Abstract
The overall goal of this work was to prepare synthetic receptor matrices that combined the Properties of antibodies (specificity and selectivity of recognition) with those of synthetic polymeric membranes (stability, durability, solvent resistance, etc.). The approach taken involved imprinting molecular recognition complexes onto membrane pore surfaces using photochemistry. Fluor-containing membranes possessing photo-imprinted surfaces can be used in competitive binding scintillation proximity assays. This would overcome the two major limitations of radioimmunoassay, i.e., antibodies would be replaced by stable synthetic receptors, and the bound radioligand would not need to be separated from the unbound radioligand because only the bound radioligand would be in close enough proximity to the fluors in the membrane to induce scintillations. Furthermore, this would permit detection of beta-emitting radioligands without using a scintillation cocktail. This would have a positive economic and environmental impact by greatly reducing the generation of “mixed” (radioactive and organic) waste, the disposal of which is difficult and expensive.
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References
M Newcomb, JL Toner, RC Helgeson and DL Cram. Host-Guest Complexation. Chiral recognition in transport as a molecular basis for a catalytic resolving machine. J Am Chem Soc 101:4941(1979).
K Johnson, RK Allemann, H Widmer and SA Benner. Synthesis, structure and activity of artificial rationally designed catalytic polypeptides. Nature 365:530 (1993).
SD Erickson, JA Simon and WC Still. Practical synthesis of a highly enantioselctive receptor for peptides. J Org Chem 58:1305 (1993).
CT Seto, JP Mathias and GM Whitesides. Molecular self-assembly through hydrogen bonding: aggregation of five molecules to form a discrete supramolecular structure. J Am Chem Soc 115:1321 (1993).
MM Conn, G Deslongchamps, J de Mendoza and J Rebek. Convergent functional groups. 13. fligh-affinity complexation of adenosine derivatives within induced binding pockets. JAm Chem Soc 115:3548 (1993).
R Curti and U Colombo. Chromatography of stereoisomers with “tailor made” compounds. J Am Chem Soc 74:3961 (1952).
G Wulff, A Sarhan and K Zabrocki. Enzyme-analogue built polymers and their use for the resolution of racemates. Tetrahedron Lett No. 44, 4329 (1973).
G Wulff, W Vesper, R Grobe-Einsler and A Sarhan. Enzyme-analogue built polymers: On the synthesis of polymers containing chiral activities and their use for the resolution of racemates. Makromol Chem 178:2799 (1977).
G Wulff, B Heide and G Helfmeier. Molecular recognition through the exact placement of functional groups on rigid matrices via a template approach. J Am Chem Soc 108:1089 (1986).
J Damen and DC Neckers. Memory of synthesized vinyl polymers for their origins. J Org Chem 45:1328 (1980).
KJ Shea and EA Thompson. Template synthesis of macromolecules. Selective functionalization of an organic polymer. J Org Chem 43:4253 (1978).
KJ Shea, EA Thompson, SD Pandey and PS Beauchamp. Template synthesis of macromolecules. Synthesis and chemistry of functionalized macroporous polydivinylbenzene. J Am Chem Soc 102:3149 (1980).
KJ Shea and TK Dougherty. Molecular recognition on synthetic amorphous surfaces. The influence of functional group positioning on the effectiveness of molecular recognition. JAm Chem Soc 108:1091 (1986).
KJ Shea and DY Sasaki. On the control of microenvironment shape of functionalized network polymers prepared by template polymerization. J Am Chem Soc 111:3442 (1989).
R Arshady and K Mosbach. Synthesis of substrate-selective polymers by host-guest polymerization. Makromol Chem 182:687 (1981).
O Norrlow, MO Mansson and K Mosbach. Improved chromatogrphy: prearranged distances between boronate groups by the molecular imprinting approach. J Chromatog 396:374 (1987).
DJ O’Shannessy, LI Andersson and K Mosbach. Molecular recognition in synthetic polymers. J Mol Recognition 2:1 (1989)
B Ekberg and K Mosbach. Molecular imrpinting: a technique for producing specific separation materials. Tibtech 7:92 (1989).
LI Andersson, DJ O’Shannessy and K Mosbach. Molecular recognition in synthetic polymers: preparation of chiral stationary phases by molecular imprinting of amino acids. J Chromatog 513:167 (1990).
LI Andersson and K Mosbach. Enantiomeric resolution on molecularly imprinted polymers prepared with only non-covalent and non-ionic interactions. J Chromatog 516:313 (1990).
LI Andersson, A Miyabayashi, DJ O’Shannessy and K Mosbach. Enantiomeric resolution of amino acids on molecularly imprinted polymers as monitored by potentiometric measurements. J Chromatog 516:323 (1990).
L Fischer, R Muller, B Ekberg and K Mosbach. Direct enantioseparation of b-adrebergic blockers using a chiral stationary phase prepared by molecular imprinting. J Am Chem Soc 113:9358 (1991).
B Sellergren and K Shea. Influence of polymer morphology on the ability of imprinted network polymers to resolve enantiomers. J Chromatog 635:31 (1993).
J Matsui, T Kato, T Takeuchi, M Suzuki, K Yokoyama, E Tamiya and I Karube. Molecular recognition in continuous polymer rods prepared by a molecular imprinting technique. Analyt Chem 65:2223 (1993).
DJ O’Shannessy, B Ekberg, LI Andersson and K Mosbach. Recent advances in the preparation and use of molecularly imprinted polymers for enatiomeric resolution of amino acid derivatives. J Chromatog 470: 391 (1989).
A Leonhardt and K Mosbach. Enzyme-mimicking polymers exhibiting specific substrate binding and catalytic functions. React Polymer 6:285 (1987).
SE Bystrom, A Borje and B Akerman. Selective reduction of steroid 3- and 17-ketones using LiAlH4 activated template polymers. J Am Chem Soc 115:2081 (1993).
M Glad, O Norrlow, B Sellergren, N Siegbahn and K Mosbach. Use of silane monomers for molecular imprinting and enzymes entrapment in polysiloxane-coated porous silica. J Chromatog 347:11 (1985).
S Mann. Molecular tectonics in biomineralization and biomimetic materials chemistry. Nature 365:499 (1993).
RK Mansfield. Ph.D. Dissertation, University of Kentucky, 1992.
G Vlatakis, LI Anderson, R Muller and K Mosbach. Drug assay using antibody mimics made by molecular imprinting. Nature 361: 645 (1993).
MJ Swanson, SG Dunkirk, JA Pietig and PE Guire. Use photochemistry to modify membranes. Chemtech 624 (Oct 1992).
H Sigrist, H Guo and B Wegmuller. Light-dependent covalent immobilization of biomolecules on inert surfaces. Bio/Technology 10:1026 (1992).
SG Dunkirk, SL Gregg, LW Duran, JD Monfils, JE Haapala, JA Marcy, DL Clapper, RA Amos and PE Guire. Photochemical coatings for the prevention of bacterial colonization. J Biomaterials Applications 6:131 (1991).
F Borle, M Sanger and H Sigrist. Planar bilayer membranes from photoactivable phospholipids. Biochim Biophys Acta 106:144 (1991).
RL Potter and BE Haley. Photoaffinity labeling of nucleotide binding sites with 8-azidopurine analogs: Techniques and applications. Meth Enzymol 91:613 (1983)
K Rajagopalan, AJ Chavan, BE Haley and DS Watt. Synthesis and application of bidentate photoaffinity cross-lining reagents. J Biol Chem 268:14230 (1993).
HE Hart and EB Greenwald. A unique radioassay using scintillation proximity beads. Mol Immunol 16:265 (1979).
S Udenfriend, LG Gerber, L Brink and S Spector. Scintillation proximity radioimmunoassay utilizing I-125 labelled ligands. Proc Natl Acad Sci USA 82:8672 (1985).
S Udenfriend, L Gerber and N Nelson. Scintillation proximity assay: A sensitive and continuous isotopic method for monitoring ligand/receptor and antigen/antibody interactions. Analyt Bichem 161:494 (1987).
N Nelson. A novel method for detection of receptors and membrane proteins by scintillation proximity assay. Analyt Biochem 165:287 (1987).
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© 1996 Springer Science+Business Media New York
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Jay, M., Mattingly, C.D. (1996). Molecular Recognition of Photoimprinted Surfaces. In: Butterfield, D.A. (eds) Biofunctional Membranes. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-2521-6_15
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DOI: https://doi.org/10.1007/978-1-4757-2521-6_15
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