Self-Assembled peptide nanofibers designed as biological enzymes for catalyzing ester hydrolysis

ACS Nano

Volumn 8, Issue 11, 2014, Pages 11715-11723

  Zhang, Chunqiu ^a   Xue, Xiangdong ^a   Luo, Quan ^b   Li, Yiwei ^a   Yang, Keni ^a   Zhuang, Xiaoxi ^a   Jiang, Yonggang ^a   Zhang, Jinchao ^c   Liu, Junqiu ^b   Zou, Guozhang ^a   Liang, Xing Jie ^a  

^a NATIONAL CENTER FOR NANOSCIENCE AND TECHNOLOGY   (China)

^b Jilin University   (China)

^c HEBEI UNIVERSITY   (China)

Author keywords

Artificial enzyme; Ester hydrolysis; Hydrogel; Nanofiber; Self assembly; Short peptide

Indexed keywords

AMINO ACIDS; BIOCOMPATIBILITY; ESTERS; HYDROGELS; HYDROLASES; HYDROLYSIS; NANOFIBERS; SELF ASSEMBLY;

AMINO ACID RESIDUES; ARTIFICIAL ENZYMES; CATALYTIC EFFICIENCIES; ESSENTIAL AMINO ACIDS; ESTER HYDROLYSIS; ORDERED NANOSTRUCTURES; SELF-ASSEMBLED PEPTIDES; STRUCTURAL ARRANGEMENT;

PEPTIDES;

NANOFIBER; PEPTIDE;

CATALYSIS; CHEMISTRY; CIRCULAR DICHROISM; HYDROLYSIS; PROTEIN SECONDARY STRUCTURE; TRANSMISSION ELECTRON MICROSCOPY;

CATALYSIS; CIRCULAR DICHROISM; HYDROLYSIS; MICROSCOPY, ELECTRON, TRANSMISSION; NANOFIBERS; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 84912535999     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn5051344     Document Type: Article

References (48)

1. Breslow, R.; Dong, S. D. Biomimetic Reactions Catalyzed by Cyclodextrins and Their Derivatives. Chem. Rev. 1998, 98, 1997-2012.
2. Kirby, A. J. Enzyme Mechanisms, Models, and Mimics. Angew. Chem., Int. Ed. Engl. 1996, 35, 706-724.
3. Qi, D.; Tann, C. M.; Haring, D.; Distefano, M. D. Generation of New Enzymes via Covalent Modification of Existing Proteins. Chem. Rev. 2001, 101, 3081-3111.
4. Murakami, Y.; Kikuchi, J. J.; Hisaeda, Y.; Hayashida, O. Artificial Enzymes. Chem. Rev. 1996, 96, 721-758.
5. Wulff, G. Enzyme-like Catalysis by Molecularly Imprinted Polymers. Chem. Rev. 2002, 102, 1-27.
6. Astruc, D.; Lu, F.; Aranzaes, J. R. Nanoparticles as Recyclable Catalysts: The Frontier between Homogeneous and Heterogeneous Catalysis. Angew. Chem., Int. Ed. 2005, 44, 7852-7872.
7. Zaramella, D.; Scrimin, P.; Prins, L. J. Self-Assembly of a Catalytic Multivalent Peptide - Nanoparticle Complex. J. Am. Chem. Soc. 2012, 134, 8396-8399.
8. Lin, Y.; Ren, J.; Qu, X. Nano-Gold as Artificial Enzymes: Hidden Talents. Adv. Mater. 2014, 26, 4200-4217.
9. Kofoed, J.; Reymond, J. L. Dendrimers as Artificial Enzymes. Curr. Opin. Chem. Biol. 2005, 9, 656-664.
10. Huang, X.; Dong, Z.; Liu, J.; Mao, S.; Xu, J.; Luo, G.; Shen, J. Selenium-Mediated Micellar Catalyst: An Efficient Enzyme Model for Glutathione Peroxidase-like Catalysis. Langmuir 2007, 23, 1518-1522.
11. Guler, M. O.; Stupp, S. I. A Self-Assembled Nanofiber Catalyst for Ester Hydrolysis. J. Am. Chem. Soc. 2007, 129, 12082-12083.
12. Rufo, C. M.; Moroz, Y. S.; Moroz, O. V.; Stohr, J.; Smith, T. A.; Hu, X.; DeGrado, W. F.; Korendovych, I. V. Short Peptides Self-Assemble To Produce Catalytic Amyloids. Nat. Chem. 2014, 6, 303-309.
13. Tang, Y.; Zhou, L.; Li, J.; Luo, Q.; Huang, X.; Wu, P.; Wang, Y.; Xu, J.; Shen, J.; Liu, J. Giant Nanotubes Loaded with Artificial Peroxidase Centers: Self-Assembly of Supramolecular Amphiphiles as a Tool To Functionalize Nanotubes. Angew. Chem., Int. Ed. 2010, 49, 3920-3924.
14. Hou, C.; Luo, Q.; Liu, J.; Miao, L.; Zhang, C.; Gao, Y.; Zhang, X.; Xu, J.; Dong, Z.; Liu, J. Construction of GPx Active Centers on Natural Protein Nanodisk/Nanotube: A New Way To Develop Artificial Nanoenzyme. ACS Nano 2012, 6, 8692-8701.
15. Huang, X.; Liu, X.; Luo, Q.; Liu, J.; Shen, J. Artificial Seleno-enzymes: Designed and Redesigned. Chem. Soc. Rev. 2011, 40, 1171-1184.
16. Gao, Y.; Zhao, F.; Wang, Q.; Zhang, Y.; Xu, B. Small Peptide Nano fibers as the Matrices of Molecular Hydrogels for Mimicking Enzymes and Enhancing the Activity of Enzymes. Chem. Soc. Rev. 2010, 39, 3425-3433.
17. Rodriguez-Llansola, F.; Miravet, J. F.; Escuder, B. A Supramolecular Hydrogel as a Reusable Heterogeneous Catalyst for the Direct Aldol Reaction. Chem. Commun. 2009, 7303-7305.
18. Terech, P.; Weiss, R. G. Low Molecular Mass Gelators of Organic Liquids and the Properties of Their Gels. Chem. Rev. 1997, 97, 3133-3160.
19. Jung, J. P.; Nagaraj, A. K.; Fox, E. K.; Rudra, J. S.; Devgun, J. M.; Collier, J. H. Co-assembling Peptides as Defined Matrices for Endothelial Cells. Biomaterials 2009, 30, 2400-2410.
20. Collier, J. H. Modular Self-Assembling Biomaterials for Directing Cellular Responses. Soft Matter 2008, 4, 2310-2315.
21. Aggeli, A.; Bell, M.; Boden, N.; Keen, J. N.; Knowles, P. F.; McLeish, T. C.; Pitkeathly, M.; Radford, S. E. Responsive Gels Formed by the Spontaneous Self-Assembly of Peptides into Polymeric β-Sheet Tapes. Nature 1997, 386, 259-262.
22. Altunbas, A.; Lee, S. J.; Rajasekaran, S. A.; Schneider, J. P.; Pochan, D. J. Encapsulation of Curcumin in Self-Assembling Peptide Hydrogels as Injectable Drug Delivery Vehicles. Biomaterials 2011, 32, 5906-5914.
23. Rudra, J. S.; Tian, Y. F.; Jung, J. P.; Collier, J. H. A Self-Assembling Peptide Acting as an Immune Adjuvant. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 622-627.
24. Huang, Z. H.; Shi, L.; Ma, J. W.; Sun, Z. Y.; Cai, H.; Chen, Y. X.; Zhao, Y. F.; Li, Y. M. A Totally Synthetic, Self-Assembling, Adjuvant-Free MUC1 Glycopeptide Vaccine for Cancer Therapy. J. Am. Chem. Soc. 2012, 134, 8730-8733.
25. Rudra, J. S.; Sun, T.; Bird, K. C.; Daniels, M. D.; Gasiorowski, J. Z.; Chong, A. S.; Collier, J. H. Modulating Adaptive Immune Responses to Peptide Self-Assemblies. ACS Nano 2012, 6, 1557-1564.
26. Collier, J. H.; Hu, B. H.; Ruberti, J. W.; Zhang, J.; Shum, P.; Thompson, D. H.; Messersmith, P. B. Thermally and Photochemically Triggered Self-Assembly of Peptide Hydrogels. J. Am. Chem. Soc. 2001, 123, 9463-9464.
27. Aggeli, A.; Bell, M.; Boden, N.; Keen, J. N.; Knowles, P. F.; McLeish, T. C.; Pitkeathly, M.; Radford, S. E. Responsive Gels Formed by the Spontaneous Self-Assembly of Peptides into Polymeric β-Sheet Tapes. Nature 1997, 386, 259-262.
28. Schneider, J. P.; Pochan, D. J.; Ozbas, B.; Rajagopal, K.; Pakstis, L.; Kretsinger, J. Responsive Hydrogels from the Intramolecular Folding and Self-Assembly of a Designed Peptide. J. Am. Chem. Soc. 2002, 124, 15030-15037.
29. Zhang, S.; Holmes, T.; Lockshin, C.; Rich, A. Spontaneous Assembly of a Self-Complementary Oligopeptide To Form a Stable Macroscopic Membrane. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 3334-3338.
30. Lashuel, H. A.; Labrenz, S. R.; Woo, L.; Serpell, L. C.; Kelly, J. W. Protofilaments, Filaments, Ribbons, and Fibrils from Peptidomimetic Self-Assembly: Implications for Amyloid Fibril Formation and Materials Science. J. Am. Chem. Soc. 2000, 122, 5262-5277.
31. El'skaia, A. V.; Soldatkin, A. P. The Basis of High-Fidelity Translation. Mol. Biol. (Moscow) 1984, 18, 1163-1180.
32. Gutfreund, H.; Sturtevant, J. M. The Mechanism of the Reaction of Chymotrypsin with p-Nitrophenyl Acetate. Biochem. J. 1956, 63, 656-661.
33. Mounter, L. A. Dialkylfluorophosphatase of Kidney. IV. Dissociation Constant of Active Groups. J. Biol. Chem. 1956, 219, 677-683.
34. Bender, M.; Turnquest, B. The Imidazole-Catalyzed Hydrolysis of p-Nitrophenyl Acetate. J. Am. Chem. Soc. 1957, 79, 1652-1655.
35. Kirsch, J.; Jencks, W. Base Catalysis of Imidazole Catalysis of Ester Hydrolysis. J. Am. Chem. Soc. 1964, 86, 833-837.
36. Komiyama, M.; Bender, M. Hydrolysis of p-Nitrotrifluoroacetanilide Catalyzed by Water and Imidazole. Bioorg. Chem. 1978, 7, 133-139.
37. Kunitake, T.; Shimada, F.; Aso, C. Imidazole Catalyses in Aqueous Systems. I. Enzyme-like Catalysis in the Hydrolysis of a Phenyl Ester by Imidazole-Containing Copolymers. J. Am. Chem. Soc. 1969, 91, 2716-2723.
38. Giusti, L.; Medeiros, M.; Ferreira, N. L.; Mora, J.; Fiedler, H. Polymers Containing Imidazole Groups as Nanoreactors for Hydrolysis of Esters. J. Phys. Org. Chem. 2014, 27, 297-302.
39. Huang, Z.; Guan, S.; Wang, Y.; Shi, G.; Cao, L.; Gao, Y.; Dong, Z.; Xu, J.; Luo, Q.; Liu, J. Self-Assembly of Amphiphilic Peptides into Bio-functionalized Nanotubes: A Novel Hydrolase Model. J. Mater. Chem. B 2013, 1, 2297-2304.
40. Collier, J. H.; Messersmith, P. B. Enzymatic Modification of Self-Assembled Peptide Structures with Tissue Transglutaminase. Bioconjugate Chem. 2003, 14, 748-755.
41. Jung, J. P.; Jones, J. L.; Cronier, S. A.; Collier, J. H. Modulating the Mechanical Properties of Self-Assembled Peptide Hydrogels via Native Chemical Ligation. Biomaterials 2008, 29, 2143-2151.
42. Caplan, M. R.; Moore, P. N.; Zhang, S.; Kamm, R. D.; Lauffenburger, D. A. Self-Assembly of a β-Sheet Protein Governed by Relief of Electrostatic Repulsion Relative to van der Waals Attraction. Biomacromolecules 2000, 1, 627-631.
43. Eisenberg, D.; Jucker, M. The Amyloid State of Proteins in Human Diseases. Cell 2012, 148, 1188-1203.
44. Colletier, J. P.; Laganowsky, A.; Landau, M.; Zhao, M.; Soriaga, A. B.; Goldschmidt, L.; Flot, D.; Cascio, D.; Sawaya, M. R.; Eisenberg, D. Molecular Basis for Amyloid-β Polymorphism. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 16938-16943.
45. Nowick, J. S. Exploring β-Sheet Structure and Interactions with Chemical Model Systems. Acc. Chem. Res. 2008, 41, 1319-1330.
46. Biancalana, M.; Koide, S. Molecular Mechanism of Thioflavin-T Binding to Amyloid Fibrils. Biochim. Biophys. Acta 2010, 1804, 1405-1412.
47. Bruice, T. C.; Sturtevant, J. M. Imidazole Catalysis. V. The Intramolecular Participation of the Imidazolyl Group in the Hydrolysis of Some Esters and the Amide of γ-(4-Imidazolyl)-butyric Acid and 4-(2′-Acetoxyethyl)-imidazole. J. Am. Chem. Soc. 1959, 81, 2860-2870.
48. Faller, L.; Sturtevant, J. M. The Kinetics of the α-Chymotrypsin-Catalyzed Hydrolysis of p-Nitrophenyl Acetate in Organic Solvent-Water Mixtures. J. Biol. Chem. 1966, 241, 4825-4834.