聚天冬酰胺衍生物药物/基因载体的合成和应用

付开乔; 张光彦; 蒋序林

doi:10.7536/PC160212

化学进展 ›› 2016, Vol. 28 ›› Issue (8) :1196-1206 DOI: 10.7536/PC160212

综述与评论

扫码查看或转发全文

聚天冬酰胺衍生物药物/基因载体的合成和应用

^1*

作者信息 +

Synthesis and Application of Polyaspartamide Derivatives for Drug/Gene Delivery

Fu Kaiqiao^1*, Zhang Guangyan^1*, Jiang Xulin²

Author information +

文章历史 +

摘要

与碳链聚合物相比，聚氨基酸类高分子由于其生物相容性好、可降解代谢、毒副作用低等优点而被广泛应用于生物医药领域。基于天冬氨酸的聚天冬酰胺衍生物，其合成方法简单多样，通过对其修饰改性可制备出具有各种环境响应性（温度、pH和还原敏感）的智能高分子，得到高效、低毒的药物/基因载体，实现可控释放、增强疗效、降低药物副作用的目的。本文重点介绍了聚天冬酰胺衍生物（特别是刺激响应性聚天冬酰胺衍生物）的合成改性方法、及其在药物和基因载体领域最新的研究进展，并对其发展前景进行了展望。

Abstract

Compared with carbon-chain polymers, poly(amino acid)s have attracted much attentions in biomedical and pharmaceutical fields because of their good biocompatibility, biodegradability and nontoxicity. Polyaspartamide derivatives based on L-aspartic acid not only can be easily synthesized, but also can be further modified with various structures to prepare intelligent material with different stimuli-responsivity (such as temperature, pH and redox), resulting in controlled release, enhancement of therapeutic effects and reduction of the drug side effects. In this review, the different synthetic strategies for preparing polyaspartamide derivatives and the up-to-date developments on polyaspartamide derivatives for drug and gene delivery systems are summarized. Besides, the future perspectives of polyaspartamide derivatives are discussed.

Contents
1 Introduction
2 Synthesis of polyaspartamide derivatives
2.1 Aminolysis reaction of PSI
2.2 ROP of N-carboxyanhydride
3 Application of polyaspartamide derivatives
3.1 Drug delivery
3.2 Gene delivery
4 Outlook

Graphical abstract

关键词

聚天冬酰胺 / 药物载体 / 基因载体 / 刺激响应性

Key words

polyaspartamide derivatives / drug delivery / gene delivery / stimuli-responsivity

引用本文

引用格式 ▾

付开乔, 张光彦, 蒋序林. 聚天冬酰胺衍生物药物/基因载体的合成和应用[J]. 化学进展, 2016, 28(8): 1196-1206 DOI:10.7536/PC160212

Fu Kaiqiao, Zhang Guangyan, Jiang Xulin. Synthesis and Application of Polyaspartamide Derivatives for Drug/Gene Delivery[J]. Progress in Chemistry, 2016, 28(8): 1196-1206 DOI:10.7536/PC160212

登录浏览全文

4963

注册一个新账户忘记密码

参考文献

原文顺序 | 出版日期 | 本文引用

[1] Prabhakar U, Maeda H, Jain R K, Sevick-Muraca E M, Zamboni W, Farokhzad O C, Barry S T, Gabizon A, Grodzinski P, Blakey D C. Cancer Res., 2013, 73:2412.
[2] Xu L, Anchordoquy T. J. Pharm. Sci-US, 2011, 100:38.
[3] Lorenzer C, Dirin M, Winkler A M, Baumann V, Winkler J. J. Control. Release, 2015, 203:1.
[4] Sun H L, Meng F H, Dias A A, Hendriks M, Feijen J, Zhong Z Y. Biomacromolecules, 2011, 12:1937.
[5] Khan W, Muthupandian S, Farah S, Kumar N, Domb A J. Macromol. Biosci., 2011, 11:1625.
[6] Hamaguchi T, Matsumura Y, Suzuki M, Shimizu K, Goda R, Nakamura I, Nakatomi I, Yokoyama M, Kataoka K, Kakizoe T. Br. J. Cancer, 2005, 92, 1240.
[7] Kato K, Chin K, Yoshikawa T, Yamaguchi K, Tsuji Y, Esaki T, Sakai K, Kimura M, Hamaguchi T, Shimada Y, Matsumura Y, Ikeda R. Invest. New Drugs, 2012, 30:1621.
[8] Morille M, Passirani C, Vonarbourg A, Clavreul A, Benoit J P. Biomaterials, 2008, 29:3477.
[9] Tomida M, Nakato T, Matsunami S, Kakuchi T. Polymer, 1997, 38:4733.
[10] Nakato T, Kusuno A, Kakuchi T. J. Polym. Sci. Part A:Polym. Chem., 2000, 38:117.
[11] Moon J R, Kim M W, Kim D, Jeong J H, Kim J H. Colloid Polym. Sci., 2011, 289:63.
[12] Das P, Jana N R. RSC Adv., 2015, 5:33586.
[13] Seo K, Lee D S, Kim S C, Kim D. J. Nanosci Nanotechno., 2010, 10:6986.
[14] Seo K, Kim D. Acta Biomater., 2010, 6:2157.
[15] Liu D E, Han H, Lu H Q, Wu G L, Wang Y N, Ma J B, Gao H. RSC Adv., 2014, 4:37130.
[16] Bach Q V, Moon J R, Lee D S, Kim J H. J. Appl. Polym. Sci., 2008, 107:509.
[17] Tachibana Y, Kurisawa M, Uyama H, Kakuchi T, Kobayashi S. Chem. Commun., 2003, 1:106.
[18] Gu X, Wang J J, Liu X F, Zhao D P, Wang Y N, Gao H, Wu G L. Soft Matter, 2013, 9:7267.
[19] Lu C C, Wang X J, Wu G L, Wang J J, Wang Y N, Gao H, Ma J B. J. Biomed. Mater. Res. A, 2014, 102A:628.
[20] Licciardi M, Campisi M, Cavallaro G, Cervello M, Azzolina A, Giammona G. Biomaterials, 2006, 27:2066.
[21] Licciardi M, Cavallaro G, Di Stefano M, Fiorica C, Giammona G. Macromol. Biosci., 2011, 11:445.
[22] Sarpietro M G, Pitarresi G, Ottimo S, Giuffrida M C, Ognibene M C, Fiorica C, Giammona G, Castellit F. Mol. Pharm., 2011, 8:642.
[23] Ognibene M C, Rocco F, Craparo E F, Picone P, Ceruti M, Giammona G. Curr. Nanosci., 2011, 7:747.
[24] Fiorica C, Senior R A, Pitarresi G, Palumbo F S, Giammona G, Deshpande P, MacNeil S. Int. J. Pharm., 2011, 414:104.
[25] Matricardi P, Pitarresi G, Palumbo F S, Di Meo C, Albanese A, Coviello T, Cencetti C, Fiorica C, Giammona G. Macromol. Res. 2011, 19:1264.
[26] Licciardi M, Cavallaro G, Amato G, Fiorica C, Giammona G. React. Funct. Polym., 2012, 72:268.
[27] Scialabba C, Rocco F, Licciardi M, Pitarresi G, Ceruti M, Giammona G. Drug Deliv., 2012, 19:307.
[28] Piccionello A P, Pitarresi G, Pace A, Triolo D, Picone P, Buscemi S, Giammona G. J. Drug Target., 2012, 20:433.
[29] Pitarresi G, Fiorica C, Palumbo F S, Calascibetta F, Giammona G. J. Biomed. Mater. Res. A, 2012, 100A:1565.
[30] Cavallaro G, Triolo D, Licciardi M, Giammona G, Chirico G, Sironi L, Dacarro G, Dona A, Milanese C, Pallavicini P. Biomacromolecules, 2013, 14:4260.
[31] Pitarresi G, Fiorica C, Palumbo F S, Rigogliuso S, Ghersi G, Giammona G. J. Biomed. Mater. Res. A, 2014, 102A:1334.
[32] Sardo C, Nottelet B, Triolo D, Giammona G, Garric X, Lavigne J P, Cavallaro G, Coudane J. Biomacromolecules, 2014, 15:4351.
[33] Pavia F C, Carrubba V L, Brucato V, Palumbo F S, Giammona G. Mat. Sci. Eng. C-Mater., 2014, 41:301.
[34] Cavallaro G, Licciardi M, Amato G, Sardo C, Giammona G, Farra R, Dapas B, Grassi M, Grassi G. Int. J. Pharm., 2014, 466:246.
[35] Cavallaro G, Craparo E F, Sardo C, Lamberti G, Barba A A, Dalmoro A. Int. J. Pharm., 2015, 495:719.
[36] Fiorica C, Palumbo F S, Pitarresi G, Giorgi M, Calascibetta F, Giammona, G. J. Pharm. Pharmacol., 2015, 67:78.
[37] Craparo E F, Licciardi M, Conigliaro A, Palumbo F S, Giammona G, Alessandro R, De Leo G, Cavallaro G. Polymer, 2015, 70:257.
[38] Craparo E F, Porsio B, Mauro N, Giammona G, Cavallaro G. Macromol. Rapid Commun., 2015, 36:1409.
[39] Craparo E F, Porsio B, Bondi M L, Giammona G, Cavallaro G. Polym. Degrad. Stabil., 2015, 119:56.
[40] Paolino D, Licciardi M, Celia C, Giammona G, Fresta M, Cavallaro G. J. Mater. Chem. B, 2015, 3:250.
[41] Mandracchia D, Denora N, Franco M, Pitarresi G, Giammona G, Trapani G. J. Biomat. Sci.-Polym. E., 2011, 22:313.
[42] Thuy V T T, Lim C W, Park J H, Ahn C H, Kim D. J. Mater. Chem. B, 2015, 3:2978.
[43] Lee M, Jeong J, Kim D. Biomacromolecules, 2015, 16:136.
[44] Yu H, Sun J, Zhang Y T, Zhang G Y, Chu Y F, Zhuo R X, Jiang X L. J. Polym. Sci. Part A:Polym. Chem., 2015, 53:1387.
[45] Yu J H, Quan J S, Huang J, Wang C Y, Sun B, Nah J W, Cho M H, Cho C S. Acta Biomater., 2009, 5:2485.
[46] Zhang M, Liu M, Xue Y N, Huang S W, Zhuo R X. Bioconjugate Chem., 2009, 20:440.
[47] Jeon Y S, Bui Q T, An J H, Chung D J, Kim J H. Polym-Korea, 2014, 38:108.
[48] Heo S, Jeon Y S, Kim Y J, Kim S H, Kim J H. J. Coat. Technol. Res., 2013, 10:811.
[49] Mukaya H E, Neuse E W, van Zyl R L, Chen C T. J. Inorg. Organomet. Polym., 2015, 25:367.
[50] Sharma A, Srivastava A. Polym. Chem., 2013, 4:5119.
[51] 杨奇志(Yang Q Z), 刘佳(Liu J), 蒋序林(Jiang X L).化学进展(Progress in Chemistry), 2010, 22(12):2377.
[52] Huynh N T, Jeon Y S, Zrinyi M, Kim J H. Polym. Int., 2013, 62:266.
[53] Lai M H, Lee S, Smith C E, Kim K, Kong H. ACS Appl. Mater. Interfaces, 2014, 6:10821.
[54] Ali S A, Kazi I W, Rahman F. Desalination, 2015, 357:36.
[55] Habraken G J M, Wilsens K H R M, Koning C E, Heise A. Polym. Chem., 2011, 2:1322.
[56] Lu Y, Chau M, Boyle A J, Liu P, Niehoff A, Weinrich D, Reilly R M, Winnik M A. Biomacromolecules, 2012, 13:1296.
[57] Yang W X, Wang L L, Zhu H, Xu R W, Wu Y X. Chinese J. Polym. Sci., 2013, 31:1706.
[58] Chu Y F, Yu H, Zhang Y T, Zhang G Y, Ma Y Y, Zhuo R X, Jiang X L. J. Polym. Sci. Part A:Polym. Chem., 2014, 52:3346.
[59] Kim Y K, Singh B, Jiang H L, Park T E, Jiang T, Park I K, Cho M H, Kang S K, Choi Y J, Cho C S. Eur. J. Pharm. Sci., 2014, 51:165.
[60] Maeda Y, Pittella F, Nomoto T, Takemoto H, Nishiyama N, Miyata K, Kataoka K. Macromol. Rapid Commun., 2014, 35:1211.
[61] Arimura H, Ohya Y, Ouchi T. Macromol. Rapid Commun., 2004, 25:743.
[62] Arimura H, Ohya Y, Ouchi T. Biomacromolecules, 2005, 6:720.
[63] Peng T, Li Y, Ahn D, Kim B S, Lee D S. Macromol. Res., 2013, 21:400.
[64] Zeng X, Guo L, Ma L F. Colloid Polym. Sci., 2015, 293:319.
[65] Matsumura Y, Hamaguchi T, Ura T, Muro K, Yamada Y, Shimada Y, Shirao K, Okusaka T, Ueno H, Ikeda M, Watanabe N. Br. J. Cancer, 2004, 91:1775.
[66] Meo C D, Cilurzo F, Licciardi M, Scialabba C, Sabia R, Paolino D, Capitani D, Fresta M, Giammona G, Villani C, Matricardi P. Pharm. Res., 2015, 32:1557.
[67] 廖荣强(Liao R Q), 刘满塑(Liu M S), 廖霞俐(Liao X L), 杨波(Yang B). 化学进展(Progress in Chemistry), 2015, 27(1):2377.
[68] 梁嘉美(Liang J M), 冯岸超(Feng A C), 袁金颖(Yuan J Y). 化学进展(Progress in Chemistry), 2015, 27(5):533.
[69] Soga O, van Nostrum C F, Fens M, Rijcken C J F, Schiffelers R M, Storm G, Hennink W E. J. Control. Release, 2005, 103:341.
[70] Rijcken C J F, Hofman J W, van Zeeland F, Hennink W E, van Nostrum C F. J. Control. Release, 2007, 124:144.
[71] Ma Y Y, Jiang X L, Zhuo R X. Mater. Lett., 2014, 121:78.
[72] Ma Y Y, Jiang X L, Zhuo R X. J. Polym. Sci. Part A:Polym. Chem., 2013, 51:3917.
[73] Zhang G Y, Zhang Y T, Chu Y F, Ma Y Y, Zhuo R X, Jiang X L. J. Polym. Sci. Part A:Polym. Chem., 2015, 53:1296.
[74] Moon J R, Jeon Y S, Zrinyi M, Kim J H. Polym. Int., 2013, 62:1218.
[75] Seo K, Chung S W, Byun Y, Kim D. Int. J. Pharm., 2012, 424:26.
[76] Ma Y Y, Zhang G Y, Li L J, Yu H, Liu J, Wang C Q, Chu Y F, Zhuo R X, Jiang X L. J. Polym. Sci. Part A:Polym. Chem., 2016, 54:879.
[77] Harada M, Bobe L, Saito H, Shibata N, Tanaka R, Hayashi T, Kato Y. Cancer Sci., 2011, 102:192.
[78] Takahashi A, Yamamoto Y, Yasunaga M, Koga Y, Kuroda J, Takigahira M, Harada M, Saito H, Hayashi T, Kato Y, Kinoshita T, Ohkohchi N, Hyodo I, Matsumura Y. Cancer Sci., 2013, 104:920.
[79] Wang X J, Wu G L, Lu C C, Zhao W P, Wang Y N, Fan Y G, Gao H, Ma J B. Eur. J. Pharm. Sci., 2012, 47:256.
[80] Liu R, Zhang Y, Zhao X, Agarwal A, Mueller L J, Feng P. J. Am. Chem. Soc., 2010, 132:1500.
[81] Tang R, Ji W, Wang C. Macromol. Biosci., 2010, 10:192.
[82] Thambi T, Deepagan V G, Yoo C K, Park J H. Polymer, 2011, 52:4753.
[83] Lavignac N, Nicholls J, Ferruti P, Duncan R. Macromol. Biosci., 2008, 9:480.
[84] Zhu S, Hong M, Tang G, Qian L, Lin J, Jiang Y, Pei Y. Biomaterials, 2010, 31:1360.
[85] Jin Y, Song L, Su Y, Zhu L, Pang Y, Qiu F, Tong G, Yan D, Zhu B, Zhu X. Biomacromolecules, 2011, 12:3460.
[86] Kim E, Kim D, Jung H, Lee J, Paul S, Selvapalam N, Yang Y, Lim N, Park C G, Kim K. Angew. Chem. Int. Ed., 2010, 49:4405.
[87] Tang L Y, Wang Y C, Li Y, Du J Z, Wang J. Bioconjugate Chem., 2009, 20:1095.
[88] Takae S, Miyata K, Oba M, Ishii T, Nishiyama N, Itaka K, Yamasaki Y, Koyama H, Kataoka K. J. Am. Chem. Soc., 2008, 130:6001.
[89] Deng B, Ma P, Xie Y. Nanoscale, 2015, 7:12773.
[90] Gyarmati1 B, Vajna B, Némethy Á, László K, Szilágyi A. Macromol. Biosci., 2013, 13:633.
[91] Gyarmati1 B, Némethy Á, Szilágyi A. RSC Adv., 2014, 4:8764.
[92] Zheng C, Zhang X G, Sun L, Zhang Z P, Li C X. J. Mater. Sci. Mater. Med., 2013, 24:931.
[93] Chu Y F, Yu H, Ma Y Y, Zhang Y T, Chen W H, Zhang G Y, Wei H, Zhang X Z, Zhuo R X, Jiang X L. J. Polym. Sci. Part A:Polym. Chem., 2014, 52:1771.
[94] Tran B N, Bui Q T, Jeon Y S, Park H S, Kim J H. Polym. Bull., 2015, 72:2605.
[95] Guo X, Huang L. Acc. Chem. Res., 2012, 45:971.
[96] Godbey W T, Wu K K, Mikos A G. J. Control. Release, 1999, 60:149.
[97] Akinc A, Thomas M, Klibanov A M, Langer R. J. Gene Med., 2005, 7:657.
[98] Godbey W T, Wu K K, Mikos A G. J. Biomed. Mater. Res., 1999, 45:268.
[99] Zhang G Y, Liu J, Yang Q Z, Zhuo R, Jiang X L. Bioconjugate Chem., 2012, 23:1290.
[100] Liu J, Xu Y, Yang Q, Li C, Hennink W E, Zhuo R X. Acta Biomater., 2013, 9:7758.
[101] Feng T S, Dong X, Tian H Y, Lam M H W, Liang H J, Wei Y, Chen X S. J. Mater. Chem. B, 2014, 2:2725.
[102] Chen J, Dong X, Feng T S, Lin L, Guo Z P, Xia J L, Tian H Y, Chen X S. Acta Biomater., 2015, 26:45.
[103] Dou X B, Hu Y, Zhao N N, Xu F J. Biomaterials, 2014, 35:3015.
[104] Cavallaro G, Licciardi M, Scirè S, Giammona G. Nanomedicine, 2009, 4:291.
[105] Cavallaro G, Scirè S, Licciardi M, Ogris M, Wagner E, Giammona G. J. Control. Release, 2008, 131:54.
[106] Di Gioia S, Sardo C, Belgiovine G, Triolo D, d'Apolito M, Castellani S, Carbone A, Giardino I, Giammona G, Cavallaro G, Conese M. Int. J. Pharm., 2015, 491:359.
[107] Miyata K, Oba M, Nakanishi M, Fukushima S, Yamasaki Y, Koyama H, Nishiyama N, Kataoka K. J. Am. Chem. Soc., 2008, 130:16287.
[108] Uchida H, Miyata K, Oba M, Ishii T, Suma T, Itaka K, Nishiyama N, Kataoka K. J. Am. Chem. Soc., 2011, 133:15524.
[109] Uchida H, Itaka K, Nomoto T, Ishii T, Suma T, Ikegami M, Miyata K, Oba M, Nishiyama N, Kataoka K. J. Am. Chem. Soc., 2014, 136:12396.
[110] Kim H J, Miyata K, Nomoto T, Zheng M, Kim A, Liu X Y, Cabral H, Christie R J, Nishiyama N, Kataoka K. Biomaterials, 2014, 35:4548.
[111] Lee Y, Ishii T, Cabral H, Kim H J, Seo J H, Nishiyama N, Oshima H, Osada K, Kataoka K. Angew. Chem. Int. Ed., 2009, 48:5309.
[112] Lee Y, Miyata K, Oba M, Ishii T, Fukushima S, Han M, Koyama H, Nishiyama N, Kataoka K. Angew. Chem. Int. Ed., 2008, 47:5163.
[113] Gao H, Takemoto H, Chen Q, Naito M, Uchida H, Liu X Y, Miyata K, Kataoka K. Chem. Commun., 2015, 51:3158.
[114] Kim H J, Ishii A, Miyata K, Lee Y, Wu S R, Oba M, Nishiyama N, Kataoka K. J. Control. Release, 2010, 145:141.
[115] Itaka K, Ishii T, Hasegawa Y, Kataoka K. Biomaterials, 2010, 31:3707.
[116] Nomoto T, Fukushima S, Kumagai M, Machitani K, Arnida, Matsumoto Y, Oba M, Miyata K, Osada K, Nishiyama N, Kataoka K. Nat. Commun., 2014, 5:3545.