PH-responsive biodegradable assemblies containing tunable phenyl-substituted vinyl ethers for use as efficient gene delivery vehicles

ACS Applied Materials and Interfaces

Volumn 5, Issue 12, 2013, Pages 5648-5658

  Kim, Hee Kwon ^a   Thompson, David H ^b   Jang, Ho Seong ^c   Chung, Yong Jin ^d   Van Den Bossche, Jeroen ^e  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b PURDUE UNIVERSITY   (United States)

^c Korea Institute of Science and Technology   (South Korea)

^d CALIFORNIA STATE POLYTECHNIC UNIVERSITY   (United States)

^e UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

acid cleavable poly(ethylene glycol) lipids; gene delivery; pH sensitive nanoparticles; protamine sulfate; vinyl ether hydrolysis

Indexed keywords

ACID-CATALYZED HYDROLYSIS; ELECTRON-DONATING GROUP; ELECTRONWITHDRAWING; GENE DELIVERY; PH SENSITIVE; PROTAMINE SULFATE; TRANSFECTION EFFICIENCY; VINYL ETHERS;

ETHERS; GENE TRANSFER; HYDROLYSIS; LIPIDS; LIPOSOMES; MOLECULAR BIOLOGY; MOTION PICTURE EXPERTS GROUP STANDARDS; POLYETHYLENE GLYCOLS;

ORGANIC POLYMERS;

BIOMATERIAL; DIPHENYL ETHER DERIVATIVE; DNA; LIPOSOME; MACROGOL DERIVATIVE; NANOPARTICLE; PHENYL VINYL ETHER; PROTAMINE; VINYL DERIVATIVE;

ANIMAL; ARTICLE; CELL STRAIN COS1; CELL STRAIN HEK293; CELL SURVIVAL; CERCOPITHECUS; CHEMISTRY; DRUG EFFECT; GENETIC TRANSFECTION; HUMAN; HYDROLYSIS; METHODOLOGY; PH; PLASMID;

ANIMALS; BIOCOMPATIBLE MATERIALS; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; COS CELLS; DNA; HEK293 CELLS; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; LIPOSOMES; NANOPARTICLES; PHENYL ETHERS; PLASMIDS; POLYETHYLENE GLYCOLS; PROTAMINES; TRANSFECTION; VINYL COMPOUNDS;

EID: 84879517827     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am400977t     Document Type: Article

References (65)

1. Mancuso, K.; Hauswirth, W. W.; Li, Q.; Connor, T. B.; Kuchenbecker, J. A.; Mauck, M. C.; Neitz, J.; Neitz, M. Nature 2009, 461, 784-788
2. Semple, S. C.; Akinc, A.; Chen, J.; Sandhu, A. P.; Mui, B. L.; Cho, C. K.; Sah, D. W. Y.; Stebbing, D.; Crosley, E. J.; Yaworski, E.; Hafez, I. M.; Dorkin, J. R.; Qin, J.; Lam, K.; Rajeev, K. G.; Wong, K. F.; Jeffs, L. B.; Nechev, L.; Eisenhardt, M. L.; Jayaraman, M.; Kazem, M.; Maier, M. A.; Srinivasulu, M.; Weinstein, M. J.; Chen, Q.; Alvarez, R.; Barros, S. A.; De, S.; Klimuk, S. K.; Borland, T.; Kosovrasti, V.; Cantley, W. L.; Tam, Y. K.; Manoharan, M.; Ciufolini, M. A.; Tracy, M. A.; de Fougerolles, A.; MacLachlan, I.; Cullis, P. R.; Madden, T. D.; Hope, M. J. Nat. Biotechnol. 2010, 20, 172-176
3. Waehler, R.; Russell, S. J.; Curiel, D. T. Nat. Rev. Genet. 2007, 8, 573-587
4. Mintzer, M. A.; Grinstaff, M. W. Chem. Soc. Rev. 2011, 40, 173-190
5. Xu, L.; Anchordoquy, T. J. Pharm. Sci. 2011, 100, 38-52
6. Wiethoff, C. M.; Middaugh, C. R. J. Pharm. Sci. 2003, 92, 203-217
7. Pack, D. W.; Hoffman, A. S.; Pun, S.; Stayton, P. S. Nat. Rev. Drug Discovery 2005, 4, 581-593
8. Watson, P.; Jones, A. T.; Stephens, D. J. Adv. Drug Delivery Rev. 2005, 57, 43-61
9. Gerweck, L. E. Semin. Radiat. Oncol. 1998, 8, 176-18
10. Mellman, I.; Fuchs, R.; Helenius, A. Annu. Rev. Biochem. 1986, 55, 663-700
11. Daleke, D. L.; Hong, K. L.; Papahadjopoulos, D. Biochim. Biophys. Acta 1990, 1024, 352-366
12. Straubinger, R. M.; Papahadjopoulos, D.; Hong, K. Biochemistry 1990, 29, 4929-4939
13. Lee, R. J.; Wang, S.; Low, P. S. Biochim. Biophys. Acta 1996, 1312, 237-242
14. Sun, H. H.; Andresen, T. L.; Benjaminsen, R. V.; Almdal, K. J. Biomed. Nanotechnol. 2009, 5, 676-682
15. Rofstad, E. K.; Mathiesen, B.; Kindem, K.; Galappathi, K. Cancer Res. 2006, 66, 6699-6707
16. Brune, K.; Graf, P. Biochem. Pharmacol. 1978, 27, 525-530
17. Masson, C.; Garinot, M.; Mignet, N.; Wetzer, B.; Mailhe, P.; Scherman, D.; Bessodes, M. J. Control. Release 2004, 99, 423-434
18. Huang, Z. H.; Guo, X.; Li, W. J.; MacKay, J. A.; Szoka, F. C. J. Am. Chem. Soc. 2006, 128, 60-61
19. Chen, H. G.; Zhang, H. Z.; McCallum, C. M.; Szoka, F. C.; Guo, X. J. Med. Chem. 2007, 50, 4269-4278
20. Remenyi, J.; Balazs, B.; Toth, S.; Falus, A.; Toth, G.; Hudecz, F. Biochem. Biophys. Res. Comm. 2003, 303, 556-561
21. Alshamkhani, A.; Duncan, R. Int. J. Pharm. 1995, 122, 107-119
22. Kale, A. A.; Torchilin, V. P. Bioconjugate Chem. 2007, 18, 363-370
23. Sawant, R. M.; Hurley, J. P.; Salmaso, S.; Kale, A.; Tolcheva, E.; Levchenko, T. S.; Torchilin, V. P. Bioconjugate Chem. 2006, 17, 943-949
24. Knorr, V.; Russ, V.; Allmendinger, L.; Ogris, M.; Wagner, E. Bioconjugate Chem. 2008, 19, 1625-1634
25. Gillies, E. R.; Goodwin, A. P.; Frechet, J. M. J. Bioconjugate Chem. 2004, 15, 1254-1263
26. Parrott, M. C.; Luft, J. C.; Byrne, J. D.; Fain, J. H.; Napier, M. E.; DeSimone, J. M. J. Am. Chem. Soc. 2010, 132, 17928-17932
27. Boomer, J. A.; Inerowicz, H. D.; Zhang, Z. Y.; Bergstrand, N.; Edwards, K.; Kim, J. M.; Thompson, D. H. Langmuir 2003, 19, 6408-6415
28. Boomer, J. A.; Qualls, M. M.; Inerowicz, H. D.; Haynes, R. H.; Patri, V. S.; Kim, J. M.; Thompson, D. H. Bioconjugate Chem. 2009, 20, 47-59
29. Felber, A. E.; Dufresne, M.-H.; Leroux, J.-C. Adv. Drug Delivery Rev. 2012, 64, 979-992
30. Hope, M. J.; Bally, M. B.; Webb, G.; Cullis, P. R. Biochim. Biophys. Acta 1985, 812, 55-65
31. Mayer, L. D.; Cullis, P. R.; Bally, M. B. Biochim. Biophys. Acta 1986, 857, 123-126
32. Lasic, D. D.; Frederik, P. M.; Stuart, M. C.; Barenholz, Y.; McIntosh, T. J. FEBS Lett. 1992, 312, 255-258
33. Haran, G.; Cohen, R.; Bar, L. K.; Barenholz, Y. Biochim. Biophys. Acta 1993, 1151, 201-215
34. Jain, R. K. Adv. Drug Delivery Rev. 2001, 46, 149-168
35. Maeda, H. Bioconjugate Chem. 2010, 21, 797-802
36. Leserman, L. D.; Barbet, J.; Kourilsky, F.; Weinstein, J. N. Nature 1980, 288, 602-604
37. Rui, Y.; Wang, S.; Low, P. S.; Thompson, D. H. J. Am. Chem. Soc. 1998, 120, 11213-11218
38. Hussain, S.; Pluckthun, A.; Allen, T. M.; Zangemeister-Wittke, U. Mol. Cancer Ther. 2007, 6, 3019-3027
39. Chen, H.; Ahn, R.; Van den Bossche, J.; Thompson, D. H.; O'Halloran, T. V. Mol. Cancer Ther. 2009, 8, 1955-1963
40. Qualls, M. M.; Thompson, D. H. Int. J. Cancer 2001, 93, 384-392
41. Harris, J. M.; Chess, R. B. Nat. Rev. Drug Discovery 2003, 2, 214-221
42. Jin, Y.; Yue, X.; Zhang, Q.; Wud, X.; Cao, Z.; Dai, Z. Acta Biomaterialia 2012, 8, 3372-3380
43. Holland, J. W.; Cullis, P. R.; Madden, T. D. Biochemistry 1996, 35, 2610-2617
44. Li, W. M.; Zue, L.; Mayer, L. D.; Bally, M. B. Biochim. Biophys. Acta 2001, 1513, 193-206
45. Auguste, D. T.; Prud'homme, R. K.; Ahl, P. L.; Meers, P.; Kohn, J. Biochim. Biophys. Acta 2003, 1616, 184-195
46. Kirpotin, D.; Hong, K. L.; Mullah, N.; Papahadjopoulos, D.; Zalipsky, S. FEBS Lett. 1996, 388, 115-118
47. Sega, E. I.; Low, P. S. Cancer Metast. Rev. 2008, 27, 655-664
48. Shin, J.; Shum, P.; Grey, J.; Fujiwara, S.; Malhotra, G. S.; González-Bonet, A. M.; Hyun, S.-H.; Moase, E.; Allen, T.M.; Thompson, D. H. Mol. Pharm. 2012, 9, 3266-3276
49. Sanchez, M.; Aranda, F. J.; Teruel, J. A.; Ortiz, A. Chem. Phys. Lipids 2011, 164, 16-23
50. Bergstrand, N.; Arfvidsson, M. C.; Kim, J. M.; Thompson, D. H.; Edwards, K. Biophys. Chem. 2003, 104, 361-379
51. Shin, J.; Shum, P.; Thompson, D. H. J. Control. Release 2003, 91, 187-200
52. Kim, H.-K.; Van den Bossche, J.; Hyun, S.-H.; Thompson, D. H. Bioconjugate Chem. 2012, 23, 2071-2077
53. Sorgi, F. L.; Bhattacharya, S.; Huang, L. Gene Ther. 1997, 4, 961-968
54. Gao, Y.; Gu, W. W.; Chen, L. L.; Xu, Z. H.; Li, Y. P. J. Control. Release 2007, 118, 381-388
55. Nie, Y.; Gunther, M.; Gu, Z.; Wagner, E. Biomaterials 2011, 32, 858-869
56. Balhorn, R.; Brewer, L.; Corzett, M. Mol. Reprod. Dev. 2000, 56, 230-234
57. Biegeleisen, K. J. Theor. Biol. 2006, 241, 533-540
58. Yuan, H.; Zhang, W.; Du, Y. Z.; Hu, F. Q. Int. J. Pharm. 2010, 392, 224-231
59. Evjen, T. J.; Nilssen, E. A.; Fowler, R. A.; Rognvaldsson, S.; Brandl, M.; Fossheim, S. L. Int. J. Pharm. 2011, 406, 114-116
60. Johnsson, M.; Edwards, K. Biophys. J. 2001, 80, 313-323
61. Klein, E.; Ciobanu, M.; Klein, J.; Machi, V.; Leborgne, C.; Vandamme, T.; Frisch, B.; Pons, F.; Kichler, A.; Zuber, G.; Lebeau, L. Bioconjugate Chem. 2010, 21, 360-371
62. Bellavance, M. A.; Poirier, M. B.; Fortin, D. Int. J. Pharm. 2010, 395, 251-259
63. Vaidya, B.; Nayak, M. K.; Dash, D.; Agrawal, G. P.; Vyas, S. P. Int. J. Pharm. 2011, 403, 254-261
64. Fujita, T.; Furuhata, M.; Hattori, Y.; Kawakami, H.; Toma, K.; Maitani, Y. J. Control. Release 2008, 129, 124-127
65. Xu, Z. H.; Gu, W. W.; Chen, L. L.; Gao, Y.; Zhang, Z. W.; Li, Y. P. Biomacromolecules 2008, 9, 3119-3126