Examination of Imprinting Process with Molsidomine as a Template

Piotr Luliński,Dorota Maciejewska

doi:10.3390/molecules14062212

Piotr Luliński, Dorota Maciejewska

Open Access

https://doi.org/10.3390/molecules14062212

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Journal: Molecules	Publication Date: Jun 17, 2009
Citations: 22	License type: CC BY 4.0

Affiliation: Medical University of Warsaw

Abstract

Eight different functional monomers were used with ethylene glycol dimethacrylate as a cross-linker and molsidomine as a template to obtain molecularly imprinted polymers (MIPs). Non-covalent interactions between molsidomine and each functional monomer in DMSO prior to thermal bulk polymerization were utilized. On the basis of calculated imprinting factors, MIP prepared with N,N’-diallyltartaramide was chosen for further investigations. Examination of interactions in the prepolymerization complex between molsidomine and N,N’-diallyltartaramide was performed using the Job method. The absorbance of isomolar solutions reaching a maximum for the molar ratio of template to monomer equal to 1:4. Scatchard analysis was used for estimation of the dissociation constants and the maximum amounts of binding sites. The polymer based on N,N’-diallyltartaramide has two classes of heterogeneous binding sites characterized by two values of Kd and two Bmax: Kd(1) = 1.17 mM-1 and Bmax(1) = 0.8 μmol/mg for the higher affinity binding sites, and Kd(2) = 200 μM-1 and Bmax(2) = 2.05 μmol/mg for the lower affinity binding sites. Furthermore, effects of pH and organic solvent on binding properties of MIP and NIP were investigated, together with release of molsidomine from both MIP and NIP.

Highlights

Molecular imprinting is a technique for preparing polymers of desired and predetermined selectivity [1]
Imprinted polymers can be applied in many areas such as chromatography or solid phase extraction (SPE) [2], as antibody mimics [3] or in catalysis [4]
Extended release is mainly achieved via interactions of the drug with complementary functional groups organized around the imprinting site in the polymer

Summary

Introduction

Molecular imprinting is a technique for preparing polymers of desired and predetermined selectivity [1]. Template molecules are removed after polymerization, leaving well-defined, three-dimensional cavities with spatially oriented functionalities, complementary to the target molecule, in the highly cross-linked polymer network. In their most common form, MIPs are prepared as a monolith which is ground and sieved to the appropriate size of particles. Selectivity of imprinted materials could be used to deliver a specific enantiomer of the drug The combination of both the recognition and release properties of MIPs, could result in their usefulness in drug delivery systems. It is well-known that after appropriate post-synthetic preparation most imprinted polymers can be used for drug delivery because they are non-toxic and biocompatible [8,9]

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