Nelson-Mendez, Andrew and Aleksanian, Samuel and Oh, Misook and Lim, Hyun-Suk and Oh, Jung Kwon (2011) Reductively degradable polyester-based block copolymers prepared by facile polycondensation and ATRP: synthesis, degradation, and aqueous micellization. Soft Matter, 7 (16). pp. 7441-7452. ISSN 1744-683X
- Published Version
Official URL: http://dx.doi.org/10.1039/c1sm05781b
Well-defined reductively degradable amphiphilic block copolymers having disulfide linkages positioned repeatedly on hydrophobic chains, thus exhibiting fast degradation, were prepared by a combination of polycondensation and ATRP. The new method consists of three synthetic steps including, (1) polycondensation of commercially available diols and diacids through carbodiimide coupling or high temperature processes to synthesize degradable polyesters with disulfides labeled on the main chain at regular intervals (ssPES–OH), (2) bromination of ssPES–OH to ssPES–Br, and (3) ATRP for chain extension of ssPES–Br with water-soluble polymethacrylate, yielding ssPES-b-polymethacrylate block copolymers (ssABPs). The reductive cleavage of disulfide linkages in reducing conditions resulted in the degradation of ssPES homopolymers; their degradation rate was significantly enhanced with the increasing amounts of disulfide linkages in ssPES–OH and reducing agents. For ATRP, gel permeation chromatography and 1H-NMR results confirmed the synthesis of well-defined ssABPs and revealed that polymerizations were well controlled. Because of their amphiphilic nature, ssABPs self-assembled in water toward the formation of core/shell micelles consisting of a hydrophobic ssPES core surrounded with polymethacrylate coronas. The effects of the corona's chain length on thermal properties and micellization in water of well-defined ssABPs were examined. Moreover, reductive (or thiol-responsive) degradation of ssABP-based micelles enabled fast release of encapsulated model drugs. Cell culture experiments confirmed nontoxicity and biocompatibility of well-defined ssABPs as effect candidates for targeted delivery applications.
|Divisions:||Concordia University > Faculty of Arts and Science > Chemistry and Biochemistry|
|Authors:||Nelson-Mendez, Andrew and Aleksanian, Samuel and Oh, Misook and Lim, Hyun-Suk and Oh, Jung Kwon|
|Journal or Publication:||Soft Matter|
|Date:||14 July 2011|
|Deposited By:||DANIELLE DENNIE|
|Deposited On:||22 Aug 2011 19:11|
|Last Modified:||24 Aug 2016 21:26|
1 A. S. Mikhail and C. Allen, J. Controlled Release, 2009, 138, 214 .
2 A. Blanazs, S. P. Armes and A. J. Ryan, Macromol. Rapid Commun., 2009, 30, 267 .
3 N. Nishiyama and K. Kataoka, Adv. Polym. Sci., 2006, 193, 67.
4 A. Harada and K. Kataoka, Prog. Polym. Sci., 2006, 31, 949 .
5 J. K. Oh, Soft Matter, 2011, 7, 5096 RSC Article .
6 C. Alexander and K. M. Shakesheff, Adv. Mater., 2006, 18, 3321.
7 N. Rapoport, Prog. Polym. Sci., 2007, 32, 962 .
8 M. Motornov, Y. Roiter, I. Tokarev and S. Minko, Prog. Polym. Sci., 2010, 35, 174 .
9 J.-M. Schumers, C.-A. Fustin and J.-F. Gohy, Macromol. Rapid Commun., 2010, 31, 1588 .
10 N. V. Tsarevsky and K. Matyjaszewski, Macromolecules, 2005, 38, 3087 .
11 J. K. Oh, C. Tang, H. Gao, N. V. Tsarevsky and K. Matyjaszewski, J. Am. Chem. Soc., 2006, 128, 5578 .
12 N. V. Tsarevsky and K. Matyjaszewski, Macromolecules, 2002, 35, 9009 .
13 L. Zhang, W. Liu, L. Lin, D. Chen and M. H. Stenzel, Biomacromolecules, 2008, 9, 3321 .
14 R. A. Petros, P. A. Ropp and J. M. DeSimone, J. Am. Chem. Soc., 2008, 130, 5008 S .
15 C. Li, J. Madsen, S. P. Armes and A. L. Lewis, Angew. Chem., Int. Ed., 2006, 45, 3510 .
16 S. Carelli, A. Ceriotti, A. Cabibbo, G. Fassina, M. Ruvo and R. Sitia, Science, 1997, 277, 1681 .
17 Y. Li, B. S. Lokitz, S. P. Armes and C. L. McCormick, Macromolecules, 2006, 39, 2726.
18 L. Zhang, J. Bernard, T. P. Davis, C. Barner-Kowollik and M. H. Stenzel, Macromol. Rapid Commun., 2008, 29, 123 .
19 Y. Li, W. Du, G. Sun and K. L. Wooley, Macromolecules, 2008, 41, 6605 .
20 C. F. van Nostrum, Soft Matter, 2011, 7, 3246 RSC .
21 M. Kang and B. Moon, Macromolecules, 2009, 42, 455 .
22 J. S. Katz, S. Zhong, B. G. Ricart, D. J. Pochan, D. A. Hammer and J. A. Burdick, J. Am. Chem. Soc., 2010, 132, 3654 .
23 J.-M. Schumers, J.-F. Gohy and C.-A. Fustin, Polym. Chem., 2010, 1, 161 RSC .
24 T.-B. Ren, Y. Feng, Z.-H. Zhang, L. Li and Y.-Y. Li, Soft Matter, 2011, 7, 2329 RSC .
25 R. P. Brinkhuis, T. R. Visser, F. P. J. T. Rutjes and J. C. M. van Hest, Polym. Chem., 2011, 2, 550 RSC .
26 Y. Wang, H. Xu and X. Zhang, Adv. Mater., 2009, 21, 2849 .
27 X. Huang, F. Du, R. Ju and Z. Li, Macromol. Rapid Commun., 2007, 28, 597 .
28 J. Babin, M. Pelletier, M. Lepage, J.-F. Allard, D. Morris and Y. Zhao, Angew. Chem., Int. Ed., 2009, 48, 3329 .
29 X. Huang, F. Du, J. Cheng, Y. Dong, D. Liang, S. Ji, S.-S. Lin and Z. Li, Macromolecules, 2009, 42, 783 .
30 W. Chen, F. Meng, F. Li, S.-J. Ji and Z. Zhong, Biomacromolecules, 2009, 10, 1727.
31 N. Fomina, C. McFearin, M. Sermsakdi, O. Edigin and A. Almutairi, J. Am. Chem. Soc., 2010, 132, 9540 .
32 D. Han, X. Tong and Y. Zhao, Macromolecules, 2011, 44, 437 .
33 K. A. Davis and K. Matyjaszewski, Adv. Polym. Sci., 2002, 159, 1.
34 K. Matyjaszewski and T. P. Davis, Handbook of Radical Polymerization, John Wiley & Sons Inc., 2002.
35 C. L. McCormick, B. S. Sumerlin, B. S. Lokitz and J. E. Stempka, Soft Matter, 2008, 4, 1760 RSC .
36 P. De, S. R. Gondi, D. Roy and B. S. Sumerlin, Macromolecules, 2009, 42, 5614 .
37 M. Barz, F. K. Wolf, F. Canal, K. Koynov, M. J. Vicent, H. Frey and R. Zentel, Macromol. Rapid Commun., 2010, 31, 1492 .
38 M. L. Becker, J. Liu and K. L. Wooley, Biomacromolecules, 2005, 6, 220 .
39 T. Diaz, A. Fischer, A. Jonquieres, A. Brembilla and P. Lochon, Macromolecules, 2003, 36, 2235.
40 R. E. Richard, M. Schwarz, S. Ranade, A. K. Chan, K. Matyjaszewski and B. Sumerlin, ACS Symp. Ser., 2006, 944, 234 .
41 X. Jiang, Z. Ge, J. Xu, H. Liu and S. Liu, Biomacromolecules, 2007, 8, 3184 .
42 M. Licciardi, Y. Tang, N. C. Billingham, S. P. Armes and A. L. Lewis, Biomacromolecules, 2005, 6, 1085.
43 V. Buetuen, S. Liu, J. V. M. Weaver, X. Bories-Azeau, Y. Cai and S. P. Armes, React. Funct. Polym., 2006, 66, 157 .
44 F. F. Wolf, N. Friedemann and H. Frey, Macromolecules, 2009, 42, 5622 .
45 P. A. Wilbon, Y. Zheng, K. Yao and C. Tang, Macromolecules, 2010, 43, 8747 .
46 M. Spasova, L. Mespouille, O. Coulembier, D. Paneva, N. Manolova, I. Rashkov and P. Dubois, Biomacromolecules, 2009, 10, 1217.
47 J. Lee, Y. H. Bae, Y. S. Sohn and B. Jeong, Biomacromolecules, 2006, 7, 1729.
48 S. Santra, C. Kaittanis and J. M. Perez, Langmuir, 2010, 26, 5364 .
49 L. Zhang, R. Guo, M. Yang, X. Jiang and B. Liu, Adv. Mater., 2007, 19, 2988 .
50 A. O. Saeed, S. Dey, S. M. Howdle, K. J. Thurecht and C. Alexander, J. Mater. Chem., 2009, 19, 4529 RSC .
51 L. Zhang, Y. Hu, X. Jiang, C. Yang, W. Lu and Y. H. Yang, J. Controlled Release, 2004, 96, 135 .
52 J. Jiang, B. Qi, M. Lepage and Y. Zhao, Macromolecules, 2007, 40, 790 .
53 J. Jiang, X. Tong, D. Morris and Y. Zhao, Macromolecules, 2006, 39, 4633
Repository Staff Only: item control page