Multistimuli-responsive supramolecular vesicles based on water-soluble pillar[6]arene and SAINT complexation for controllable drug release

Journal of the American Chemical Society

Volumn 136, Issue 30, 2014, Pages 10762-10769

  Cao, Yu ^a   Hu, Xiao Yu ^a   Li, Yan ^b   Zou, Xiaochun ^a,c   Xiong, Shuhan ^a   Lin, Chen ^a   Shen, Ying Zhong ^c   Wang, Leyong ^a  

^a NANJING UNIVERSITY   (China)

^b SOUTHEAST UNIVERSITY   (China)

^c NANJING UNIVERSITY OF AERONAUTICS AND ASTRONAUTICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; CONTROLLED DRUG DELIVERY; EXPERIMENTS;

ACIDIC CONDITIONS; ANTICANCER DRUG; CONTROLLABLE DRUG RELEASE; HOST-GUEST COMPLEXATIONS; INTERNAL VOLUME; MODEL SUBSTRATES; THERAPEUTIC EFFECTS; VESICULAR STRUCTURE;

SUPRAMOLECULAR CHEMISTRY;

CALCEIN; CALCIUM; DOXORUBICIN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; DELAYED RELEASE FORMULATION; PILLAR(6)ARENE; QUATERNARY AMMONIUM DERIVATIVE; WATER;

ACIDITY; ANIMAL CELL; ARTICLE; CANCER CELL; COMPLEX FORMATION; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG STABILITY; ENCAPSULATION; HUMAN; HUMAN CELL; NONHUMAN; PH; SOLUBILITY; TEMPERATURE SENSITIVITY; 3T3 CELL LINE; ANIMAL; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG RELEASE; MCF 7 CELL LINE; METABOLISM; MOUSE; NEOPLASMS;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; CALCIUM; DELAYED-ACTION PREPARATIONS; DOXORUBICIN; DRUG LIBERATION; HUMANS; MCF-7 CELLS; MICE; NEOPLASMS; NIH 3T3 CELLS; QUATERNARY AMMONIUM COMPOUNDS; SOLUBILITY; WATER;

EID: 84905248212     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja505344t     Document Type: Article

References (73)

1. Scarzello, M.; Chupin, V.; Wagenaar, A.; Stuart, M. C. A.; Engberts, J. B. F. N.; Hulst, R. Biophys. J. 2005, 88, 2104
2. Jiao, D.; Geng, J.; Loh, X. J.; Das, D.; Lee, T.-C.; Scherman, O. A. Angew. Chem., Int. Ed. 2012, 51, 9633
3. Ahl, P. L.; Chen, L.; Perkins, W. R.; Minchey, S. R.; Boni, L. T.; Taraschi, T. F.; Janoff, A. S. Biochim. Biophys. Acta, Biomembr. 1994, 1195, 237
4. Menger, F. M.; Gabrielson, K. J. Am. Chem. Soc. 1994, 116, 1567
5. Menger, F. M.; Seredyuk, V. A. J. Am. Chem. Soc. 2003, 125, 11800
6. Dwars, T.; Paetzold, E.; Oehme, G. Angew. Chem., Int. Ed. 2005, 44, 7174
7. Boussif, O.; Lezoualc'h, F.; Zanta, M. A.; Mergny, M. D.; Scherman, D.; Demeneix, B.; Behr, J. P. Proc. Natl. Acad. Sci. U. S. A. 1995, 92, 7297
8. Guo, D.-S.; Wang, K.; Wang, Y.-X.; Liu, Y. J. Am. Chem. Soc. 2012, 134, 10244
9. Nalluri, S. K. M.; Voskuhl, J.; Bultema, J. B.; Boekema, E. J.; Ravoo, B. J. Angew. Chem., Int. Ed. 2011, 50, 9747
10. Ta, T.; Convertine, A. J.; Reyes, C. R.; Stayton, P. S.; Porter, T. M. Biomacromolecules 2010, 11, 1915
11. Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. J. Am. Chem. Soc. 2013, 135, 10542
12. Yu, G.; Zhou, X.; Zhang, Z.; Han, C.; Mao, Z.; Gao, C.; Huang, F. J. Am. Chem. Soc. 2012, 134, 19489
13. Yu, G.; Xue, M.; Zhang, Z.; Li, J.; Han, C.; Huang, F. J. Am. Chem. Soc. 2012, 134, 13248
14. Yu, G.; Han, C.; Zhang, Z.; Chen, J.; Yan, X.; Zheng, B.; Liu, S.; Huang, F. J. Am. Chem. Soc. 2012, 134, 8711
15. Lee, M.; Lee, S.-J.; Jiang, L.-H. J. Am. Chem. Soc. 2004, 126, 12724
16. Wang, C.; Guo, Y.; Wang, Y.; Xu, H.; Zhang, X. Chem. Commun. 2009, 5380
17. Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F. J. Am. Chem. Soc. 2012, 134, 15712
18. Saito, G.; Swanson, J. A.; Lee, K.-D. Adv. Drug Delivery Rev. 2003, 55, 199
19. Wang, K.; Guo, D.-S.; Wang, X.; Liu, Y. ACS Nano 2011, 5, 2880
20. Gao, L.; Zheng, B.; Yao, Y.; Huang, F. Soft Matt. 2013, 9, 7314
21. Sun, Y.-L.; Yang, B.-J.; Zhang, S. X.-A.; Yang, Y.-W. Chem.-Eur. J. 2012, 18, 9212
22. Sun, Y.-L.; Yang, Y.-W.; Chen, D.-X.; Wang, G.; Zhou, Y.; Wang, C.-Y.; Stoddart, J. F. Small 2013, 9, 3224
23. Ogoshi, T.; Hashizume, M.; Yamagishi, T.-a.; Nakamoto, Y. Chem. Commun. 2010, 46, 3708
24. Ma, Y.; Ji, X.; Xiang, F.; Chi, X.; Han, C.; He, J.; Abliz, Z.; Chen, W.; Huang, F. Chem. Commun. 2011, 47, 12340
25. Li, C.; Ma, J.; Zhao, L.; Zhang, Y.; Yu, Y.; Shu, X.; Li, J.; Jia, X. Chem. Commun. 2013, 49, 1924
26. Nusselder, J. J. H.; Engberts, J. B. F. N. J. Org. Chem. 1991, 56, 5522
27. Fadnavis, N. W.; Engberts, J. B. F. N. J. Org. Chem. 1982, 47, 2923
28. Sudhoelter, E. J. R.; Engberts, J. B. F. N.; Hoekstra, D. J. Am. Chem. Soc. 1980, 102, 2467
29. van der Woude, I.; Wagenaar, A.; Meekel, A. A. P.; ter Beest, M. B. A.; Ruiters, M. H. J.; Engberts, J. B. F. N.; Hoekstra, D. Proc. Natl. Acad. Sci. U. S. A. 1997, 94, 1160
30. Meekel, A. A. P.; Wagenaar, A.; Šmisterová, J.; Kroeze, J. E.; Haadsma, P.; Bosgraaf, B.; Stuart, M. C. A.; Brisson, A.; Ruiters, M. H. J.; Hoekstra, D.; Engberts, J. B. F. N. Eur. J. Org. Chem. 2000, 665
31. Roosjen, A.; Šmisterová, J.; Driessen, C.; Anders, J. T.; Wagenaar, A.; Hoekstra, D.; Hulst, R.; Engberts, J. B. F. N. Eur. J. Org. Chem. 2002, 1271
32. Hulst, R.; Muizebelt, I.; Oosting, P.; van der Pol, C.; Wagenaar, A.; Šmisterová, J.; Bulten, E.; Driessen, C.; Hoekstra, D.; Engberts, J. B. F. N. Eur. J. Org. Chem. 2004, 835
33. Šmisterová, J.; Wagenaar, A.; Stuart, M. C. A.; Polushkin, E.; ten Brinke, G.; Hulst, R.; Engberts, J. B. F. N.; Hoekstra, D. J. Biol. Chem. 2001, 276, 47615
34. Duzgunes, N.; Straubinger, R. M.; Baldwin, P. A.; Friend, D. S.; Papahadjopoulos, D. Biochemistry 1985, 24, 3091
35. Zhou, Y.; Yan, D. Angew. Chem., Int. Ed. 2005, 44, 3223
36. Ravoo, B. J.; Kevelam, J.; Weringa, W. D.; Engberts, J. B. F. N. J. Phys. Chem. B 1998, 102, 11001
37. Zhou, Y.; Yan, D. J. Am. Chem. Soc. 2005, 127, 10468
38. Ellens, H.; Bentz, J.; Szoka, F. C. Biochemistry 1985, 24, 3099
39. Ravoo, B. J.; Engberts, J. B. F. N. J. Chem. Soc., Perkin Trans. 2 2001, 1869
40. Menger, F. M.; Angelova, M. I. Acc. Chem. Res. 1998, 31, 789
41. Bentz, J.; Duezguenes, N. Biochemistry 1985, 24, 5436
42. Duzgunes, N.; Paiement, J.; Freeman, K. B.; Lopez-Straubinger, N. G.; Wilschut, J.; Papahadjopoulos, D. Biochemistry 1984, 23, 3486
43. Newmark, H. L.; Wargovich, M. J.; Bruce, W. R. J. Natl. Cancer Inst. 1984, 72, 1323
44. Durham, A. H.; Walton, J. Biosci. Rep. 1982, 2, 15
45. Berridge, M. J.; Bootman, M. D.; Lipp, P. Nature 1998, 395, 645
46. Bunn, P. A.; Dienhart, D. G.; Chan, D.; Puck, T. T.; Tagawa, M.; Jewett, P. B.; Braunschweiger, E. Proc. Natl. Acad. Sci. U. S. A. 1990, 87, 2162
47. Monteith, G. R.; McAndrew, D.; Faddy, H. M.; Roberts-Thomson, S. J. Nat. Rev. Cancer 2007, 7, 519
48. Kuiper, J. M.; Stuart, M. C. A.; Engberts, J. B. F. N. Langmuir 2007, 24, 426
49. Scarzello, M.; Wagenaar, A.; Stuart, M. C. A.; Hoekstra, D.; Engberts, J. B. F. N.; Hulst, R. J. Am. Chem. Soc. 2005, 127, 10420
50. Liu, Y.; Li, X.-Y.; Zhang, H.-Y.; Li, C.-J.; Ding, F. J. Org. Chem. 2007, 72, 3640
51. Guo, D.-S.; Chen, S.; Qian, H.; Zhang, H.-Q.; Liu, Y. Chem. Commun. 2010, 46, 2620
52. Guo, D.-S.; Wang, L.-H.; Liu, Y. J. Org. Chem. 2007, 72, 7775
53. Wiese, G. R.; Healy, T. W. Trans. Faraday Soc. 1970, 66, 490
54. Sakagami, H.; Kamata, A.; Nishimura, H.; Kasahara, J.; Owada, Y.; Takeuchi, Y.; Watanabe, M.; Fukunaga, K.; Kondo, H. Eur. J. Neurosci. 2005, 22, 2697
55. Ravoo, B. J.; Weringa, W. D.; Engberts, J. B. F. N. Cell Biol. Int. 2000, 24, 787
56. Keller, P. M.; Person, S.; Snipes, W. J. Cell. Sci. 1977, 28, 167
57. Tristram-Nagle, S.; Wiener, M. C.; Yang, C. P.; Nagle, J. F. Biochemistry 1987, 26, 4288
58. Blandamer, M. J.; Briggs, B.; Cullis, P. M.; Engberts, J. B. F. N. Chem. Soc. Rev. 1995, 24, 251
59. Blandamer, M. J.; Briggs, B.; Cullis, P. M.; Engberts, J. B. F. N.; Wagenaar, A.; Smits, E.; Hoekstra, D.; Kacperska, A. J. Chem. Soc., Faraday Trans. 1994, 90, 2709
60. Janoff, A. S.; Minchey, S. R.; Perkins, W. R.; Boni, L. T.; Seltzer, S. E.; Adams, D. F.; Blau, M. Invest. Radiol. 1991, 26, S167
61. Sudhoelter, E. J. R.; De Grip, W. J.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1982, 104, 1069
62. Nusselder, J. J. H.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1989, 111, 5000
63. Danhier, F.; Feron, O.; Préat, V. J. Controlled Release 2010, 148, 135
64. Fukumura, D.; Jain, R. K. J. Cell. Biochem. 2007, 101, 937
65. Rofstad, E. K.; Mathiesen, B.; Kindem, K.; Galappathi, K. Cancer Res. 2006, 66, 6699
66. Vaupel, P.; Kallinowski, F.; Okunieff, P. Cancer Res. 1989, 49, 6449
67. Gabizon, A.; Catane, R.; Uziely, B.; Kaufman, B.; Safra, T.; Cohen, R.; Martin, F.; Huang, A.; Barenholz, Y. Cancer Res. 1994, 54, 987
68. Allen, T. M.; Hansen, C.; Martin, F.; Redemann, C.; Yau-Young, A. Biochim. Biophys. Acta, Biomembr. 1991, 1066, 29
69. Dash, A. K.; Cudworth, G. C. J. Pharmacol. Toxicol. Methods 1998, 40, 1
70. Sethi, T.; Rozengurt, E. Cancer Res. 1991, 51, 1674
71. Nygren, P.; Larsson, R.; Gruber, A.; Peterson, C.; Bergh, J. Br. J. Cancer 1991, 64, 1011
72. Bergmann, J.; Junghahn, I.; Brachwitz, H.; Langen, P. Anticancer Res. 1994, 14, 1549
73. Bergner, A.; Huber, R. M. Anticancer Agents Med. Chem. 2008, 8, 705