Cyclodextrin-based host-guest supramolecular nanoparticles for delivery: From design to applications

Accounts of Chemical Research

Volumn 47, Issue 7, 2014, Pages 2017-2025

  Hu, Qi Da ^a,b   Tang, Gu Ping ^a,c   Chu, Paul K ^c  

^a ZHEJIANG UNIVERSITY   (China)

^b THE SECOND AFFILIATED HOSPITAL OF ZHEJIANG UNIVERSITY SCHOOL OF MEDICINE   (China)

^c CITY UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84904438951     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500055s     Document Type: Article

References (55)

1. Chen, G.; Jiang, M. Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly Chem. Soc. Rev. 2011, 40, 2254-2266
2. Nimse, S. B.; Kim, T. Biological applications of functionalized calixarenes Chem. Soc. Rev. 2013, 42, 366-386
3. Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Functionalized cucurbiturils and their applications Chem. Soc. Rev. 2007, 36, 267-279
4. Meek, S. T.; Greathouse, J. A.; Allendorf, M. D. Metal-organic frameworks: A rapidly growing class of versatile nanoporous materials Adv. Mater. 2011, 23, 249-267
5. Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F. Pillararenes, a new class of macrocycles for supramolecular chemistry Acc. Chem. Res. 2012, 45, 1294-1308
6. Dong, S.; Luo, Y.; Yan, X.; Zheng, B.; Ding, X.; Yu, Y.; Ma, Z.; Zhao, Q.; Huang, F. A dual-responsive supramolecular polymer gel formed by crown ether based molecular recognition Angew. Chem., Int. Ed. 2011, 50, 1905-1909
7. Wang, F.; Han, C.; He, C.; Zhou, Q.; Zhang, J.; Wang, C.; Li, N.; Huang, F. Self-sorting organization of two heteroditopic monomers to supramolecular alternating copolymers J. Am. Chem. Soc. 2008, 130, 11254-11255
8. Yan, X.; Xu, D.; Chi, X.; Chen, J.; Dong, S.; Ding, X.; Yu, Y.; Huang, F. A multiresponsive, shape-persistent, and elastic supramolecular polymer network gel constructed by orthogonal self-assembly Adv. Mater. 2011, 24, 362-369
9. Ortiz Mellet, C.; Garcia Fernandez, J. M.; Benito, J. M. Cyclodextrin-based gene delivery systems Chem. Soc. Rev. 2011, 40, 1586-1608
10. Mintzer, M. A.; Simanek, E. E. Nonviral vectors for gene delivery Chem. Rev. 2009, 109, 259-302
11. Tang, G. P.; Guo, H. Y.; Alexis, F.; Wang, X.; Zeng, S.; Lim, T. M.; Ding, J.; Yang, Y. Y.; Wang, S. Low molecular weight polyethylenimines linked by β-cyclodextrin for gene transfer into the nervous system J. Gene Med. 2006, 8, 736-744
12. Hu, Y.; Yuan, W.; Zhao, N. N.; Ma, J.; Yang, W. T.; Xu, F. J. Supramolecular pseudo-block gene carriers based on bioreducible star polycations Biomaterials 2013, 34, 5411-5422
13. Wang, H.; Liu, K.; Chen, K. J.; Lu, Y.; Wang, S.; Lin, W. Y.; Guo, F.; Kamei, K.; Chen, Y. C.; Ohashi, M.; Wang, M.; Garcia, M. A.; Zhao, X. Z.; Shen, C. K.; Tseng, H. R. A rapid pathway toward a superb gene delivery system: Programming structural and functional diversity into a supramolecular nanoparticle library ACS Nano 2010, 4, 6235-6243
14. Ping, Y.; Hu, Q.; Tang, G.; Li, J. FGFR-targeted gene delivery mediated by supramolecular assembly between β-cyclodextrin-crosslinked PEI and redox-sensitive PEG Biomaterials 2013, 34, 6482-6494
15. Davis, M. E.; Zuckerman, J. E.; Choi, C. H.; Seligson, D.; Tolcher, A.; Alabi, C. A.; Yen, Y.; Heidel, J. D.; Ribas, A. Evidence of RNAi in humans from systemically administered siRNA via targeted nanoparticles Nature 2010, 464, 1067-1070
16. Dong, R.; Zhou, L.; Wu, J.; Tu, C.; Su, Y.; Zhu, B.; Gu, H.; Yan, D.; Zhu, X. A supramolecular approach to the preparation of charge-tunable dendritic polycations for efficient gene delivery Chem. Commun. 2011, 47, 5473-5475
17. Burckbuchler, V.; Wintgens, V.; Leborgne, C.; Lecomte, S.; Leygue, N.; Scherman, D.; Kichler, A.; Amiel, C. Development and characterization of new cyclodextrin polymer-based DNA delivery systems Bioconjugate Chem. 2008, 19, 2311-2320
18. Wang, H.; Wang, S.; Su, H.; Chen, K. J.; Armijo, A. L.; Lin, W. Y.; Wang, Y.; Sun, J.; Kamei, K.; Czernin, J.; Radu, C. G.; Tseng, H. R. A supramolecular approach for preparation of size-controlled nanoparticles Angew. Chem., Int. Ed. 2009, 48, 4344-4348
19. Wang, S.; Chen, K. J.; Wu, T. H.; Wang, H.; Lin, W. Y.; Ohashi, M.; Chiou, P. Y.; Tseng, H. R. Photothermal effects of supramolecularly assembled gold nanoparticles for the targeted treatment of cancer cells Angew. Chem., Int. Ed. 2010, 49, 3777-3781
20. Bartlett, D. W.; Su, H.; Hildebrandt, I. J.; Weber, W. A.; Davis, M. E. Impact of tumor-specific targeting on the biodistribution and efficacy of siRNA nanoparticles measured by multimodality in vivo imaging Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 15549-15554
21. Luo, Z.; Cai, K.; Hu, Y.; Li, J.; Ding, X.; Zhang, B.; Xu, D.; Yang, W.; Liu, P. Redox-responsive molecular nanoreservoirs for controlled intracellular anticancer drug delivery based on magnetic nanoparticles Adv. Mater. 2012, 24, 431-435
22. Li, J. M.; Wang, Y. Y.; Zhao, M. X.; Tan, C. P.; Li, Y. Q.; Le, X. Y.; Ji, L. N.; Mao, Z. W. Multifunctional QD-based co-delivery of siRNA and doxorubicin to HeLa cells for reversal of multidrug resistance and real-time tracking Biomaterials 2012, 33, 2780-2790
23. Jing, J.; Szarpak-Jankowska, A.; Guillot, R.; Pignot-Paintrand, I.; Picart, C.; Auzély-Velty, R. Cyclodextrin/paclitaxel complex in biodegradable capsules for breast cancer treatment Chem. Mater. 2013, 25, 3867-3873
24. Zhang, J. X.; Ellsworth, K.; Ma, P. X. Hydrophobic pharmaceuticals mediated self-assembly of β-cyclodextrin containing hydrophilic copolymers: Novel chemical responsive nano-vehicles for drug delivery J. Controlled Release 2010, 145, 116-123
25. Zhang, J. X.; Ma, P. X. Polymeric core-shell assemblies mediated by host-guest interactions: Versatile nanocarriers for drug delivery Angew. Chem., Int. Ed. 2009, 48, 964-968
26. Zhou, Q.; Guo, X.; Chen, T.; Zhang, Z.; Shao, S. J.; Luo, C.; Li, J. R.; Zhou, S. B. Target-specific cellular uptake of folate-decorated biodegradable polymer micelles J. Phys. Chem. B 2011, 115, 12662-12670
27. Quan, C. Y.; Chen, J. X.; Wang, H. Y.; Li, C.; Chang, C.; Zhang, X. Z.; Zhuo, R. X. Core-shell nanosized assemblies mediated by the α-β cyclodextrin dimer with a tumor-triggered targeting property ACS Nano 2010, 4, 4211-4219
28. Fan, H.; Hu, Q. D.; Xu, F. J.; Liang, W. Q.; Tang, G. P.; Yang, W. T. In vivo treatment of tumors using host-guest conjugated nanoparticles functionalized with doxorubicin and therapeutic gene pTRAIL Biomaterials 2012, 33, 1428-1436
29. Hu, Q. L.; Li, W.; Hu, X. R.; Hu, Q. D.; Shen, J.; Jin, X.; Zhou, J.; Tang, G. P.; Chu, P. K. Synergistic treatment of ovarian cancer by co-delivery of survivin shRNA and paclitaxel via supramolecular micellar assembly Biomaterials 2012, 33, 6580-6591
30. Hu, Q. D.; Fan, H.; Ping, Y.; Liang, W. Q.; Tang, G. P.; Li, J. Cationic supramolecular nanoparticles for co-delivery of gene and anticancer drug Chem. Commun. 2011, 47, 5572-5574
31. Luo, G. F.; Xu, X. D.; Zhang, J.; Yang, J.; Gong, Y. H.; Lei, Q.; Jia, H. Z.; Li, C.; Zhuo, R. X.; Zhang, X. Z. Encapsulation of an adamantane- doxorubicin prodrug in pH-responsive polysaccharide capsules for controlled release ACS Appl. Mater. Interfaces 2012, 4, 5317-5324
32. Zhang, J.; Ma, P. X. Cyclodextrin-based supramolecular systems for drug delivery: Recent progress and future perspective Adv. Drug Delivery Rev. 2013, 65, 1215-1233
33. Zhang, J. X.; Sun, H. L.; Ma, P. X. Host-guest interaction mediated polymeric assemblies: Multifunctional nanoparticles for drug and gene delivery ACS Nano 2010, 4, 1049-1059
34. Bandara, H. M.; Burdette, S. C. Photoisomerization in different classes of azobenzene Chem. Soc. Rev. 2012, 41, 1809-1825
35. Wang, Y.; Ma, N.; Wang, Z.; Zhang, X. Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with α-cyclodextrin Angew. Chem., Int. Ed. 2007, 46, 2823-2826
36. Moon, C.; Kwon, Y. M.; Lee, W. K.; Park, Y. J.; Yang, V. C. In vitro assessment of a novel polyrotaxane-based drug delivery system integrated with a cell-penetrating peptide J. Controlled Release 2007, 124, 43-50
37. Mitragotri, S.; Lahann, J. Physical approaches to biomaterial design Nat. Mater. 2009, 8, 15-23
38. Chen, Y.; Pang, Y.; Wu, J. L.; Su, Y.; Liu, J. Y.; Wang, R. B.; Zhu, B. S.; Yao, Y. F.; Yan, D. Y.; Zhu, X. Y.; Chen, Q. Controlling the particle size of interpolymer complexes through host-guest interaction for drug delivery Langmuir 2010, 26, 9011-9016
39. Kulkarni, A.; DeFrees, K.; Hyun, S. H.; Thompson, D. H. Pendant polymer:amino-β-cyclodextrin:siRNA guest:host nanoparticles as efficient vectors for gene silencing J. Am. Chem. Soc. 2012, 134, 7596-7599
40. Zhang, Z. X.; Liu, K. L.; Li, J. A thermoresponsive hydrogel formed from a star-star supramolecular architecture Angew. Chem., Int. Ed. 2013, 52, 6180-6184
41. Chen, Y.; Pang, X. H.; Dong, C. M. Dual stimuli-responsive supramolecular polypeptide-based hydrogel and reverse micellar hydrogel mediated by host-guest chemistry Adv. Funct. Mater. 2010, 20, 579-586
42. Adeli, M.; Fard, A. K.; Abedi, F.; Chegeni, B. K.; Bani, F. Thermo- and pH-sensitive dendrosomes as bi-phase drug delivery systems Nanomedicine 2013, 9, 1203-1213
43. Liu, R.; Zhang, Y.; Feng, P. Y. Multiresponsive supramolecular nanogated ensembles J. Am. Chem. Soc. 2009, 131, 15128-15129
44. Zhang, J.; Yuan, Z. F.; Wang, Y.; Chen, W. H.; Luo, G. F.; Cheng, S. X.; Zhuo, R. X.; Zhang, X. Z. Multifunctional envelope-type mesoporous silica nanoparticles for tumor-triggered targeting drug delivery J. Am. Chem. Soc. 2013, 135, 5068-5073
45. Tarn, D.; Ashley, C. E.; Xue, M.; Carnes, E. C.; Zink, J. I.; Brinker, C. J. Mesoporous silica nanoparticle nanocarriers: Biofunctionality and biocompatibility Acc. Chem. Res. 2013, 46, 792-801
46. Meng, H.; Xue, M.; Xia, T.; Zhao, Y. L.; Tamanoi, F.; Stoddart, J. F.; Zink, J. I.; Nel, A. E. Autonomous in vitro anticancer drug release from mesoporous silica nanoparticles by pH-sensitive nanovalves J. Am. Chem. Soc. 2010, 132, 12690-12697
47. Zhang, Z.; Ding, J.; Chen, X.; Xiao, C.; He, C.; Zhuang, X.; Chen, L.; Chen, X. Intracellular pH-sensitive supramolecular amphiphiles based on host-guest recognition between benzimidazole and β-cyclodextrin as potential drug delivery vehicles Polym. Chem. 2013, 4, 3265-3271
48. Yan, H.; Teh, C.; Sreejith, S.; Zhu, L.; Kwok, A.; Fang, W.; Ma, X.; Nguyen, K. T.; Korzh, V.; Zhao, Y. Functional mesoporous silica nanoparticles for photothermal-controlled drug delivery in vivo Angew. Chem., Int. Ed. 2012, 51, 8373-8377
49. Li, W. Y.; Wang, Y. X.; Chen, L. N.; Huang, Z. X.; Hu, Q. L.; Ji, J. Light-regulated host-guest interaction as a new strategy for intracellular PEG-detachable polyplexes to facilitate nuclear entry Chem. Commun. 2012, 48, 10126-10128
50. Lee, J. H.; Chen, K. J.; Noh, S. H.; Garcia, M. A.; Wang, H.; Lin, W. Y.; Jeong, H.; Kong, B. J.; Stout, D. B.; Cheon, J.; Tseng, H. R. On-demand drug release system for in vivo cancer treatment through self-assembled magnetic nanoparticles Angew. Chem., Int. Ed. 2013, 52, 4384-4388
51. Yan, Q.; Yuan, J. Y.; Cai, Z. N.; Xin, Y.; Kang, Y.; Yin, Y. W. Voltage-responsive vesicles based on orthogonal assembly of two homopolymers J. Am. Chem. Soc. 2010, 132, 9268-9270
52. Wang, Y.; Gao, S.; Ye, W. H.; Yoon, H. S.; Yang, Y. Y. Co-delivery of drugs and DNA from cationic core-shell nanoparticles self-assembled from a biodegradable copolymer Nat. Mater. 2006, 5, 791-796
53. Davis, M. E. The first targeted delivery of siRNA in humans via a self-assembling, cyclodextrin polymer-based nanoparticle: From concept to clinic Mol. Pharmaceutics 2009, 6, 659-668
54. Salvati, A.; Pitek, A. S.; Monopoli, M. P.; Prapainop, K.; Bombelli, F. B.; Hristov, D. R.; Kelly, P. M.; Aberg, C.; Mahon, E.; Dawson, K. A. Transferrin-functionalized nanoparticles lose their targeting capabilities when a biomolecule corona adsorbs on the surface Nat. Nanotechnol. 2013, 8, 137-143
55. Allen, T. M.; Cullis, P. R. Liposomal drug delivery systems: From concept to clinical applications Adv. Drug Delivery Rev. 2013, 65, 36-48