A calix[4]arene derivative and its selective interaction with drugs (clofibric acid, diclofenac and aspirin)

Namor, Angela F. Danil de; Nuaim, Maan Al; Salas, José Villanueva; Bryant, Sophie; Howlin, Brendan J.

doi:10.1016/j.ejps.2016.12.027

Cited by 5 publications

(4 citation statements)

References 39 publications

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“…In an attempt to explore the field of supramolecular chemistry, Danil de Namor et al (2017) reported the selective interaction of a calix [4]arene derivative, 5,11,17,23-tetratert-butyl, 25,27-bis[amino ethoxy]26,28-dihydroxycalix[4] arene with clofibric acid, diclofenac and aspirin. It was demonstrated that the calix[4]-based receptor is a suitable extracting agent for the two former drugs but its extracting ability for aspirin was found to be very weak.…”

Section: Introductionmentioning

confidence: 99%

Amine-modified silica for removing aspirin from water

Namor

Nuaim

Fairclough

et al. 2021

Int. J. Environ. Sci. Technol.

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The synthesis and structural characterisation (Fourier transform infrared, FTIR spectrometry, scanning electron microscopy, SEM and energy-dispersive X-ray, EDX) of amino-modified silicates (unloaded L1, and aspirin-loaded, L2) are reported. The optimal conditions for the extraction of aspirin from water by the modified silicate material were determined as a function of the mass of the extracting agent and the pH of the aqueous solution. The optimum mass was found to be 0.08–0.10 g with 99.9% removal of aspirin. Maximum extraction of aspirin by the material was observed at pH 4. The kinetics, the removal capacity of the material, as well as its recycling, were investigated. The results indicate that (i) the process is fast and (ii) the removal capacity for the drug is greater than that of previously reported materials and (iii)the modified silicate can be easily recycled. These data along with the low cost involved in the production of the material led to the conclusion that the modified silicate has the required potential for industrial use. Molecular simulation calculations suggest that one unit of aspirin interacts with one unit of the modified silicate L1 through hydrogen bond formation between the amine functional group of the silicate and the oxygen donor atoms of aspirin. Final conclusions are given.

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Section: Introductionmentioning

confidence: 99%

Amine-modified silica for removing aspirin from water

Namor

Nuaim

Fairclough

et al. 2021

Int. J. Environ. Sci. Technol.

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“…It is important to be able to monitor and determine the effects of drugs on both humans and the environment. By its recognition ability of calixarene compounds, it has achieved successful results in the detection and separation of drugs in wastewater [ 30 , 31 ]. Calixarenes are good sensors for some drugs as well as providing excellent selectivity, sensitivity and stability for long-term use [ 32 – 35 ].…”

Section: Introductionmentioning

confidence: 99%

The supramolecularly complexes of calix[4]arene derivatives toward favipiravir antiviral drug (used to treatment of COVID-19): a DFT study on the geometry optimization, electronic structure and infrared spectroscopy of adsorption and sensing

Yüksel

Köse

Fellah

2021

J Incl Phenom Macrocycl Chem

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While the world is in search of a vaccine that can cure COVID-19 disease, favipiravir is the most commonly used antiviral drug in the treatment of patients during the pandemic process. In this study, we investigated the host–guest interaction between the popular supramolecule calix[4]arene derivatives and the favipiravir drug by using the DFT (Density Functional Theory) method. The B3LYP hybrid method and 6-31G (d,p) basis set were utilized to determine the optimized structures of the host and guest molecules and their complexes. The negative adsorption energy (∆E) and adsorption enthalpy (∆H) calculated for the complexes formed between calix[4]arene compounds and favipiravir drug molecule mentioned that adsorption of favipiravir molecule was an exothermic process on calix[4]arene structures. On the other hand, among the calixarene derivatives in the study, Gibbs free energy change (∆G) value for the adsorption was only negative on calix[4]arene4 molecule. The infrared spectroscopy (IR) calculations were performed by examining the C=O, O–H and NH 2 vibrational frequencies to see the adsorption behavior in the favipiravir-calix[4]arene complex. After adsorption of the favipiravir molecule, HOMO–LUMO gap values decreased significantly for the structures and therefore electrical conductivity increased proportionally. In addition, sensor response factors, Fermi energy levels and workfunction changes of calix[4]arene derivatives were calculated and examined. Charge transfer between the four calix[4]arene compounds and the favipiravir molecule has occurred after adsorption. This attributes that calix[4]arene derivatives can be used as a well-suited favipiravir sensor (electronic and workfunction) and adsorbent at room temperature. Based on the calculations made to see the solvent effect on the adsorption of favipiravir it was determined that it did not affect the interaction between the drug molecule and the calix[4]arene compound too much and the adsorption energy turned into a slightly less negative value.

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“…The NMR studies of NaDN solutions were used to detect related complexes with cyclodextrin 58 , 59 and with calix[4]arene. 60 NMR and IR spectroscopy techniques were used to evaluate the quality of generic NaDN tablets. 61 The IR spectrum of the aqueous solution of NaDN has not been published yet, based on the available data.…”

Section: Introductionmentioning

confidence: 99%

Hydration of the Carboxylate Group in Anti-Inflammatory Drugs: ATR-IR and Computational Studies of Aqueous Solution of Sodium Diclofenac

Levina

Penkov

Rodionova³

et al. 2018

ACS Omega

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Diclofenac (active ingredient of Voltaren) has a significant, multifaceted role in medicine, pharmacy, and biochemistry. Its physical properties and impact on biomolecular structures still attract essential scientific interest. However, its interaction with water has not been described yet at the molecular level. In the present study, we shed light on the interaction between the steric hindrance (the intramolecular N–H···O bond, etc.) carboxylate group (−CO2–) with water. Aqueous solution of sodium declofenac is investigated using attenuated total reflection-infrared (ATR-IR) and computational approaches, i.e., classical molecular dynamics (MD) simulations and density functional theory (DFT). Our coupled classical MD simulations, DFT calculations, and ATR-IR spectroscopy results indicated that the −CO2– group of the diclofenac anion undergoes strong specific interactions with the water molecules. The combined experimental and theoretical techniques provide significant insights into the spectroscopic manifestation of these interactions and the structure of the hydration shell of the −CO2– group. Moreover, the developed methodology for the theoretical analysis of the ATR-IR spectrum could serve as a template for the future IR/Raman studies of the strong interaction between the steric hindrance −CO2– group of bioactive molecules with the water molecules in dilute aqueous solutions.

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A calix[4]arene derivative and its selective interaction with drugs (clofibric acid, diclofenac and aspirin)

Cited by 5 publications

References 39 publications

Amine-modified silica for removing aspirin from water

Amine-modified silica for removing aspirin from water

The supramolecularly complexes of calix[4]arene derivatives toward favipiravir antiviral drug (used to treatment of COVID-19): a DFT study on the geometry optimization, electronic structure and infrared spectroscopy of adsorption and sensing

Hydration of the Carboxylate Group in Anti-Inflammatory Drugs: ATR-IR and Computational Studies of Aqueous Solution of Sodium Diclofenac

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