苯丙氨酸二肽类分子自组装:分子设计、结构调控与材料应用
赵君1, 黄仁亮*2, 齐崴*1,3, 王跃飞1, 苏荣欣1,3, 何志敏1
化学进展 ›› 2014, Vol. 26 ›› Issue (09) :1445-1459
苯丙氨酸二肽类分子自组装:分子设计、结构调控与材料应用
Self-Assembly of Diphenylalanine Based Peptides:Molecular Design, Structural Control and Applications
近年来,苯丙氨酸二肽类分子的自组装研究受到了广泛关注,已成为超分子化学、生物材料科学研究的前沿领域之一。苯丙氨酸二肽类纳米组装体因具有结构多样、易功能化以及良好的生物相容性等优点,在纳米制造、组织修复等方面展示出巨大的应用潜力。本文从分子设计、组装结构调控与材料应用三个层次系统综述了苯丙氨酸二肽类分子自组装的研究进展。首先总结了苯丙氨酸二肽类分子的修饰改性,包括乙酰基、芳香环、氨基酸、短肽等基团。然后,重点介绍了苯丙氨酸二肽类分子自组装的调控策略和方法,如溶剂、界面、气相、多组分共组装和酶催化组装。最后,介绍了苯丙氨酸二肽类自组装材料在纳米材料合成、传感检测、药物传递及组织修复等方面的应用现状,并分析了该领域今后的发展方向。
The supramolecular self-assembly of diphenylalanine(FF)-based peptides have been the focus of considerable research in the field of supramolecular chemistry and biomaterials over the past few years. Due to the structural diversity, facile functionalization and excellent biocompatibility, the diphenylalanine-based assemblies are extremely attractive as building blocks for various applications such as nanofabrication and tissue engineering. This review aims to introduce the recent advances in the self-assembly of diphenylalanine-based peptides, from the molecular design, structural control and applications. Specifically, we summarize the diphenylalanine-based peptides with different chemical groups, such as acetyl, aromatic ring, amino acid, and short peptides. Meanwhile, we highlight the various strategies and methods for controlling the self-assembly behavior and structure of assemblies, including solvent, interface, vapor, co-assembly and enzymatic assembly. Moreover, we introduce the applications of the diphenylalanine-based nanomaterials, such as the templates for nanomaterials fabrication, elements in sensors, carriers for drug delivery and scaffolds for tissue engineering & regeneration. In addition, the problems existed in this field and the key issues for further research were also discussed in this review.
Contents
1 Introduction
2 Molecular design of FF-based peptides
3 Structural control of FF-based assemblies
3.1 pH and temperature
3.2 Solvents
3.3 Interfaces
3.4 Vapors
3.5 Co-assembly
3.6 Enzymatic self-assembly
4 Applications of FF-based nanomaterials
4.1 Nanofabrication
4.2 Sensors
4.3 Drug delivery
4.4 Tissue engineering and regeneration
4.5 Other applications
5 Conclusion and outlook
苯丙氨酸二肽
diphenylalanine
[1] Yan X, Zhu P, Li J. Chem. Soc. Rev., 2010, 39: 1877.
[2] Gao X Y, Matsui H. Adv. Mater., 2005, 17: 2037.
[3] Scanlon S, Aggeli A. Nano Today, 2008, 3: 22.
[4] Yang Y, Khoe U, Wang X, Akihiro H, Hidenori Y, Zhang S. Nano Today, 2009, 4: 193.
[5] 黄仁亮(Huang R L), 齐崴(Qi W), 姜楠(Jiang N), 苏荣欣(Su R X), 何志敏(He Z M). 化学进展(Progress in Chemistry), 2010, 22: 2328.
[6] 孟庆斌(Meng Q B), 刘克良(Liu K L). 化学进展(Progress in Chemistry), 2009, 21: 2411.
[7] Gazit E. Chem. Soc. Rev., 2007, 36: 1263.
[8] Luo Z, Zhang S. Chem. Soc. Rev., 2012, 41: 4736.
[9] Raeburn J, Cardoso A Z, Adams D J. Chem. Soc. Rev., 2013, 42: 5143.
[10] Reches M, Gazit E. Science, 2003, 300: 625.
[11] Yang Z, Liang G, Xu B. Acc. Chem. Res., 2008, 41: 315.
[12] Wang Y F, Huang R L, Qi W, Wu Z J, Su R X, He Z M. Nanotechnology, 2013, 24.
[13] Huang R L, Qi W, Su R X, Zhao J, He Z M. Soft Matter, 2011, 7: 6418.
[14] Huang R, Wu S, Li A, Li Z. J. Mater. Chem. A, 2014, 2: 1672.
[15] Wang Y, Qi W, Huang R, Su R, He Z. RSC Adv., 2014, 4: 15340.
[16] Huang R L, Su R X, Qi W, Zhao J, He Z M. Nanotechnology, 2011, 22: 7.
[17] Huang R, Qi W, Feng L, Su R, He Z. Soft Matter, 2011, 7: 6222.
[18] Yan X, He Q, Wang K, Duan L, Cui Y, Li J. Angew. Chem.-Int. Edit., 2007, 46: 2431.
[19] Song Y, Challa S R, Medforth C J, Qiu Y, Watt R K, Pena D, Miller J E, van Swol F, Shelnutt J A. Chem. Commun., 2004, 1044.
[20] Gupta M, Bagaria A, Mishra A, Mathur P, Basu A, Ramakumar S, Chauhan V S. Adv. Mater., 2007, 19: 858.
[21] Vegners R, Shestakova I, Kalvinsh I, Ezzell R M, Janmey P A. J. Pept. Sci., 1995, 1: 371.
[22] Ryu J, Park C B. Adv. Mater., 2008, 20: 3754.
[23] Yan X H, Cui Y, He Q, Wang K W, Li J B. Chem. Mater., 2008, 20: 1522.
[24] Su Y, Yan X H, Wang A H, Fei J B, Cui Y, He Q, Li J B. J. Mater. Chem., 2010, 20: 6734.
[25] Reches M, Gazit E. Phys. Biol., 2006, 3: S10.
[26] Adler-Abramovich L, Kol N, Yanai I, Barlam D, Shneck R Z, Gazit E, Rousso I. Angew. Chem.-Int. Edit., 2010, 49: 9939.
[27] Amdursky N, Molotskii M, Gazit E, Rosenman G. Appl. Phys. Lett., 2009, 94: 261907.
[28] Reches M, Gazit E. Nano Lett., 2004, 4: 581.
[29] Reches M, Gazit E. Isr. J. Chem., 2005, 45: 363.
[30] Jayawarna V, Smith A, Gough J E, Ulijn R V. Biochem. Soc. Trans., 2007, 35: 535.
[31] Kuang Y, Du X, Zhou J, Xu B. Adv. Healthcare Mater., 2014: doi: 10.1002/adhm.201300645.
[32] Smith A M, Williams R J, Tang C, Coppo P, Collins R F, Turner M L, Saiani A, Ulijn R V. Adv. Mater., 2008, 20: 37.
[33] Mahler A, Reches M, Rechter M, Cohen S, Gazit E. Adv. Mater., 2006, 18: 1365.
[34] Orbach R, Adler-Abramovich L, Zigerson S, Mironi-Harpaz I, Seliktar D, Gazit E. Biomacromolecules, 2009, 10: 2646.
[35] Yang Z M, Xu K M, Guo Z F, Guo Z H, Xu B. Adv. Mater., 2007, 19: 3152.
[36] Williams R J, Smith A M, Collins R, Hodson N, Das A K, Ulijn R V. Nat. Nanotechnol., 2009, 4: 19.
[37] Chronopoulou L, Lorenzoni S, Masci G, Dentini M, Togna A R, Togna G, Bordi F, Palocci C. Soft Matter, 2010, 6: 2525.
[38] Yang Z, Liang G, Guo Z, Guo Z, Xu B. Angew. Chem.-Int. Edit., 2007, 46: 8216.
[39] Li J, Gao Y, Kuang Y, Shi J, Du X, Zhou J, Wang H, Yang Z, Xu B. J. Am. Chem. Soc., 2013, 135: 9907.
[40] Yang Z M, Liang G L, Wang L, Xu B. J. Am. Chem. Soc., 2006, 128: 3038.
[41] Zhou J, Du X, Gao Y, Shi J, Xu B. J. Am. Chem. Soc., 2014, 136: 2970.
[42] Roy S, Banerjee A. Soft Matter, 2011, 7: 5300.
[43] Sun Z, Li Z, He Y, Shen R, Deng L, Yang M, Liang Y, Zhang Y. J. Am. Chem. Soc., 2013, 135: 13379.
[44] Kim J, Han T H, Kim Y I, Park J S, Choi J, Churchill D G, Kim S O, Ihee H. Adv. Mater., 2010, 22: 583.
[45] Kumaraswamy P, Lakshmanan R, Sethuraman S, Krishnan U M. Soft Matter, 2011, 7: 2744.
[46] Tang C, Smith A M, Collins R F, Ulijn R V, Saiani A. Langmuir, 2009, 25: 9447.
[47] Jayawarna V, Ali M, Jowitt T A, Miller A F, Saiani A, Gough J E, Ulijn R V. Adv. Mater., 2006, 18: 611.
[48] Na N, Mu X Y, Liu Q L, Wen J Y, Wang F F, Ouyang J. Chem. Commun., 2013, 49: 10076.
[49] Gorbitz C H. Chem. Commun., 2006, 2332.
[50] Yan X, Li J, Möhwald H. Adv. Mater., 2011, 23: 2796.
[51] Park J S, Han T H, Oh J K, Kim S O. Macromolecular Chemistry and Physics, 2009, 210: 1283.
[52] Ryu J, Lim S Y, Park C B. Adv. Mater., 2009, 21: 1577.
[53] Amdursky N, Molotskii M, Gazit E, Rosenman G. J. Am. Chem. Soc., 2010, 132: 15632.
[54] Han T H, Kim J, Park J S, Park C B, Ihee H, Kim S O. Adv. Mater., 2007, 19: 3924.
[55] Zhu P, Yan X, Su Y, Yang Y, Li J. Chemistry, 2010, 16: 3176.
[56] Reches M, Gazit E. Nat. Nanotechnol., 2006, 1: 195.
[57] Du M, Zhu P, Yan X, Su Y, Song W, Li J. Chemistry, 2011, 17: 4238.
[58] Ryu J, Park C B. Angew. Chem.-Int. Edit., 2009, 48: 4820.
[59] Ryu J, Kim S W, Kang K, Park C B. ACS Nano, 2010, 4: 159.
[60] Ryu J, Park C B. Biotechnol. Bioeng., 2010, 105: 221.
[61] Ryu J, Park C B. Chem. Mater., 2008, 20: 4284.
[62] Adler-Abramovich L, Aronov D, Beker P, Yevnin M, Stempler S, Buzhansky L, Rosenman G, Gazit E. Nat. Nanotechnol., 2009, 4: 849.
[63] Lee J S, Yoon I, Kim J, Ihee H, Kim B, Park C B. Angew. Chem.-Int. Edit., 2011, 50: 1164.
[64] Rissanou A N, Georgilis E, Kasotakis E, Mitraki A, Harmandaris V. J. Phys. Chem. B, 2013, 117: 3962.
[65] Yan X, Su Y, Li J, Früh J, Möhwald H. Angew. Chem.-Int. Edit., 2011, 50: 11186.
[66] Hendler N, Sidelman N, Reches M, Gazit E, Rosenberg Y, Richter S. Adv. Mater., 2007, 19: 1485.
[67] Capito R M, Azevedo H S, Velichko Y S, Mata A, Stupp S I. Science, 2008, 319: 1812.
[68] Rozkiewicz D I, Myers B D, Stupp S I. Angew. Chem.-Int. Edit., 2011, 50: 6324.
[69] Yuran S, Razvag Y, Reches M. ACS Nano, 2012, 6: 9559.
[70] Maity S, Nir S, Reches M. J. Mater. Chem. B, 2014, 2: 2583.
[71] Zou Q, Zhang L, Yan X, Wang A, Ma G, Li J, Möhwald H, Mann S. Angew. Chem.-Int. Edit., 2014, 53: 2366.
[72] Kim J H, Ryu J, Park C B. Small, 2011, 7: 718.
[73] Kozhevnikov I V. Chem. Rev., 1998, 98: 171.
[74] Rhule J T, Hill C L, Judd D A, Schinazi R F. Chem. Rev., 1998, 98: 327.
[75] Sadakane M, Steckhan E. Chem. Rev., 1998, 98: 219.
[76] Yan X, Zhu P, Fei J, Li J. Adv. Mater., 2010, 22: 1283.
[77] Ma H, Fei J, Cui Y, Zhao J, Wang A, Li J. Chem. Commun., 2013, 49: 9956.
[78] Zhou M, Smith A M, Das A K, Hodson N W, Collins R F, Ulijn R V, Gough J E. Biomaterials, 2009, 30: 2523.
[79] Berillo D, Mattiasson B, Galaev I Y, Kirsebom H. J. Colloid Interface Sci., 2012, 368: 226.
[80] Pont G, Chen L, Spiller D G, Adams D J. Soft Matter, 2012, 8: 7797.
[81] Liu Y, Cheng Y, Wu H C, Kim E, Ulijn R V, Rubloff G W, Bentley W E, Payne G F. Langmuir, 2011, 27: 7380.
[82] Fleming S, Debnath S, Frederix P W J M, Hunt N T, Ulijn R V. Biomacromolecules, 2014, 15: 1171.
[83] Abul-Haija Y M, Roy S, Frederix P W J M, Javid N, Jayawarna V, Ulijn R V. Small, 2014, 10: 973.
[84] Yang Z, Gu H, Fu D, Gao P, Lam J K, Xu B. Adv. Mater., 2004, 16: 1440.
[85] Yang Z, Xu B. Chem. Commun., 2004, 2424.
[86] Toledano S, Williams R J, Jayawarna V, Ulijn R V. J. Am. Chem. Soc., 2006, 128: 1070.
[87] Hughes M, Xu H, Frederix P W J M, Smith A M, Hunt N T, Tuttle T, Kinloch I A, Ulijn R V. Soft Matter, 2011, 7: 10032.
[88] Qin X, Xie W, Tian S, Cai J, Yuan H, Yu Z, Butterfoss G L, Khuong A C, Gross R A. Chem. Commun., 2013, 49: 4839.
[89] Das A K, Collins R, Ulijn R V. Small, 2008, 4: 279.
[90] Yang Z, Ho P L, Liang G, Chow K H, Wang Q, Cao Y, Guo Z, Xu B. J. Am. Chem. Soc., 2006, 129: 266.
[91] Gao Y, Shi J, Yuan D, Xu B. Nat. Commun., 2012, 3: 1033.
[92] Gao J, Wang H, Wang L, Wang J, Kong D, Yang Z. J. Am. Chem. Soc., 2009, 131: 11286.
[93] Huaimin W, Chunhua R, Zhijian S, Ling W, Xuemei C, Zhimou Y. Nanotechnology, 2010, 21: 225606.
[94] Huaimin W, Zhihong W, Donghui S, Jingyu W, Jie G, Ling W, Deling K, Zhimou Y. Nanotechnology, 2010, 21: 155602.
[95] Wang H, Shi Y, Wang L, Yang Z. Chem. Soc. Rev., 2013, 42: 891.
[96] Zhang X, Chu X, Wang L, Wang H, Liang G, Zhang J, Long J, Yang Z. Angew. Chem.-Int. Edit., 2012, 51: 4388.
[97] Wang H, Wang Z, Yi X, Long J, Liu J, Yang Z. Chem. Commun., 2011, 47: 955.
[98] Ulijn R V. J. Mater. Chem., 2006, 16: 2217.
[99] Gao Y, Yang Z, Kuang Y, Ma M L, Li J, Zhao F, Xu B. Biopolymers, 2010, 94: 19.
[100] Lakshmanan A, Zhang S, Hauser C A. Trends Biotechnol., 2012, 30: 155.
[101] Han T H, Lee W J, Lee D H, Kim J E, Choi E Y, Kim S O. Adv. Mater., 2010, 22: 2060.
[102] Ryu J, Kim S W, Kang K, Park C B. Adv. Mater., 2010, 22: 5537.
[103] Han T H, Oh J K, Park J S, Kwon S H, Kim S W, Kim S O. J. Mater. Chem., 2009, 19: 3512.
[104] Han T H, Moon H S, Hwang J O, Seok S I, Im S H, Kim S O. Nanotechnology, 2010, 21: 185601.
[105] Andersen K B, Castillo-Leon J, Bakmand T, Svendsen W E. Jpn. J. Appl. Phys., 2012, 51.
[106] Li P, Chen X, Yang W. Langmuir, 2013, 29: 8629.
[107] McQuade D T, Pullen A E, Swager T M. Chem. Rev., 2000, 100: 2537.
[108] Gerard M, Chaubey A, Malhotra B D. Biosens. Bioelectron., 2002, 17: 345.
[109] Yemini M, Reches M, Rishpon J, Gazit E. Nano Lett., 2005, 5: 183.
[110] Yemini M, Reches M, Gazit E, Rishpon J. Anal. Chem., 2005, 77: 5155.
[111] Adler-Abramovich L, Badihi-Mossberg M, Gazit E, Rishpon J. Small, 2010, 6: 825.
[112] Sasso L, Vedarethinam I, Emneus J, Svendsen W E, Castillo-Leon J. J. Nanosci. Nanotechnol., 2012, 12: 3077.
[113] Amdursky N, Molotskii M, Aronov D, Adler-Abramovich L, Gazit E, Rosenman G. Nano Lett., 2009, 9: 3111.
[114] Amdursky N, Gazit E, Rosenman G. Adv. Mater., 2010, 22: 2311.
[115] Kim J H, Lim S Y, Nam D H, Ryu J, Ku S H, Park C B. Biosens. Bioelectron., 2011, 26: 1860.
[116] Yan X, Cui Y, Qi W, Su Y, Yang Y, He Q, Li J. Small, 2008, 4: 1687.
[117] Liang G, Yang Z, Zhang R, Li L, Fan Y, Kuang Y, Gao Y, Wang T, Lu W W, Xu B. Langmuir, 2009, 25: 8419.
[118] Silva R F, Araujo D R, Silva E R, Ando R A, Alves W A. Langmuir, 2013, 29: 10205.
[119] Wang X M, Horii A, Zhang S G. Soft Matter, 2008, 4: 2388.
[120] Palmer L C, Newcomb C J, Kaltz S R, Spoerke E D, Stupp S I. Chem. Rev., 2008, 108: 4754.
[121] Lee J S, Ryu J, Park C B. Soft Matter, 2009, 5: 2717.
[122] Handelman A, Lavrov S, Kudryavtsev A, Khatchatouriants A, Rosenberg Y, Mishina E, Rosenman G. Adv. Optical Mater., 2013, 1: 875.
[123] Kim J H, Lee M, Lee J S, Park C B. Angew. Chem. Int. Edit., 2012, 51: 517.
[124] Adler-Abramovich L, Gazit E. J. Pept. Sci., 2008, 14: 217.
[125] Kuang Y, Gao Y, Xu B. Chem. Commun., 2011, 47: 12625.
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