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

Abstract

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.

Density Functional Theory Study on the Reactivity and Stability of Calix[n]arene-paba Complexes: Drug Sensor Application

“…The same behavior is shown by C6-PABA, where the last two complexes with larger interaction distances denote a larger band gap reduction compared to pure C6 and PABA molecules. Furthermore, the band gap reduction obtained in this work suggests the existence of charge transfer interaction between the host and guest molecules, which means successful complex formation by calixarenes and PABA [61]. By the way, the reduced change in band gap shown by the C4-PABA and C6-PABA, indicating the increase in conductivity, might be studied in the future to explore their potential application beyond drug sensors [31].…”

DFT/TDDFT calculations of geometry optimization, electronic structure and spectral properties of clevudine and telbivudine for treatment of chronic hepatitis B

“…The HOMO is the highest energy orbital occupied by electrons, making it an electron donor. Moreover, HOMO and LUMO are very significant quantum chemical parameters to predict the reactivity of the compounds 25 – 27 . They are used to study significant chemical reactivity descriptors, including ionization potential (IP), electron affinity (EA), electronegativity (EN), chemical hardness (η), chemical potential (μ), chemical softness (S), electrophilicity index (ω), electron-accepting capability (ω+), electron-donating capability (ω−), nucleophilicity index (N), additional electronic charge (∆Nmax), optical softness (σo) and dipole moment (DM) 18 .…”

Energy Band Gap Investigation using First Principle Simulation and Tauc Plot Method of Calixarene and Calixarene-Drug Inclusion Complexes

“…In this view, calixarene-based nanosensors have been reported to display significant responses towards various guest molecules such as cation (Supian et al, 2022), anion (Edwards et al, 2021), and neutral molecule (Fort & Scott, 2016) based on the optimized structural and geometrical factors (Panchal et al, 2020). Furthermore, calixarene can remarkably act as a receptor for trapping or encapsulating chemical entities (Gassoumi et al, 2019), forming hostguest complexes, which continuously increases the interest as a significant host molecule in many fields of supramolecular chemistry (Fahmy et al, 2020), particularly in drug delivery and drug sensor systems (Yuksel et al, 2021). (Español & Villamil, 2019) Calixarene is an ideal host molecule for various therapeutic guest drugs due to its unique architecture macromolecule composed of an upper rim with a para-substituent phenolic ring, a lower rim with a phenolic hydroxyl group, and a hydrophobic π electron-rich core cavity (Figure 2).…”