Self-assembly of Peptide Amphiphiles and Their Applications†

doi:10.7503/cjcu20140859

Abstract

Abstract:

Due to good biocompatibility, straight forward chemical modification and inherent molecular recognition, peptides have been very attractive biological building blocks for self-assembly. Amphiphilic peptides are of special interesting with the advantages of abundant molecular structures, unique structures of assemblies and special biological functions. In this work, the recent progress in the study and application of the self-assembly of amphiphilic peptides was reviewed. Several kinds of amphiphilic peptides were introduced. Moreover, the molecular structures of amphiphilic peptides, the behavior and mechanism of self-assembly, the structure and property of assemblies and their applications in nanotechnology and biomedical field were also demonstrated in detail.

Key words: Amphiphilic peptide, Self-assembly, Morphology, Nano structure, Biological functional material

CLC Number:

O631

TrendMD:

WANG Jianxun, QIN Siyong, CAI Tengteng, ZHANG Xianzheng, ZHUO Renxi. Self-assembly of Peptide Amphiphiles and Their Applications^†[J]. Chem. J. Chinese Universities, 2015, 36(2): 201.

Figures/Tables 8

Fig.1 Schematic illustration of the self-assembly of surfactant-like peptides into nano-structures[4,6] (A) Copyright from American Chemical Society; (B) copyight from the Royal Society of Chemistry.

Fig.2 Structural models of peptide amphiphiles proposed by Kunitake[15](A) and schematic illustration of the self-assembly of PAs[20](B) (A) Copyright from the Royal Society of Chemistry; (B) copyright from Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Fig.3 TEM images of quadruple helix fibers(A), single fibers[26](B), PA before(C) and after(D) photoirradiation[27] and cell survival and morphology of NPCs encapsulated in IKVAV gels[31](E1—E3) (A) Copyright from American Chemical Society; (B) copyright from Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; (C) copyright from American Association for the Advancement of Science. Cell survival determined by LIVE/DEAD cell assay at 1 d(E1), 7 d(E2) and 22 d(E3).

Fig.4 Schematic depiction of the formation of gold nanoparticle double helices facilitated by the self-assembling peptide(A), TEM images of left-handed gold nanoparticle double helices(B, C) and tomographic 3D reconstruction image of the double helices[35](D) Copyright from American Chemical Society.

Fig.5 Proposed hierarchical self-assembly mechanisms of CPs2(A) and CPs3(B)[48] Copyright from the Royal Society of Chemistry.

Fig.6 Complexes formation, internalization and cellular trafficking process of PA gene delivery[52](A) and schematic illustration of MENPs self-assembly of PA-DOX and the targeted release of DOX in tumor cells[53](B) (A) Copyright from Elsevier B.V; (B) copyright from American Chemical Society.

Fig.7 GG-C7-GG assembled into helical ribbons in pH=8 and GG-C7-GG assembled into tubule structures in pH=3(A) and proposed assembly mechanism[54](B) Copyright from American Chemical Society.

Fig.8 Schemaic representation and TEM images of nanofibril formed by 2C12-Lys-Aβ(12—17)(a), twisted ribbon formed by C12-Aβ(11—17)-C12 at low pH(b), lamellae formed by C12-Aβ(11—17)-C12 at high pH(c)[73](A), TEM image of neutral(C12CCP)n/DNA complexes(B) and pharmocokinetics and biodistribution of various DNA complexes following injection of plasmid into the jugular vein of mice[76](C) Copyright from American Chemical Society.

References 79

[1]	Mandal D., Shirazi A. N., Parang K., Org. Biomol. Chem., 2014, 12(22), 3544—3561
[2]	Ma X., Meng Q. B., Kou Y. Y., Liang Y. J., Guo L., Ni C. H., Liu K. L., Chem. J. Chinese Universities, 2011, 32(8), 1774—1778
	(马鑫, 孟庆斌, 寇莹莹, 梁远军, 郭磊, 倪才华, 刘克良. 高等学校化学学报, 2011, 32(8), 1774—1778)
[3]	Vauthey S., Santoso S., Gong H., Watson N., Zhang S. G., Proc. Natl. Acad. Sci. USA, 2002, 99(8), 5355—5360
[4]	Santoso S., Hwang W., Hartman H., Zhang S., Nano Lett., 2002, 2(7), 687—691
[5]	Von-Maltzahn G., Vauthey S., Santoso S., Zhang S., Langmuir, 2003, 19(10), 4332—4337
[6]	Zhao X., Zhang S., Chem. Soc. Rev., 2006, 35(11) , 1105—1110
[7]	Khoe U., Yang Y. L., Zhang S. G., Macromol. Biosci., 2008, 8(11), 1060—1067
[8]	Zhao X., Pan F., Xu H., Yaseen M., Shan H., Hauser C. A., Zhang S., Lu J. R., Chem. Soc. Rev., 2010, 39(9), 3480—3498
[9]	Xu H., Wang J., Han S. Y., Wang J. Q., Yu D. Y., Zhang H. Y., Xia D. H., Zhao X. B., Waigh T. A., Lu J. R., Langmuir, 2009, 25(5), 5115—4123
[10]	Zhao X. J., Nagai Y., Reeves P. J., Kiley P., Khorana H. G., Zhang S. G., Proc. Natl. Acad. Sci. USA, 2006, 103(47), 17707—17712
[11]	Matsumoto K., Vaughn M., Bruce B. D., Koutsopoulos S., Zhang S. G., J. Phys. Chem. B, 2009, 113(1), 75—83
[12]	Yeh J. I., Du S., Tortajada A., Paulo J., Zhang S., Biochemistry, 2005, 44(51), 16912—16919
[13]	Chen C. X., Pan F., Zhang S. Z., Hu J., Cao M. W., Wang J., Xu H., Zhao X. B., Lu J. R., Biomacromolecules, 2010, 11(2), 402—411
[14]	Kou Y. Y., Meng Q. B., Liu K. L., Chem. J. Chinese Universities, 2012, 33(11), 2476—2480
	(寇莹莹, 孟庆斌, 刘克良. 高等学校化学学报, 2012, 33(11), 2476—2480)
[15]	Kokkoli E., Mardilovich A., Wedekind A., Rexeisen E. L., Garg A., Craig J. A., Soft Matter, 2006, 2(12), 1015—1024
[16]	Behanna H. A., Donners J. J. J. M., Gordon A. C., Stupp S. I., J. Am. Chem. Soc., 2005, 127(4), 1193—1200
[17]	Hartgerink J. D., Beniash E., Stupp S. I., Proc. Natl. Acad. Sci. USA, 2002, 99(8), 5133—5138
[18]	Velichko Y. S., Stupp S. I., de la Cruz M. O., J. Phys. Chem. B, 2008, 112(8), 2326—2334
[19]	Cui H. G., Webber M. J., Stupp S. I., Biopolymers, 2010, 94(1), 1—18
[20]	Stendahl J. C., Rao M. S., Guler M. O., Stupp S. I., Adv. Funct. Mater., 2006, 16(4), 499—508
[21]	Beniash E., Hartgerink J. D., Storrie H., Stendahl J. C., Stupp S. I., Acta Biomater., 2005, 1(4), 387—397
[22]	Tsonchev S., Niece K. L., Schatz G. C., Ratner M. A., Stupp S. I., J. Phys. Chem. B, 2008, 112(2), 441—447
[23]	Niece K. L., Hartgerink J. D., Donners J. J. J. M., Stupp S. I., J. Am. Chem. Soc., 2003, 125(24), 7146—7147
[24]	Hartgerink J. D., Beniash E., Stupp S. I., Science, 2001, 294(5547), 1684—1688
[25]	Sone E. D., Stupp S. I., Chem. Mater., 2011, 23(8), 2005—2007
[26]	Muraoka T., Cui H., Stupp S. I., J. Am. Chem. Soc., 2008, 130(10), 2946—2947
[27]	Muraoka T., Koh C. Y., Cui H., Stupp S. I., Angew. Chem. Int. Ed., 2009, 48(32), 5946—5949
[28]	Storrie H., Guler M. O., Abu-Amara S. N., Volberg T., Rao M., Geiger B., Stupp S. I., Biomaterials, 2007, 28(31), 4608—4618
[29]	Hosseinkhani H., Hosseinkhani M., Tian F., Kobayashi H., Tabata Y., Biomaterials, 2006, 27(29), 5089—5098
[30]	Hosseinkhani H., Hosseinkhani M., Khademhosseini A., Kobayashi H., Tabata Y., Biomaterials, 2006, 27(34), 5836—5844
[31]	Silva G. A., Czeisler C., Niece K. L., Beniash E., Harrington D. A., Kessler J. A., Stupp S. I., Science, 2004, 303(5662), 1352—1355
[32]	Jun H. W., Yuwono V., Paramonov S. E., Hartgerink J. D., Adv. Mater., 2005, 17(21), 2612—2617
[33]	Zhang S., Greenfield M. A., Mata A., Palmer L. C., Bitton R., Mantei J. R., Aparicio C., de la Cruz M. O., Stupp S. I., Nat. Mater., 2010, 9(7), 594—601
[34]	Cui H. G., Muraoka T., Cheetham A. G., Stupp S. I., Nano Lett., 2009, 9(3), 945—951
[35]	Chen C. L., Zhang P. J., Rosi N. L., J. Am. Chem. Soc., 2008, 130(41), 13555—13557
[36]	Deng M. L., Yu D. F., Hou Y. B., Wang Y. L., J. Phys. Chem. B, 2009, 113(41), 8539—8644
[37]	Gore T., Dori Y., Talmon Y., Tirrell M., Bianco-Peled H., Langmuir, 2001, 17(17), 5352—5360
[38]	Lockwood N. A., Haseman J. R., Tirrell M. V., Hamyo K. H., Biochem. J., 2004, 378(1), 93—103
[39]	Versluis F., Tomatsu I., Kehr S., Fregonese C., Tepper A. W. J. W., Stuart M. C., Ravoo B. J., Koning R. I., Kros A., J. Am. Chem. Soc., 2009, 131(37), 13186—13187
[40]	Jiao D. Z., Geng J., Loh X. J., Das D., Lee T. C., Scherman O. A., Angew. Chem. Int. Ed., 2012, 51(38), 9633—9637
[41]	Ahmed S., Mondal J., H., Behera N., Das D., Langmuir, 2013, 29(46), 14274—14283
[42]	Fry H. C., Carcia J. M., Medina M. J., Ricoy U. M., Gosztola D. J., Nikiforov M. P., Palmer L. C., Stupp S. I., J. Am. Chem. Soc., 2012, 134(36), 14646—14649
[43]	Ziserman L., Lee H. Y., Raghavan S. R., Mor A., Danino D., J. Am. Chem. Soc., 2011, 133(8), 2511—2517
[44]	Velichko Y. S., Mantei J. R., Bitton R., Carvajal D., Shull K. R., Stupp S. I., Adv. Funct. Mater., 2012, 22(2), 369—377
[45]	Ting C. L., Frischknecht A. L., Stevens M. J., Spoerke E. D., J. Phys. Chem. B, 2014, 118(29), 8624—8630
[46]	Jin Y., Xu X. D., Chen C. S., Cheng S. X., Zhang X. Z., Zhuo R. X., Macromol. Rappid Commun., 2008, 29(21), 1726—1731
[47]	Xu X. D., Jin Y., Liu Y., Zhang X. Z., Zhuo R. X., Colloids Surf. B Biointer., 2010, 81(1), 329—335
[48]	Qin S. Y., Chu Y. F., Tao L., Xu S. S., Li Z. Y., Zhuo R. X., Zhang X. Z., Soft Matter, 2011, 7(18), 8635—8641
[49]	Qin S. Y., Xu S. S., Zhuo R. X., Zhang X. Z., Langmuir, 2012, 28(4), 2083—2090
[50]	Chen J. X., Wang H. Y., Li C., Han K., Zhang X. Z., Zhuo R. X., Biomaterials, 2011, 32(6), 1678—1684
[51]	Wang H. Y., Chen J. X., Sun Y. X., Deng J. Z., Li C., Zhang X. Z., Zhuo R. X., J. Control. Release, 2011, 155(1), 26—33
[52]	Han K., Yang J., Chen S., Chen J. X., Liu C. W., Li C., Cheng H., Zhuo R. X., Zhang X. Z., Int. J. Pharm., 2012, 436(1), 555—563
[53]	Chen J. X., Xu X. D., Chen W. H., Zhang X. Z., ACS Appl. Mater. & Interf., 2014, 6(1), 593—598
[54]	Matsui H., Gologan B., J. Phys. Chem. B, 2000, 104(15), 3383—3386
[55]	Matsui H., Douberly G. E., Langmuir, 2001, 17(25), 7918—7922
[56]	Porrata P., Goun E., Matsui H., Chem. Mater., 2002, 14(10), 4378—4381
[57]	Qin S., Wang Q., Pei Y., Peng M., Zhuo R., Zhang X., Chin. J. Chem., 2014, 32(1), 22—26
[58]	Djalai R., Chen Y. F., Matsui H., J. Am. Chem. Soc., 2003, 125(19), 5873—5879
[59]	Banerjee I. A., Yu L., Matsui H., Proc. Natl. Acad. Sci. USA, 2003, 100(25), 14678—14682
[60]	Yu L., Banerjee I. A., Matsui H., Adv. Mater., 2004, 16(6), 709—712
[61]	Banerjee I. A., Yu L., Matsui H., J. Am. Chem. Soc., 2003, 125(32), 9542—9543
[62]	Nuraje N., Banerjee I. A., MacCuspie R. I., Yu L. T., Matsui H., J. Am. Chem. Soc., 2004, 126(26), 8088—8089
[63]	Matsui H., MacCuspie R. I., Nano Lett., 2001, 1(12), 671—675
[64]	Rica R. D. L., Mendoza E., Lechuga L. M., Matsui H., Angew. Chem. Int. Ed., 2008, 47(50), 9752—9755
[65]	Claussen R. C., Rabatic B. M., Stupp S. I., J. Am. Chem. Soc., 2003, 125(42), 12680—12681
[66]	Kogiso M., Okada Y., Hanada T., Yase K., Shimizu T., Biochim. Biophys. Acta, 2000, 1475(3), 346—352
[67]	Kogiso M., Okada Y., Yase K., Shimizu T., J. Colloid Interf. Sci., 2004, 273(2), 394—399
[68]	Hait S. K., Moulik S. P., Curr. Sci., 2002, 82(9), 1101—1111
[69]	Danino D., Talmon Y., Levy H., Beinert G., Zana R., Science, 1995, 269(5229), 1420—1421
[70]	Yamamoto Y., Fukushima T., Suna Y., Ishii N., Saeki A., Seki S., Tagawa S., Taniguchi M., Kawai T., Aida T., Science, 2006, 314(5806), 1761—1763
[71]	Menger F. M., Peresypkin A. V., J. Am. Chem. Soc., 2003, 125(18), 5340—5345
[72]	Rubio J., Alfonso I., Bru M., Burguete M. I., Luis S. V., Tetrahedron Lett., 2010, 51(45), 5861—5867
[73]	Rubio J., Alfonso I., Burguete M. I., Luis S. V., Soft Matter, 2011, 7(22), 10737—10748
[74]	He C. Q., Han Y. H., Fan Y. X., Deng M. L., Wang Y. L., Langmuir, 2012, 28(7), 3391—3396
[75]	Kirby A. J., Camilleri P., Engberts J. B. F. N., Feiters M. C., Nolte R. J. M., Soderman O., Bersma M. , Bell P. C., Kremer A., McGregor C., Perrin C., Ronsin G., Eijk M. C. P. V., Angew. Chem. Int. Ed., 2003, 42(13), 1448—1457
[76]	Chittimalla C., Zammut-Italiano L., Zuber G., Behr J. P., J. Am. Chem. Soc., 2005, 127(32), 11436—11441
[77]	Wang J. X., Zhang Y. X., Li J. L., Xu X. D., Zhuo R. X., Zhang X. Z., Soft Matter, 2012, 8(37), 9523—9525
[78]	Wang J. X., Lei Q., Luo G. F., Cai T. T., Li J. L., Cheng S. X., Zhuo R. X., Zhang X. Z., Langmuir, 2013, 29(23), 6996—7004
[79]	Wang J. X., Cai T. T., Li J. L., Zhuo R. X., Zhang X. Z., RSC Adv., 2014, 4(29), 14993—14996
	(Ed.: D, Z)