超两亲分子在药物转运体系构筑中的应用
收稿日期: 2017-11-17
修回日期: 2017-12-04
网络出版日期: 2017-12-08
基金资助
国家自然科学基金（No.21572101）资助项目.
Applications of Supramolecular Amphiphilc for the Construction of Drug Delivery Systems
Received date: 2017-11-17
Revised date: 2017-12-04
Online published: 2017-12-08
Supported by
Project supported by the National Natural Science Foundation of China (No. 21572101).
邵为 , 刘昕 , 王婷婷 , 胡晓玉 . 超两亲分子在药物转运体系构筑中的应用[J]. 有机化学, 2018 , 38(5) : 1107 -1118 . DOI: 10.6023/cjoc201711027
Stimuli-responsive supramolecular drug delivery systems (SDDSs) self-assembled by supra-amphiphiles have received tremendous attentions in cancer therapy due to various advantages of SDDSs, such as enhanced drug bioavailability, prolonged blood circulation and retention time, improved drug stability and so on. The construction of smart supramolecular drug delivery systems based on the different structural characteristics of macrocyclic compounds are reviewed and their recent applications in anti-cancer drug delivery are described. Advantages and drawbacks of the current supramolecular drug delivery systems are also discussed, along with the opportunities and challenges in future.
Key words： supra-amphiphile; macrocycles; nanocarrier; drug delivery system
[1] Isrealachvili, J. N.; Mitchell, D. J.; Ninham, B. W. J. Chem. Soc. 1976, 72, 1525.
[2] Zhang, S.; Moussodia, R. O.; Sun, H. J.; Leowanawat, P.; Muncan, A.; Nusbaum, C. D.; Chelling, K. M.; Heiney, P. A.; Klein, M. L.; Andre, S.; Roy, R.; Gabius, H.-J.; Percec, V. Angew. Chem., Int. Ed. 2014, 53, 10899.
[3] Sorrenti, A.; Illa, O.; Ortuno, R. M. Chem. Soc. Rev. 2013, 42, 8200.
[4] Fu, T.; Ao, L.; Gao, Z.; Zhang, X.; Wang, F. Chin. Chem. Lett. 2016, 27, 1147.
[5] Zhang, S.; Wang, Q.; Cheng, M.; Qian, X.; Yang, Y.; Jiang, J.; Wang, L. Chin. Chem. Lett. 2015, 26, 885.
[6] Wu, X.; Gao, L.; Sun, J.; Hu, X-Y.; Wang, L. Chin. Chem. Lett. 2016, 27, 1655.
[7] Wu, X.; Duan, Q.; Ni, M.; Hu, X-Y.; Wang, L. Chin. J. Org. Chem. 2014, 34, 437(in Chinese). (吴旋, 段群鹏, 倪梦飞, 胡晓玉, 王乐勇, 有机化学, 2014, 34, 437.)
[8] Hou, N.-N.; Sun, Q.; Zhang, N.; Ni, M.-F.; Lin, C.; Wang, L.-Y. Acta Polym. Sin. 2017, 86(in Chinese). (候娜娜, 孙强, 张宁, 倪梦飞, 林晨, 王乐勇, 高分子学报, 2017, 86.)
[9] Rybtchinski, B. ACS Nano 2011, 5, 6791.
[10] Sun, G.; Nie, C.; Zhao, X.; Li, Z. Chin. J. Org. Chem. 2017, 37, 1757(in Chinese). (孙广军, 聂承斌, 赵新, 黎占亭, 有机化学, 2017, 37, 1757.)
[11] Ji, X.-F.; Xia, D.-Y.; Yan, X.-Z.; Wang, H.; Huang, F.-H. Acta Polym. Sin. 2017, 9(in Chinese). (吉晓帆, 夏丹玉, 颜徐州, 王虎, 黄飞鹤, 高分子学报, 2017, 9.)
[12] Zhang, X.; Wang, C. Chem. Soc. Rev. 2011, 40, 94.
[13] Kang, Y.; Liu, K.; Zhang, X. Langmuir 2014, 30, 5989.
[14] Guo, D.; Liu, Y. Acc. Chem. Res. 2014, 47, 1925.
[15] Yu, G.; Jie, K.; Huang, F. Chem. Rev. 2015, 115, 7240.
[16] Ji, X.; Li, Y.; Wang, H.; Zhao, R.; Tang, G.; Huang, F. Polym. Chem. 2015, 6, 5021.
[17] Nakahata, M.; Takashima, Y.; Hashidzume, A.; Harada, A. Angew. Chem., Int. Ed. 2013, 52, 5731.
[18] Zhu, K.; He, J.; Li, S.; Liu, M.; Wang, F.; Zhang, M.; Abliz, Z.; Yang, H.; Li, N.; Huang, F. J. Org. Chem. 2009, 74, 3905.
[19] Talotta, C.; Gaeta, C.; Qi, Z.; Schalley, C. A.; Neri, P. Angew. Chem., Int. Ed. 2013, 52, 7437.
[20] Yan, X.; Wei, P.; Zhang, M.; Chi, X.; Liu, J.; Huang, F. Org. Lett. 2011, 13, 6370.
[21] Li, Y.; Flood, A. H. Angew. Chem., Int. Ed. 2008, 47, 2649.
[22] Liu, M.; Li, S.; Hu, M.; Wang, F.; Huang, F. Org. Lett. 2010, 12, 760.
[23] Yoon, D.-W.; Gross, D. E.; Lynch, V. M.; Sessler, J. L.; Hay, B. P.; Lee, C.-H. Angew. Chem., Int. Ed. 2008, 47, 5038.
[24] Dong, S.; Zheng, B.; Wang, F.; Huang, F. Acc. Chem. Res. 2014, 47, 1982.
[25] Zhang, M.; Zhu, K.; Huang, F. Chem. Commun. 2010, 46, 8131.
[26] Selvapalam, N.; Ryu, S. H.; Kim, K. Nat. Chem. 2011, 3, 154.
[27] Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J. B.; Zavalij, P. Y.; Briken, V.; Isaacs, L. Nat. Chem. 2012, 4, 503.
[28] Wisner, J. A.; Beer, P. D.; Berry, N. G.; Tomapatanaget, B. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 4983.
[29] Yu, G.; Zhang, Z.; He, J.; Abliz, Z.; Huang, F. Eur. J. Org. Chem. 2012, 5902.
[30] Hubbard, A. L.; Davidson, G. J. E.; Patel, R. H.; Wisner, J. A.; Loeb, S. J. Chem. Commun. 2004, 138.
[31] Niu, Z.; Huang, F.; Gibson, H. W. J. Am. Chem. Soc. 2011, 133, 2836.
[32] Villiers, V. C. R. Acad. Sci. 1891, 112, 536.
[33] Irie, T.; Uekama, K. J. Pharm. Sci. 1997, 86, 147.
[34] Brewster, M. E.; Loftsson, T. Adv. Drug Delivery Rev. 2007, 59, 645.
[35] Zhang, Z.; Ding, J.; Chen, X.; Xiao, C.; He, C.; Zhuang, X.; Chen, L.; Chen, X. Polym. Chem. 2013, 4, 3265.
[36] Quan, C.; Chen, J.; Wang, H.; Li, C.; Chang, C.; Zhang, X.; Zhuo, R. ACS Nano 2010, 4, 4211.
[37] Ma, M.; Guan, Y.; Zhang, C.; Hao, J.; Xing, P.; Su, J.; Li, S.; Chu, X.; Hao, A. Colloids Surf., A 2014, 454, 38.
[38] Wang, Y.; Wang, H.; Chen, Y.; Liu, X.; Jin, Q.; Ji, J. Colloids Surf., B 2014, 121, 189.
[39] Yang, Y.; Zhang, Y.; Chen, Y.; Chen, J.; Liu, Y. J. Med. Chem. 2013, 56, 9725.
[40] Yhaya, F.; Lim, J.; Kim, Y.; Liang, M.; Gregory, A. M.; Stenzel, M. H. Macromolecules 2011, 44, 8433.
[41] Peng, L.; Feng, A.; Zhang, H.; Wang, H.; Jian, C.; Liu, B.; Gao, W.; Yuan, J. Polym. Chem. 2014, 5, 1751.
[42] Ma, M.; Shang, W.; Xing, P.; Li, S.; Chu, X.; Hao, A.; Liu, G.; Zhang, Y. Carbohydr. Res. 2015, 402, 208.
[43] Samanta, A.; Stuart, M. C. A.; Ravoo, B. J. J. Am. Chem. Soc. 2012, 134, 19909.
[44] Gourevich, D.; Dogadkin, O.; Volovick, A.; Wang, L.; Gnaim, J.; Cochran, S.; Melzer, A. J. Controlled Release 2013, 170, 316.
[45] Gutsche, C. D. Calixarenes, The Royal Society of Chemistry, Cambridge, 1989.
[46] Stewart, D. R.; Gutsche, C. D. J. Am. Chem. Soc. 1999, 121, 4136.
[47] Wang, Y.; Liu, Y. Acta Chim. Sinica 2015, 73, 984(in Chinese). (王以轩, 刘育, 化学学报, 2015, 73, 984.)
[48] Wang, K.; Guo, D.; Wang, X.; Liu, Y. ACS Nano 2011, 5, 2880.
[49] Guo, D.; Wang, K.; Wang, Y.; Liu, Y. J. Am. Chem. Soc. 2012, 134, 10244.
[50] Wang, K.; Guo, D.; Zhao, M.; Liu, Y. Chem.-Eur. J. 2016, 22, 1475.
[51] Qin, Z.; Guo, D.; Gao, X.; Liu, Y. Soft Matter 2014, 10, 2253.
[52] Behrend, R.; Meyer, E.; Rusche, F. Liebigs Ann. Chem. 1905, 339, 1.
[53] Freeman, W. A.; Mock, W. L.; Shih, N. Y. J. Am. Chem. Soc. 1981, 103, 7367.
[54] Park, K. M.; Lee, D. W.; Sarkar, B.; Jung, H.; Kim, J.; Ko, Y. H.; Lee, K. E.; Jeon, H.; Kim, K. Small 2010, 6, 1430.
[55] Loh, X. J.; Barrio, J.; Toh, P.; Lee, T. C.; Jiao, D.; Rauwald, U.; Appel, E. A.; Scherman, O. A. Biomacromolecules 2012, 13, 84.
[56] Wang, Y.; Li, D.; Wang, H.; Chen, Y.; Han, H.; Jin, Q.; Ji, J. Chem. Commun. 2014, 50, 9390.
[57] Pennakalathil, J.; Jahja, E.; Özdemir, E. S.; Konu, O.; Tuncel, D. Biomacromolecules 2014, 15, 3366.
[58] Jiao, D.; Geng, J.; Loh, X. J.; Das, D.; Lee, T. C.; Scherman, O. A. Angew. Chem., Int. Ed. 2012, 51, 9633.
[59] Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[60] Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. J. Am. Chem. Soc. 2013, 135, 10542.
[61] Cao, Y.; Hu, X.-Y.; Li, Y.; Zou, X.; Xiong, S.; Lin, C.; Shen, Y. Z.; Wang, L. J. Am. Chem. Soc. 2014, 136, 10762.
[62] Hu, X.-Y.; Jia, K.; Cao, Y.; Li, Y.; Qin, S.; Zhou, F.; Lin, C.; Zhang, D.; Wang, L. Chem.-Eur. J. 2015, 21, 1208.
[63] Chang, Y.; Yang, K.; Wei, P.; Huang, S.; Pei, Y.; Zhao, W.; Pei, Z. Angew. Chem., Int. Ed. 2014, 53, 13126.
[64] Yang, K.; Chang, Y.; Wen, J.; Lu, Y.; Pei, Y.; Cao, S.; Wang, F.; Pei, Z. Chem. Mater. 2016, 28, 1990.
[65] Yang, K.; Pei, Y.; Wen, J.; Pei, Z. Chem. Commun. 2016, 52, 9316.
[66] Huang, X.; Du, X. ACS Appl. Mater. Interfaces 2014, 53, 20430.
[67] Yao, Y.; Wang, Y.; Zhao, R.; Shao, L.; Tang, R.; Huang, F. J. Mater. Chem. B 2016, 4, 2691.
[68] Yu, G.; Yu, W.; Shao, L.; Zhang, Z.; Chi, X.; Mao, Z.; Gao, C.; Huang, F. Adv. Funct. Mater. 2016, 26, 8999.
[69] Liu, X.; Shao, W.; Zheng, Y.; Yao, C.; Peng, L.; Zhang, D.; Hu, X.-Y.; Wang, L. Chem. Commun. 2017, 53, 8596.
[70] Merzel, R. L.; Chen, J. J.; Marsh, E. N. G.; Holl, M. M. B. Chin. Chem. Lett. 2015, 26, 426.
[71] Zhou, Y.; Li, H.; Yang, Y. Chin. Chem. Lett. 2015, 26, 825.
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