Immobilization of ferrocene-modified SNAP-fusion proteins

International Journal of Molecular Sciences

Volumn 14, Issue 2, 2013, Pages 4066-4080

  Wasserberg, Dorothee ^a   Uhlenheuer, Dana A ^b   Neirynck, Pauline ^b   Cabanas Danés, Jordi ^a   Schenkel, Jan Hendrik ^c   Ravoo, Bart Jan ^c   An, Qi ^a   Huskens, Jurriaan ^a   Milroy, Lech Gustav ^b   Brunsveld, Luc ^b   Jonkheijm, Pascal ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Cucurbituril; Cyclodextrin; Ferrocene; Host guest chemistry; Protein immobilization; Protein modifications

Indexed keywords

6 O BENZYLGUANINE; BETA CYCLODEXTRIN; BIS FERROCENE BENZYLGUANINE; CUCURBITURIL; CYAN FLUORESCENT PROTEIN; FERROCENE; FERROCENE BENZYLGUANINE; HYBRID PROTEIN; SOLUBLE N ETHYLMALEIMIDE SENSITIVE FACTOR ATTACHMENT PROTEIN; TERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL LABELING; MOLECULAR INTERACTION; PROTEIN ASSEMBLY; PROTEIN BINDING; PROTEIN IMMOBILIZATION; PROTEIN MODIFICATION; SURFACE PROPERTY;

EID: 84875090864     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms14024066     Document Type: Article

References (37)

1. Wong, L.S.; Khan, F.; Micklefield, J. Selective covalent protein immobilization: Strategies and applications. Chem. Rev. 2009, 109, 4025-4053.
2. Weinrich, D.; Jonkheijm, P.; Niemeyer, C.; Waldmann, H. Applications of protein biochips in biomedical and biotechnological research. Angew. Chem. Int. Ed. 2009, 10, 7744-7751.
3. Colpo, P.; Ruiz, A.; Ceriotti, L.; Rossi, F. Surface functionalization for protein and cell patterning. Adv. Biochem. Eng. Biotechnol. 2010, 117, 109-130.
4. Hanefeld, U.; Gardossi, L.; Magner, E. Understanding enzyme immobilization. Chem. Soc. Rev. 2009, 38, 453-468.
5. Yang, L.; Gómez-Casado, A.; Young, J.F.; Nguyen, H.D.; Cabanas-Danés, J.; Huskens, J.; Brunsveld, L.; Jonkheijm, P. Reversible and oriented immobilization of ferrocene-modified proteins. J. Am. Chem. Soc. 2012, 134, 19199-19206.
6. Escalante, M.; Zhao, Y.; Ludden, M.J.W.; Vermeij, R.; Olsen, J.D.; Berenschot, E.; Hunter, C.N.; Huskens, J.; Subramaniam, V.; Otto, C. Nanometer arrays of functional light harvesting antenna complexes by nanoimprint lithography and host-guest interactions. J. Am. Chem. Soc. 2008, 130, 8892-8893.
7. Hwang, I.; Baek, K.; Jung, M.; Kim, Y.; Park, K.M.; Lee, D.-W.; Selvapalam, N.; Kim, K. Noncovalent immobilization of proteins on a solid surface by cucurbit[7]uril-ferrocenemethylammonium pair, a potential replacement of biotin-avidin pair. J. Am. Chem. Soc. 2007, 129, 4170-4171.
8. Ludden, M.J.W.; Li, X.; Greve, J.; van Amerongen, A.; Escalante, M.; Subramaniam, V.; Reinhoudt, D.N.; Huskens, J. Assembly of bionanostructures onto beta-cyclodextrin molecular printboards for antibody recognition and lymphocyte cell counting. J. Am. Chem. Soc. 2008, 130, 6964-6973.
9. Ludden, M.L.W.; Mulder, A.; Schulze, K.; Subramaniam, V.; Tampé, R.; Huskens, J. Anchoring of histidine-tagged proteins to molecular printboards: Self-assembly, thermodynamic modeling, and patterning. Chem. Eur. J. 2008, 14, 2044-2051.
10. González-Campo, A.; Brasch, M.; Uhlenheuer, D.; Gómez-Casado, A.; Yang, L.; Brunsveld, L.; Huskens, J.; Jonkheijm, P. Supramolecularly oriented immobilization of proteins using cucurbit[8]uril. Langmuir 2012, doi:10.1021/la303987c.
11. González-Campo, A.; Eker, B.; Gardeniers, H.J.G.E.; Huskens, J.; Jonkheijm, P. A supramolecular approach to enzyme immobilization in micro-channels. Small 2012, 8, 3531-3537.
12. Felici, M.; Marzá-Pérez, M.; Hatzakis, N.S.; Nolte, R.J.M.; Feiters, M.C. Beta-Cyclodextrin-appended giant amphiphile: Aggregation to vesicle polymersomes and immobilisation of enzymes. Chem. Eur. J. 2008, 14, 9914-9920.
13. Zhang, L.; Wu, Y.; Brunsveld, L. A synthetic supramolecular construct modulating protein assembly in cells. Angew. Chem. Int. Ed. 2007, 46, 1798-1802.
14. Uhlenheuer, D.A.; Wasserberg, D.; Nguyen, H.; Zhang, L.; Blum, C.; Subramaniam, V.; Brunsveld, L. Modulation of protein dimerization by a supramolecular host-guest system. Chem. Eur. J. 2009, 15, 8779-8790.
15. Uhlenheuer, D.A.; Young, J.F.; Nguyen, H.D.; Scheepstra, M.; Brunsveld, L. Cucurbit[8]uril induced heterodimerization of methylviologen and naphthalene functionalized proteins. Chem. Commun. 2011, 47, 6798-6800.
16. Uhlenheuer, D.; Milroy, L.-G.; Neirynck, P.; Brunsveld, L. Strong supramolecular control over protein self-assembly using a polyamine decorated beta-cyclodextrin as synthetic recognition element. J. Mater. Chem. 2011, 21, 18919-18922.
17. Young, J.F.; Nguyen, H.D.; Yang, L.; Huskens, J.; Jonkheijm, P.; Brunsveld, L. Strong and reversible monovalent supramolecular protein immobilization. ChemBioChem 2010, 1, 180-183.
18. Keppler, A., Gendreizig, S.; Gronemeyer, T.; Pick, H.; Vogel, H.; Johnsson, K. A general method for the covalent labeling of fusion proteins with small molecules in vivo. Nat. Biotechn. 2002, 21, 86-89.
19. Juillerat, A.; Gronemeyer, T.; Keppler, A.; Gendreizig, S.; Pick, H.; Vogel, H.; Johnsson, K. Directed evolution of O6-alkylguanine-DNA alkyltransferase for efficient labeling of fusion proteins with small molecules in vivo. Chem. Biol. 2003, 10, 313-317.
20. Hinner, M.J.; Johnsson, K. How to obtain labeled proteins and what to do with them. Curr. Opin. Biotechnol. 2010, 21, 766-776.
21. Kindermann, M.; George, N.; Johnsson, N.; Johnsson, K. Covalent and selective immobilization of fusion proteins. J. Am. Chem. Soc. 2003, 125, 7810-7811.
22. Sielaff, I.; Arnold, A.; Godin, G.; Tugulu, S.; Klok, H.A.; Johnsson, K. Protein function microarrays based on self-immobilizing and self-labeling fusion proteins. ChemBioChem 2006, 7, 194-202.
23. Iversen, L.; Cherouati, N.; Berthing, T.; Stamou, D.; Martinez, K.L. Templated protein assembly on micro-contact-printed surface patterns. Use of the SNAP-tag protein functionality. Langmuir 2008, 24, 6375-6381.
24. Recker, T.; Haamann, D.; Schmitt, A.; Kuster, A.; Klee, D.; Barth, S.; Muller-Newen, G. Directed covalent immobilization of fluorescently labeled cytokines. Bioconj. Chem. 2011, 22, 1210-1220.
25. Engin, S.; Trouillet, V.; Franz, C.M.; Welle, A.; Bruns, M.; Wedlich, D. Benzylguanine thiol self-assembled monolayers for the immobilization of SNAP-tag proteins on microcontact-printed surface structures. Langmuir 2010, 26, 6097-6101.
26. Uhlenheuer, D.A.; Wasserberg, D.; Haase, C.; Nguyen, H.D.; Schenkel, J.H.; Huskens, J.; Ravoo, B.J.; Jonkheijm, P.; Brunsveld, L. Directed supramolecular surface assembly of SNAP-tag fusion proteins. Chem. Eur. J., 2012, 18, 6788-6794.
27. Falvey, P.; Lim, C.W.; Darcy, R.; Revermann, T.; Karst, U.; Giesbers, M.; Marcelis, A.T.M.; Lazar, A.; Coleman, A.W.; Reinhoudt, D.N.; et al. Bilayer vesicles of amphiphilic cyclodextrins: Host membranes that recognize guest molecules. Chem. Eur. J. 2005, 11, 1171-1180.
28. Valeur, E.; Bradley, M. Amide bond formation: beyond the myth of coupling reagents. Chem. Soc. Rev. 2009, 38, 606-631.
29. Lemercier, G.; Gendreizig, S.; Kindermann, M.; Johnsson, K. Inducing and sensing protein-protein interactions in living cells by selective cross-linking. Angew. Chem. Int. Ed. 2007, 46, 4281-4284.
30. Uhlenheuer, D.A. Supramolecular control over protein assembly, PhD Thesis, Eindhoven University of Technology, Eindhoven, The Netherlands, 19 September 2011.
31. Rijkers, D.T.; van Esse, G.W.; Merkx, R.; Brouwer, A.J.; Jacobs, H.J.; Pieters, R.J.; Liskamp, R.M. Efficient microwave-assisted synthesis of multivalent dendrimeric peptides using cycloaddition reaction (click) chemistry. Chem. Commun. 2005, 4581-4583.
32. Kobayashi, T.; Komatsu, T.; Terai, T.; Hanaoka, K.; Nagano, T.; Urano, Y.; Kamiya, M.; Campos, C.; Gonzalez-Gaitan, M. Highly activatable and environment-insensitive optical highlighters for selective spatiotemporal imaging of target proteins. J. Am. Chem. Soc. 2012, 134, 11153-11160.
33. Meldal, M.; Tornøe, C.W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 2008, 108, 2952-3015.
34. Onclin, S.; Mulder, A.; Huskens, J.; Ravoo, B.J.; Reinhoudt, D.N. Molecular printboards: monolayers of beta-cyclodextrins on silicon oxide surfaces. Langmuir 2004, 20, 5460-5466.
35. Beulen, M.W.; Bügler, J.; de Jong, M.R.; Lammerink, B.; Huskens, J.; Schönherr, H.; Vancso, G.J.; Boukamp, B.A.; Wieder, H.; Offenhäuser, A.; et al. Host-guest interactions at self-assembled monolayers of cyclodextrins on gold. Chem. Eur. J. 2000, 6, 1176-1183.
36. Gomez-Casado, A.; Jonkheijm, P.; Huskens, J. Recognition properties of cucurbit[7]uril self-assembled monolayers studied with force spectroscopy. Langmuir 2011, 27, 11508-11513.
37. Alker, D.; Ashton, P.R.; Harding, V.D.; Königer, R.; Stoddart, J.F. Amino acid derivatives of beta-cyclodextrin. J. Org. Chem. 1996, 61, 903-908.