Research Progress on the Phthalocyanine Based Targeting Photosensitizers in Photodynamic Therapy
Received date: 2016-10-17
Online published: 2016-12-05
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21136002, 21421005).
In recent years,photodynamic therapy (PDT) technology,as a noninvasive method of treating malignant tumors and age-related macular degeneration,which is different from the traditional cancer treatments,has drawn more and more attention of scientists.PDT treatment relies on the combination of photosensitizer,oxygen and light,when the photosensitizer is irradiated by special light,it can generate singlet oxygen,which is a cytotoxic agent can eradicate tumors via vasculature damage and cell damage,and sometimes the response of immune system.Due to its special advantages,i.e small traumatic,low toxicity,good compatibility,collaborative surgical treatment and repeatable treatment etc.,PDT is widely used in many kinds of tumor treatments.Current practice of photodynamic therapy is limited to a few functionalized photosensitizers,for example porphyrins,however these compounds has several disadvantageous properties such as low absorption in the tissue transparency window (650~900 nm),prolonged skin photosensitivity,and slow clearance rate from body.This has inspired efforts to develop more effective PDT photosensitizers with improved photophysical characteristics and special targeting advantages.So in this review,the authors briefly outline the theories of PDT as well as the development process of photosensitizer,and summarize the characteristics of ideal photosensitizer.At present,the third generation photosensitizers mainly based on phthalocyanines have become a research highlight in PDT.However,how to improve the targeting of photosensitizer so as to achieve precise photodynamic efficiency is still an urgent problem to be solved.Therefore,this review mainly summarizes the recent research on phthalocyanine based targeting photosensitizers.In addition,the development of key research directions in the future has also been pointed out.According to the present researches,in the aspects of PDT,overcoming the limitation of cancer hypoxic microenvironment,developing Type I independently from oxygen,and penetrating more deeply targeting photosensitizers possess enormous potential,and they may become a kind of photosensitizer with excellent performance in the field of photodynamic therapy.
Key words： photodynamic therapy; phthalocyanine; targeting; photosensitizer
Li Mingle , Peng Xiaojun . Research Progress on the Phthalocyanine Based Targeting Photosensitizers in Photodynamic Therapy[J]. Acta Chimica Sinica, 2016 , 74(12) : 959 -968 . DOI: 10.6023/A16100553
[1] Bonnett, R. Chem. Soc. Rev. 1995, 24, 19.
[2] Dolmans, D.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer. 2003, 3, 380.
[3] Weinberg, B. D.; Allison, R. R.; Sibata, C.; Parent, T.; Downie, G. Photodiagn. Photodyn. 2010, 7, 50.
[4] Wang, X.-L.; Wang, H.-W.; Guo, M.-X.; Xu, S.-Z. Photodiagn. Photodyn. 2008, 5, 127.
[5] Moghissi, K.; Dixon, K.; Thorpe, J. A. C.; Stringer, M.; Moore, P. J. Eur. J. Cardio-Thorac. 2000, 17, 95.
[6] Kato, H.; Harada, M.; Ichinose, S.; Usuda, J.; Tsuchida, T.; Okunaka, T. Photodiagn. Photodyn. 2004, 1, 49.
[7] Cai, J.; Liu, J.-L. Modern Oncology 2006, 14, 1312. (蔡君, 刘剑仑, 现代肿瘤医学, 2006, 14, 1312.)
[8] Ethirajan, M.; Chen, Y.; Joshi, P.; Pandey, R. K. Chem. Soc. Rev. 2011, 40, 340.
[9] Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. J. Natl. Cancer Inst. 1998, 90, 889.
[10] Foote, C. S. Science 1968, 162, 963.
[11] Henderson, B. W.; Dougherty, T. J. Photodiagn. Photodyn. 1992, 55, 145.
[12] Juzeniene, A.; Nielsen, K. P.; Moan, J. J. Environ. Pathol. Tox. 2006, 25, 7.
[13] Brancaleon, L.; Moseley, H. Laser. Med. Sci. 2002, 17, 173.
[14] Juzeniene, A.; Juzenas, P.; Ma, L. W.; Iani, V.; Moan, J. Laser. Med. Sci. 2004, 19, 139.
[15] Szeimies, R. M.; Morton, C. A.; Sidoroff, A.; Braathen, L. R. Acta Derm-Venereol. 2005, 85, 483.
[16] Agostinis, P.; Berg, K.; Cengel, K. A.; Foster, T. H.; Girotti, A. W.; Gollnick, S. O.; Hahn, S. M.; Hamblin, M. R.; Juzeniene, A.; Kessel, D.; Korbelik, M.; Moan, J.; Mroz, P.; Nowis, D.; Piette, J.; Wilson, B. C.; Golab, J. Ca-Cancer. J. Clin. 2011, 61, 250.
[17] Dougherty, T. J.; Potter, W. R.; Weishaupt, K. R. Progress in Clinical and Biological Research, New York, 1984, 170, 301.
[18] Felsher, D. W. Nat. Rev. Cancer 2003, 3, 375.
[19] Bellnier, D. A.; Dougherty, T. J. J. Clin. Laser. Med. Sur. 1996, 14, 311.
[20] Moreira, L. M.; dos Santos, F. V.; Lyon, J. P.; Maftoum-Costa, M.; Pacheco-Soares, C.; da Silva, N. S. Aust. J. Crop. Sci. 2008, 61, 741.
[21] Wang, L.-Y.; Cao, D.-R. Chin. J. Org. Chem. 2012, 32, 2248. (汪凌云, 曹德榕, 有机化学, 2012, 32, 2248.)
[22] Li, M.-R.; Cai, X.-Q.; Zhu, Y.-F.; Liu, K.-G.; Hu, M.-L. Acta Chim. Sinica 2011, 69, 425. (李美容, 蔡晓庆, 朱易峰, 刘宽冠, 胡茂林, 化学学报, 2011, 69, 425.)
[23] Maruani, A.; Savoie, H.; Bryden, F.; Caddick, S.; Boyle, R.; Chudasama, V. Chem. Commun. (Cambridge, U. K.) 2015, 51, 15304.
[24] Liu, K.; Xing, R.; Zou, Q.; Ma, G.; Moehwald, H.; Yan, X. Angew. Chem., Int. Ed. 2016, 55, 3036.
[25] Du, J.-Z.; Du, X.-J.; Mao, C.-Q.; Wang, J. J. Am. Chem. Soc. 2011, 133, 17560.
[26] Ke, M.-R.; Ng, D. K. P.; Lo, P.-C. Chem. Commun. 2012, 48, 9065.
[27] Li, X. S.; Ke, M. R.; Huang, W.; Ye, C. H.; Huang, J. D. Chemistry 2015, 21, 3310.
[28] Cavani, F.; Trifirò, F.; Vaccari, A. Catal. Today 1991, 11, 173.
[29] Iarashi, K.; Kashiwagi, K. Int. J. Biochem. Cell. Biol. 2010, 42, 39.
[30] Seiler, N.; Delcros, J. G.; Moulinoux, J. P. Int. J. Biochem. Cell. Biol. 1996, 28, 843.
[31] Casero, R. A., Jr.; Woster, P. M. J. Med. Chem. 2009, 52, 4551.
[32] Holley, J. L.; Mather, A.; Wheelhouse, R. T.; Cullis, P. M.; Hartley, J. A.; Bingham, J. P.; Cohen, G. M. Cancer. Res. 1992, 52, 4190.
[33] Papadopoulou, M. V.; Rosenzweig, H. S.; Bloomer, W. D. Bioorg. Med. Chem. Lett. 2004, 14, 1519.
[34] Yuan, Z. M.; Egorin, M. J.; Rosen, D. M.; Simon, M. A.; Callery, P. S. Cancer Res. 1994, 54, 742.
[35] Delcros, J. G.; Tomasi, S.; Carrington, S.; Martin, B.; Renault, J.; Blagbrough, I. S.; Uriac, P. J. Med. Chem. 2002, 45, 5098.
[36] Battaglia, A.; Guerrini, A.; Baldelli, E.; Fontana, G.; Varchi, G.; Samori, C.; Bombardelli, E. Tetrahedron Lett. 2006, 47, 2667.
[37] Samor, C.; Guerrini, A.; Varchi, G.; Beretta, G. L.; Fontana, G.; Bornbardelli, E.; Carenini, N.; Zunino, F.; Bertucci, C.; Fiori, J.; Battaglia, A. Bioconjugate Chem. 2008, 19, 2270.
[38] Jiang, X.-J.; Lo, P.-C.; Yeung, S.-L.; Fong, W.-P.; Ng, D. K. P. Chem. Commun. 2010, 46, 3188.
[39] Jiang, X.-J.; Yeung, S.-L.; Lo, P.-C.; Fong, W.-P.; Ng, D. K. P. J. Med. Chem. 2011, 54, 320.
[40] Lau, J. T. F.; Jiang, X.-J.; Ng, D. K. P.; Lo, P.-C. Chem. Commun. 2013, 49, 4274.
[41] Lau, J. T. F.; Lo, P.-C.; Jiang, X.-J.; Wang, Q.; Ng, D. K. P. J. Med. Chem. 2014, 57, 4088.
[42] Zorlu, Y.; Dumoulin, F.; Bouchu, D.; Ahsen, V.; Lafont, D. Tetrahedron Lett. 2010, 51, 6615.
[43] Lv, F.; He, X.; Wu, L.; Liu, T. Bioorg. Med. Chem. Lett. 2013, 23, 1878.
[44] Liu, J.-Y.; Lo, P.-C.; Fong, W.-P.; Ng, D. K. P. Org. Biomol. Chem. 2009, 7, 1583.
[45] Mori, S.; Yoshiyama, H.; Tokunaga, E.; Iida, N.; Hayashi, M.; Obata, T.; Tanaka, M.; Shibata, N. J. Fluor. Chem. 2015, 174, 137.
[46] Chen, Y.; Liu, Y. Chem. Soc. Rev. 2010, 39, 495.
[47] Hapiot, F.; Tilloy, S.; Monflier, E. Chem. Rev. 2006, 106, 767.
[48] Leng, X.; Choi, C.-F.; Luo, H.-B.; Cheng, Y.-K.; Ng, D. K. P. Org. Lett. 2007, 9, 2497.
[49] Lau, J. T. F.; Lo, P.-C.; Tsang, Y.-M.; Fong, W.-P.; Ng, D. K. P. Chem. Commun. 2011, 47, 9657.
[50] Lourenco, L. M. O.; Pereira, P. M. R.; Maciel, E.; Valega, M.; Domingues, F. M. J.; Domingues, M. R. M.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S.; Fernandes, R.; Tome, J. P. C. Chem. Commun. 2014, 50, 8363.
[51] Chen, Z.; Xu, P.; Chen, J.; Chen, H.; Hu, P.; Chen, X.; Lin, L.; Huang, Y.; Zheng, K.; Zhou, S.; Li, R.; Chen, S.; Liu, J.; Xue, J.; Huang, M. Acta Biomater. 2014, 10, 4257.
[52] Ke, M.-R.; Yeung, S.-L.; Fong, W.-P.; Ng, D. K. P.; Lo, P.-C. Chem.-Eur. J. 2012, 18, 4225.
[53] Sibrian-Vazquez, M.; Jensen, T. J.; Vicente, M. G. H. Org. Biomol. Chem. 2010, 8, 1160.
[54] Ranyuk, E.; Cauchon, N.; Klarskov, K.; Guerin, B.; van Lier, J. E. J. Med. Chem. 2013, 56, 1520.
[55] Master, A. M.; Livingston, M.; Oleinick, N. L.; Sen Gupta, A. Mol. Pharm. 2012, 9, 2331.
[56] Zhang, F.-L.; Huang, Q.; Zheng, K.; Li, J.; Liu, J.-Y.; Xue, J.-P. Chem. Commun. 2013, 49, 9570.
[57] Mitsunaga, M.; Ogawa, M.; Kosaka, N.; Rosenblum, L. T.; Choyke, P. L.; Kobayashi, H. Nat. Med. 2011, 17, 1685.
[58] Zhang, S.; Yang, L.; Ling, X.; Shao, P.; Wang, X.; Edwards, W. B.; Bai, M. Acta Biomater. 2015, 28, 160.
[59] Austin, C. J. D.; Kahlert, J.; Kassiou, M.; Rendina, L. M. Int. J. Biochem Cell. Biol. 2013, 45, 1212.
[60] Hardwick, M.; Cavalli, L. R.; Barlow, K. D.; Haddad, B. R.; Papadopoulos, V. Cancer Genet. Cytogen. 2002, 139, 48.
[61] Maaser, K.; Grabowski, P.; Sutter, A. P.; Höpfner, M.; Foss, H. D.; Stein, H.; Berger, G.; Gavish, M.; Zeitz, M.; Scherübl, H. Clin. Cancer Res. 2002, 8, 3205.
[62] Zhang, S.; Jia, N.; Shao, P.; Tong, Q.; Xie, X. Q.; Bai, M. Chem. Biol. 2014, 21, 338.
[63] Li, Y.; Wang, J.; Zhang, X.; Guo, W.; Li, F.; Yu, M.; Kong, X.; Wu, W.; Hong, Z. Org. Biomol. Chem. 2015, 13, 7681.
[64] Fulda, S.; Galluzzi, L.; Kroemer, G. Nat. Rev. Drug. Disscov. 2010, 9, 447.
[65] Ge, Y.; Weng, X.; Tian, T.; Ding, F.; Huang, R.; Yuan, L.; Wu, J.; Wang, T.; Guo, P.; Zhou, X. RSC Adv. 2013, 3, 12839.
[66] Shen, X.-M.; Zheng, B.-Y.; Huang, X.-R.; Wang, L.; Huang, J.-D. Dalton Trans. 2013, 42, 10398.
[67] Yang, X.-M.; Zheng, B.-Y.; Cai, Y.; Lin, A.-L.; Shen, X.-M.; Zhang, H.-H.; Huang, J.-D. Spectrosc. Spect. Anal. 2015, 35, 457. (杨晓梅, 郑碧远, 蔡悦, 林爱兰, 沈小敏, 张汉辉, 黄剑东, 光谱学与光谱分析, 2015, 35, 457.)
[68] Shen, X.-M.; Jiang, X.-J.; Zhu, Y.-J.; Zhang, H.-H.; Huang, J.-D. Spectrosc. Spect. Anal. 2013, 33, 2148. (沈小敏, 蒋雄杰, 朱尉娇, 张汉辉, 黄剑东, 光谱学与光谱分析, 2013, 33, 2148.)
[69] Wiseman, H.; Halliwell, B. Biochem. J. 1996, 313, 17.
[70] Mao, J.; Zhang, Y.; Zhu, J.; Zhang, C.; Guo, Z. Chem. Commun. 2009, 908.
[71] Abrahamse, H.; Hamblin, M. R. Biochem. J. 2016, 473, 347.
[72] Ogawa, K.; Kobuke, Y. BioMed. Res. Int. 2013, 2013, 125658.
[73] Gollavelli, G.; Ling, Y.-C. Biomaterials 2014, 35, 4499.
/
| 〈 |
|
〉 |
