Theoretical investigation on functional monomer and solvent selection for molecular imprinting of tramadol

Fonseca, Matheus Cecílio; Nascimento, Clébio S.; Borges, Keyller Bastos

doi:10.1016/j.cplett.2015.12.061

Cited by 51 publications

(12 citation statements)

References 29 publications

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“…Khan et al designed a new computational model capable of understanding the nature of the interaction between the template and the functional monomers by using the DFT/B3LYP method . Borges et al investigated the MIP formation for tramadol and dinotefuran with distinct functional monomers for the evaluation of the interaction process of tramadol and dinotefuran in distinct solvents employing DFT calculations at the B3LYP/6‐311G(d,p) level . Diñeiro et al used DFT/B3LYP method to design the MIPs for voltammetric sensing of homovanillic acid .…”

Section: Introductionmentioning

confidence: 99%

Quantum mechanical studies on dioxin‐imprinted polymer precursor composites: Fundamental insights to enhance the binding strength and selectivity of biomarkers

Khan

Pal

2018

J of Molecular Recognition

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We present a benchmark study of binding energies for dioxin-imprinted polymer complexes. A density functional theory approach was used for screening the polymerization precursors in the rational design of molecularly imprinted polymers (MIPs). Tetrachlorodibenzo-p-dioxin (TCDD) was taken as an imprinted molecule. The geometry optimization, natural bond orbital charge, and molecular electrostatic potential of TCDD and acrylamide (AM) were studied at the M062X level and 6-31G(d,p) belonging to one of the hybrid density functional theories. The results of molecular electrostatic potential and natural bond orbital charge analysis were comparable. Among the studied functional monomers-AM, methacrylic acid (MAA), itaconic acid, and vinyl pyridine-AM was confirmed as the best functional monomer, because the strongest interaction (the maximum number of hydrogen bonds and the lowest binding energy) occurs between TCDD and AM. The stability property was excellent when the ratio of TCDD and AM was 1:4. The polarizable continuum model was used for solvent calculations. Computational results showed that acetonitrile plays an important role in the MIP formation, as it seems to control the size and the shape of the cavity. The atoms in molecule and Becke surface method have also been applied to understand the nature and strength of the hydrogen bonding interactions in complexes. TCDD-AM complexes were found involving C-O···Cl and N-H···Cl hydrogen bonds. Good correlations have been established between hydrogen bond lengths versus atoms in molecule topological parameter like electron density ρ(r) and its Laplacian ▽ ρ(r) at the bond critical points. On ground of theoretical results, a series of MIPs were synthesized. The MIP prepared using TCDD as the template, the functional monomer (AM), and the cross-linker (TRIM) in acetonitrile solvent exhibited the highest adsorption capacity for TCDD. The maximum binding capacity of TCDD on the MIP was 3.7 μg/mg. This research work can provide a theoretical reference for the fabrication and characterization of novel TCDD-MIPs for environmental applications.

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Section: Introductionmentioning

confidence: 99%

Quantum mechanical studies on dioxin‐imprinted polymer precursor composites: Fundamental insights to enhance the binding strength and selectivity of biomarkers

Khan

Pal

2018

J of Molecular Recognition

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“…The structures of the template, functional monomers, and monomer-template complex were computationally modeled using Gaussian simulation software. Then, optimizing the structures through DFT at the B3LYP/6-31G+(d,p) basis set level [41]. The most stable configuration were obtained when the calculated molecular lattice point data in the command window is not changing and the completed state is displayed, which can be used as the initial configuration for subsequent studies.…”

Section: Computational Detailsmentioning

confidence: 99%

Theoretical Insight into the Interaction between Chloramphenicol and Functional Monomer (Methacrylic Acid) in Molecularly Imprinted Polymers

Xie

Xiao

et al. 2020

IJMS

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Molecular imprinting technology is a promising method for detecting chloramphenicol (CAP), a broad-spectrum antibiotic with potential toxicity to humans, in animal-derived foods. This work aimed to investigate the interactions between the CAP as a template and functional monomers required for synthesizing efficient molecularly imprinted polymers for recognition and isolation of CAP based on density functional theory. The most suitable monomer, methacrylic acid (MAA), was determined based on interaction energies and Gibbs free energy changes. Further, the reaction sites of CAP and MAA was predicted through the frontier molecular orbitals and molecular electrostatic potentials. Atoms in molecules topology analysis and non-covalent interactions reduced density gradient were applied to investigate different types of non-covalent and inter-atomic interactions. The simulation results showed that CAP was the main electron donor, while MAA was the main electron acceptor. Moreover, the CAP–MAA complex simultaneously involved N-H···O and C=O···H double hydrogen bonds, where the strength of the latter was greater than that of the former. The existence of hydrogen bonds was also confirmed by theoretical and experimental hydrogen nuclear magnetic resonance and Fourier transform infrared spectroscopic analyses. This research can act as an important reference for intermolecular interactions and provide strong theoretical guidance regarding CAP in the synthesis of molecularly imprinted polymers.

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“…Density functional theory (DFT) method was employed in order to analyze the different types of information that can be obtained through the computational design of MIPs and to explore the many computational resources that can be employed for better understanding of the system at a molecular level. All of the calculations were performed using B3LYP/6-31G(d,p) [18,41,42] level of theory, using Gaussian 09 [43] software. Aiming to predict the possible interaction sites of the monomers (see Table 1) and the template molecule (MDMA) (Fig.…”

Section: Selection Of the Most Appropriate Functional Monomermentioning

confidence: 99%

Computational design of synthetic receptors for drug detection: interaction between molecularly imprinted polymers and MDMA (3,4-methylenedioxymethamphetamine)

Sales

Ramalho

2020

Theor Chem Acc

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For many decades, synthetic receptors have been used as sensor elements and are a promising alternative to natural receptors, which, despite its great selectivity, are so complex and instable. The rational design of this kind of receptors is currently one of the most researched topics in molecular recognition. Molecular imprinted polymers (MIPs) have become a growing highlight in polymer chemistry, once they possess a wide range of applications and can be used in several environments, due to their high chemical and thermal stability. The aim of this study was to perform a rational design for the MIP preparation, for 3,4-methylenedioxymethamphetamine (MDMA) detection. The theoretical measurements were employed at several stages of the process, using DFT and B3LYP/6-31G(d,p) level of theory, by means of optimization and frequency calculations. Among the several functional monomers tested, the itaconic acid was the most appropriated for MIP preparation with MDMA template, and the proper molar ratio found theoretically was 3:1 (itaconic acid/MDMA). In the preparation of pre-polymerization complex, polar solvents were found to perform a better stabilization, mainly those which are not protic solvents. As cross-linking agents, the better results were obtained for trimethylolpropane trimethacrylate and ethylene glycol dimethacrylate molecules, respectively. Finally, selectivity tests showed a high affinity of the studied MIP for MDMA and chemically similar molecules. The proposal theoretical strategy yielded novel, experimentally testable hypotheses for the design of MIPs. Additionally, from the theoretical point of view, the set of computational analyses presented in this paper constitutes a very useful protocol to predict optimal experimental conditions, which can considerably reduce the time and cost on the MIPs preparation.

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Theoretical investigation on functional monomer and solvent selection for molecular imprinting of tramadol

Cited by 51 publications

References 29 publications

Quantum mechanical studies on dioxin‐imprinted polymer precursor composites: Fundamental insights to enhance the binding strength and selectivity of biomarkers

Quantum mechanical studies on dioxin‐imprinted polymer precursor composites: Fundamental insights to enhance the binding strength and selectivity of biomarkers

Theoretical Insight into the Interaction between Chloramphenicol and Functional Monomer (Methacrylic Acid) in Molecularly Imprinted Polymers

Computational design of synthetic receptors for drug detection: interaction between molecularly imprinted polymers and MDMA (3,4-methylenedioxymethamphetamine)

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