)A series of novel cationic porphyrin derivatives were designed and synthesized and their antimicrobial activities were investigated.The structures of compounds obtained were confirmed by IR,UV-vis,~1H NMR and MS analysis.
In this work,40 compouds were synthesized,among them 9 intermediates and 28 new porphyrins.
(3)Bioactivities showed that the anticancer activities of compounds 17a～17c toward liver cancer cell SMCC-7721 and colon carcinoma cell Volo were similar to that of ftorafur(p＜0.01);however,the anticancer activities of metal compounds 18a～18c were 2.2,2.6 and 2.3 times,comparing with anticancer drug ftorafur in clinic;All new synthetic nitroimidazole porphyrin derivatives as novel radiosensitizers also exhibited good activity to the cancer cell of the cervix,especially,their metallo-complexes 33～38, the value of inhibition rate reaches 95%when they were exposured by x-ray at a dose of 4 Gy;In addition,compounds 40a,40b and 41a～41c showed the strong antibacterial activity against S.aureus and moderate antifungal activity against C.albicans. Compound 41a also showed strong activity against S.aureus and E.coli.It is found that cationic compounds gave better antibacterial activity than neutral compounds.The results in antibacterial activity showed that these compounds as new antibacterial agents are promising for further work in this area.
引文
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