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Progress in Chemistry 2014, Vol. 26 Issue (11): 1849-1858 DOI: 10.7536/PC140707 Previous Articles   Next Articles

• Review •

Zwitterions in Surface Engineering of Biomedical Nanoparticles

Chen Yangjun, Liu Xiangsheng, Wang Haibo, Wang Yin, Jin Qiao*, Ji Jian*   

  1. Key Laboratory of Macromolecular Synthesis and Functionalization, Ministry of Education, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
  • Received: Revised: Online: Published:
  • Supported by:

    The work was supported by the National Natural Science Foundation of China (No. 51333005, 21174126, 51103126, 21374095, 51303154, 51025312)

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Surface engineering of biomedical nanoparticles is of great importance to maintain nano-stability, resist nonspecific biomolecular adsorption so as to enhance in vivo circulation time. Cell membrane mimicking zwitterions can form superhydrophilic antifouling surface which helps to maintain colloidal stability and resist immune elimination via electrostatically induced hydration. The stealthy surface prolongs the blood circulation time to reach "passive targeting", further "active targeting" is also available if combined with stimuli-responsive or bioactive molecules. Hence "zwitteration" has been developed as a new surface engineering strategy of biomedical nanoparticles. This review mainly talks about surface engineering of inorganic nanoparticles with small molecular and polymeric zwitterions, zwitterionic polymeric assemblies as drug delivery system and zwitterionic polymeric prodrugs. Introduction of special properities and applications of mixed-charge materials is also involved.

Contents
1 Introduction
2 Surface design of inorganic nanoparticles with zwitterions
2.1 Small molecular zwitterions
2.2 Polymeric zwitterions
3 Zwitterionic polymeric assemblies for drug delivery
3.1 Drug non-covalently loaded assemblies
3.2 Polymeric prodrugs
4 Mixed-charged materials
5 Conclusion and outlook

Key words: zwitterion, nano-biointerface, biocompatibility, drug delivery, mixed charge

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[1] Caruso F, Hyeon T, Rotello V M. Chem. Soc. Rev., 2012, 41: 2537.
[2] Liu Y Y, Miyoshi H, Nakamura M. Int. J. Cancer, 2007, 120: 2527.
[3] Sanhai W R, Sakamoto J H, Canady R, Ferrari M. Nat. Nanotech., 2008, 3: 242.
[4] Fang C, Bhattarai N, Sun C, Zhang M Q. Small, 2009, 5: 1637.
[5] Maeda H, Wu J, Sawa T, Matsumura Y, Hori K. J. Control. Release, 2000, 65: 271.
[6] Naahidi S, Jafari M, Edalat F, Raymond K, Khademhosseini A, Chen P. J. Control. Release, 2013, 166: 182.
[7] Estephan Z G, Schlenoff P S, Schlenoff J B. Langmuir, 2011, 27: 6794.
[8] 刘红艳(Liu H Y), 周健(Zhou J). 化学进展(Progress in Chemistry), 2012, 24(11): 2187.
[9] Lewis A L. Colloids Surf., B, 2000, 18: 261.
[10] Gong Y K, Winnik F M. Nanoscale, 2012, 4: 360.
[11] Cao Z Q, Jiang S Y. Nano Today, 2012, 7: 404.
[12] Chien H W, Xu X, Ella-Menye J R, Tsai W B, Jiang S Y. Langmuir, 2012, 28: 17778.
[13] Wu J, Lin W F, Wang Z, Chen S F, Chang Y. Langmuir, 2012, 28: 7436.
[14] Zhai X Y, Wang W, Wang C D, Wang Q, Liu W G. J. Mater. Chem., 2012, 22: 23576.
[15] Holmlin R E, Chen X X, Chapman R G, Takayama S, Whitesides G M. Langmuir, 2001, 17: 2841.
[16] Bernards M T, Cheng G, Zhang Z, Chen S F, Jiang S Y. Macromolecules, 2008, 41: 4216.
[17] Chen S F, Jiang S Y. Adv. Mater., 2008, 20: 335.
[18] Jiang S Y, Cao Z Q. Adv. Mater., 2010, 22: 920.
[19] Iwasaki Y, Ishihara K. Anal. Bioanal. Chem., 2005, 381: 534.
[20] Matsuno R, Ishihara K. Nano Today, 2011, 6: 61.
[21] Garcia K P, Zarschler K, Barbaro L, Barreto J A, O'Malley W, Spiccia L, Stephan H, Graham B. Small, DOI: 10.1002/smll.201303540.
[22] Boisselier E, Astruc D. Chem. Soc. Rev., 2009, 38: 1759.
[23] Qiao R R, Yang C H, Gao M Y. J. Mater. Chem., 2009, 19: 6274.
[24] Blaszykowski C, Sheikh S, Thompson M. Chem. Soc. Rev., 2012, 41: 5599.
[25] Kim S T, Saha K, Kim C, Rotello V M. Acc. Chem. Res., 2013, 46: 681.
[26] Choi H S, Liu W, Misra P, Tanaka E, Zimmer J P, Itty Ipe B, Bawendi M G, Frangioni J V. Nat. Biotechnol., 2007, 25: 1165.
[27] Rosen J E, Gu F X. Langmuir, 2011, 27: 10507.
[28] Liu W H, Choi H S, Zimmer J P, Tanaka E, Frangioni J V, Bawendi M. J. Am. Chem. Soc., 2007, 129: 14530.
[29] Breus V V, Heyes C D, Tron K, Nienhaus G U. ACS Nano, 2009, 3: 2573.
[30] Chung Y C, Chiu Y H, Wu Y W, Tao Y T. Biomaterials, 2005, 26: 2313.
[31] Chung Y C, Chen I H, Chen C J. Biomaterials, 2008, 29: 1807.
[32] Jin Q, Xu J P, Ji J, Shen J C. Chem. Commun., 2008, 3058.
[33] Zhou W B, Shao J Y, Jin Q, Wei Q S, Tang J G, Ji J. Chem. Commun., 2010, 46: 1479.
[34] Zhou W B, Liu X S, Ji J. J. Mater. Chem., 2012, 22: 13969.
[35] Ohyanagi T, Nagahori N, Shimawaki K, Hinou H, Yamashita T, Sasaki A, Jin T, Iwanaga T, Kinjo M, Nishimura S. J. Am. Chem. Soc., 2011, 133: 12507.
[36] Liu X S, Zhu H G, Jin Q, Zhou W B, Colvin V L, Ji J. Adv. Healthcare Mater., 2013, 2: 352.
[37] Muro E, Pons T, Lequeux N, Fragola A, Sanson N, Lenkei Z, Dubertret B. J. Am. Chem. Soc., 2010, 132: 4556.
[38] Aldeek F, Muhammed M A H, Palui G, Zhan N Q, Mattoussi H. ACS Nano, 2013, 7: 2509.
[39] Zhan N Q, Palui G, Grise H, Tang H L, Alabugin I, Mattoussi H. ACS Appl. Mater. Interfaces, 2013, 5: 2861.
[40] Estephan Z G, Jaber J A, Schlenoff J B. Langmuir, 2010, 26: 16884.
[41] Estephan Z G, Hariri H H, Schlenoff J B. Langmuir, 2013, 29: 2572.
[42] Wei H, Insin N, Lee J, Han H S, Cordero J M, Liu W H, Bawendi M G. Nano Lett., 2012, 12: 22.
[43] Wei H, Bruns O T, Chen O, Bawendi M G. Integr. Biol., 2013, 5: 108.
[44] Zhou Z J, Wang L R, Chi X Q, Bao J F, Yang L J, Zhao W X, Chen Z, Wang X M, Chen X Y, Gao J H. ACS Nano, 2013,7: 3287.
[45] Kim C K, Ghosh P, Pagliuca C, Zhu Z J, Menichetti S, Rotello V M. J. Am. Chem. Soc., 2009, 131: 1360.
[46] Agasti S S, Chompoosor A, You C C, Ghosh P, Kim C K, Rotello V M. J. Am. Chem. Soc., 2009, 131: 5728.
[47] Yang W, Zhang L, Wang S L, White A D, Jiang S Y. Biomaterials, 2009, 30: 5617.
[48] Zhang L, Xue H, Gao C, Carr L, Wang J, Chu B, Jiang S. Biomaterials, 2010, 31, 6582.
[49] Yuan J J, Armes S P, Takabayashi Y, Prassides K, Leite C A P, Galembeck F, Lewis A L. Langmuir, 2006, 22: 10989.
[50] Yuan J J, Schmid A, Armes S P, Lewis A L. Langmuir, 2006, 22: 11022.
[51] Giovanelli E, Muro E, Sitbon G, Hanafi M, Pons T, Dubertret B, Lequeux N. Langmuir, 2012, 28: 15177.
[52] Chen X J, Lawrence J, Parelkar S, Emrick T. Macromolecules, 2013, 46: 119.
[53] Liu X S, Huang H Y, Liu G Y, Zhou W B, Chen Y J, Jin Q, Ji J. Nanoscale, 2013,5: 3982.
[54] Ma H, Hyun J, Stiller P, Chilkoti A. Adv. Mater., 2004, 16: 338.
[55] Huang C J, Brault N D, Li Y T, Yu Q M, Jiang S Y. Adv. Mater., 2012, 24: 1834.
[56] Jia G W, Cao Z Q, Xue H, Xu Y S, Jiang S Y. Langmuir, 2009, 25: 3196.
[57] Yang W, Liu S J, Bai T, Keefe A J, Zhang L, Ella-Menye J R, Li Y T, Jiang S Y. Nano Today, 2014, 9: 10.
[58] Zhang X A, Lin W F, Chen S F, Xu H, Gu H C. Langmuir, 2011, 27: 13669.
[59] Kataoka K, Harada A, Nagasaki Y. Adv. Drug Delivery Rev., 2001, 47: 113.
[60] Larson N, Ghandehari H. Chem. Mater., 2012, 24: 840.
[61] Du J Z, Tang Y Q, Lewis A L, Armes S P. J. Am. Chem. Soc., 2005, 127: 17982.
[62] Pearson R T, Warren N J, Lewis A L, Armes S P, Battaglia G. Macromolecules, 2013, 46: 1400.
[63] Sugihara S, Blanazs A, Armes S P, Ryan A J, Lewis A L. J. Am. Chem. Soc., 2011, 133: 15707.
[64] Massignani M, LoPresti C, Blanazs A, Madsen J, Armes S P, Lewis A L, Battaglia G. Small, 2009, 5: 2424.
[65] Ukawa M, Akita H, Masuda T, Hayashi Y, Konno T, Ishihara K, Harashima H. Biomaterials, 2010, 31: 6355.
[66] Goda T, Goto Y, Ishihara K. Biomaterials, 2010, 31: 2380.
[67] Tu S, Chen Y W, Qiu Y B, Zhu K, Luo X L. Macromol. Biosci., 2011, 11: 1416.
[68] Xu J P, Ji J, Chen W D, Shen J C. J. Control. Release, 2005, 107: 502.
[69] Liu G Y, Jin Q, Liu X S, Lv L P, Chen C J, Ji J. Soft Matter, 2011, 7: 662.
[70] Wang H B, Xu F M, Wang Y, Liu X S, Jin Q, Ji J. Polym. Chem., 2013, 4: 3012.
[71] Cao Z Q, Yu Q M, Xue H, Cheng G, Jiang S Y. Angew. Chem. Int. Ed., 2010, 49: 3771.
[72] Zhang S Y, Zou J, Zhang F W, Elsabahy M, Felder S E, Zhu J H, Pochan D J, Wooley K L. J. Am. Chem. Soc., 2012, 134: 18467.
[73] Cao J, Xiu K M, Zhu K, Chen Y W, Luo X L. J. Biomed. Mater. Res., Part A, 2012, 100: 2079.
[74] Cao J, Lu A J, Li C L, Cai M T, Chen Y W, Li S, Luo X L. Colloids Surf., B, 2013, 112: 35.
[75] Zhai S Y, Ma Y H, Chen Y Y, Li D, Cao J, Liu Y J, Cai M T, Xie X X, Chen Y W, Luo X L. Polym. Chem., 2014, 5: 1285.
[76] Kratz F, Müller I A, Ryppa C, Warnecke A. ChemMedChem, 2007, 3: 20.
[77] Lee E S, Na K, Bae Y H. J. Control. Release, 2003, 91: 103.
[78] Bae Y, Fukushima S, Harada A, Kataoka K. Angew. Chem. Int. Ed., 2003, 42: 4640.
[79] Bae Y, Nishiyama N, Fukushima S, Koyama H, Yasuhiro M, Kataoka K. Bioconjugate Chem., 2005, 16: 122.
[80] Meng F H, Zhong Z Y, Feijen J. Biomacromolecules, 2009, 10: 197.
[81] Joralemon M J, McRae S, Emrick T. Chem. Commun., 2010, 46: 1377.
[82] Chen X J, McRae S, Parelkar S, Emrick T. Bioconjugate Chem., 2009, 20: 2331.
[83] McRae Page S, Martorella M, Parelkar S, Kosif I, Emrick T. Mol. Pharm., 2013, 10: 2684.
[84] Chen X J, Parelkar S S, Henchey E, Schneider S, Emrick T. Bioconjugate Chem., 2012, 23: 1753.
[85] McRae Page S, Henchey E, Chen X J, Schneider S, Emrick T. Mol. Pharm., 2014, 11: 1715.
[86] Wang H B, Xu F M, Li D D, Liu X S, Jin Q, Ji J. Polym. Chem., 2013, 4: 2004.
[87] Wang Y, Wang H B, Chen Y J, Liu X S, Jin Q, Ji J. Chem. Commun., 2013, 49: 7123.
[88] Liu X S, Huang H Y, Jin Q, Ji J. Langmuir, 2011, 27: 5242.
[89] Liu X S, Jin Q, Ji Y, Ji J. J. Mater. Chem., 2012, 22: 1916.
[90] Bonitatibus P J, Torres A S, Kandapallil B, Lee B D, Goddard G D, Colborn R E, Marino M E. ACS Nano, 2012, 6: 6650.
[91] Yang H, Heng X P, Hu J W. RSC Adv., 2012, 2: 12648.
[92] Pillai P P, Huda S, Kowalczyk B, Grzybowski B A. J. Am. Chem. Soc., 2013, 135: 6392.
[93] Liu X S, Chen Y J, Li H, Huang N, Jin Q, Ren K F, Ji J. ACS Nano, 2013, 7: 6244.
[94] Mi L, Bernards M T, Cheng G, Yu Q, Jiang S Y. Biomaterials, 2010, 31: 2919.
[95] Xu M, Zhao Y F, Feng M. Langmuir, 2012, 28: 11310.
[96] Li J G, Wang T, Wu D L, Zhang X Q, Yan J T, Du S, Guo Y F, Wang J T, Zhang A F. Biomacromolecules, 2008, 9: 2670.
[97] Huang Y, Tang Z H, Zhang X F, Yu H Y, Sun Y H, Pang X, Chen X S. Biomacromolecules, 2013, 14: 2023.
[98] Yuan Y Y, Mao C Q, Du X J, Du J Z, Wang F, Wang J. Adv. Mater., 2012, 24: 5476.
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