A Novel Molecular Imprint Polymer Synthesis for Solid Phase Extraction of Andrographolide

Abstract

The use of molecularly imprinted polymers for Solid phase micro-extraction (SPME) of bioactive compounds are getting popularity. The interest on efficient extraction process of andrographolide from the plant is increasing due to their vast therapeutic applications. In this study, andrographolide imprinted MIP was prepared by precipitation polymerization method using the non-covalent technique to use as sorbent materials for solid phase extraction of the bioactive compound. HyperChem 8.0.10 software was used to investigate and optimize the template and functional monomer ratio in the pre-polymerization system to synthesize the imprinted polymers. Molecular modeling gives information about molecular interactions and the Gibbs free energies of the pre-polymerization complex. Based on the computational study, andrographolide, methacrylic acid (MAA) and ethylene glycol dimethacrylate (EGDMA) were used as the template, functional monomer, and cross-linker, respectively at the 1:3:20 ratios. The MIPs were characterized by kinetic study and imprinting factor. The binding parameters for the recognition of andrographolide were studied using Langmuir, Freundlich and Langmuir-Freundlich adsorption isotherm models. Andrographolide MIP contains the maximum number of binding sites with the adsorption capacity of 149.59 μg/g. The SPME experimental data best fit with Langmuir-Freundlich isotherm model with the R2 value of 0.997. This research shows that the MIPs prepared by precipitation polymerization gives a good extraction capability using SPME method.

An Update on Molecularly Imprinted Polymer Design through a Computational Approach to Produce Molecular Recognition Material with Enhanced Analytical Performance

“…AM1 has been used to design MIPs by Ishak et al [ 56 ], while PM3 has been used by Li et al [ 57 ], Krishnan et al [ 60 ], Ao et al [ 58 ], Schwarz et al [ 59 ] and Peng et al [ 61 ]. The semiempirical approach has generally been used to calculate the binding energy of prepolymerization complexes.…”

“…Schwarz et al [ 60 ] used PM3 to aid the selection of the comonomer type as well as to choose the comonomer to template ratios for the formation of the prepolymerization complex to design a MIP that recognizes phytosterol. N , N I -dimethylacrylamide ( N , N I -DMAAM) was selected as the functional monomer due to its great binding energy (−8.867 kcal/mol); it formed a stable complex with stigmasteryl methacrylate as a polymerizable template.…”

Design, synthesis, and characterization of molecularly imprinted solid phase extraction for alpha Mangostin analysis in blood sample

“…Possible conformations of AM and each monomer were designed and simulated to allow the lowest energy during the simulation in a vacuum state. 25 The template-monomer complexes were prepared by attaching AA, MMAA, IA, AAM, MAM, 2VP, 4VP, and AL functional monomers to AM as the template molecule, and the complex structures were optimized using the PM3 method at the ground state by minimizing the binding energy of the molecules.…”

“…The more negative the atomic charge pulled by the H atom, the stronger the hydrogen bond is formed. 25,43 The carboxyl functional group (-COOH) in acid functional monomers, such as AA, MMAA, and IA, is an excellent donor and acceptor of hydrogen bonds to form interactions with AM. In the functional monomers AAM and MAM, the amide functional group (-CONH 2 ) plays a role in the formation of hydrogen bonds with AM.…”

“…23 The critical aspect of forming MIP is the selection of a suitable monomer so that it can interact with the template molecule in a particular molecular ratio. 24 A computational approach can be used to reduce processing steps in selecting monomers from several monomers to be used in MIP production 25,26 and predict the interactions that occur in the system used in pre-polymerization. 27,28 In this study, Molecularly Imprinted polymer-Solid Phase Extraction (MI-SPE) materials were designed and synthesized for the extraction of α-mangostin from biological fluids by combining the method of the molecular imprinting technique and Molecular Dynamic (MD) simulations.…”