Supramolecular Assemblies of Multi-Charged Cyclodextrins

doi:10.6023/cjoc202004040

Abstract

As a class of macrocyclic host with excellent water solubility, low biotoxicity and high charge density, multi-charged cyclodextrins have been extensively studied because they can interact with organic/inorganic/biological molecules through multiple synergistic forces such as the hydrophobic cavities and electrostatic interactions to construct the smart supramolecular assemblies with stable topology, functional diversity and stimulus responsiveness. The latest research progress of pH-, photo-, enzyme-, redox-, magnetic-and multi-stimulus responsive smart supramolecular assemblies, which are constructed by typical positively/negatively charged and amphiphilic multi-charged cyclodextrins including their application in the fields of drug delivery, controlled release and sensory detection is introduced, and the challenges and future developments of multi-charged cyclodextrin smart supramolecular assemblies are discussed.

Key words: multi-charged cyclodextrin, supramolecular assembly, stimulus responsiveness, smart material

Cite this article

Zhang Yi, Liu Yu. Supramolecular Assemblies of Multi-Charged Cyclodextrins[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3802-3811.

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References

[1] (a) Crini, G. Chem. Rev. 2014, 114, 10940.
(b) Chen, Y.; Zhang, Y. M.; Liu, Y. Chem. Commun. 2010, 46, 5622.
(c) Lai, W.-F.; Rogach, A. L.; Wong, W.-T. Chem. Soc. Rev. 2017, 46, 6379.
(d) Prochowicz, D.; Kornowicz, A.; Lewiński, J. Chem. Rev. 2017, 117, 13461.
(e) Chen, G.; Jiang, M. Chem. Soc. Rev. 2011, 40, 2254.
(f) Chen, H.; Liu, X.; Dou, Y.; He, B.; Liu, L.; Wei, Z.; Li, J.; Wang, C.; Mao, C.; Zhang, J.; Wang, G. Biomaterials 2013, 34, 4159.
(g) Schmidt, B.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2017, 56, 8350.
(h) Kolesnichenko, I. V.; Anslyn, E. V. Chem. Soc. Rev. 2017, 46, 2385.
(i) Chen, Y.; Liu, Y. Chem. Soc. Rev. 2010, 39, 495.
(j) Zhang, Y.; Liang, L.; Chen, Y.; Chen, X. M.; Liu, Y. Soft Matter 2018, 15, 73.
(k) Yu, Q.; Zhang, Y.-M.; Liu, Y.-H.; Xu, X.; Liu, Y. Sci. Adv. 2018, 4, eaat2297.
(l) Pinalli, R.; Pedrini, A.; Dalcanale, E. Chem. Soc. Rev. 2018, 47, 7006.
(m) Zhang, W.; Deng, W. Chin. J. Org. Chem. 2018, 38, 3002(in Chinese). (张薇, 邓维, 有机化学, 2018, 38, 3002.)
(n) Chen, Y. Q.; Gui, X.; Duan, Z. B.; Zhu, L. J.; Xiang, Y. Z.; Xia, D. H. Chin. J. Org. Chem. 2019, 39, 1284(in Chinese). (陈雅琪, 桂鑫, 段尊斌, 朱丽君, 项玉芝, 夏道宏, 有机化学, 2019, 39, 1284.)
(o) Qie, S. Y.; Hao, Y.; Liu, Z. J.; Wang, J.; Xi, J. N. Acta Chim. Sinica 2020, 78, 232(in Chinese). (郄淑燕, 郝莹, 刘宗建, 王锦, 席家宁, 化学学报, 2020, 78, 232.)
[2] Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
[3] (a) Li, Z.; Zhang, Y.-M.; Wang, H.-Y.; Li, H.; Liu, Y. Macromolecules 2017, 50, 1141.
(b) Zhang, Y.; Chen, Y.; Li, J.; Liang, L.; Liu, Y. Acta Chim. Sinica 2018, 76, 622(in Chinese). (张依, 陈湧, 李晶晶, 梁璐, 刘育, 化学学报, 2018, 76, 622.)
(c) Niu, J.; Chen, Y.; Liu, Y. Chin. J. Org. Chem. 2019, 39, 151(in Chinese). (牛杰, 陈湧, 刘育, 有机化学, 2019, 39, 151.)
[4] (a) Eliseev, A. V.; Schneider, H.-J. Angew. Chem., Int. Ed. 1993, 32, 1331.
(b) Steffen, A.; Thiele, C.; Tietze, S.; Strassnig, C.; Kämper, A.; Lengauer, T.; Wenz, G.; Apostolakis, J. Chem.-Eur. J. 2007, 13, 6801.
[5] (a) Zhang, Y. M.; Liu, Y. H.; Liu, Y. Adv. Mater. 2020, 32, e1806158.
(b) Liao, R.; Lv, P.; Wang, Q.; Zheng, J.; Feng, B.; Yang, B. Biomater. Sci. 2017, 5, 1736.
(c) Yao, X.; Mu, J.; Zeng, L.; Lin, J.; Nie, Z.; Jiang, X.; Huang, P. Mater. Horiz. 2019, 6, 846.
[6] (a) Bom, A.; Bradley, M.; Cameron, K.; Clark, J. K.; Van Egmond, J.; Feilden, H.; Maclean, E. J.; Muir, A. W.; Palin, R.; Rees, D. C.; Zhang, M.-Q. Angew. Chem., Int. Ed. 2002, 41, 265.
(b) Adam, J. M.; Bennett, D. J.; Bom, A.; Clark, J. K.; Feilden, H.; Hutchinson, E. J.; Palin, R.; Prosser, A.; Rees, D. C.; Rosair, G. M.; Stevenson, D.; Tarver, G. J.; Zhang, M.-Q. J. Med. Chem. 2002, 45, 1806.
[7] Jones, S. T.; Cagno, V.; Janeček, M.; Ortiz, D.; Gasilova, N.; Piret, J.; Gasbarri, M.; Constant, D. A.; Han, Y.; Vuković, L.; Král, P.; Kaiser, L.; Huang, S.; Constant, S.; Kirkegaard, K.; Boivin, G.; Stellacci, F.; Tapparel, C. Sci. Adv. 2020, 6, eaax9318.
[8] Sun, H.-L.; Zhang, Y.-M.; Chen, Y.; Liu, Y. Sci. Rep. 2016, 6, 27.
[9] Li, J. J.; Chen, Y.; Yu, J.; Cheng, N.; Liu, Y. Adv. Mater. 2017, 29, 1701905.
[10] (a) Shi, R.-J.; Chen, Y.; Hou, X.-F.; Liu, Y. RSC Adv. 2016, 6, 15175.
(b) Zhao, D.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2015, 26, 829.
[11] Díaz-Moscoso, A.; Balbuena, P.; Gómez-García, M.; Ortiz Mellet, C.; Benito, J. M.; Le Gourriérec, L.; Di Giorgio, C.; Vierling, P.; Mazzaglia, A.; Micali, N.; Defaye, J.; García Fernández, J. M. Chem. Commun. 2008, 2001.
[12] Zhao, F.; Yin, H.; Zhang, Z.; Li, J. Biomacromolecules 2013, 14, 476.
[13] Wang, J.; Chen, Y.; Cheng, N.; Feng, L.; Gu, B.-H.; Liu, Y. ACS Appl. Bio Mater. 2019, 2, 5898.
[14] (a) Lu, Y.; De Vries, W. C.; Overeem, N. J.; Duan, X.; Zhang, H.; Zhang, H.; Pang, W.; Ravoo, B. J.; Huskens, J. Angew. Chem., Int. Ed. 2019, 58, 159.
(b) Schibilla, F.; Holthenrich, A.; Song, B.; Linard Matos, A. L.; Grill, D.; Rota Martir, D.; Gerke, V.; Zysman-Colman, E.; Ravoo, B. J. Chem. Sci. 2018, 9, 7822.
(c) Himmelein, S.; Lewe, V.; Stuart, M. C. A.; Ravoo, B. J. Chem. Sci. 2014, 5, 1054.
[15] Ravoo, B. J.; Darcy, R. Angew. Chem., Int. Ed. 2000, 39, 4324.
[16] (a) Mohan Nalluri, S. K.; Bultema, J. B.; Boekema, E. J.; Ravoo, B. J. Chem. Sci. 2011, 2, 2383.
(b) Samanta, A.; Ravoo, B. J. Chem.-Eur. J. 2014, 20, 4966.
(c) Samanta, A.; Stuart, M. C. A.; Ravoo, B. J. J. Am. Chem. Soc. 2012, 134, 19909.
(d) Nalluri, S. K. M.; Bultema, J. B.; Boekema, E. J.; Ravoo, B. J. Chem.-Eur. J. 2011, 17, 10297.
(e) Moratz, J.; Stricker, L.; Engel, S.; Ravoo, B. J. Macromol. Rapid Commun. 2018, 39, 1700256.
[17] Sukegawa, T.; Furuike, T.; Niikura, K.; Yamagishi, A.; Monde, K.; Nishimura, S.-I. Chem. Commun. 2002, 430.
[18] Donohue, R.; Mazzaglia, A.; Ravoo, B. J.; Darcy, R. Chem. Commun. 2002, 2864.
[19] (a) O'mahony, A. M.; Doyle, D.; Darcy, R.; Cryan, J. F.; O'driscoll, C. M. Eur. J. Pharm. Sci. 2012, 47, 896.
(b) Méndez-Ardoy, A.; Guilloteau, N.; Di Giorgio, C.; Vierling, P.; Santoyo-González, F.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2011, 76, 5882.
[20] Li, P. Y.; Chen, Y.; Chen, C. H.; Liu, Y. Chem. Commun. 2019, 55, 11790.
[21] (a) Zan, M.; Li, J.; Luo, S.; Ge, Z. Chem. Commun. 2014, 50, 7824.
(b) Zhao, D.; Yi, X.; Xu, J.; Yuan, G.; Zhuo, R.; Li, F. J. Mater. Chem. B 2017, 5, 2823.
(c) Durmaz, Y. Y.; Lin, Y.-L.; Elsayed, M. E. H. Adv. Funct. Mater. 2013, 23, 3885.
[22] Cheng, J. G.; Yu, H. J.; Chen, Y.; Liu, Y. Bioorg. Med. Chem. 2018, 26, 2287.
[23] Cheng, J.-G.; Zhang, Y.-M.; Liu, Y. ChemNanoMat 2018, 4, 758.
[24] Tardy, B. L.; Tan, S.; Dam, H. H.; Ejima, H.; Blencowe, A.; Qiao, G. G.; Caruso, F. Nanoscale 2016, 8, 15589.
[25] Liang, L.; Chen, Y.; Chen, X.-M.; Zhang, Y.; Liu, Y. Chin. Chem. Lett. 2018, 29, 989.
[26] Chen, X. M.; Chen, Y.; Hou, X. F.; Wu, X.; Gu, B. H.; Liu, Y. ACS Appl. Mater. Interfaces 2018, 10, 24987.
[27] (a) Gayam, S. R.; Venkatesan, P.; Sung, Y.-M.; Sung, S.-Y.; Hu, S.-H.; Hsu, H.-Y.; Wu, S.-P. Nanoscale 2016, 8, 12307.
(b) Lee, J.; Oh, E.-T.; Yoon, H.; Woo Kim, C.; Han, Y.; Song, J.; Jang, H.; Joo Park, H.; Kim, C. Nanoscale 2017, 9, 6901.
(c) Cheng, Y.-J.; Luo, G.-F.; Zhu, J.-Y.; Xu, X.-D.; Zeng, X.; Cheng, D.-B.; Li, Y.-M.; Wu, Y.; Zhang, X.-Z.; Zhuo, R.-X.; He, F. ACS Appl. Mater. Interfaces 2015, 7, 9078.
[28] Hu, P.; Chen, Y.; Li, J. J.; Liu, Y. Chem.-Asian J. 2016, 11, 505.
[29] Hou, X.-F.; Chen, Y.; Liu, Y. Soft Matter 2015, 11, 2488.
[30] Han, X.; Chen, Y.; Sun, H.-L.; Liu, Y. Asian J. Org. Chem. 2018, 7, 870.
[31] Guan, X.; Chen, Y.; Wu, X.; Li, P.; Liu, Y. Chem. Commun. 2019, 55, 953.
[32] (a) Zhao, Q.; Lian, Z.; Gao, X.; Yan, Y.; Huang, J. Langmuir 2016, 32, 11973.
(b) Mandl, G. A.; Rojas-Gutierrez, P. A.; Capobianco, J. A. Chem. Commun. 2018, 54, 5847.
(c) Stricker, L.; Fritz, E.-C.; Peterlechner, M.; Doltsinis, N. L.; Ravoo, B. J. J. Am. Chem. Soc. 2016, 138, 4547.
[33] Zhao, X.; Chen, Y.; Guan, X. R.; Li, P. Y.; Zhou, W. L.; Liu, Y. ChemistrySelect 2019, 4, 13241.
[34] Li, Z.-Y.; Chen, Y.; Wu, H.; Liu, Y. ChemistrySelect 2018, 3, 3203.
[35] Liu, Z.; Qiao, J.; Tian, Y.; Wu, M.; Niu, Z.; Huang, Y. Langmuir 2014, 30, 8938.
[36] Liu, J.; Xu, L.; Jin, Y.; Qi, C.; Li, Q.; Zhang, Y.; Jiang, X.; Wang, G.; Wang, Z.; Wang, L. ACS Appl. Mater. Interfaces 2016, 8, 14200.
[37] Chen, X.; Qiu, Y. K.; Owh, C.; Loh, X. J.; Wu, Y. L. Nanoscale 2016, 8, 18876.
[38] Wen, Y.; Zhang, Z.; Li, J. Adv. Funct. Mater. 2014, 24, 3874.
[39] (a) Yang, C.; Wang, X.; Li, H.; Goh, S. H.; Li, J. Biomacromolecules 2007, 8, 3365.
(b) Yamashita, A.; Kanda, D.; Katoono, R.; Yui, N.; Ooya, T.; Maruyama, A.; Akita, H.; Kogure, K.; Harashima, H. J. Control. Release 2008, 131, 137.
[40] Ooya, T.; Choi, H. S.; Yamashita, A.; Yui, N.; Sugaya, Y.; Kano, A.; Maruyama, A.; Akita, H.; Ito, R.; Kogure, K.; Harashima, H. J. Am. Chem. Soc. 2006, 128, 3852.
[41] Tamura, A.; Yui, N. Biomaterials 2013, 34, 2480.
[42] Schroeder, T. B. H.; Houghtaling, J.; Wilts, B. D.; Mayer, M. Adv. Mater. 2018, 30, 1705322.
[43] (a) Badruddoza, A. Z. M.; Bhattarai, B.; Suri, R. P. S. ACS Sustainable Chem. Eng. 2017, 5, 9223.
(b) Lu, A.-H.; Salabas, E. L.; Schüth, F. Angew. Chem., Int. Ed. 2007, 46, 1222.
[44] Samanta, A.; Ravoo, B. J. Angew. Chem., Int. Ed. 2014, 53, 12946.
[45] Awasthi, A. A.; Singh, P. K. J. Phys. Chem. B 2017, 121, 6208.
[46] Singh, G.; Singh, P. K. Langmuir 2019, 35, 14628.
[47] Hu, P.; Chen, Y.; Liu, Y. Chem. Commun. 2015, 51, 10839.

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