Hostname: page-component-78c5997874-dh8gc Total loading time: 0 Render date: 2024-11-10T08:56:06.586Z Has data issue: false hasContentIssue false
  • English
  • Français

Oligonucleotide Imprinting in Aqueous Environment

Published online by Cambridge University Press:  01 February 2011

Dolly Batra  and
Kenneth J. Shea
Dolly Batra
Affiliation:
Department of Chemistry University of California, Irvine Irvine, CA 92697
Kenneth J. Shea
Affiliation:
Department of Chemistry University of California, Irvine Irvine, CA 92697
Get access

Abstract

The development of synthetic receptors that recognize nucleotide bases and their derivatives is an important area of research [1-3]. Applications are envisioned in separation science, biosensors, drug therapy and genetic engineering. Previously in this laboratory, we have developed a molecularly imprinted synthetic receptor for 9-ethyladenine (9-EA). The network polymer has an affinity for adenine and its derivatives with an average association constant (Ka) of 75,000 M–1 in CHCl3 [4]. When a 9-EA imprinted polymer was used as the chromatographic support, adenine eluted at 27 minutes using 92.5/5/0/2.5 CH3CN/H2O/CH3CO2H as the mobile phase, while cytosine, guanine and thymine derivatives all eluted close to the void volume (2.0 min). In addition, imprinted polymers have been made with complementary binding sites for cytosine and guanine [5], as well as other nucleotide base analogues [6].

The extension of these results to construct robust receptors for oligonucleotides requires fundamental changes in imprinting strategies. Most importantly, since oligonucleotides are water soluble, strategies that employ EGDMA/MAA formulations in organic solvents will need to be replaced with those that do not compromise the interactions between template (the oligo) and functional monomer.

Initially, the imprinting of a 2'-deoxyadenosine dimer (1) was attempted. Due to the hydrophilicity of a DNA oligomer, it was difficult to find a suitable organic solvent that would solubilize the oligomers without disrupting the template's interaction with the polymer matrix [7]. To combat the solubility problems and to insure the homogeniety of the polymerization solution, we examined various polymer formulations with organic and/or aqueous-based solvents that would dissolve the template without disrupting these key interactions.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 723: Symposia M/O – Molecularly Imprinted Materials – Chemical and Biological Sensors-Materials and Devices , 2002 , M5.3
Copyright
Copyright © Materials Research Society 2002

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

1. Sessler, J. L., Furuta, H., Kral, V., Supramol. Chem. 1, 209–20 (1993).Google Scholar
2. Jorgensen, W. L., Chemtracts: Org. Chem. 2, 53–5 (1989).Google Scholar
3. Rebek, J. Jr, Chemtracts: Org. Chem. 1, 59–60 (1988).Google Scholar
4. Spivak, D. A., Gilmore, M. A., Shea, K. J., J. Am. Chem. Soc. 119, 4388–93 (1997).Google Scholar
5. Spivak, D. A., Shea, K. J., Macromolecules 31, 2160–5 (1998).Google Scholar
6. Yano, K., Tanabe, K., Takeuchi, T., Matsui, J., Ikebukuro, K., Karube, I., Anal. Chim. Acta 363, 111–7 (1998).Google Scholar
7. Spivak, D. A., Ph.D. Thesis. University of California, Irvine, Irvine, CA, (1995).Google Scholar
8. Beaucage, S. L., Iyer, R. P., Tetrahedron 48, 2223–311 (1992).Google Scholar
9. Shuto, S., Kanazaki, M., Ichikawa, S., Minakawa, N., Matsuda, A., J. Org. Chem. 63, 746–54 (1998).Google Scholar
10. Ellman, J. A., Mendel, D., Anthony-Cahill, S., Noren, C. J., Schultz, P. G., Methods Ensymol. 202, 301–37. (1991).Google Scholar
11. Mathew, J., Buchardt, O., Bioconj. Chem. 6, 524–8 (1995).Google Scholar
12. Shea, K. J., Stoddard, G. J., Shavelle, D. M., Wakui, F., Choate, R. M., Macromolecules 23, 4497–507 (1990).Google Scholar
13. Hart, B. R., Ph. D. Thesis. University of California, Irvine, Irvine, CA, (2001).Google Scholar
14. Hocking, M. B., Klimchuk, K. A., Lowen, S., J. Polym. Sci., Part A: Polym. Chem. 38, 3128–45 (2000).Google Scholar
15. Sellergren, B., Shea, K. J., J. Chromatogr. A 690, 29–39 (1995).Google Scholar