Advanced

Preparation of molecularly imprinted polymers using anacardic acid monomers derived from cashew nut shell liquid

Philip, JosephYN LU ; Buchweishaija, Joseph; Mkayula, Lupituko L. and Ye, Lei LU (2007) In Journal of Agricultural and Food Chemistry 55(22). p.8870-8876
Abstract
The objective of this work was to use monomers from cashew (Anacardium occidentale L.) nut shells to develop molecularly imprinted polymers. Cashew nut shell liquid (CNSL) is a cheap and renewable agro byproduct consisting of versatile monomers. Solvent-extracted CNSL contains over 80% anacardic acid (AnAc) with more than 90% degree of unsaturation in its C-15 side chain. From AnAc monomer, anacardanyl acrylate (AnAcr) and anacardanyl methacrylate (AnMcr) monomers were synthesized and their chemical structures were characterized by Fourier transform IR and NMR. Different imprinted bulk polymers based on AnAc, AnAcr, and AnMcr functional monomers have been prepared. In the present study, each functional monomer was separately copolymerized... (More)
The objective of this work was to use monomers from cashew (Anacardium occidentale L.) nut shells to develop molecularly imprinted polymers. Cashew nut shell liquid (CNSL) is a cheap and renewable agro byproduct consisting of versatile monomers. Solvent-extracted CNSL contains over 80% anacardic acid (AnAc) with more than 90% degree of unsaturation in its C-15 side chain. From AnAc monomer, anacardanyl acrylate (AnAcr) and anacardanyl methacrylate (AnMcr) monomers were synthesized and their chemical structures were characterized by Fourier transform IR and NMR. Different imprinted bulk polymers based on AnAc, AnAcr, and AnMcr functional monomers have been prepared. In the present study, each functional monomer was separately copolymerized in toluene with ethylene glycol dimethacrylate and divinylbenzene as cross-linkers, using racemic propranolol as a model template. While the AnAc based polymer revealed a meager rebinding ability, the imprinted polymers made from AnAcr and AnMcr displayed highly specific propranolol binding. At a polymer concentration of 2 mg/mL, AnAcr and AnMcr based imprinted polymers were able to bind over 50% of trace propranolol (initial concentration 1.2 nM). Under the same condition propranolol uptake by the two nonimprinted control polymers was less than 20%. Chiral recognition properties of these polymers were further confirmed using tritium-labeled (S)-propranolol as a tracer in displacement experiments, suggesting that the apparent affinity of the imprinted chiral sites for the correct enantiomer is at least 10 times that of the mismatched (R)-propranolol. Moreover, cross reactivity studies of these polymers showed that the (S)-imprinted sites have higher cross-reactivity toward (R,S)metoprolol than (R)-propranolol and (R)-timolol. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
propranolol, timolol, anacardanyl methacrylate, anacarclanyl acrylate, molecular imprinting, anacardic acid, metoprolol
in
Journal of Agricultural and Food Chemistry
volume
55
issue
22
pages
8870 - 8876
publisher
The American Chemical Society
external identifiers
  • wos:000250479500008
  • scopus:36148970478
ISSN
0021-8561
DOI
10.1021/jf0718289
language
English
LU publication?
yes
id
f59dcb2b-844c-476e-ae06-f13376d807c7 (old id 653122)
date added to LUP
2007-12-18 16:30:22
date last changed
2017-02-26 03:34:16
@article{f59dcb2b-844c-476e-ae06-f13376d807c7,
  abstract     = {The objective of this work was to use monomers from cashew (Anacardium occidentale L.) nut shells to develop molecularly imprinted polymers. Cashew nut shell liquid (CNSL) is a cheap and renewable agro byproduct consisting of versatile monomers. Solvent-extracted CNSL contains over 80% anacardic acid (AnAc) with more than 90% degree of unsaturation in its C-15 side chain. From AnAc monomer, anacardanyl acrylate (AnAcr) and anacardanyl methacrylate (AnMcr) monomers were synthesized and their chemical structures were characterized by Fourier transform IR and NMR. Different imprinted bulk polymers based on AnAc, AnAcr, and AnMcr functional monomers have been prepared. In the present study, each functional monomer was separately copolymerized in toluene with ethylene glycol dimethacrylate and divinylbenzene as cross-linkers, using racemic propranolol as a model template. While the AnAc based polymer revealed a meager rebinding ability, the imprinted polymers made from AnAcr and AnMcr displayed highly specific propranolol binding. At a polymer concentration of 2 mg/mL, AnAcr and AnMcr based imprinted polymers were able to bind over 50% of trace propranolol (initial concentration 1.2 nM). Under the same condition propranolol uptake by the two nonimprinted control polymers was less than 20%. Chiral recognition properties of these polymers were further confirmed using tritium-labeled (S)-propranolol as a tracer in displacement experiments, suggesting that the apparent affinity of the imprinted chiral sites for the correct enantiomer is at least 10 times that of the mismatched (R)-propranolol. Moreover, cross reactivity studies of these polymers showed that the (S)-imprinted sites have higher cross-reactivity toward (R,S)metoprolol than (R)-propranolol and (R)-timolol.},
  author       = {Philip, JosephYN and Buchweishaija, Joseph and Mkayula, Lupituko L. and Ye, Lei},
  issn         = {0021-8561},
  keyword      = {propranolol,timolol,anacardanyl methacrylate,anacarclanyl acrylate,molecular imprinting,anacardic acid,metoprolol},
  language     = {eng},
  number       = {22},
  pages        = {8870--8876},
  publisher    = {The American Chemical Society},
  series       = {Journal of Agricultural and Food Chemistry},
  title        = {Preparation of molecularly imprinted polymers using anacardic acid monomers derived from cashew nut shell liquid},
  url          = {http://dx.doi.org/10.1021/jf0718289},
  volume       = {55},
  year         = {2007},
}