Self-assembled monolayers that transduce enzymatic activities to electrical signals

Angewandte Chemie - International Edition

Volumn 42, Issue 27, 2003, Pages 3121-3124

  Yeo, Woon Seok ^a   Mrksich, Milan ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Cyclic voltammetry; Enzymes; Interfaces; Redox chemistry; Self assembly

Indexed keywords

ELECTRIC SIGNAL SYSTEMS; ENZYMES; SUBSTRATES;

REDOX-ACTIVE PRODUCT;

SELF ASSEMBLY;

BENZOQUINONE; CUTINASE; ENZYME; ETHYLENE GLYCOL DERIVATIVE; FERROUS CHLORIDE; HYDROQUINONE; SERINE PROTEINASE; VALERIC ACID DERIVATIVE;

ARTICLE; CYCLIC POTENTIOMETRY; ELECTRIC POTENTIAL; ENZYME ACTIVITY; MASS SPECTROMETRY; SIGNAL TRANSDUCTION;

CARBOXYLIC ESTER HYDROLASES; ELECTRIC STIMULATION; KINETICS; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENOLS; SIGNAL TRANSDUCTION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; VALERATES;

EID: 0042812119     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250862     Document Type: Article

References (26)

1. a) M. Mrksich, G. M. Whitesides, Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 55;
2. b) A. K. Dillow, M. Tirrell, Curr. Opin. Solid State Mater Sci. 1998, 3, 252;
3. c) M. Mrksich, Chem. Soc. Rev. 2000, 29, 267;
4. d) I. Willner, E. Katz, Angew. Chem. Int. Ed. 2000, 39, 1180;
5. e) D. R. Jung, R. Kapur, T. Adams, K. A. Giuliano, M. Mrksich, H. G. Craighead, D. L. Taylor, Crit. Rev. Biotechnol. 2001, 21, 111.
6. a) T. Okano, N. Yamata, J. Sakai, Y. Sakurai, Biomaterials 1995, 16, 297-303;
7. b) T. O. Collier, J. M. Anderson, A. Kikuchi, T. Okano, J. Biomed. Mater. Res. 2002, 59, 136.
8. a) R. Blonder, E. Katz, I. Willner, V. Wray, A. F. Bückmann, J. Am. Chem. Soc. 1997, 119, 11747;
9. b) R. Blonder, S. Levi, G. Tao, I. Ben-Dov, I. Willner, J. Am. Chem. Soc. 1997, 119, 10467.
10. a) M. N. Yousaf, M. Mrksich, J. Am. Chem. Soc. 1999, 121, 4286;
11. b) C. D. Hodneland, M. Mrksich, J. Am. Chem. Soc. 2000, 122, 4235;
12. c) W.-S. Yeo, C. D. Hodneland, M. Mrksich, ChemBioChem 2001, 2, 590.
13. a) M. N. Yousaf, B. T. Houseman, M. Mrksich, Proc. Natl. Acad. Sci. USA 2001, 98, 5992;
14. b) M. N. Yousaf, B. T. Houseman, M. Mrksich, Angew. Chem. Int. Ed. 2001, 40, 1093.
15. C. Martinez, P. De Geus, M. Lauwereys, G. Matthyssens, C. Cambilau, Nature 1992, 356, 6370.
16. a) Y. Sato, M. Fujita, F. Mizutani, K. Uosaki, J. Electroanal. Chem. 1996, 409, 145;
17. b) M. N. Yousaf, E. W. L. Chan, M. Mrksich, Angew. Chem. Int. Ed. 2000, 39, 1943;
18. c) Y. Kwon, M. Mrksich, J. Am. Chem. Soc. 2002, 124, 806.
19. 1H NMR spectra.
20. -1 solution in acetonitrile) as a matrix. Sodium adducts of disulfides are the major species that are observed in MALDI spectra of the SAMs of alkanethiolates: see J. Su, M. Mrksich, Angew. Chem. Int. Ed. 2002, 41, 4715, and J. L. Trevor, K. R. Lykke, M. J. Pellin, L. Hanley, Langmuir 1998, 14, 1664.
21. -1 solution in acetonitrile) as a matrix. Sodium adducts of disulfides are the major species that are observed in MALDI spectra of the SAMs of alkanethiolates: see J. Su, M. Mrksich, Angew. Chem. Int. Ed. 2002, 41, 4715, and J. L. Trevor, K. R. Lykke, M. J. Pellin, L. Hanley, Langmuir 1998, 14, 1664.
22. -1. All experiments used a custom-designed electrochemical cell with the monolayer as the working electrode, a Pt wire as the counter electrode, and an Ag/AgCl reference electrode.
23. 1H NMR spectra. For the synthetic scheme and experimental details, see Supporting Information.
24. The density of 4-hydroxyphenyl valerate for this monolayer was approximately 9%, as determined by integration of the area under the redox wave after the enzymatic reaction was completed. This analysis assumes that the 4-hydroxyphenyl valerate was quantitatively converted to hydroquinone.
25. For the protocols used to prepare cutinase and the inhibitor, see; C. D. Hodneland, Y. S. Lee, D. -H. Min, M. Mrksich, Proc. Natl. Acad. Sci. USA 2002, 99, 5048.
26. For each monolayer, the density of hydroquinone on the surface was determined by integration of the areas under the redox waves in the cyclic voltammograms.