超两亲分子在药物转运体系构筑中的应用

doi:10.6023/cjoc201711027

摘要/Abstract

由超分子两亲化合物自组装形成的具有刺激响应性的纳米药物转运体系由于其能够有效提高药物的生物利用率、延长药物在血液中的循环和滞留时间、增加体系的稳定性等优点，近年来在以恶性肿瘤为代表的疾病的治疗和研究领域倍受关注.针对几类大环化合物的结构特征，主要概述了近年来基于其构筑的超分子两亲体在智能药物转运体系中的应用概况，分析了现阶段超分子纳米药物转运体系的优缺点，并指出其未来发展面临的机遇与挑战.

关键词: 超两亲分子, 大环化合物, 纳米组装体, 药物转运

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

引用此文

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.

Shao Wei, Liu Xin, Wang Tingting, Hu Xiao-Yu. Applications of Supramolecular Amphiphilc for the Construction of Drug Delivery Systems[J]. Chin. J. Org. Chem., 2018, 38(5): 1107-1118.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[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.