Noncovalent immobilization of proteins on a solid surface by cucurbit[7]uril-ferrocenemethylammonium pair, a potential replacement of biotin-avidin pair

Journal of the American Chemical Society

Volumn 129, Issue 14, 2007, Pages 4170-4171

  Hwang, Ilha ^a   Baek, Kangkyun ^a   Jung, Minseon ^a   Kim, Youngkook ^a   Kyeng, Min Park ^a   Lee, Don Wook ^a   Selvapalam, Narayanan ^a   Kim, Kimoon ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; AVIDIN; BIOTIN; FERROCENE DERIVATIVE; STREPTAVIDIN; URACIL DERIVATIVE;

ADSORPTION; ARTICLE; CHEMICAL BOND; CYCLIC POTENTIOMETRY; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; PROTEIN IMMOBILIZATION; SOLID; SURFACE PROPERTY;

BIOTIN; BRIDGED COMPOUNDS; FERROUS COMPOUNDS; GLUCOSE; GOLD; IMIDAZOLES; MOLECULAR STRUCTURE; PROTEINS; SURFACE PLASMON RESONANCE;

EID: 34247109133     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071130b     Document Type: Article

References (50)

1. (a) Green, N. M. Adv. Prot. Chem. 1975, 29, 85-133.
2. (b) Green, N. M. Methods Enzymol. 1990, 184, 51-67.
3. Swamy, M. J. Biochem. Mol. Biol. Int. 1995, 36, 219-225.
4. (a) Bayer, E. A.; Wilchek, M. J. Chromatogr. 1990, 510, 3-11.
5. (b) Wilchek, M.; Bayer, E. A. Methods Enzymol. 1990, 184, 5-13, 14-45.
6. Savage, D.; Mattson, G.; Desai, S.; Nielander, G.; Morgensen, S.; Conklin, E. Avidin-Biotin Chemistry: A Handbook; Pierce Chemical Company: Rockford, IL, 1992.
7. (a) Reznik, G. O.; Vajda, S.; Cantor, C. R.; Sano, T. Bioconjugate Chem. 2001, 12, 1000-1004.
8. (b) Lesaicherre, M.-L.; Lue, R. Y. P.; Chen, G. Y. J.; Zhu, Q.; Yao, S. Q. J. Am. Chem. Soc. 2002, 124, 8768-8769.
9. (c) Ripel, M.; Enander, K.; Liedberg, B.; Schäferling, M.; Kruschina, M.; Ortigao, F. Langmuir 2002, 18, 7016-7023.
10. (d) Ladd, J.; Boozer, C.; Yu, Q.; Chen, S.; Homola, J.; Jiang, S. Langmuir 2004, 20, 8090-8095.
11. (e) Park, T. J.; Lee, K.-B.; Lee, S. J.; Park, J. P.; Lee, Z.-W.; Lee, S. Y.; Choi, I. S. J. Am. Chem. Soc. 2004, 126, 10512-10513.
12. (f) Kim, K.; Yang, H.; Jon, S.; Kim, E.; Kwak, J. J. Am. Chem. Soc. 2004, 126, 15368-15369.
13. (g) Tao, S.-C.; Zhu, H. Nat. Biotechnol. 2006, 24, 1253-1254.
14. (h) Christman, K. L.; Requa, M. V.; Enriquez-Rios, V. D.; Ward, S. C.; Bradley, K. A.; Turner, K. L.; Maynard, H. D. Langmuir 2006, 22, 7444-7450.
15. (a) Freeman, W. A.; Mock, W. L.; Shih, N.-Y. J. Am. Chem. Soc. 1981, 103, 7367-7368.
16. (b) Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540-541.
17. (c) Day, A.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66, 8094-8100.
18. (d) Liu, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 16798-16799.
19. Reviews on cucurbit[n]uril: (a) Mock, W. L. Top. Curr. Chem. 1995, 175, 1-24.
20. (b) Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621-630.
21. (c) Kim, K.; Kim, H.-J. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Ed.; Marcel Dekker Inc.: New York, 2004; pp 390-397.
22. (d) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870.
23. (a) Jeon, W. S.; Moon, K.; Park, S. H.; Chun, H.; Ko, Y. H.; Lee, J. Y.; Lee, E. S.; Samal, S.; Selvapalam, S.; Rekharsky, M. V.; Sindelar, V.; Sobransingh, D.; Inoue, Y.; Kaifer, A. E.; Kim, K. J. Am. Chem. Soc. 2005, 127, 12984-12989.
24. (b) Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959-15967.
25. Jon, S. Y.; Selvapalam, N.; Oh, D. H.; Kang, J.-K.; Kim, S.-Y.; Jeon, Y. J.; Lee, J. W.; Kim, K. J. Am. Chem. Soc. 2003, 125, 10186-10187.
26. (a) Jeon, Y. J.; Kim, H.; Jon, S.; Selvapalam, N.; Oh, D. H.; Seo, I.; Park, C.-S.; Jung, S. R.; Koh, D.-S.; Kim, K. J. Am. Chem. Soc. 2004, 126, 15944-15945.
27. (b) Lee, H.-K.; Park, K. M.; Jeon, Y. J.; Kim, D.; Oh, D. H.; Kim, H. S.; Park, C. K.; Kim, K. J. Am. Chem. Soc. 2005, 127, 5006-5007.
28. (c) Kim, D.; et al. Angew. Chem., Int. Ed. 2007, 46 (DOI: 10.1002/anie.200604526).
29. Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267-279.
30. Noncovalent immobilization of molecules on a surface using multiple β-cyclodextrin-adamantane (or ferrocene) interaction has been reported: Ludden, M. J. W.; Reinhoudt, D. N.; Huskens, J. Chem. Soc. Rev. 2006, 35, 1122-1134.
31. -1), however, this method relies on multiple host-guest interactions using multivalent guests such as adamantyl-functionalized dendrimers. Immobilization of streptavidin using this approach was recently reported: Ludden, M. J. W.; Péter, M.; Reinhoudt, D. N.; Huskens, J. Small 2006, 2, 1192-1202.
32. 9 with some modifications, contains ∼6 allyloxy groups at the "equator" of CB[7]: see Supporting Information for details.
33. (a) Lee, J. K.; Lee, K.-B.; Kim, D. J.; Choi, I. S. Langmuir 2003, 19, 8141-8143.
34. (b) Rutenberg, I. M.; Scherman, O. A.; Grubbs, R. H.; Jiang, W.; Garfunkel, E.; Bao, Z. J. Am. Chem. Soc. 2004, 126, 4062-4063.
35. (c) Brooksby, P. A.; Anderson, K. H.; Downard, A. J.; Abell, A. D. Langmuir 2006, 22, 9304-9312.
36. (a) Prime, K. L.; Whitesides, G. M. Science 1991, 252, 1164-1167.
37. (b) Pale-Grosdemange, C.; Simon, E. S.; Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 12-20.
38. (c) Prime, K. L.; Whitesides, G. M. Am. Chem. Soc. 1993, 115, 10714-10721.
39. (d) Mrksich, M. Chem. Soc. Rev. 2000, 29, 267-273.
40. (e) Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103-1169.
41. Willner, I.; Katz, E. Angew. Chem., Int. Ed. 2000, 39, 1180-1218.
42. (a) Degani, Y.; Heller, A. J. Phys. Chem. 1987, 91, 1285-1292.
43. (b) Degani, Y.; Heller, A. J. Am. Chem. Soc. 1988, 110, 2615-2620.
44. (c) Schuhmann, W.; Ohara, T. J.; Schmidt, H.-L.; Heller, A. J. Am. Chem. Soc. 1991, 113, 1394-1397.
45. (a) Blonder, R.; Katz, E.; Cohen, Y.; Itzhak, N.; Riklin, A.; Willner, I. Anal. Chem. 1996, 68, 3151-3157.
46. (b) Blonder, R.; Levi, S.; Tao, G.; Ben-Dov, I.; Willner, I. J. Am. Chem. Soc. 1997, 119, 10467-10478.
47. (a) Franchina, J. G.; Lackowski, W. M.; Dermody, D. L.; Crooks, R. M.; Bergbreiter, D. E.; Sirkar, K.; Russell, R. J.; Pishko, M. V. Anal. Chem. 1997, 71, 3133-3139.
48. (b) Yoon, H. C.; Hong, M.-Y.; Kim, H.-S. Langmuir 2001, 17, 1234-1239.
49. Based on the SPR data and size of the protein, we estimated that one or two CB[7]-FA pairs are involved in immobilization of each FA-GOx on the surface.
50. -1, which is ∼20% of that in solution. The origin of the reduction in the activity is not clear at the moment, but it may be due to the inefficiency of the electron transfer between FA-GOx and the electrode surface.