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Computational Insights on Sulfonamide Imprinted Polymers

Isarankura-Na-Ayudhya, Chartchalerm; Nantasenamat, Chanin; Buraparuangsang, Prasit LU ; Piacham, Theeraphon LU ; Ye, Lei LU ; Bülow, Leif LU and Prachayasittikul, Virapong (2008) In Molecules 13(12). p.3077-3091
Abstract
Molecular imprinting is one of the most efficient methods for preparing synthetic receptors that possess user defined recognition properties. Despite general success of non-covalent imprinting for a large variety of templates, some groups of compounds remain difficult to tackle due to their structural complexity. In this study we investigate preparation of molecularly imprinted polymers that can bind sulfonamide compounds, which represent important drug candidates. Compared to the biological system that utilizes metal coordinated interaction, the imprinted polymer provided pronounced selectivity when hydrogen bond interaction was employed in an organic solvent. Computer simulation of the interaction between the sulfonamide template and... (More)
Molecular imprinting is one of the most efficient methods for preparing synthetic receptors that possess user defined recognition properties. Despite general success of non-covalent imprinting for a large variety of templates, some groups of compounds remain difficult to tackle due to their structural complexity. In this study we investigate preparation of molecularly imprinted polymers that can bind sulfonamide compounds, which represent important drug candidates. Compared to the biological system that utilizes metal coordinated interaction, the imprinted polymer provided pronounced selectivity when hydrogen bond interaction was employed in an organic solvent. Computer simulation of the interaction between the sulfonamide template and functional monomers pointed out that although methacrylic acid had strong interaction energy with the template, it also possessed high non-specific interaction with the solvent molecules of tetrahydrofuran as well as being prone to self-complexation. On the other hand, 1-vinylimidazole was suitable for imprinting sulfonamides as it did not cross-react with the solvent molecules or engage in self-complexation structures. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Sulfonamide, Molecular imprinting, Molecularly Imprinted polymer, Molecular modeling
in
Molecules
volume
13
issue
12
pages
3077 - 3091
publisher
Molecular Diversity Preservation International
external identifiers
  • wos:000261948300013
  • scopus:58149260362
ISSN
1420-3049
DOI
10.3390/molecules13123077
language
English
LU publication?
yes
id
f6324d7d-5e34-42c2-ba6d-7018eb5cc962 (old id 1376912)
date added to LUP
2009-04-24 11:14:09
date last changed
2017-09-10 03:53:02
@article{f6324d7d-5e34-42c2-ba6d-7018eb5cc962,
  abstract     = {Molecular imprinting is one of the most efficient methods for preparing synthetic receptors that possess user defined recognition properties. Despite general success of non-covalent imprinting for a large variety of templates, some groups of compounds remain difficult to tackle due to their structural complexity. In this study we investigate preparation of molecularly imprinted polymers that can bind sulfonamide compounds, which represent important drug candidates. Compared to the biological system that utilizes metal coordinated interaction, the imprinted polymer provided pronounced selectivity when hydrogen bond interaction was employed in an organic solvent. Computer simulation of the interaction between the sulfonamide template and functional monomers pointed out that although methacrylic acid had strong interaction energy with the template, it also possessed high non-specific interaction with the solvent molecules of tetrahydrofuran as well as being prone to self-complexation. On the other hand, 1-vinylimidazole was suitable for imprinting sulfonamides as it did not cross-react with the solvent molecules or engage in self-complexation structures.},
  author       = {Isarankura-Na-Ayudhya, Chartchalerm and Nantasenamat, Chanin and Buraparuangsang, Prasit and Piacham, Theeraphon and Ye, Lei and Bülow, Leif and Prachayasittikul, Virapong},
  issn         = {1420-3049},
  keyword      = {Sulfonamide,Molecular imprinting,Molecularly Imprinted polymer,Molecular modeling},
  language     = {eng},
  number       = {12},
  pages        = {3077--3091},
  publisher    = {Molecular Diversity Preservation International},
  series       = {Molecules},
  title        = {Computational Insights on Sulfonamide Imprinted Polymers},
  url          = {http://dx.doi.org/10.3390/molecules13123077},
  volume       = {13},
  year         = {2008},
}