PH- and redox-responsive poly(ethylene glycol) and cholesterol-conjugated poly(amido amine)s based micelles for controlled drug delivery

Macromolecular Bioscience

Volumn 14, Issue 3, 2014, Pages 347-358

  Cheng, Weiren ^a   Kumar, Jatin N ^a   Zhang, Yong ^b   Liu, Ye ^a  

^a INSTITUTE OF MATERIALS RESEARCH AND ENGINEERING   (Singapore)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

drug delivery systems; poly(amido amine)s; redox polymers; self assembly; stimuli responsive polymers

Indexed keywords

ADDITION REACTIONS; AGGREGATES; CELLS; CHOLESTEROL; CONTROLLED DRUG DELIVERY; DYNAMIC LIGHT SCATTERING; FUNCTIONAL POLYMERS; GEL PERMEATION CHROMATOGRAPHY; POLYETHYLENE GLYCOLS; SELF ASSEMBLY; TRANSMISSION ELECTRON MICROSCOPY;

CYTOTOXICITY IN VITRO; DRUG DELIVERY SYSTEM; GEL PERMEATION CHROMATOGRAPHY (GPC); MICHAEL ADDITION POLYMERIZATION; POLYAMIDOAMINES; REDOX POLYMERS; SECONDARY AMINO GROUP; STIMULI-RESPONSIVE POLYMER;

MICELLES;

4 (AMINOMETHYL)PIPERIDINE; ACRYLAMIDE DERIVATIVE; CHOLESTEROL; DITHIOTHREITOL; DOXORUBICIN; MACROGOL; N,N CYSTAMINEBIS(ACRYLAMIDE); PIPERIDINE DERIVATIVE; POLYAMIDOAMINE; UNCLASSIFIED DRUG; ANTINEOPLASTIC ANTIBIOTIC; DELAYED RELEASE FORMULATION; MACROGOL DERIVATIVE; MICELLE; POLYAMINE;

AQUEOUS SOLUTION; ARTICLE; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CELL KILLING; CELL STRAIN MCF 7; CELLULAR DISTRIBUTION; CHEMICAL STRUCTURE; CONJUGATE; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; CYTOTOXICITY TEST; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; GEL PERMEATION CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; LIGHT SCATTERING; MICELLE; MICHAEL ADDITION; OXIDATION REDUCTION REACTION; PH; PROTON NUCLEAR MAGNETIC RESONANCE; TRANSMISSION ELECTRON MICROSCOPY; CELL SURVIVAL; CHEMICAL PHENOMENA; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG EFFECTS; PARTICLE SIZE; SYNTHESIS; TUMOR CELL LINE;

ACRYLAMIDES; ANTIBIOTICS, ANTINEOPLASTIC; CELL LINE, TUMOR; CELL SURVIVAL; CHOLESTEROL; DELAYED-ACTION PREPARATIONS; DOXORUBICIN; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MICELLES; OXIDATION-REDUCTION; PARTICLE SIZE; POLYAMINES; POLYETHYLENE GLYCOLS;

EID: 84896348244     PISSN: 16165187     EISSN: 16165195     Source Type: Journal    
DOI: 10.1002/mabi.201300339     Document Type: Article

References (74)

1. L. Brannon-Peppas, J. O. Blanchette, Adv. Drug Delivery Rev. 2004, 56, 1649.
2. I. Brigger, C. Dubernet, P. Couvreur, Adv. Drug Delivery Rev. 2002, 54, 631.
3. A. Gabizon, R. Isacson, E. Libson, B. Kaufman, B. Uziely, R. Catane, C. G. Ben-Dor, E. Rabello, Y. Cass, T. Peretz, A. Sulkes, R. Chisin, Y. Barenholz, Acta Oncol. 1994, 33, 779.
4. M. R. Green, G. M. Manikhas, S. Orlov, B. Afanasyev, A. M. Makhson, P. Bhar, M. J. Hawkins, Ann. Oncol. 2006, 17, 1263.
5. E. S. Gil, S. M. Hudson, Prog. Polym. Sci. 2004, 29, 1173.
6. M. A. C. Stuart, W. T. S. Huck, J. Genzer, M. Müller, C. Ober, M. Stamm, G. B. Sukhorukov, I. Szleifer, V. V. Tsukruk, M. Urban, F. Winnik, S. Zauscher, I. Luzinov, S. Minko, Nat. Mater. 2010, 9, 101.
7. C. De Las Heras Alarcon, S. Pennadam, C. Alexander, Chem. Soc. Rev. 2005, 34, 276.
8. K. Na, V. T. Sethuraman, Y. H. Bae, Anti-Cancer Agents Med. Chem. 2006, 6, 525.
9. C. M. Schilli, M. Zhang, E. Rizzardo, S. H. Thang, Y. K. Chong, K. Edwards, G. Karlsson, A. H. E. Müller, Macromolecules 2004, 37, 7861.
10. M. Nakayama, T. Okano, T. Miyazaki, F. Kohori, K. Sakai, M. Yokoyama, J. Controlled Release 2006, 115, 46.
11. R. A. Cairns, I. S. Harris, T. W. Mak, Nat. Rev. Cancer 2011, 11, 85.
12. R. M. Sawant, J. P. Hurley, S. Salmaso, A. Kale, E. Tolcheva, T. S. Levchenko, V. P. Torchilin, Bioconjugate Chem. 2006, 17, 943.
13. Y. Bae, S. Fukushima, A. Harada, K. Kataoka, Angew. Chem. Int. Ed. 2003, 42, 4640.
14. Y. Bae, N. Nishiyama, S. Fukushima, H. Koyama, M. Yasuhiro, K. Kataoka, Bioconjugate Chem. 2005, 16, 122.
15. K. Kataoka, T. Matsumoto, M. Yokoyama, T. Okano, Y. Sakurai, S. Fukushima, K. Okamoto, G. S. Kwon, J. Controlled Release 2000, 64, 143.
16. M. Hrubý, C. Konák, K. Ulbrich, J. Controlled Release 2005, 103, 137.
17. J. Rodríguez-Hernández, S. Lecommandoux, J. Am. Chem. Soc. 2005, 127, 2026.
18. E. S. Lee, K. Na, Y. M. Bae, Nano Lett. 2005, 5, 325.
19. J. C. Leroux, E. Roux, D. Le Garrec, K. Hong, D. C. Drummond, J. Controlled Release 2001, 72, 71.
20. D. Liu, H. Hu, J. Zhang, X. Zhao, X. Tang, D. Chen, Chem. Pharm. Bull. 2011, 59, 63.
21. J. Yao, Y. Ruan, T. Zhai, J. Guan, G. Tang, H. Li, S. Dai, Polymer 2011, 52, 3396.
22. F. Q. Schafer, G. R. Buettner, Free Radic. Biol. Med. 2001, 30, 1191.
23. Z. Djuric, V. K. Malviya, G. Deppe, J. Malone, D. L. McGunagle, L. K. Heilbrun, B. A. Reading, W. D. Lawrence, J. Cancer Res. Clin. Oncol. 1990, 116, 379.
24. G. K. Balendiran, R. Dabur, D. Fraser, Cell Biochem. Funct. 2004, 22, 343.
25. J. M. Estrela, A. Ortega, E. Obrador, Crit. Rev. Clin. Lab. Sci. 2006, 43, 143.
26. A. A. Stavrovskaya, Biochem. Moscow 2000, 65, 95.
27. a) Y. Sun, X. Yan, T. Yuan, J. Liang, Y. Fan, Z. Gu, X. Zhang, Biomaterials 2010, 31, 7124
28. b) J. Chen, X. Z. Qiu, J. Ouyang, J. M. Kong, W. Zhong, M. M. Q. Xing, Biomacromolecules 2011, 12, 3601.
29. S. Cerritelli, D. Velluto, J. A. Hubbell, Biomacromolecules 2007, 8, 1966.
30. B. Remant, B. Thapa, P. Xu, Mol. Pharm. 2012, 9, 2719.
31. H. Sun, B. Guo, R. Cheng, F. Meng, H. Liu, Z. Zhong, Biomaterials 2009, 30, 6358.
32. J. H. Ryu, R. Roy, J. Ventura, S. Thayumanavan, Langmuir 2010, 26, 7086.
33. H. Sun, B. Guo, X. Li, R. Cheng, F. Meng, H. Liu, Z. Zhong, Biomacromolecules 2010, 11, 848.
34. L. Y. Tang, Y. C. Wang, Y. Li, J. Z. Du, J. Wang, Bioconjugate Chem. 2009, 20, 1095.
35. H. Kim, S. Kim, C. Park, H. Lee, H. J. Park, C. Kim, Adv. Mater. 2010, 22, 4280.
36. Y. Yan, A. P. R. Johnston, S. J. Dodds, M. M. J. Kamphuis, C. Ferguson, R. G. Parton, E. C. Nice, J. K. Heath, F. Caruso, ACS Nano 2010, 4, 2928.
37. A. N. Koo, K. H. Min, H. J. Lee, S. U. Lee, K. Kim, I. Chan Kwon, S. H. Cho, S. Y. Jeong, S. C. Lee, Biomaterials 2012, 33, 1489.
38. K. Wang, G. F. Luo, Y. Liu, C. Li, S. X. Cheng, R. X. Zhuo, X. Z. Zhang, Polym. Chem. 2012, 3, 1084.
39. Y. J. Pan, Y. Y. Chen, D. R. Wang, C. Wei, J. Guo, D. R. Lu, C. C. Chu, C. C. Wang, Biomaterials 2012, 33, 6570.
40. Y. L. Li, L. Zhu, Z. Liu, R. Cheng, F. Meng, J. H. Cui, S. J. Ji, Z. Zhong, Angew. Chem. Int. Ed. 2009, 48, 9914.
41. A. N. Koo, H. J. Lee, S. E. Kim, J. H. Chang, C. Park, C. Kim, J. H. Park, S. C. Lee, Chem. Commun. 2008, 48, 6570.
42. J. O. Kim, G. Sahay, A. V. Kabanov, T. K. Bronich, Biomacromolecules 2010, 11, 919.
43. Y. Li, K. Xiao, J. Luo, W. Xiao, J. S. Lee, A. M. Gonik, J. Kato, T. A. Dong, K. S. Lam, Biomaterials 2011, 32, 6633.
44. H. H. Bae, M. Y. Cho, J. H. Hong, H. Poo, M. H. Sung, Y. T. Lim, J. Microbiol. Biotechnol. 2012, 22, 1782.
45. R. B. Arote, H. L. Jiang, Y. K. Kim, M. H. Cho, Y. J. Choi, C. S. Cho, Expert Opin. Drug Delivery 2011, 8, 1237.
46. L. V. Christensen, C. W. Chang, J. K. Won, W. K. Sung, Z. Zhong, C. Lin, J. F. J. Engbersen, J. Feijen, Bioconjugate Chem. 2006, 17, 1233.
47. X. Wang, Y. He, J. Wu, C. Gao, Y. Xu, Biomacromolecules 2010, 11, 245.
48. R. Wang, L. Zhou, Y. Zhou, G. Li, X. Zhu, H. Gu, X. Jiang, H. Li, J. Wu, L. He, X. Guo, B. Zhu, D. Yan, Biomacromolecules 2010, 11, 489.
49. Z. Q. Yu, J. J. Yan, Y. Z. You, Q. H. Zhou, Int. J. Nanomed. 2012, 7, 5819.
50. D. Wu, X. J. Loh, Y. L. Wu, C. L. Lay, Y. Liu, J. Am. Chem. Soc. 2010, 132, 15140.
51. Y. Liu, D. Wu, Y. Ma, G. Tang, S. Wang, C. He, T. Chung, S. Goh, Chem. Commun. 2003, 9, 2630.
52. D. Wu, Y. Liu, C. He, T. Chung, S. H. Goh, Macromolecules 2004, 37, 6763.
53. D. Wu, Y. Liu, L. Chen, C. He, T. S. Chung, S. H. Goh, Macromolecules 2005, 38, 5519.
54. D. Wang, Y. Liu, C. Y. Hong, C. Y. Pan, Polymer 2006, 47, 3799.
55. D. Wu, Y. Liu, C. B. He, Macromolecules 2008, 41, 18.
56. C. L. Lay, H. Q. Liu, D. Wu, Y. Liu, Chem. Eur. J. 2010, 16, 3001.
57. a) C. Lin, Z. Zhong, M. C. Lok, X. Jiang, W. E. Hennink, J. Feijen, J. F. J. Engbersen, J. Controlled Release 2006, 116, 130
58. b) W. Zhang, Y. Li, L. Liu, Q. Sun, X. Shuai, W. Zhu, Y. Chen, Biomacromolecules 2010, 11, 1331
59. c) L. Cheng, D. Cao, Langmuir 2009, 25, 2749.
60. B. D. Mather, K. Viswanathan, K. M. Miller, T. E. Long, Prog. Polym. Sci. 2006, 31, 487.
61. S. Cohen, G. Couéb, D. Beno, R. Korenstein, J. F. J. Engbersen, Biomaterials 2012, 33, 614.
62. E. Emilitri, E. Ranucci, P. Ferruti, J. Polym. Sci., Part A 2005, 43, 1404.
63. A. Manfredi, E. Ranucci, M. Suardi, P. Ferruti, J. Bioact. Compat. Polym. 2007, 22, 219.
64. D. D. Lasic, D. Papahadjopoulos, Medical Applications of Liposomes, Elsevier Science B.V., Amsterdam, The Netherlands 1998.
65. G. Prencipe, S. M. Tabakman, K. Welsher, Z. Liu, A. P. Goodwin, L. Zhang, J. Henry, H. Dai, J. Am. Chem. Soc. 2009, 131, 4783.
66. J. V. M. Weaver, Y. Tang, S. Liu, P. D. Iddon, R. Grigg, N. C. Billingham, S. P. Armes, R. Hunter, S. P. Rannard, Angew. Chem. Int. Ed. 2004, 43, 1389.
67. Y. Li, B. S. Lokitz, C. L. McCormick, Angew. Chem. Int. Ed. 2006, 45, 5792.
68. C. L. Lay, H. R. Tan, X. Lu, Y. Liu, Chem. Eur. J. 2011, 17, 2504.
69. H. Hussain, B. H. Tan, C. S. Gudipati, C. B. He, Y. Liu, T. P. Davis, Langmuir 2009, 25, 5557.
70. Y. Ping, D. Wu, J. N. Kumar, W. Cheng, C. L. Lay, Y. Liu, Biomacromolecules 2013, 14, 2083.
71. J. Panyam, V. Labhasetwar, Pharm. Res. 2003, 20, 212.
72. A. K. Larsen, A. E. Escargueil, A. Skladanowski, Pharmacol. Ther. 2000, 85, 217.
73. H. Jin, D. A. Heller, R. Sharma, M. S. Strano, ACS Nano 2009, 3, 149.
74. H. Carvalho, L. M. Garrido, R. L. A. Furlan, G. Padilla, M. Agnoletto, T. Guecheva, J. A. P. Henriques, J. Saffi, C. F. M. Menck, Cancer Chemother. Pharmacol. 2010, 65, 989.