Cholinesterase-responsive supramolecular vesicle

Journal of the American Chemical Society

Volumn 134, Issue 24, 2012, Pages 10244-10250

  Guo, Dong Sheng ^a   Wang, Kui ^a   Wang, Yi Xuan ^a   Liu, Yu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALZHEIMERS DISEASE; AMPHIPHILICS; CONTROLLED RELEASE; DRUG DELIVERY SYSTEM; ENZYMATIC CATALYSIS; GUEST MOLECULES; HIGH SPECIFICITY; MACROCYCLICS; SPECIFIC SITES; THERAPEUTIC AGENTS;

BIOLOGICAL MATERIALS; DRUG DELIVERY; ENZYMES; NEURODEGENERATIVE DISEASES;

SUPRAMOLECULAR CHEMISTRY;

4 SULFONATOCALIX[4]ARENE; CHOLINE DERIVATIVE; CHOLINESTERASE; MYRISTOCHOLINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; SUPRAMOLECULAR CHEMISTRY;

CALIXARENES; CELL LINE; CHOLINE; CHOLINESTERASES; DELAYED-ACTION PREPARATIONS; HUMANS; MACROCYCLIC COMPOUNDS; PHENOLS;

EID: 84862549614     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303280r     Document Type: Article

References (67)

1. Samantaray, S.; Sharma, R.; Chattopadhyaya, T.; Gupta, K. S. D.; Ralhan, R. J. Cancer Res. Clin. Oncol. 2004, 130, 37-44
2. Spaltenstein, A.; Kamierski, W. M.; Miller, J. F.; Samano, V. Curr. Top. Med. Chem. 2005, 5, 1589-1607
3. Guo, T.; Hobbs, D. W. Curr. Med. Chem. 2006, 13, 1811-1829
4. Um, S. H.; Lee, J. B.; Park, N.; Kwon, S. Y.; Umbach, C. C.; Luo, D. Nat. Mater. 2006, 5, 797-801
5. Williams, R. J.; Smith, A. M.; Collins, R.; Hodson, N.; Das, A. K.; Ulijn, R. V. Nat. Nanotechnol. 2009, 4, 19-24
6. Morimoto, N.; Ogino, N.; Narita, T.; Kitamura, S.; Akiyoshi, K. J. Am. Chem. Soc. 2007, 129, 458-459
7. Amir, R. J.; Zhong, S.; Pochan, D. J.; Hawker, C. J. J. Am. Chem. Soc. 2009, 131, 13949-13951
8. Alemdaroglu, F. E.; Wang, J.; Börsch, M.; Berger, R.; Herrmann, A. Angew. Chem., Int. Ed. 2008, 47, 974-976
9. Chien, M.-P.; Rush, A. M.; Thompson, M. P.; Gianneschi, N. C. Angew. Chem., Int. Ed. 2010, 49, 5076-5080
10. Yang, Z. M.; Liang, G. L.; Xu, B. Acc. Chem. Res. 2008, 41, 315-326
11. Yang, Z. M.; Liang, G. L.; Wang, L.; Xu, B. J. Am. Chem. Soc. 2006, 128, 3038-3043
12. Azagarsamy, M. A.; Sokkalingam, P.; Thayumanavan, S. J. Am. Chem. Soc. 2009, 131, 14184-14185
13. Raghupathi, K. R.; Azagarsamy, M. A.; Thayumanavan, S. Chem.-Eur. J. 2011, 17, 11752-11760
14. Ulijn, R. V. J. Mater. Chem. 2006, 16, 2217-2225
15. Thornton, P. D.; Mart, R. J.; Ulijn, R. V. Adv. Mater. 2007, 19, 1252-1256
16. Lutolf, M. P.; Hubbell, J. A. Nat. Biotechnol. 2005, 23, 47-55
17. Kühnle, H.; Börner, H. G. Angew. Chem., Int. Ed. 2009, 48, 6431-6434
18. Wang, Y.; Xu, H.; Zhang, X. Adv. Mater. 2009, 21, 2849-2864
19. Zhang, X.; Wang, C. Chem. Soc. Rev. 2011, 40, 94-101
20. Wang, C.; Chen, Q.; Wang, Z.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 8612-8615
21. Xing, Y.; Wang, C.; Han, P.; Wang, Z.; Zhang, X. Langmuir 2012, 28, 6032-6036
22. Savariar, E. N.; Ghosh, S.; González, D. C.; Thayumanavan, S. J. Am. Chem. Soc. 2008, 130, 5416-5417
23. Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 4094-4104
24. Zhang, X.; Chen, Z.; Würthner, F. J. Am. Chem. Soc. 2007, 129, 4886-4887
25. Wang, Y.; Ma, N.; Wang, Z.; Zhang, X. Angew. Chem., Int. Ed. 2007, 46, 2823-2826
26. Wang, C.; Yin, S.; Chen, S.; Xu, H.; Wang, Z.; Zhang, X. Angew. Chem., Int. Ed. 2008, 47, 9049-9052
27. Ko, Y. H.; Kim, E.; Hwang, I.; Kim, K. Chem. Commun. 2007, 1305-1315
28. Bize, C.; Garrigues, J.-C.; Blanzat, M.; Rico-Lattes, I.; Bistri, O.; Colasson, B.; Reinaud, O. Chem. Commun. 2010, 46, 586-588
29. Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267-279
30. Liu, Y.; Chen, Y. Acc. Chem. Res. 2006, 39, 681-691
31. Harada, A.; Takashima, Y.; Yamaguchi, H. Chem. Soc. Rev. 2009, 38, 875-882
32. Guo, D.-S.; Liu, Y. Chem. Soc. Rev. 2012, in press.
33. Uekama, K.; Hirayama, F.; Irie, T. Chem. Rev. 1998, 98, 2045-2076
34. Perret, F.; Lazar, A. N.; Coleman, A. W. Chem. Commun. 2006, 42, 2425-2438
35. Perret, F.; Coleman, A. W. Chem. Commun. 2011, 47, 7303-7319
36. Wang, K.; Guo, D.-S.; Zhang, H.-Q.; Li, D.; Zheng, X.-L.; Liu, Y. J. Med. Chem. 2009, 52, 6402-6412
37. Uzunova, V. D.; Cullinane, C.; Brix, K.; Nau, W. M.; Day, A. I. Org. Biomol. Chem. 2010, 8, 2037-2042
38. Jeon, Y. J.; Bharadwaj, P. K.; Choi, S. W.; Lee, J. W.; Kim, K. Angew. Chem., Int. Ed. 2002, 41, 4474-4476
39. Jing, B.; Chen, X.; Wang, X.; Yang, C.; Xie, Y.; Qiu, H. Chem.-Eur. J. 2007, 13, 9137-9142
40. Zeng, J.; Shi, K.; Zhang, Y.; Sun, X.; Zhang, B. Chem. Commun. 2008, 3753-3755
41. Yan, Q.; Yuan, J.; Cai, Z.; Xin, Y.; Kang, Y.; Yin, Y. J. Am. Chem. Soc. 2010, 132, 9268-9270
42. Wang, K.; Guo, D.-S.; Liu, Y. Chem.-Eur. J. 2010, 16, 8006-8011
43. Wang, K.; Guo, D.-S.; Wang, X.; Liu, Y. ACS Nano 2011, 5, 2880-2894
44. Basilio, N.; García-Río, L. Chem.-Eur. J. 2009, 15, 9315-9319
45. Francisco, V.; Basilio, N.; García-Río, L.; Leis, J. R.; Maques, E. F.; Vázquez-Vázquez, C. Chem. Commun. 2010, 46, 6551-6553
46. Basilio, N.; Martín-Pastor, M.; García-Río, L. Langmuir 2012, 28, 6561-6568
47. Wang, M.; Gu, X.; Zhang, G.; Zhang, D.; Zhu, D. Anal. Chem. 2009, 81, 4444-4449
48. Li, Y.; Bai, H.; Li, C.; Shi, G. ACS Appl. Mater. Interfaces 2011, 3, 1306-1310
49. It is well-established that SC4A exhibits especially strong binding affinity and high molecular selectivity toward organic cations; see, for example: Guo, D.-S.; Wang, K.; Liu, Y. J. Inclusion Phenom. Macrocyclic Chem. 2008, 62, 1-21
50. Mueller, A.; OBrien, D. F. Chem. Rev. 2002, 102, 727-757
51. Vriezema, D. M.; Aragonès, M. C.; Elemans, J. A. A. W.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Chem. Rev. 2005, 105, 1445-1489
52. Zhou, S.; Burger, C.; Chu, B.; Sawamura, M.; Nagahama, N.; Toganoh, M.; Hackler, U. E.; Isobe, H.; Nakamura, E. Science 2001, 291, 1944-1947
53. Zhang, X.; Rehm, S.; Safont-Sempere, M. M.; Würthner, F. Nat. Chem. 2009, 1, 623-629
54. Whitehouse, P. J.; Price, D. L.; Struble, R. G.; Clark, A. W.; Coyle, J. T.; Delon, M. R. Science 1982, 215, 1237-1239
55. Koo, E. H.; Lansbury, P. T.; Kelly, J. W. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9989-9990
56. Selkoe, D. J. Physiol. Rev. 2001, 81, 741-746
57. Guo, D.-S.; Uzunova, V. D.; Su, X.; Liu, Y.; Nau, W. M. Chem. Sci. 2011, 2, 1722-1734
58. Ahlström, B.; Chelminska-Bertilsson, M.; Thompson, R. A.; Edebo, L. Antimicrob. Agents Chemother. 1995, 39, 50-55
59. Scherlund, M.; Brodin, A.; Malmsten, M. J. Colloid Interface Sci. 2000, 229, 365-374
60. Wen, X.; Franses, E. I. J. Colloid Interface Sci. 2000, 231, 42-51
61. Groth, C.; Nydén, M.; Persson, K. C. Langmuir 2007, 23, 3000-3008
62. Rehm, M.; Frank, M.; Schatz, J. Tetrahedron Lett. 2009, 50, 93-96
63. Lee, M.; Lee, S.-J.; Jiang, L.-H. J. Am. Chem. Soc. 2004, 126, 12724-12725
64. Hotz, J.; Meier, W. Langmuir 1998, 14, 1031-1036
65. Egelhaaf, S. U.; Schurtenberger, P. J. Phys. Chem. 1994, 98, 8560-8573
66. Chécot, F.; Lecommandoux, S.; Gnanou, Y.; Klox, H.-A. Angew. Chem., Int. Ed. 2002, 41, 1339-1343
67. Arena, G.; Contino, A.; Lombardo, G. G.; Sciotto, D. Thermochim. Acta 1995, 264, 1-11