Ionic liquid crosslinkers for chiral imprinted nanoGUMBOS

Suzana Hamdan; Leonard Moore Jr; Jason Lejeune; Farhana Hasan; Trevor K Carlisle; Jason E Bara; D L Gin; Andrew L LaFrate; R D Noble; David A Spivak; Isiah M Warner

doi:10.1016/j.jcis.2015.10.033

Ionic liquid crosslinkers for chiral imprinted nanoGUMBOS

J Colloid Interface Sci. 2016 Feb 1:463:29-36. doi: 10.1016/j.jcis.2015.10.033. Epub 2015 Oct 22.

Authors

Affiliations

¹ Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
² Department of Chemistry & Biochemistry, University of Colorado, Boulder, CO 80309, USA.
³ Department of Chemical & Biological Engineering, University of Colorado, Boulder, CO 80309, USA.
⁴ Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA. Electronic address: dspivak@lsu.edu.

PMID: 26513734
DOI: 10.1016/j.jcis.2015.10.033

Abstract

Molecularly imprinted polymers (MIPs) are an important class of selective materials for molecular specific sensors and separations. Molecular imprinting using non-covalent interactions in aqueous conditions still remains a difficult challenge due to interruption of hydrogen-bonding or electrostatic interactions water. Newly developed crosslinking ionic liquids are demonstrated herein to overcome problems of synthesizing aqueous MIPs, adding to previous examples of ionic liquids used as monomers in non-aqueous conditions or used as MIP solvents. Vinylimidazole ionic liquid crosslinkers were synthesized and subsequently explored as matrix supports for fabrication of molecularly imprinted polymeric nanoGUMBOS (nanoparticles derived from a group of uniform materials based on organic salts). Each of the four crosslinkers incorporated a unique functional spacer between the vinylimidazole groups, and the performance of the corresponding molecularly imprinted polymers was evaluated using chiral recognition as the diagnostic. High uptake values for l-tryptophan were found in the 13-87μmol/g range; and chiral recognition was determined via binding ratios of l-tryptophan over d-tryptophan that ranged from 5:1 to 13:1 for polymers made using different crosslinkers. Not only are these materials good for chiral recognition, but the results highlight the utility of these materials for imprinting aqueous templates such as biological targets for theranostic agents.

Keywords: Aqueous molecular imprinting; Chiral amino acids; Chiral recognition; Ionic liquid crosslinkers; NanoGUMBOS; Polymeric ionic liquids.