Hostname: page-component-cd9895bd7-gbm5v Total loading time: 0 Render date: 2024-12-27T02:04:34.842Z Has data issue: false hasContentIssue false
  • English
  • Français

Molecular Imprinting of 3-Hydroxybenzoic Acid: Special and General Binding Sites

Published online by Cambridge University Press:  01 February 2011

Yue Hu  and
Robert A. Orwoll
Yue Hu
Affiliation:
Departments of Applied Science and Chemistry, College of William and Mary, Williamsburg, VA 23187–8795, U.S.A
Robert A. Orwoll
Affiliation:
Departments of Applied Science and Chemistry, College of William and Mary, Williamsburg, VA 23187–8795, U.S.A
Get access

Abstract

A resin, imprinted with 3-hydroxybenzoic acid (3HBA), was synthesized from acrylamide (AA, the functional monomer) and ethylene glycol dimethacrylate (EGDMA, the crosslinking agent). Batch analyses showed that the imprinted polymer has a special affinity for the meta-substituted 3HBA, but not for its para-substituted isomer (4HBA) nor for benzoic acid (BA). These results are consistent with the principle that an imprinted resin's ability to recognize is dependent on the target's size, shape, and functionality. Another resin, prepared from AA and EGDMA but in the absence of a template, had similar affinities for 3HBA, 4HBA, and BA; and thus it could not differentiate among the three. The results can be interpreted with a simple two-binding-site model with one site special for 3HBA and the other being more general with similar affinities for 3HBA, 4HBA and BA. The binding of 3HBA to the imprinted resin is characterized by an association constant and the density of each kind of site using a two-site Scatchard equation. The binding sites common to both the imprinted resin and the non-imprinted reference resin were found to have greater affinity but are less numerous than the sites unique to the imprinted resin.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 787: Symposium G – Molecularly Imprinted Materials , 2003 , G3.4
Copyright
Copyright © Materials Research Society 2004

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

1. Yu, C.; Mosbach, K. J. Chromatogr., A, 2000, 888, 63.Google Scholar
2. Chen, W. Y.; Chen, C. S.; Lin, F. Y. J. Chromatogr., A, 2001, 923, 1.Google Scholar
3. Kirsch, N.; Alexander, C.; Lubke, M.; Whitecombe, M. J.; Vulfson, E. N. Polymer, 2000, 41, 5583.Google Scholar
4. Katz, A.; Davis, M. E. Macromolecules, 1999, 32, 4113.Google Scholar
5. Andersson, H. S.; Karlsson, J. G.; Piletsky, S. A.; Koch-Schmidt, A.; Mosbach, K.; Nicholls, I. A. J. Chromatogr., A, 1999, 848, 39.Google Scholar
6. Komiyama, M.; Takeuchi, T.; Mukawa, T.; Asanuma, H. Molecular Imprinting; WILEY-VCH: Weinheim, 2003; Chapter 4.Google Scholar
7. Quaglia, M.; Chenon, K.; Hall, A. J.; Lorenzi, E. D.; Sellergren, B. J. Am. Chem. Soc., 2001, 123, 2146.Google Scholar
8. Zhang, T.; Liu, F.; Chen, W.; Wang, J.; Li, K. Anal. Chim. Acta, 2001, 450, 53.Google Scholar
9. Zhu, Q.; Haupt, K.; Knopp, D.; Niessner, R. Anal. Chim. Acta, 2002, 468, 217.Google Scholar
10. Yamamura, H. I.; Kuhar, M. J. Neurotranmitter Receptor Binding, 2nd edition; Raven Press: New York, 1985; Chapter 3.Google Scholar
11. Connors, K. A.; Binding Constants; John Wiley & Sons: New York, 1987; Chapter 2.Google Scholar
12. Spivak, D.; Gilmore, M. A.; Shea, K. J. J. Am. Chem. Soc., 1997, 119, 4388.Google Scholar
13. Armstrong, D. W.; Schneiderheinze, J. M.; Hwang, Y. S.; Sellergren, B. Anal. Chem.; 1998, 70, 3717.Google Scholar
14. Garland, C. W.; Niber, J. W.; Shoemaker, D. P. Experiments in Physical Chemistry, 7th edition; The McGraw-Hill Companies, Inc., 2003; Chapter 22.Google Scholar
15. Hu, Y.; Orwoll, R. A.; manuscript, in preparation.Google Scholar