Citation: Peng Kaimei, Ding Wei, Tu Weiping, Hu Jianqing, Liu Chao, Jian Yang. Construction of Guanidinium-rich Polymers and Their Applications[J]. Acta Chimica Sinica, ;2016, 74(9): 713-725. doi: 10.6023/A16030147 shu

Construction of Guanidinium-rich Polymers and Their Applications

Peng Kaimei ^a ,
Ding Wei ^a ,
Tu Weiping ^a ,
Hu Jianqing ^a,*,, ,
Liu Chao ^b ,
Jian Yang ^b,*,,

a.
Guangdong Provincial Key Laboratory for Green Chemical Product Technology, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, Guangdong, China
b.
Aleo BME, Inc. 200 Innovation Blvd, Suite 210A, State College, PA 16803, USA

Corresponding author: Hu Jianqing, glennhu@scut.edu.cn Jian Yang, glennhu@scut.edu.cn
Received Date: 26 March 2016

Fund Project: National Natural Science Foundation of China 50903031International Science & Technology Cooperation Program of Guangzhou 2012J5100043

Figures(11)

Antimicrobial is closely related to public life and efficient delivery of drug and gene is an indispensable means for the modern medicine. However, guanidinium-rich polymer has particular function in antimicrobial and delivery, such as the bactericidal mode of guanidinium-rich polymer is the non-specific interaction—electrostatic interaction, which is the driving force of the movement for the process of guanidinium-rich polymer getting close to the cell membrane of microbes, and from the perspective of biological evolution, which make bacterial hard to evolve resistance. On the other hand, the tight double-hydrogen bonded structure between guanidino and phosphate in the cell membrane phospholipids is the foundation for guanidinium-rich polymer exhibiting excellent performance on delivery, which will be an important grasp for the guanidinium-rich polymer and its carrying molecules entering the mammalian cell membrane. Moreover, relatively lower toxicity or nontoxicity of guanidinium-rich polymer for the mammalian cells remove the obstacle of applications. Therefore, this paper is based on available literature, sums up the fabrication methods of guanidinium-rich polymer, reviews the applications in microbial inhibition and delivery of drug or gene.
- guanidinium-rich polymer,
- microbial inhibition,
- drug delivery,
- gene delivery
1. [1]
  Cornell, R. J.; Donaruma, L. G. J. Med Chem. 1965, 8, 388. doi: 10.1021/jm00327a025
2. [2]
  Vogl, O.; Tirrell, D. J. Macromol. Sci., Part A 1979, 13, 415. doi: 10.1080/00222337908068110
3. [3]
  Panarin, E. F.; Solovskii, M. V.; Ékzemplyarov, O. N. Pharm. Chem. J. 1971, 5, 406. doi: 10.1007/BF00772413
4. [4]
  Siedenbiedel, F.; Tiller, J. C. Polymers 2012, 4, 46. doi: 10.3390/polym4010046
5. [5]
  Gillings, M. R. Front. Microbiol. 2013, 4, 4.
6. [6]
  Ganewatta, M. S.; Tang, C. Polymer 2015, 63, A1. doi: 10.1016/j.polymer.2015.03.007
7. [7]
  Wender, P. A.; Galliher, W. C.; Goun, E. A.; Jones, L. R.; Pillow, T. H. Adv. Drug Delivery Rev. 2008, 60, 452. doi: 10.1016/j.addr.2007.10.016
8. [8]
  Gabriel, G. J.; Som, A.; Madkour, A. E.; Eren, T.; Tew, G. N. Mater. Sci. Eng., R 2007, 57, 28. doi: 10.1016/j.mser.2007.03.002
9. [9]
  Onda, M.; Yoshihara, K.; Koyano, H.; Ariga, K.; Kunitake, T. J. Am. Chem. Soc. 1996, 118, 8524. doi: 10.1021/ja960991+
10. [10]
  Gilbert, P.; Moore, L. E. J. Appl. Microbiol. 2005, 99, 703. doi: 10.1111/jam.2005.99.issue-4
11. [11]
  Michl, T. D.; Locock, K. E. S.; Stevens, N. E.; Hayball, J. D.; Vasilev, K.; Postma, A.; Qu, Y.; Traven, A.; Haeussler, M.; Meagher, L.; Griesser, H. J. Polym. Chem. 2014, 5, 5813. doi: 10.1039/C4PY00652F
12. [12]
  Mattheis, C.; Wang, H.; Meister, C.; Agarwal, S. Macromol. Biosci. 2013, 13, 242. doi: 10.1002/mabi.201200217
13. [13]
  Lim, N.; Goh, D.; Bunce, C.; Xing, W.; Fraenkel, G.; Poole, T. R.; Ficker, L. Am. J. Ophthalmol. 2008, 145, 130. doi: 10.1016/j.ajo.2007.08.040
14. [14]
  Kima, B. R.; Andersona, J. E.; Muellera, S. A.; Gainesb, W. A.; Kendall, A. M. Water Res. 2002, 36, 4433. doi: 10.1016/S0043-1354(02)00188-4
15. [15]
  Motta, G. J.; Milne, C. T.; Corbett, L. Q. Ostomy Wound Manage. 2004, 50, 48.
16. [16]
  Kawabata, A.; Taylor, J. Dyes and Pigments 2006, 68, 197. doi: 10.1016/j.dyepig.2005.01.017
17. [17]
  Woodcock, P. M. Industrial Biocides, John Wiley & Sons, USA, 1988.
18. [18]
  Krebs, F. C.; Miller, S. R.; Ferguson, M. L.; Labib, M.; Rando, R. F.; Wigdahl, B. Biomed. Pharmacother. 2005, 59, 438. doi: 10.1016/j.biopha.2005.07.007
19. [19]
  Lindgren, M.; Hällbrink, M.; Prochiantz, A.; Langel, Ü. Trends Pharmacol. Sci. 2000, 21, 99. doi: 10.1016/S0165-6147(00)01447-4
20. [20]
  Fischer, P. M.; Krausz, E.; Lane, D. P. Bioconjugate Chem. 2001, 12, 825. doi: 10.1021/bc0155115
21. [21]
  Albert, M.; Feiertag, P.; Hayn, G.; Saf, R.; Honig, H. Biomacromolecules 2003, 4, 1811. doi: 10.1021/bm0342180
22. [22]
  Wei, D.; Ma, Q.; Guan, Y.; Hu, F.; Zheng, A.; Zhang, X.; Teng, Z.; Jiang, H. Mat. Sci. Eng. C-Mater. 2009, 29, 1776. doi: 10.1016/j.msec.2009.02.005
23. [23]
  Kurzer, F.; Pitchfork, E. D. Fortschr. Chem. Forsch., 1968, 10, 375.
24. [24]
  Pregozen, D.; Park Ridge N. J. US 5141803A, 1992 [Chem. Abstr. 1991, 114, 84358].
25. [25]
  Zhang, Y. M.; Jiang, J. M.; Chen, Y. M. Polymer 1999, 40, 6189. doi: 10.1016/S0032-3861(98)00828-3
26. [26]
  Lebrini, M.; Bentiss, F.; Chihib, N.-E.; Jama, C.; Hornez, J. P.; Lagrenée, M. Corros. Sci. 2008, 50, 2914. doi: 10.1016/j.corsci.2008.07.003
27. [27]
  Bentiss, F.; Lebrini, M.; Chihib, N.-E.; Abdalah, M.; Jama, C.; Lagrenée, M.; Al-Deyab, S. S.; Hammouti, B. Int. J. Electrochem. Sci. 2012, 7, 3947.
28. [28]
  Li, W.; Wang, H.; Ding, Y.; Scheithauer, E. C.; Goudouri, O.-M.; Grünewald, A.; Detsch, R.; Agarwal, S.; Boccaccini, A. R. J. Mater. Chem. B 2015, 3, 3367. doi: 10.1039/C5TB00044K
29. [29]
  Oledzka, E.; Sokolowski, K.; Sobczak, M.; Kolodziejski, W. Polym. Int. 2011, 60, 787.
30. [30]
  Wang, H.; Synatschke, C. V.; Raup, A.; Jérôme, V.; Freitag, R.; Agarwal, S. Polym. Chem. 2014, 5, 2453. doi: 10.1039/c3py01467c
31. [31]
  Schuchardt, U.; Vargas, R. M.; Gelbard, G. J. Mol. Catal. A-Chem. 1996, 109, 37. doi: 10.1016/1381-1169(96)00014-3
32. [32]
  Wang, J.; Li, S.; Zhang, S. Macromolecules 2010, 43, 3890. doi: 10.1021/ma100260a
33. [33]
  Kim, D. S.; Labouriau, A.; Guiver, M. D.; Kim, Y. S. Chem. Mater. 2011, 23, 3795. doi: 10.1021/cm2016164
34. [34]
  Sahariah, P.; Oskarsson, B. M.; Hjalmarsdottir, M. A.; Masson, M. Carbohydr. Polym. 2015, 127, 407. doi: 10.1016/j.carbpol.2015.03.061
35. [35]
  Gabriel, G. J.; Madkour, A. E.; Dabkowski, J. M.; Nelson, C. F.; Nusslein, K.; Tew, G. N. Biomacromolecules 2008, 9, 2980. doi: 10.1021/bm800855t
36. [36]
  Locock, K. E. S.; Michl, T. D.; Stevens, N.; Hayball, J. D.; Vasilev, K.; Postma, A.; Griesser, H. J.; Meagher, L.; Haeussler, M. ACS Macro Lett. 2014, 3, 319. doi: 10.1021/mz5001527
37. [37]
  Gasparini, G.; Bang, E. K.; Molinard, G.; Tulumello, D. V.; Ward, S.; Kelley, S. O.; Roux, A.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2014, 136, 6069. doi: 10.1021/ja501581b
38. [38]
  Funhoff, A. M.; Nostrum, C. F.; Lok, M. C.; Fretz, M. M.; Crommelin, D. J. A.; Hennink, W. E. Bioconjugate Chem. 2004, 15, 1212. doi: 10.1021/bc049864q
39. [39]
  Nimesh, S.; Chandra, R. Eur. J. Pharm. Biopharm. 2008, 68, 647. doi: 10.1016/j.ejpb.2007.09.008
40. [40]
  Bromberg, L.; Hatton, T. A. Polymer 2007, 48, 7490. doi: 10.1016/j.polymer.2007.10.040
41. [41]
  Cai, Z. S.; Sun, Y. M.; Zhu, X. M.; Zhao, L. L.; Yue, G. G. Polym. Bull. 2013, 70, 1085. doi: 10.1007/s00289-012-0883-y
42. [42]
  Zhang, Q.; Li, S.; Zhang, S. Chem. Commun. 2010, 46, 7495. doi: 10.1039/c0cc01834a
43. [43]
  Hu, Y.; Du, Y.; Yang, J.; Kennedy, J.; Wang, X.; Wang, L. Carbohydr. Polym. 2007, 67, 66. doi: 10.1016/j.carbpol.2006.04.015
44. [44]
  Kim, K. Y.; Lin, Y. T.; Mosher, H. S. Tetrahedron Lett. 1988, 29, 3183. doi: 10.1016/0040-4039(88)85116-5
45. [45]
  Zheng, A. N.; Guan, Y.; Wei, D. F.; Lu, H. CN 1350022, 2002 [Chem. Abstr. 2004, 140, 200279].
46. [46]
  Zheng, A. N.; Guan, Y.; Wei, D. F.; Lu, H. EP 1486519, 2004 [Chem. Abstr. 2003, 139, 277486].
47. [47]
  Zheng, A. N.; Guan, Y.; Wei, D. F.; Lu, H. US 7282538, 2005 [Chem. Abstr. 2003, 139, 277486].
48. [48]
  Zheng, A. N.; Guan, Y.; Wei, D. F.; Lu, H. US 7531225, 2007 [Chem. Abstr. 2003, 139, 277486].
49. [49]
  Zheng, A. N.; Guan, Y.; Wei, D. F.; Lu, H. CN 1351086, 2002 [Chem. Abstr. 2003, 139, 101825].
50. [50]
  Zheng, A. N.; Guan, Y. CN 1569923, 2005 [Chem. Abstr. 2005, 144, 7557].
51. [51]
  Guan, Y.; Xiao, H.; Sullivan, H.; Zheng, A. Carbohydr. Polym. 2007, 69, 688. doi: 10.1016/j.carbpol.2007.02.013
52. [52]
  Xu, X.; Zheng, A.; Zhou, X.; Guan, Y.; Pan, Y.; Xiao, H. J. Appl. Polym. Sci. 2015, 132, 42214.
53. [53]
  Zheng, A. N.; Guan, Y.; Wei, D. F.; Lu, H. CN 1445270, 2003 [Chem. Abstr. 2003, 139, 277486].
54. [54]
  Wang, W. G.; Zheng, A. N.; Wang, Q.; Gu, H. L.; Yuan, W. D.; Fei, H. S.; Zhang, Q.; Gan, Z. C.; Xiao, H.; Yang, G. F. CN 203449992, 2014 [Chem. Abstr. 2014, 160, 428922].
55. [55]
  Wei, D. F.; Zheng, A. N.; Xiao, R.; Hu, F. Z. CN 101209228, 2008 [Chem. Abstr. 2008, 149, 160569].
56. [56]
  Zheng, A. N.; Wei, D. F.; Ma, Q. X.; Hu, F. Z. CN 101210062, 2008 [Chem. Abstr. 2008, 149, 177165].
57. [57]
  Duan, H.-F.; Guo, X.; Li, S.-H.; Lin, Y.-J.; Zhang, S.-B.; Xie, H.-B. Chin. J. Org. Chem. 2006, 26, 1335 (in Chinese). (段海峰, 郭旭, 李胜海, 林英杰, 张所波, 谢海波, 有机化学, 2006, 26, 1335.)
58. [58]
  Cao, L.-H.; Lian, Z.-B. Acta Chim. Sinica 2007, 65, 349 (in Chinese). (曹玲华, 连召斌, 化学学报, 2007, 65, 349.)
59. [59]
  Maccari, G.; Sanfilippo, S.; De Luca, F.; Deodato, D.; Casian, A.; Lang, M. C. D.; Zamperini, C.; Dreassi, E.; Rossolini, G. M.; Docquier, J. D.; Botta, M. Bioorg. Med. Chem. Lett. 2014, 24, 5525. doi: 10.1016/j.bmcl.2014.09.081
60. [60]
  Wender, P. A.; Huttner, M. A.; Staveness, D.; Vargas, J. R.; Xu, A. F. Mol. Pharm. 2015, 12, 742. doi: 10.1021/mp500581r
61. [61]
  Geffers, C.; Gastmeier, P. Dtsch. Arztebl. Int. 2011, 108, 87.
62. [62]
  Fraise, A. P. J. Antimicrob. Chemoth. 2002, 49, 11.
63. [63]
  Tashiroa, T. Macromol. Mater. Eng. 2001, 286, 63. doi: 10.1002/(ISSN)1439-2054
64. [64]
  Tiller, J. C.; Liao, C. J.; Lewis, K.; Klibanov, A. M. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 5981. doi: 10.1073/pnas.111143098
65. [65]
  Percival, A. Hosp. Pharm. 1997, 4, 193.
66. [66]
  Kaehn, K. Skin Pharmacol. Physiol. 2010, 23, 7. doi: 10.1159/000318237
67. [67]
  Ikeda, T.; Tazuke, S.; Watanabe, M. Biochim. Biophys. Acta 1983, 735, 380. doi: 10.1016/0005-2736(83)90152-9
68. [68]
  Ikeda, T.; Ledwith, A.; Bamford, C. H.; Hann, R. A. Biochim. Biophys. Acta 1984, 769, 57. doi: 10.1016/0005-2736(84)90009-9
69. [69]
  Ikeda, T.; Tazuke, S.; Bamford, C. H. J. Chem. Res. 1985, 6, 180.
70. [70]
  Ikeda, T.; Tazuke, S.; Bamford, C. H.; Ledwith, A. Bull. Chem. Soc. Jpn. 1985, 58, 705. doi: 10.1246/bcsj.58.705
71. [71]
  Zhou, Z. X.; Wei, D. F.; Guan, Y.; Zheng, A. N.; Zhong, J. J. J. Appl. Microbiol. 2010, 108, 898. doi: 10.1111/jam.2010.108.issue-3
72. [72]
  Qian, L.; Xiao, H.; Zhao, G.; He, B. ACS Appl. Mater. Interfaces 2011, 3, 1895. doi: 10.1021/am200094u
73. [73]
  Davies, G. E.; Francis, J.; Martin, A. R.; Rose, F. L.; Swain, G. Br. J. Pharmacol. Chemother. 1954, 9, 192. doi: 10.1111/(ISSN)1476-5381a
74. [74]
  Willenegger, H. Unfallchirurg 1994, 20, 94. doi: 10.1007/BF02588150
75. [75]
  Buxbaum, A.; Kratzer, C.; Graninger, W.; Georgopoulos, A. J. Antimicrob. Chemother. 2006, 58, 193. doi: 10.1093/jac/dkl206
76. [76]
  Kaehn, K.; Eberlein, T. EWMA J. 2008, 8, 13.
77. [77]
  Qian, L. Y.; Li, X.; Sun, S. L.; Xiao, H. N. J. Biobased Mater. Bio. 2011, 5, 219. doi: 10.1166/jbmb.2011.1137
78. [78]
  Zhou, Z.; Zheng, A.; Zhong, J. Acta Biochim. Biophys. Sin. 2011, 43, 729. doi: 10.1093/abbs/gmr067
79. [79]
  Zhang, Y. W.; Chen, Y.; Zhao, J. X. Aust. J. Chem. 2014, 67, 142. doi: 10.1071/CH13295
80. [80]
  Wei, D.; Chen, Y.; Zhang, Y. Carbohydr. Polym. 2016, 136, 543. doi: 10.1016/j.carbpol.2015.09.086
81. [81]
  Pan, Y.; Xiao, H.; Zhao, G.; He, B. Polym. Bull. 2008, 61, 541. doi: 10.1007/s00289-008-0977-8
82. [82]
  Qian, L.; Guan, Y.; He, B.; Xiao, H. Polymer 2008, 49, 2471. doi: 10.1016/j.polymer.2008.03.042
83. [83]
  Nikkola, J.; Liu, X.; Li, Y.; Raulio, M.; Alakomi, H. L.; Wei, J.; Tang, C. Y. J. Membrane Sci. 2013, 444, 192. doi: 10.1016/j.memsci.2013.05.032
84. [84]
  Walczak, M.; Richert, A.; Burkowska-But, A. J. Ind. Microbiol. Biotechnol. 2014, 41, 1719. doi: 10.1007/s10295-014-1505-5
85. [85]
  Mei, Y.; Yao, C.; Li, X. Biofouling 2014, 30, 313. doi: 10.1080/08927014.2013.871540
86. [86]
  Tollar, M.; Štol, M.; Kliment, K. J. Biomed. Mater. Res. 1969, 3, 305. doi: 10.1002/(ISSN)1097-4636
87. [87]
  Quinn, K. J.; Courtney, J. M. Br. Polym. J. 1988, 20, 25. doi: 10.1002/(ISSN)1934-256X
88. [88]
  Sun, S.; An, Q.; Li, X.; Qian, L.; He, B.; Xiao, H. Bioresour. Technol. 2010, 101, 5693. doi: 10.1016/j.biortech.2010.02.046
89. [89]
  Guan, Y.; Qian, L.; Xiao, H.; Zheng, A. Cellulose 2008, 15, 609. doi: 10.1007/s10570-008-9208-6
90. [90]
  Ziaee, Z.; Qian, L.; Guan, Y.; Fatehi, P.; Xiao, H. J. Biomater. Sci. Polym. Ed. 2010, 21, 1359. doi: 10.1163/092050609X12517190417795
91. [91]
  Wei, D. F.; Zhou, R. H.; Zhang, Y. W.; Guan, Y.; Zheng, A. N. J. Appl. Polym. Sci. 2013, 130, 419. doi: 10.1002/app.39163
92. [92]
  Pan, Y.; Xiao, H.; Cai, P.; Colpitts, M. Carbohydr. Polym. 2016, 135, 94. doi: 10.1016/j.carbpol.2015.08.046
93. [93]
  Wei, D.; Zhou, R.; Guan, Y.; Zheng, A.; Zhang, Y. J. Appl. Polym. Sci. 2013, 127, 666. doi: 10.1002/app.37849
94. [94]
  Zhang, D.; Xiao, H. ACS Appl. Mater. Interfaces 2013, 5, 3464. doi: 10.1021/am400585m
95. [95]
  Wang, H.; Wei, D.; Ziaee, Z.; Xiao, H.; Zheng, A.; Zhao, Y. Ind. Eng. Chem. Res. 2015, 54, 1824. doi: 10.1021/ie504393t
96. [96]
  Li, S.; Wei, D.; Guan, Y.; Zheng, A. Eur. Polym. J. 2014, 51, 120. doi: 10.1016/j.eurpolymj.2013.12.004
97. [97]
  Ikeda, T.; Yamaguchi, H.; Tazuke, S. Antimicrob. Agents Chemother. 1984, 26, 139. doi: 10.1128/AAC.26.2.139
98. [98]
  Locock, K. E.; Michl, T. D.; Valentin, J. D.; Vasilev, K.; Hayball, J. D.; Qu, Y.; Traven, A.; Griesser, H. J.; Meagher, L.; Haeussler, M. Biomacromolecules 2013, 14, 4021. doi: 10.1021/bm401128r
99. [99]
  Casal, E.; Corzo, N.; Moreno, F. J.; Olano, A. J. Agric. Food Chem. 2005, 53, 1201. doi: 10.1021/jf040256e
100. [100]
  Hsieh, C. Y.; Hsieh, H. J.; Liu, H. C.; Wang, D. M.; Hou, L. T. Dent. Mater. 2006, 22, 622. doi: 10.1016/j.dental.2005.05.012
101. [101]
  Tapia, C.; Corbalán, V.; Costa, E.; Gai, M. N.; Yazdani-Pedram, M. Biomacromolecules 2005, 6, 2389. doi: 10.1021/bm050227s
102. [102]
  Batista, M. K. S.; Pinto, L. F.; Gomes, C. A. R.; Gomes, P. Carbohydr. Polym. 2006, 64, 299. doi: 10.1016/j.carbpol.2005.11.040
103. [103]
  Jung, E. J.; Youn, D. K.; Lee, S. H.; No, H. K.; Ha, J. G.; Prinyawiwatkul, W. Int. J. Food Sci. Tech. 2010, 45, 676. doi: 10.1111/j.1365-2621.2010.02186.x
104. [104]
  Rúnarsson, Ö. V.; Holappa, J.; Nevalainen, T.; Hjálmarsdóttir, M.; Järvinen, T.; Loftsson, T.; Einarsson, J. M.; Jónsdóttir, S.; Valdimarsdóttir, M.; Másson, M. Eur. Polym. J. 2007, 43, 2660. doi: 10.1016/j.eurpolymj.2007.03.046
105. [105]
  Liu, W. G.; Zhang, J. R.; Cao, Z. Q.; Xu, F. Y.; Yao, K. D. J. Mater. Sci-Mater. M. 2004, 15, 1199. doi: 10.1007/s10856-004-5672-1
106. [106]
  Xiao, B.; Wan, Y.; Zhao, M.; Liu, Y.; Zhang, S. Carbohydr. Polym. 2011, 83, 144. doi: 10.1016/j.carbpol.2010.07.032
107. [107]
  Zhu, D.; Zhang, H.; Bai, J.; Liu, W.; Leng, X.; Song, C.; Yang, J.; Li, X.; Jin, X.; Song, L.; Liu, L.; Li, X.; Zhang, Y.; Yao, K. Chinese Sci. Bull. 2007, 52, 3207. doi: 10.1007/s11434-007-0455-y
108. [108]
  Liu, L.; Bai, Y.; Song, C. Zhu, D.; Song, L.; Zhang, H.; Dong, X.; Leng, X. J. Nanopart. Res. 2009, 12, 1637.
109. [109]
  Tang, H.; Zhang, P.; Kieft, T. L.; Ryan, S. J.; Baker, S. M.; Wiesmann, W. P.; Rogelj, S. Acta Biomater. 2010, 6, 2562. doi: 10.1016/j.actbio.2010.01.002
110. [110]
  Zhai, X.; Sun, P.; Luo, Y.; Ma, C.; Xu, J.; Liu, W. J. Appl. Polym. Sci. 2011, 121, 3569. doi: 10.1002/app.34156
111. [111]
  Zhao, X.; Qiao, Z. Z.; He, J. X. J. Eng. Fiber. Fabr. 2010, 5, 16.
112. [112]
  Zhao, X.; He, J. X.; Zhan, Y. Z. Polym. J. 2009, 41, 1030. doi: 10.1295/polymj.PJ2009087
113. [113]
  Cai, Z. S.; Sun, Y. M., Yang, C. S.; Zhu, X. M. J. Appl. Polym. Sci. 2012, 125, 1146. doi: 10.1002/app.v125.2
114. [114]
  Sang, W.; Tang, Z.; He, M. Y.; Hua, Y. P.; Xu, Q. Int. J. Biol. Macromol. 2015, 75, 489. doi: 10.1016/j.ijbiomac.2015.01.009
115. [115]
  Budhathoki-Uprety, J.; Peng, L.; Melander, C.; Novak, B. M. ACS Macro Lett. 2012, 1, 370. doi: 10.1021/mz200116k
116. [116]
  Liu, K.; Xu, Y.; Lin, X.; Chen, L.; Huang, L.; Cao, S.; Li, J. Carbohydr. Polym. 2014, 110, 382. doi: 10.1016/j.carbpol.2014.03.086
117. [117]
  Groll, A. H.; Lumb, J. Future Microbiol. 2012, 7, 179. doi: 10.2217/fmb.11.154
118. [118]
  Kyle, A. A.; Dahl, M. V. Am. J. Clin. Dermatol. 2004, 5, 443. doi: 10.2165/00128071-200405060-00009
119. [119]
  Klepser, M. E. Pharmacotherapy 2006, 26, 68S. doi: 10.1592/phco.26.6part2.68S
120. [120]
  Manetti, F.; Castagnolo, D.; Raffi, F.; Zizzari, A. T.; Rajamaki, S.; D'Arezzo, S.; Visca, P.; Cona, A.; Fracasso, M. E.; Doria, D.; Posteraro, B.; Sanguinetti, M.; Fadda, G.; Botta, M. J. Med. Chem. 2009, 52, 7376. doi: 10.1021/jm900760k
121. [121]
  Sanguinetti, M.; Sanfilippo, S.; Castagnolo, D.; Sanglard, D.; Posteraro, B.; Donzellini, G.; Botta, M. ACS Med. Chem. Lett. 2013, 4, 852. doi: 10.1021/ml400187w
122. [122]
  Wilkinson, R. A.; Pincus, S. H.; Shepard, J. B.; Walton, S. K.; Bergin, E. P.; Labib, M.; Teintze, M. Antimicrob. Agents Chemother. 2011, 55, 255. doi: 10.1128/AAC.00709-10
123. [123]
  Thakkar, N.; Pirrone, V.; Passic, S.; Keogan, S.; Zhu, W.; Kholodovych, V.; Welsh, W.; Rando, R.; Labib, M.; Wigdahl, B.; Krebs, F. C. Antimicrob. Agents Chemother. 2010, 54, 1965. doi: 10.1128/AAC.00934-09
124. [124]
  Pan, Y.; Xue, Y.; Snow, J.; Xiao, H. Macromol. Chem. Phys. 2015, 216, 511. doi: 10.1002/macp.v216.5
125. [125]
  Schmidt, N.; Mishra, A.; Lai, G. H.; Wong, G. C. FEBS Lett. 2010, 584, 1806. doi: 10.1016/j.febslet.2009.11.046
126. [126]
  Schug, K. A.; Lindner, W. Chem. Rev. 2005, 105, 67. doi: 10.1021/cr040603j
127. [127]
  Schmidt, N. W.; Lis, M.; Zhao, K.; Lai, G. H.; Alexandrova, A. N.; Tew, G. N.; Wong, G. C. J. Am. Chem. Soc. 2012, 134, 19207. doi: 10.1021/ja308459j
128. [128]
  Wender, P. A.; Mitchell, D. J.; Pattabiraman, K.; Pelkey, E. T.; Steinman, L.; Rothbard, J. B. Proc. Natl. Acad. Sci. U. S. A. 2000, 97, 13003. doi: 10.1073/pnas.97.24.13003
129. [129]
  Tung, C. H.; Weissleder, R. Adv. Drug Delivery Rev. 2003, 55, 281. doi: 10.1016/S0169-409X(02)00183-7
130. [130]
  Wender, P. A.; Rothbard, J. B.; Jessop, T. C.; Kreider, E. L.; Wylie, B. L. J. Am. Chem. Soc. 2002, 124, 13382. doi: 10.1021/ja0275109
131. [131]
  Cooley, C. B.; Trantow, B. M.; Nederberg, F.; Kiesewetter, M. K.; Hedrick, J. L.; Waymouth, R. M.; Wender, P. A. J. Am. Chem. Soc. 2009, 131, 16401. doi: 10.1021/ja907363k
132. [132]
  Green, M.; Loewenstein, P. M. Cell 1988, 55, 1179. doi: 10.1016/0092-8674(88)90262-0
133. [133]
  Bang, E. K.; Gasparini, G.; Molinard, G.; Roux, A.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2013, 135, 2088. doi: 10.1021/ja311961k
134. [134]
  Elbashir, S. M.; Harborth, J.; Lendeckel, W.; Yalcin, A.; Weber, K.; Tusch, T. Nature 2001, 411, 494. doi: 10.1038/35078107
135. [135]
  Davidson, B. L.; McCray, P. B. Nat. Rev. Genet. 2011, 12, 329. doi: 10.1038/nrg2968
136. [136]
  Geihe, E. I.; Cooley, C. B.; Simon, J. R.; Kiesewetter, M. K.; Edward, J. A.; Hickerson, R. P.; Kaspar, R. L.; Hedrick, J. L.; Waymouth, R. M.; Wender, P. A. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 13171. doi: 10.1073/pnas.1211361109
137. [137]
  Ono, R. J.; Lee, A. L. Z.; Chin, W.; Goh, W. S.; Lee, A. Y. L.; Yang, Y. Y.; Hedrick, J. L. ACS Macro Lett. 2015, 4, 886. doi: 10.1021/acsmacrolett.5b00527
138. [138]
  deRonde, B. M.; Torres, J. A.; Minter, L. M.; Tew, G. N. Biomacromolecules 2015, 16, 3172. doi: 10.1021/acs.biomac.5b00795
139. [139]
  Rutz, S.; Scheffold, A. Arthritis Res. Ther. 2004, 6, 78.
140. [140]
  Mantei, A.; Rutz, S.; Janke, M.; Kirchhoff, D.; Jung, U.; Patzel, V.; Voge, U.; Rudel, T.; Andreou, I.; Weber, M.; Scheffold, A. Eur. J. Immunol. 2008, 38, 2616. doi: 10.1002/eji.200738075
141. [141]
  Freeley, M.; Long, A. Biochem. J. 2013, 455, 133. doi: 10.1042/BJ20130950
142. [142]
  Treat, N. J.; Smith, D.; Teng, C.; Flores, J. D.; Abel, B. A.; York, A. W.; Huang, F.; McCormick, C. L. ACS Macro Lett. 2012, 1, 100. doi: 10.1021/mz200012p
143. [143]
  Tabujew, I.; Freidel, C.; Krieg, B.; Helm, M.; Koynov, K.; Mullen, K.; Peneva, K. Macromol. Rapid Commun. 2014, 35, 1191. doi: 10.1002/marc.v35.13
144. [144]
  Mumper, R. J.; Wang, J.; Claspell, J. M.; Rolland, A. P. Proceedings of the 22nd International Symposium on Controlled Release of Bioactive Materials, Elsevier, Amsterdam, 1995, 22, 178.
145. [145]
  Kim, T. H.; Jiang, H. L.; Jere, D.; Park, I. K.; Cho, M. H.; Nah, J. W.; Choi, Y. J.; Akaike, T.; Cho, C. S. Prog. Polym. Sci. 2007, 32, 726. doi: 10.1016/j.progpolymsci.2007.05.001
146. [146]
  Kolonko, E. M.; Kiessling, L. L. J. Am. Chem. Soc. 2008, 130, 5626. doi: 10.1021/ja8001716
147. [147]
  Kim, S. H.; Jeong, J. H.; Kim, T.; Kim, S. W.; Bull, D. A. Mol. Pharm. 2008, 6, 718.
148. [148]
  Wender, P. A.; Kreider, E.; Pelkey, E. T.; Rothbard, J.; VanDeusen, C. L. Org. Lett. 2005, 7, 4815. doi: 10.1021/ol051496y
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