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    陈帅, 庞瑞淇, 刘思奕, 洪晨雨, 马绍花, 杲云, 田佳. 卟啉半遥爪聚合物的制备及其在光动力疗法中的应用探讨[J]. 华东理工大学学报(自然科学版), 2020, 46(3): 349-359. DOI: 10.14135/j-cnki.1006-3080.20190309001
    引用本文: 陈帅, 庞瑞淇, 刘思奕, 洪晨雨, 马绍花, 杲云, 田佳. 卟啉半遥爪聚合物的制备及其在光动力疗法中的应用探讨[J]. 华东理工大学学报(自然科学版), 2020, 46(3): 349-359. DOI: 10.14135/j-cnki.1006-3080.20190309001
    CHEN Shuai, PANG Ruiqi, LIU Siyi, HONG Chenyu, MA Shaohua, GAO Yun, TIAN Jia. Synthesis of Porphyrin Semitelechelic Polymers and Application in Photodynamic Therapy[J]. Journal of East China University of Science and Technology, 2020, 46(3): 349-359. DOI: 10.14135/j-cnki.1006-3080.20190309001
    Citation: CHEN Shuai, PANG Ruiqi, LIU Siyi, HONG Chenyu, MA Shaohua, GAO Yun, TIAN Jia. Synthesis of Porphyrin Semitelechelic Polymers and Application in Photodynamic Therapy[J]. Journal of East China University of Science and Technology, 2020, 46(3): 349-359. DOI: 10.14135/j-cnki.1006-3080.20190309001

    卟啉半遥爪聚合物的制备及其在光动力疗法中的应用探讨

    Synthesis of Porphyrin Semitelechelic Polymers and Application in Photodynamic Therapy

    • 摘要: 通过“点击化学”偶联反应将不同分子量(Mn=1 000,2 000,5 000)的亲水性高分子聚乙二醇(PEG)与卟啉光敏剂(TPP)键合在一起,成功合成了一系列水溶性很好的卟啉半遥爪聚合物光敏剂(TPP-PEG),并探讨了高分子链长对TPP-PEG的单线态氧(1O2)产率和细胞毒性的影响。相比于自由的卟啉小分子,这类亲水高分子光敏剂在水溶液中以单个分子存在,有效地减少了卟啉分子之间的π-π堆积,提高了光敏剂的1O2产率,同时改善了生物相容性。以1,3-二苯基异苯并呋喃(DPBF)为捕获剂检测1O2,结果表明,接枝分子量分别为1 000、2 000、5 000 的TPP-PEG光敏剂的1O2产率比卟啉小分子如四苯基卟啉的1O2产率有显著提高,而且1O2产率随着PEG链长的增加而降低。HeLa细胞的毒性实验证明TPP-PEG几乎没有暗毒性,并且在655 nm光照下表现出很好的光毒性,证明TPP-PEG可以作为潜在的大分子光敏剂用于光动力疗法。

       

      Abstract: Porphyrin and its derivatives, which are widely existed in organisms and participate in essential physiological processes, are well-known and promising photosensitizers. However, many drawbacks, such as strong hydrophobicity and self-quenching induced by aggregation, have greatly limited their applications in photodynamic therapy (PDT). Herein, a series of water-soluble porphyrin semitelechelic polymers (TPP-PEG) were successfully synthesized via click reaction between hydrophilic polyethylene glycol chains with various molecular weight (PEG, Mn=1 000, 2 000, 5 000) and tetraphenyl porphyrin unit (TPP). Compared with small porphyrin molecules, these PEGlated porphyrin semitelechelic polymers exhibit excellent solubility in aqueous solution, greatly reducing the intermolecular π-π stacking and thereby enhancing the singlet oxygen generation. In addition, the introduction of PEG chains also improves the biocompatibility of the porphyrin photosensitizer. Using 1,3-diphenylisobenzofuran (DPBF) as the 1O2 detecting probe, the UV-vis absorption intensity results show that the 1O2 generation of TPP-PEG are faster and more extensive than the free TPP molecules. Additionally, the results indicate that the 1O2 generation capability of TPP-PEG decreases with the increase of the lergth of PEG chain. The Thiazolyl Blue Tetrazolium Bromide method (MTT) assay results of dark cytotoxicity and phototoxicity in HeLa cells also confirmed that TPP-PEG possesses good biocompatibility and high cytotoxicity under light irradiation.

       

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