Page 72 - 《精细化工》2022年第3期

·494· 精细化工 FINE CHEMICALS 第 39 卷

在不加入光敏剂的情况下，仅接受激光照射的细胞 26(34): 6257-6269.
存活率高于 90%，证明了激光照射技术自身不会引 [9] JOSEFSEN L B, BOYLE R W. Unique diagnostic and therapeutic
roles of porphyrins and phthalocyanines in photodynamic therapy,
入额外的毒性，具有一定的安全性。上述结果显示， imaging and theranostics[J]. Theranostics, 2012, 2(9): 916-966.
该 P-5O 纳米粒具有较高的细胞光毒性以及较低的 [10] LU X M (卢晓梅), ZHAO M (赵萌), HUANG W (黄维). Synthesis
of near-infrared poly(IB-alt-MAnh)-aza-BODIPY and its application
细胞暗毒性，有望用于肿瘤的 PDT。
in photoacoustic imaging[J]. Acta Polymerica Sinica (高分子学报),
2018, 49(11): 1451-1459.
3 结论 [11] SCHMITT J, HEITZ V, SOUR A, et al. Diketopyrrolopyrrole-
porphyrin conjugates with high two-photon absorption and singlet
通过引入亲水柔性醚链的策略合成了一系列聚 oxygen generation for two-photon photodynamic therapy[J].
Angewandte Chemie International Edition, 2015, 54(1): 169-173.
卟啉，系统地研究了具有不同链长的聚卟啉在不同
[12] CELLI J P, SPRING B Q, RIZVI I, et al. Imaging and photodynamic
聚合条件下的水溶性，并通过条件筛选确定最优聚 therapy: Mechanisms, monitoring, and optimization[J]. Chemical
合条件，即以温度为 110 ℃、溶剂为 DMF、时间为 Reviews, 2010, 110(5): 2795-2838.
[13] TIAN J ( 田佳 ), ZHANG W A ( 张伟 安 ). Construction and
48 h 以及 TCPP 单体浓度为 0.063 mol/L 得到水溶性 applications of well-defined porphyrin-containing polymers[J]. Acta
良好的 P-5O。卟啉聚合物在水中以疏水的卟啉端为 Polymerica Sinica (高分子学报), 2019, 50(7): 653-670.
核、醚基柔性链为亲水端在去离子水中以无载体的 [14] WANG D, NIU L J, QIAO Z Y, et al. Synthesis of self-assembled
porphyrin nanoparticle photosensitizers[J]. ACS Nano, 2018, 12(4):
形式自组装成纳米粒，并对其单线态氧产率、纳米 3796-3803.
粒稳定性以及体外光暗毒性进行了研究。结果表明， [15] SKIDAN I, DHOLAKIA P, TORCHILIN V. Photodynamic therapy
of experimental B-16 melanoma in mice with tumor-targeted
在 P-5O 中引入长柔性醚链结构能够有效抑制疏水
5,10,15,20-tetraphenylporphin-loaded PEG-PE micelles[J]. Journal
性卟啉单体的 ACQ 效应以及提高其水溶性，P-5O of Drug Targeting, 2008, 16(6): 486-493.
的单线态氧产率是 TCPP 单体的 1.95 倍。除此以外， [16] HUANG Z. A review of progress in clinical photodynamic therapy
[J]. Technology in Cancer Research & Treatment, 2005, 4(3): 283-293.
P-5O 纳米粒在模拟的人体生理环境下具有很好的 [17] GU B B, WU W B, XU G X, et al. Precise two-photon photodynamic
稳定性，且在肿瘤细胞及正常细胞中均具有较低的 therapy using an efficient photosensitizer with aggregation-induced
暗毒性。在肿瘤细胞中，P-5O 纳米粒在激光照射下 emission characteristics[J]. Advanced Materials, 2017, 29(28):
1701076.
可诱导出较强的光毒性，细胞存活率显著下降至 [18] LUBY B M, WALSH C D, ZHENG G. Advanced photosensitizer
30%以下。针对该纳米粒的细胞内吞机制、细胞内 activation strategies for smarter photodynamic therapy beacons[J].
Angewandte Chemie International Edition, 2019, 58(9): 2558-2569.
分布及体内 PDT 的研究正在进行中，该类水溶性聚
[19] FAN H H, YAN G B, ZHAO Z L, et al. A smart photosensitizer-
卟啉纳米粒的研制在未来开发光动力抗肿瘤药物方 manganese dioxide nanosystem for enhanced photodynamic therapy
面具有广阔的应用前景。 by reducing glutathione levels in cancer cells[J]. Angewandte
Chemie International Edition, 2016, 55(18): 5477-5482.
参考文献： [20] LIU K, XING R R, ZOU Q L, et al. Simple peptide-tuned
self-assembly of photosensitizers towards anticancer photodynamic
[1] ETHIRAJAN M, CHEN Y H, JOSHI P, et al. The role of porphyrin therapy[J]. Angewandte Chemie International Edition, 2016, 55(9):
chemistry in tumor imaging and photodynamic therapy[J]. Chemical 3036-3039.
Society Reviews, 2011, 40(1): 340-362. [21] LUCKY S S, SOO K C, ZHANG Y. Nanoparticles in photodynamic
[2] ZHOU Z J, SONG J B, NIE L M, et al. Reactive oxygen species therapy[J]. Chemical Reviews, 2015, 115(4): 1990-2042.
generating systems meeting challenges of photodynamic cancer [22] ARUNKUMAR E, SUDEEP P K, KAMAT P V, et al. Singlet oxygen
therapy[J]. Chemical Society Reviews, 2016, 45(23): 6597-6626. generation using iodinated squaraine and squaraine-rotaxane dyes[J].
[3] HE H, ZHU R Y, SUN W, et al. Selective cancer treatment via New Journal of Chemistry, 2007, 31(5): 677-683.
photodynamic sensitization of hypoxia-responsive drug delivery[J]. [23] DALLAGNOL J C C, DUCATTI D R B, BARREIRA S M W, et al.
Nanoscale, 2018, 10(6): 2856-2865. Synthesis of porphyrin glycoconjugates bearing thiourea, thiocarb
[4] CASTANO A P, MROZ P, HAMBLIN M R. Photodynamic therapy amate and carbamate connecting groups: Influence of the linker on
and anti-tumour immunity[J]. Nature Reviews Cancer, 2006, 6(7): chemical and photophysical properties[J]. Dyes and Pigments, 2014,
535-545. 107: 69-80.
[5] DANIELL M D, HILL J S. A history of photodynamic therapy[J]. [24] LAU J T F, LO P C, TSANG Y M, et al. Unsymmetrical
Australian & New Zealand Journal of Surgery, 1991, 61(5): 340-348. β-cyclodextrin-conjugated silicon(Ⅳ ) phthalocyanines as highly
[6] ACKROYD R, KELTY C, BROWN N, et al. The history of potent photosensitisers for photodynamic therapy[J]. Chemical
photodetection and photodynamic therapy[J]. Photochemistry & Communications, 2011, 47(34): 9657-9659.
Photobiology, 2001, 74(5): 656-669. [25] ZHAO P, HUANG J W, MEI W J, et al. DNA binding and
[7] LIPSON R L, BALDES E J, OLSEN A M. Hematoporphyrin photocleavage specificities of a group of tricationic
derivative: A new aid for endoscopic detection of malignant metalloporphyrins[J]. Spectrochimica Acta. Part A, Molecular and
disease[J]. Journal of Thoracic and Cardiovascular Surgery, 1961, Biomolecular Spectroscopy, 2010, 75(3): 1108-1114.
42(5): 623-629. [26] KRALOVA J, SYNYTSYA A, POUCKOVA P, et al. Novel porphyrin
[8] LIU L H, QIU W X, LI B, et al. A red light activatable conjugates with a potent photodynamic antitumor effect: Differential
multifunctional prodrug for image-guided photodynamic therapy and efficacy of mono- and bis-β-cyclodextrin derivatives in vitro and in
cascaded chemotherapy[J]. Advanced Functional Materials, 2016, vivo[J]. Photochemistry and Photobiology, 2006, 82: 432-438.