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Open AccessArticle

Rapid, High Affinity Binding by a Fluorescein Templated Copolymer Combining Covalent, Hydrophobic, and Acid–Base Noncovalent Crosslinks

1
Tekscan, Inc., 307 W. First St., Boston, MA 02127, USA
2
Department of Chemistry, University of New Hampshire, Durham NH 03824, USA
3
Boston Analytical, 14 Manor Parkway, Salem, NH 03079, USA
4
Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA
*
Author to whom correspondence should be addressed.
Sensors 2018, 18(5), 1330; https://doi.org/10.3390/s18051330
Received: 8 February 2018 / Revised: 19 April 2018 / Accepted: 19 April 2018 / Published: 25 April 2018
(This article belongs to the Special Issue Polymer-Based Sensors for Bioanalytes)
A new type of biomimetic templated copolymer has been prepared by reverse addition fragmentation chain transfer polymerization (RAFT) in dioxane. The initial formulation includes the template fluorescein, N-isopropylacrylamide (NIPAM, 84 mol %), methacrylic acid (MAA, 5-mol %), 4-vinylpyridine (4-VP, 9 mmol %), and N,N′-methylenebis(acrylamide) (MBA, 2 mol %). PolyNIPAM is a thermosensitive polymer that comes out of aqueous solution above its lower critical solution temperature forming hydrophobic ‘crosslinks’. MAA and 4-VP interact in dioxane forming acid–base crosslinks. The excess 4-VP serves as a recognition monomer organizing around the template fluorescein to form a binding site that is held in place by the noncovalent and covalent crosslinks. The MBA is a covalent crosslinker. The RAFT agent in the resulting copolylmer was reduced to a thiol and attached to gold nanoparticles. The gold nanoparticle bound copolymer binds fluorescein completely in less than two seconds with an affinity constant greater than 108 M−1. A reference copolymer prepared with the same monomers by the same procedure binds fluorescein much more weakly. View Full-Text
Keywords: templates; moleculary imprinted polymers; poly(N-isopropylacrylamide); noncovalent crosslinks; fluorescein; binding affinity; binding kinetics templates; moleculary imprinted polymers; poly(N-isopropylacrylamide); noncovalent crosslinks; fluorescein; binding affinity; binding kinetics
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MDPI and ACS Style

Grenier, C.J.; Timberman, A.; Yang, R.; Csoros, J.; Papantones, A.; Deravi, L.F.; Seitz, W.R. Rapid, High Affinity Binding by a Fluorescein Templated Copolymer Combining Covalent, Hydrophobic, and Acid–Base Noncovalent Crosslinks. Sensors 2018, 18, 1330. https://doi.org/10.3390/s18051330

AMA Style

Grenier CJ, Timberman A, Yang R, Csoros J, Papantones A, Deravi LF, Seitz WR. Rapid, High Affinity Binding by a Fluorescein Templated Copolymer Combining Covalent, Hydrophobic, and Acid–Base Noncovalent Crosslinks. Sensors. 2018; 18(5):1330. https://doi.org/10.3390/s18051330

Chicago/Turabian Style

Grenier, Casey J.; Timberman, Anthony; Yang, Rongfang; Csoros, John; Papantones, Alex; Deravi, Leila F.; Seitz, W. R. 2018. "Rapid, High Affinity Binding by a Fluorescein Templated Copolymer Combining Covalent, Hydrophobic, and Acid–Base Noncovalent Crosslinks" Sensors 18, no. 5: 1330. https://doi.org/10.3390/s18051330

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