Exploiting biocatalysis in the synthesis of supramolecular polymers

Advances in Polymer Science

Volumn 237, Issue , 2010, Pages 127-143

  Roy, Sangita ^a   Ulijn, Rein V ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Biocatalysis; Enzymes; Molecular hydrogel; Peptides; Self assembly; Supramolecular polymers

Indexed keywords

EID: 79953291478     PISSN: 00653195     EISSN: None     Source Type: Book Series    
DOI: 10.1007/12-2010-75     Document Type: Review

References (75)

1. Lehn JM (1995) Supramolecular chemistry-concepts and perspectives. VCH Weinheim
2. Lehn JM (2002) Supramolecular polymer chemistry-scope and perspectives. Polym Int 51:825-839
3. Mart RJ, Osborne RD, Stevens MM, Ulijn RV (2006) Peptide-based stimuli-responsive biomaterials. Soft Matter 2:822-835
4. Jayawarna V, Ali M, Jowitt TA, Miller AF, Saiani A, Gough JE, Ulijn RV (2006) Nanostructured hydrogels for three-dimensional cell culture through self-assembly of fluorenylmethoxycarbonyl-dipeptides. Adv Mater 18:611-614
5. Silva GA, Czeisler C, Niece KL, Beniash E, Harrington DA, Kessler JA, Stupp SL (2004) Selective differentation of neural progenitor cells by high-epitope density nanofibers. Science 303:1352-1355
6. Holmes TC, de Lacalle S, Su X, Liu G, Rich A, Zhang S (2000) Extensive neurite outgrowth and active synapse formation on self-assembling peptide scaffolds. Proc Natl Acad Sci 97:6728-6733
7. 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
8. Matsumoto S, Yamaguchi S, Ueno S, Komatsu H, Ikeda M, Ishizuka K, Iko Y, Tabata KV, Aoki H, Ito S, Noji H, Hamachi I (2008) Photo gel-sol/sol-gel transition and its patterning of a supramolecular hydrogel as stimuli-responsive. Biomaterials 14:3977-3986
9. Muraoka T, Cui H, Stupp SI (2008) Quadruple helix formation of a photoresponsive peptide amphiphile and its light-triggered dissociation into single fibers. J Am Chem Soc 130:2946-2947
10. Yang Z, Liang G, Xu B (2008) Enzymatic hydrogelation of small molecules. Acc Chem Res 41:315-326
11. Ulijn RV (2006) Enzyme responsive materials: a new class of smart biomaterials. J Mat Chem 16:2217-2225
12. Colombo M, Brittingham RJ, Klement JF, Majsterek I, Birk DE, Uitto J, Fertala A (2003) Procollagen VII self-assembly depends on site-specific interactions and is promoted by cleavage of the NC2 domain with procollagen C-proteinase. Biochemistry 42:11434-11442
13. Kessler E, Takahara K, Biniaminov L, Brusel M, Greenspan DS (1996) Bone morphogenetic protein-1: the type I procollagen C-proteinase. Science 271:360-362
14. Prockop DJ, Kivirikko KI (1995) Collagens: molecular biology, diseases, and potentials for therapy. Annu Rev Biochem 64:403-434
15. Feratala A, Sieron A, Hojima Y, Ganguli A, Prockop DJ (1994) Self-assembly into fibrils of collagen II by enzymic cleavage of recombinant procollagen II. Lag period, critical concentration, and morphology of fibrils differ from collagen I. J Biol Chem 269:11584-11589
16. Kadler K, Hojima Y, Prockop DJ (1987) Assembly of collagen fibrils de novo by cleavage of the type I pC-collagen with procollagen C-proteinase. Assay of critical concentration demonstrates that collagen self-assembly is a classical example of an entropy-driven process. J Biol Chem 262:15696-15701
17. Lodish H, Berk A, Matsudaira P, Kaiser CA, Krieger M, Scott, MP, Zipursky SL, Darnell J (2003) Molecular cell biology, 5th edn. Freeman, New York
18. Wu L.-Q, Payne GF (2004) Biofabrication: the use of biological materials and biocatalysts to construct nanostructured assemblies. Trends Biotechnol 22:593-599
19. Hu BH, Messersmith PB (2003) Rational design of transglutaminase substrate peptides for rapid enzymatic formation of hydrogels. J Am Chem Soc 125:14298-14299
20. Sperinde JJ, Griffith LG (1997) Synthesis and characterization of enzymatically-cross-linked poly(ethylene glycol) hydrogels. Macromolecules 30:5255-5264
21. Williams RJ, Smith AM, Collins R, Hodson N, Das AK, Ulijn RV (2009) Enzyme-assisted self-assembly under thermodynamic control. Nat Nanotechnol 4:19-24
22. Das AK, Collins R, Ulijn RV (2008) Exploiting enzymatic (reversed) hydrolysis in directed self-assembly of peptide nanostructures. Small 4:279-287
23. Toledano S, Williams RJ, Jayawarna V, Ulijn RV (2006) Enzyme-triggered self-assembly of peptide hydrogels via reversed hydrolysis. J Am Chem Soc 128:1070-1071
24. Yang Z, Ma M, Xu B (2009) Using matrix metalloprotease-9 (MMP-9) to trigger supramolecular hydrogelation. Soft Matter 5:2546-2548
25. Adler-Abramovich L, Perry R, Sagi A, Gazit E, Shabat D (2007) Controlled assembly of peptide nanotubes triggered by enzymatic activation of self-immolative dendrimers. Chembiochem 8:859-862
26. Dos Santos S, Chandravarkar A, Mandal B, Mimna R, Murat K, Saucede L, Tella P, Tuchscherer G, Mutter M (2005) Switch-peptides: controlling self-Assembly of amyloid ?-derived peptides in vitro by consecutive triggering of acyl migrations. J Am Chem Soc 127:11888-11889
27. Yang Z, Gu H, Fu D, Gao P, Lam JK, Xu B (2004) Enzymatic formation of supramolecular hydrogels. Adv Mater 16:1440-1444
28. Winkler S, Wilson D, Kaplan DL (2000) Controlling beta-sheet assembly in genetically engineered silk by enzymatic phosphorylation/dephosphorylation. Biochemistry 39:12739-12746
29. Kühnle H, Börner HG, (2009) Biotransformation on polymer-peptide conjugates: a versatile tool to trigger microstructure formation. Angew Chem Int Ed 48:6431-6434
30. Amir RJ, Zhong S, Pochan DJ, Hawker CJ (2009) Enzymatically triggered self-assembly of block copolymers. J Am Chem Soc 131:13949-13951
31. Reches M, Gazit E (2003) Casting metal nanowires within discrete self-assembled peptide nanotubes. Science 300:625-627
32. Plunkett KN, Berkowski KL,Moore JS (2005) Chymotrypsin responsive hydrogel: application of a disulfide exchange protocol for the preparation of methacrylamide containing peptides Biomacromolecules 6:632-637
33. Lutolf MP, Raeber GP, Zisch AH, Tirelli N, Hubbell JA (2003) Cell-responsive synthetic hydrogels. Adv Mater 15:888-892
34. Van Bommel KJC, Stuart MCA, Feringa BL, Van Esch J (2005) Two-stage enzyme mediated drug release from LMWG hydrogels. Org Biomol Chem 3:2917-2920
35. Jun HW, Yuwono V, Paramonov, SE, Hartgerink JD (2005) Enzyme-mediated degradation of peptide-amphiphile nanofiber networks. Adv Mater 17:2612-2617
36. Chau Y, Luo Y, Cheung ACY, Nagai Y, Zhang SG, Kobler JB, Zeitels SM, Langer R (2008) Incorporation of a matrix metalloproteinase-sensitive substrate into self-assembling peptides as a model for biofunctional scaffolds. Biomaterials 29:1713-1719
37. Yang Z, Liang G, Wang L, Xu B (2006) Using a kinase/phosphatase switch to regulate a supramolecular hydrogel and forming the supramoleclar hydrogel in vivo. J Am Chem Soc 128:3038-3043
38. Um SH, Lee JB, Park N, Kwon SY, Umbach CC, Luo D (2006) Enzyme-catalysed assembly of DNA hydrogel. Nat Mater 5:797-801
39. Zhang SG (2003) Fabrication of novel biomaterials through molecular self-assembly. Nat Biotechnol 21:1171-1178
40. Whitesides GM, Grzybowski BA (2002) Self-assembly at all scales. Science 295:2418-2421
41. Grzybowski BA, Wilmer CE, Kim J, Browne KP, Bishop KJM (2009) Self-assembly: from crystals to cells. Soft Matter 5:1110-1128
42. Hirst AR, Coates IA, Boucheteau TR, Miravet JF, Escuder B, Castelletto V, Hamley IW, Smith DK (2008) Low-molecular-weight gelators: elucidating the principles of gelation based on gelator solubility and a cooperative self-assembly model. J Am Chem Soc 130:9113-9121
43. Rughani RV, Schneider JR (2008) Molecular design of beta-hairpin peptides for material construction. MRS Bull 33:530-535
44. de Loos M, Feringa BL, van Esch JH (2005) Design and application of self-assembled low molecular weight hydrogels. Eur J Org Chem 3615-3631
45. Kobayashi H, Friggeri A, Koumoto K, Amaike M, Shinkai S, Reinhoudt DN (2002) Molecular design of "super" hydrogelators: understanding the gelation process of azobenzene-based sugar derivatives in water. Org Lett 4:1423-1426
46. Woolfson DN, Ryadnov MG (2006) Peptide-based fibrous biomaterials: some things old, new and borrowed. Curr Opin Chem Biol 10:559-567
47. Yanlian Y, Ulung K, Xiumei W, Horii A, Yokoi H, Zhang S (2009) Designer self-assembling peptide nanomaterials. Nano Today 4:193-210
48. Estroff LA, Hamilton AD (2004) Water gelation by small organic molecules. Chem Rev 104:1201-1218
49. Reches M, Gazit E (2006) Controlled patterning of aligned self-assembled peptide nanotubes. Nat Nanotechnol 1:195-200
50. 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 x-interlocked ?-sheets. Adv Mater 20:37-41
51. Smith AM, Ulijn RV (2008) Designing peptide based nanomaterials. Chem Soc Rev 37:664-675
52. Adams DJ, Butler MF, Frith WJ, Kirkland M, Mullen L, Sanderson P (2009) A new method for maintaining homogeneity during liquid-hydrogel transitions using low molecular weight hydrogelators. Soft Matter 5:1856-1862
53. Vegners R, Shestakova I, Kalvinsh I, Ezzell RM, Janmey PA (1995) Use of a gel-forming dipeptide derivative as a carrier for antigen presentation. J Pept Sci 1:371-378
54. Tang C, Smith AM, Collins RF, Ulijn RV, Saiani A (2009) Fmoc-diphenylalanine selfassembly mechanism induces apparent pK(a) shifts. Langmuir 25:9447-9453
55. Thornton K, Smith AM, Merry CLR, Ulijn RV (2009) Controlling stiffness in nanostructured hydrogels produced by enzymatic dephosphorylation. Biochem Soc Trans 37:660-664
56. Yang ZM, Liang GL, Xu B (2007) Enzymatic control of the self-assembly of small molecules: a new way to generate supramolecular hydrogels. Soft Matter 3:515-520
57. Engler AJ, Sen S, Sweeney HL, Discher DE (2006) Matrix elasticity directs stem cell lineage specification. Cell 126:677-689
58. Ulijn RV, De Martin L, Gardossi L, Halling PJ (2003) Biocatalysis with mainly undissolved solid substrates. Curr Org Chem 7:1333-1346
59. Klibanov AM (2001) Improving enzymes by using them in organic solvents. Nature 409:241-246
60. Halling PJ, Ulijn RV, Flitsch SL (2005) Understanding enzyme action on immobilized substrates. Curr Opin Biotechnol 16:385-392
61. Corbett PT, Leclaire J, Vial L, West KR, Wietor J-L, Sanders JKM, Otto S (2006) Dynamic combinatorial chemistry. Chem Rev 106:3652-3711
62. Rowan SJ, Cantrill SJ, Cousins GRL, Sanders JKM, Stoddart JF (2002) Dynamic covalent chemistry. Angew Chem Int Ed 41:898-952
63. Sreenivasachary N, Lehn JM (2005) Gelation-driven component selection in the generation of constitutional dynamic hydrogels based on guanine-quartet formation. Proc Nat Acad Sci 102:5938-5943
64. Otto S, Furlan RLE, Sanders JKM (2002) Selection and amplification of hosts from dynamic combinatorial libraries of macrocyclic disulfides. Science 297:590-593
65. Ludlow RF, Otto S (2008) Systems chemistry. Chem Soc Rev 37:101-108
66. Bilgiçer B, Xing X, Kumar K (2001) Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores. J Am Chem Soc 123:11815-11816
67. Krishnan-Ghosh Y, Balasubramanian S (2003) Dynamic covalent chemistry on selftemplating peptides: formation of a disulfide-linked-hairpin mimic. Angew Chem Int Ed 42:2171-2173
68. Case MA, McLendon GL (2000) A virtual library approach to investigate protein folding and internal packing. J Am Chem Soc 122:8089-8090
69. Das AK, Hirst A, Ulijn RV (2009) Evolving nanomaterials using enzyme-driven dynamic peptide libraries (eDPL). Faraday Discuss 143:293-303
70. Zhou M, Smith AM, Das AK, Hodson NW, Collins RF, Ulijn RV, Gough JE (2009) Selfassembled peptide-based hydrogels as scaffolds for anchorage dependent cells. Biomaterials 30:2523-2530
71. Jayawarna V, Richardson SM, Hirst A, Hodson NW, Saiani A, Gough JE, Ulijn RV (2009) Introducing chemical functionality in Fmoc-peptide gels for cell culture. Acta Biomater 5:934-943
72. Gao Y, Kuang Y, Guo ZF, Guo Z, Krauss IJ, Xu B (2009) Enzyme-instructed self-assembly confers nanofibers and a supramolecular hydrogel of taxol derivative. J Am Chem Soc 131:13576-13577
73. Yang ZM, Xu B (2004) A simple visual assay based on small molecule hydrogels for detecting inhibitors of enzymes. Chem Commun 2424-2425
74. Yang ZM, Liang GL, Ma ML, Gao Y, Xu B (2007) In vitro and in vivo enzymatic formation of supramolecular hydrogels based on self-assembled nanofibers of a beta-amino acid derivative. Small 3:558-562
75. Yang ZM, Xu KM, Guo ZF, Guo ZH, Xu B (2007) Intracellular enzymatic formation of nanofibers results in hydrogelation and regulated cell death. Adv Mater 19:3152-3156