Abstract
Peptide-based organogels/hydrogels are flexible and versatile in biological and nanotechnological applications. These supramolecular gels consisted of supramolecular fibrous networks formed through non-covalent interactions, including hydrogen bonding, hydrophobic, electrostatic, π–π stacking, and van der Waals interactions. In this chapter, we present the assembly, structures, and governing interactions of these supramolecular gels based on a broad range of peptides. We also highlight the potential applications of these supramolecular gels in tissue engineering, drug delivery, templates for nanofabrication, and detergent of waste water, etc.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Wang J, Liu K, Xing R, Yan X (2016) Peptide self-assembly: thermodynamics and kinetics. Chem Soc Rev 45:5589–5604
Whitesides GM, Grzybowski B (2002) Self-assembly at all scales. Science 295(5564):2418–2421
Mahadevi AS, Sastry GN (2016) Cooperativity in noncovalent interactions. Chem Rev 116:2775–2825
Zhang S (2003) Fabrication of novel biomaterials through molecular self-assembly. Nat Biotechnol 21(10):1171–1178
Evd Linden, Venema P (2007) Self-assembly and aggregation of proteins. Curr Opin Colloid Interface Sci 12:158–165
Hauser CA, Zhang S (2010) Nanotechnology: peptides as biological semiconductors. Nature 468(7323):516–517
Ulijn RV, Woolfson DN (2010) Peptide and protein based materials in 2010: from design and structure to function and application. Chem Soc Rev 39(9):3349–3350
Löwik DW, Leunissen E, Van den Heuvel M, Hansen M, van Hest JC (2010) Stimulus responsive peptide based materials. Chem Soc Rev 39(9):3394–3412
Seabra AB, Duran N (2013) Biological applications of peptides nanotubes: an overview. Peptides 39:47–54
Adler-Abramovich L, Gazit E (2014) The physical properties of supramolecular peptide assemblies: from building block association to technological applications. Chem Soc Rev 43(20):6881–6893
Aono M, Ariga K (2016) The way to nanoarchitectonics and the way of nanoarchitectonics. Adv Mater 28(6):989–992
Shimizu T, Masuda M, Minamikawa H (2005) Supramolecular nanotube architectures based on amphiphilic molecules. Chem Rev 105(4):1401–1443
Yan X, Zhu P, Li J (2010) Self-assembly and application of diphenylalanine-based nanostructures. Chem Soc Rev 39(6):1877–1890
Hauser CAE, Zhang S (2010) Designer self-assembling peptide nanofiber biological materials. Chem Soc Rev 39:2780–2790
Boyle AL, Woolfson DN (2011) De novo designed peptides for biological applications. Chem Soc Rev 40(8):4295–4306
Fleming S, Ulijn RV (2014) Design of nanostructures based on aromatic peptide amphiphiles. Chem Soc Rev 43(23):8150–8177
De Santis E, Ryadnov MG (2015) Peptide self-assembly for nanomaterials: the old new kid on the block. Chem Soc Rev 44:8288–8300
Yan C, Pochan DJ (2010) Rheological properties of peptide-based hydrogels for biomedical and other applications. Chem Soc Rev 39(9):3528–3540
Johnson EK, Adams DJ, Cameron PJ (2011) Peptide based low molecular weight gelators. J Mater Chem 21(7):2024–2027
Dasgupta A, Mondal JH, Das D (2013) Peptide hydrogels. Rsc Adv 3(24):9117–9149
Raeburn J, Cardoso AZ, Adams DJ (2013) The importance of the self-assembly process to control mechanical properties of low molecular weight hydrogels. Chem Soc Rev 42(12):5143–5156
Tomasini C, Castellucci N (2013) Peptides and peptidomimetics that behave as low molecular weight gelators. Chem Soc Rev 42(1):156–172
Fichman G, Gazit E (2014) Self-assembly of short peptides to form hydrogels: design of building blocks, physical properties and technological applications. Acta Biomater 10(4):1671–1682
Jonker AM, Lowik DWPM, Hest JCMv (2012) Peptide- and protein-based hydrogels. Chem Mater 24:759–773
Rodriguez LMDL, Hemar Y, Cornish J, Brimble MA (2016) Structure-mechanical property correlations of hydrogel forming b-sheet peptides. Chem Soc Rev 45:4797–4828
Naskar J, Palui G, Banerjee A (2009) Tetrapeptide-based hydrogels: for encapsulation and slow release of an anticancer drug at physiological pH. J Phys Chem B 113:11787–11792
Woolfson DN, Ryadnov MG (2006) Peptide-based fibrous biomaterials: some things old, new and borrowed. Curr Opin Chem Biol 10:559–567
Banwell EF, Abelardo ES, Adams DJ, Birchall MA, Corrigan A, Donald A, Kirkland M, Serpell LC, Butler MF, Woolfson ND (2009) Rational design and application of responsive a-helical peptide hydrogels. Nat Mater 8:596–600
Lu Y, Derreumaux P, Guo Z, Mousseau N, Wei G (2009) Thermodynamics and dynamics of amyloid peptide oligomerization are sequence dependent. Proteins 75(4):954–963
Houton KA, Morris KL, Chen L, Schmidtmann M, Jones JTA, Serpell LC, Lloyd GO, Adams DJ (2012) On crystal versus fiber formation in dipeptide hydrogelator systems. Langmuir 28(25):9797–9806
Sasselli IR, Halling PJ, Ulijn RV, Tuttle T (2016) Supramolecular fibers in gels can be at thermodynamic equilibrium: a simple packing model reveals preferential fibril formation versus crystallization. ACS Nano 10(2):2661–2668
Zhu P, Yan X, Su Y, Yang Y, Li J (2010) Solvent-induced structural transition of self-assembled dipeptide: from organogels to microcrystals. Chem Eur J 16(10):3176–3183
Wang J, Liu K, Yan L, Wang A, Bai S, Yan X (2016) Trace solvent as a predominant factor to tune dipeptide self-assembly. ACS Nano 10(2):2138–2143
Moyer TJ, Finbloom JA, Chen F, Toft DJ, Cryns VL, Stupp SI (2014) pH and amphiphilic structure direct supramolecular behavior in biofunctional assemblies. J Am Chem Soc 136(42):14746–14752
Liu XC, Zhu PL, Fei JB, Zhao J, Yan XH, Li JB (2015) Synthesis of peptide-based hybrid nanobelts with enhanced color emission by heat treatment or water induction. Chem Eur J 21(26):9461–9467
Webber MJ, Newcomb CJ, Bitton R, Stupp SI (2011) Switching of self-assembly in a peptide nanostructure with a specific enzyme. Soft Matter 7(20):9665–9672
Guilbaud J-B, Rochas C, Miller AF, Saiani A (2013) Effect of enzyme concentration of the morphology and properties of enzymatically triggered peptide hydrogels. Biomacromolecules 14(5):1403–1411
Lan Y, Corradini M, Weiss R, Raghavan S, Rogers M (2015) To gel or not to gel: correlating molecular gelation with solvent parameters. Chem Soc Rev 44:6035–6058
Diehn KK, Oh H, Hashemipour R, Weiss RG, Raghavan SR (2014) Insights into organogelation and its kinetics from Hansen solubility parameters. toward a priori predictions of molecular gelation. Soft Matter 10(15):2632–2640
Reches M, Gazit E (2003) Casting metal nanowires within discrete self-assembled peptide nanotubes. Science 300(5619):625–627
Pappas CG, Frederix PWJM, Mutasa T, Fleming S, Abul-Haija YM, Kelly SM, Gachagan A, Kalafatovic D, Trevino J, Ulijn RV, Bai S (2015) Alignment of nanostructured tripeptide gels by directional ultrasonication. Chem Commun 51(40):8465–8468
Jayawarna V, Ali M, Jowitt TA, Miller AE, Saiani A, Gough JE, Ulijn RV (2006) Nanostructured hydrogels for three-dimensional cell culture through self-assembly of fluorenylmethoxycarbonyl-dipeptides. Adv Mater 18(5):611–614
Smith AM, Williams RJ, Tang C, Coppo P, Collins RF, Turner ML, Saiani A, Ulijn RV (2008) Fmoc-diphenylalanine self assembles to a hydrogel via a novel architecture based on p-p interlocked b-sheets. Adv Mater 20:37–41
Tang C, Smith AM, Collins RF, Ulijn RV, Saiani A (2009) Fmoc-diphenylalanine self-assembly mechanism induces apparent pK(a) shifts. Langmuir 25(16):9447–9453
Mahler A, Reches M, Rechter M, Cohen S, Gazit E (2006) Rigid, self-assembled hydrogel composed of a modified aromatic dipeptide. Adv Mater 18(11):1365–1370
Yang Z, Liang G, Xu B (2006) Supramolecular hydrogels based on b-amino acid derivatives. Chem Commun 738–740
Toledano S, Williams RJ, Jayawarna V, Ulijn RV (2006) Enzyme-triggered self-assembly of peptide hydrogels via reversed hydrolysis. J Am Chem Soc 128(4):1070–1071
Das AK, Collins R, Ulijn RV (2008) Exploiting enzymatic (reversed) hydrolysis in directed self-assembly of peptide nanostructures. Small 2:279–287
Orbach R, Adler-Abramovich L, Zigerson S, Mironi-Harpaz I, Seliktar D, Gazit E (2009) Self-assembled fmoc-peptides as a platform for the formation of nanostructures and hydrogels. Biomacromol 10:2646–2651
Ma M, Kuang Y, Gao Y, Zhang Y, Gao P, Xu B (2010) Aromatic-aromatic interactions induce the self-assembly of pentapeptidic derivatives in water to form nanofibers and supramolecular hydrogels. J Am Chem Soc 132(8):2719–2728
Hughes M, Frederix PWJM, Raeburn J, Birchall LS, Sadownik J, Coomer FC, Lin IH, Cussen EJ, Hunt NT, Tuttle T, Webb SJ, Adams DJ, Ulijn RV (2012) Sequence/structure relationships in aromatic dipeptide hydrogels formed under thermodynamic control by enzyme-assisted self-assembly. Soft Matter 8(20):5595–5602
Gao Y, Yang Z, Kuang Y, Ma M-L, Li J, Zhao F, Xu B (2010) Enzyme-instructed self-assembly of peptide derivatives of form nanofibers and hydrogels. Biopolymers 94:19–31
Cheng G, Castelletto V, Jones RR, Connon CJ, Hamley IW (2011) Hydrogelation of self-assembling RGD-based peptides. Soft Matter 7:1326–1333
Cui HG, Webber MJ, Stupp SI (2010) Self-assembly of peptide amphiphiles: from molecules to nanostructures to biomaterials. Biopolymers 94(1):1–18
Claussen RC, Rabatic BM, Stupp SI (2003) Aqueous self-assembly of unsymmetric peptide bolaamphiphiles into nanofibers with hydrophilic cores and surfaces. J Am Chem Soc 125:12680–12681
Stendahl JC, Rao MS, Guler MO, Stupp SI (2006) Intermolecular forces in the self-assembly of peptide amphiphile nanofibers. Adv Funct Mater 16(4):499–508
Schneider JP, Pochan DJ, Ozbas B, Rajagopal K, Pakstis L, Kretsinger J (2002) Responsive hydrogels from the intramolecular folding and self-assembly of a designed peptide. J Am Chem Soc 124:15030–15037
Pochan DJ, Schneider JP, Kretsinger J, Ozbas B, Rajagopal K, Haines L (2003) Thermally reversible hydrogels via intramolecular folding and consequent self-assembly of a de novo designed peptide. J Am Chem Soc 125:11802–11803
Haines LA, Rajagopal K, Ozbas B, Salick DA, Pochan DJ, Schneider JP (2005) Light-activated hydrogel formation via the triggered folding and self-assembly of a designed peptide. J Am Chem Soc 127:17025–17029
Yucel T, Micklitsch CM, Schneider JP, Pochan DJ (2008) Direct observation of early-time hydrogelation in b-hairpin peptide self-assembly. Macromolecules 41:5763–5772
Hule RA, Nagarkar RP, Hammouda B, Schneider JP, Pochan DJ (2009) Dependence of self-assembled peptide hydrogel network structure on local fibril nanostructure. Macromolecules 42:7137–7145
Nagy KJ, Giano MC, Jin A, Pochan DJ, Schneider JP (2011) Enhanced mechanical rigidity of hydrogels formed from enantiomeric peptide assemblies. J Am Chem Soc 133:14975–14977
Rubio J, Alfonso I, Burguete MI, Luis SV (2012) Interplay between hydrophilic and hydrophobic interactions in the self-assembly of a gemini amphiphilic pseudopeptide: from nano-spheres to hydrogels. Chem Commun 48:2210–2212
Nebot VJ, Armengol J, Smets J, Prieto SF, Escuder B, Miravet JF (2012) Molecular hydrogels from bolaform amino acid derivatives: a structure-properties study based on the thermodynamics of gel solubilization. Chem EurJ 18:4063–4072
Nowak AP, Breedveld V, Pakstis L, Ozbas B, Pine DJ, Pochan D, Deming TJ (2002) Rapidly recovering hydrogel scaffolds from self-assembling diblock copolypeptide amphiphiles. Nature 417:424–428
Breedveld V, Nowak AP, Sato J, Deming TJ, Pine DJ (2004) Rheology of block copolypeptide solutions: hydrogels with tunable properties. Macromolecules 37:3943–3953
Deming TJ (2005) Polypeptide hydrogels via a unique assembly mechanism. Soft Matter 1:28–35
Li Z, Deming TJ (2010) Tunable hydrogel morphology via self-assembly of amphiphilic pentablock copolypeptides. Soft Matter 6:2546–2551
Glassman MJ, Olsen BD (2015) Arrested phase separation of elastin-like polypeptide solutions yields stiff, thermoresponsive gels. Biomacromol 16:3762–3773
Caliari SR, Burdick JA (2016) A practical guide to hydrogels for cell culture. Nat Methods 13:405–414
Wang H, Heilshorn SC (2015) Adaptable hydrogel networks with reversible linkages for tissue engineering. Adv Mater 27:3717–3736
Hilderbrand AM, Ovadia EM, Rehmann MS, Kharkar PM, Guo C, Kloxin AM (2016) Biomaterials for 4D stem cell culture. Curr Opin Solid State Mater Sci 20:212–224
Chen G, Chen J, Liu Q, Ou C, Gao J (2015) Enzymatic formation of a meta-stable supramolecular hydrogel for 3D cell culture. Rsc Adv 5:30675–30678
Ryan DM, Nilsson BL (2012) Self-assembled amino acids and dipeptides as noncovalent hydrogels for tissue engineering. Polym Chem 3:18–33
Slaughter BV, Khurshid SS, Fisher OZ, Khademhosseini A, Peppas NA (2009) Hydrogels in regenerative medicine. Adv Mater 21:3307–3329
Mata A, Hsu L, Capito R, Aparicio C, Henriksonc K, Stupp SI (2009) Micropatterning of bioactive self-assembling gels. Soft Matter 5:1228–1236
Kisiday J, Jin M, Kurz B, Hung H, Semino C, Zhang S, Grodzinsky AJ (2002) Self-assembling peptide hydrogel fosters chondrocyte extracellular matrix production and cell division: implications for cartilage tissue repair. Proc Natl Acad Sci U S A 99(15):9996–10001
Kisiday J, Jin M, Kurz B, Hung H, Semino C, Zhang S, Grodzinsky AJ (2002) Self-assembling peptide hydrogel fosters chondrocyte extracellular matrix production and cell division: implications for cartilage tissue repair. Proc Natl Acad Sci U S A 99:9996–10001
Salick DA, Kretsinger JK, Pochan DJ, Schneider JP (2007) Inherent antibacterial activity of a peptide-based b-hairpin hydrogel. J Am Chem Soc 129:14793–14799
Zhou M, Smith AM, Das AK, Hodson NW, Collins RF, Ulijn RV, Gough JE (2009) Self-assembled peptide-based hydrogels as scaffolds for anchorage-dependent cells. Biomaterials 30:2523–2530
Jayawarna V, Richardson SM, Hirst AR, Hodson NW, Saiani A, Gough JE, Ulijn RV (2009) Introducing chemical functionality in Fmoc-peptide gels for cell culture. Acta Biomater 5:934–943
Tian YF, Devgun JM, Collier JH (2011) Fibrillized peptide microgels for cell encapsulation and 3D cell culture. Soft Matter 7:6005–6011
Wieduwild R, Krishnan S, Chwalek K, Boden A, Nowak M, Drechsel D, Werner C, Zhang Y (2015) Noncovalent hydrogel beads as microcarriers for cell culture. Angew Chem Int Ed 54(13):3962–3966
Zamuner A, Cavo M, Scaglione S, Messina GML, Russo T, Gloria A, Marletta G, Dettin M (2016) Design of decorated self-assembling peptide hydrogels as architecture for mesenchymal stem cells. Materials 9:727
Loo Y, Hauser CAE (2016) Bioprinting synthetic self-assembling peptide hydrogels for biomedical applications. Biomed Mater 11:014103
Zhang SM, Greenfield MA, Mata A, Palmer LC, Bitton R, Mantei JR, Aparicio C, de la Cruz MO, Stupp SI (2010) A self-assembly pathway to aligned monodomain gels. Nat Mater 9(7):594–601
Bysell H, Månsson R, Hansson P, Malmsten M (2011) Microgels and microcapsules in peptide and protein drug delivery. Adv Drug Del Rev 63:1172–1185
Wang H, Feng Z, Xu B D-amino acid-containing supramolecular nanofibers for potential cancer therapeutics. Adv Drug Del Rev. doi: https://doi.org/10.1016/j.addr.2016.04.008
Williams RJ, Hall TE, Glattauer V, White J, Pasic PJ, Sorensen AB, Waddington L, McLean KM, Currie PD, Hartley PG (2011) The in vivo performance of an enzyme-assisted self-assembled peptide/protein hydrogel. Biomaterials 32(22):5304–5310
Gao J, Zheng WT, Kong DL, Yang ZM (2011) Dual enzymes regulate the molecular self-assembly of tetra-peptide derivatives. Soft Matter 7(21):10443–10448
Ruana L, Zhanga H, Luoa H, Liua J, Tanga F, Shi Y-K, Zhaoa X (2009) Designed amphiphilic peptide forms stable nanoweb, slowly releases encapsulated hydrophobic drug, and accelerates animal hemostasis. Proc Natl Acad Sci U S A 106(13):5105–5110
Li J, Gao Y, Kuang Y, Shi J, Du X, Zhou J, Wang H, Yang Z, Xu B (2013) Dephosphory-lation of D-peptide derivatives to form biofunctional, supramolecular nanofibers/hydrogels and their potential applications for intracellular imaging and intratumoral chemotherapy. J Am Chem Soc 135:9907–9914
Kuang Y, Shi J, Li J, Yuan D, Alberti KA, Xu Q, Xu B (2014) Pericellular hydrogel/nanonets inhibit cancer cells. Angew Chem Int Ed 53:8104–8107
Ischakov R, Adler-Abramovich L, Buzhansky L, Shekhter T, Gazit E (2013) Peptide-based hydrogel nanoparticles as effective drug delivery agents. Biorg Med Chem 21:3517–3522
Xing RR, Liu K, Jiao TF, Zhang N, Ma K, Zhang RY, Zou QL, Ma GH, Yan XH (2016) An injectable self-assembling collagen-gold hybrid hydrogel for combinatorial antitumor photothermal/photodynamic therapy. Adv Mater 28:3669–3676
Thornton PD, Mart RJ, Webbb SJ, Ulijn RV (2008) Enzyme-responsive hydrogel particles for the controlled release of proteins: designing peptide actuators to match payload. Soft Matter 4:821–827
Maity I, Rasale DB, Das AK (2012) Sonication induced peptide-appended bolaamphiphile hydrogels for in situ generation and catalytic activity of Pt nanoparticles. Soft Matter 8:5301–5308
Dutta S, Shome A, Kar T, Das PK (2011) Counterion-induced modulation in the antimicrobial activity and biocompatibility of amphiphilic hydrogelators: influence of in-situ-synthesized Ag-nanoparticle on the bactericidal property. Langmuir 27:5000–50008
Sharma KP, Harniman R, Farrugia T, Briscoe WH, Perriman AW, Mann S (2016) Dynamic behavior in enzyme-polymer surfactant hydrogel films. Adv Mater 28:1597–1602
Yan X, Cui Y, He Q, Wang K, Li J (2008) Organogels based on self-assembly of diphenylalanine peptide and their application to immobilize quantum dots. Chem Mater 20(4):1522–1526
Adhikari B, Nanda J, Banerjee A (2011) Pyrene-containing peptide-based fluorescent organogels: inclusion of graphene into the organogel. Chem Eur J 17:11488–11496
Afrasiabi R, Kraatz H-B (2013) Small-peptide-based organogel kit: towards the development of multicomponent self-sorting organogels. Chem Eur J 19:15862–15871
Sone ED, Zubarev ER, Stupp SI (2002) Semiconductor nanohelices templated by supramolecular ribbons. Angew Chem Int Ed 41:1706–1709
Ray S, Das AK, Banerjee A (2006) Smart oligopeptide gels: in situ formation and stabilization of gold and silver nanoparticles within supramolecular organogel networks. Chem Commun 26:2816–2818
Liu Y, Wang Y, Jin L, Chen T, Yin B (2016) MPTTF-containing tripeptide-based organogels: receptor for 2, 4, 6-trinitrophenol and multiple stimuli-responsive properties. Soft Matter 12:934–945
Acknowledgements
This work was supported by the National Natural Science Foundation of China (Project Nos. 21522307, 21473208, and 91434103), the Talent Fund of the Recruitment Program of Global Youth Experts, and the Chinese Academy of Sciences (CAS).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2018 Springer Nature Singapore Pte Ltd.
About this chapter
Cite this chapter
Wang, J., Yan, X. (2018). Peptide-Based Hydrogels/Organogels: Assembly and Application. In: Li, B., Jiao, T. (eds) Nano/Micro-Structured Materials for Energy and Biomedical Applications. Springer, Singapore. https://doi.org/10.1007/978-981-10-7787-6_6
Download citation
DOI: https://doi.org/10.1007/978-981-10-7787-6_6
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-10-7786-9
Online ISBN: 978-981-10-7787-6
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)