Theoretical Investigation on Biological Activity of Phenacetin and Its Derivatives via DFT and Docking Approach

Oyebamiji, Abel Kolawole; Adeleke, B. B.

doi:10.9734/csji/2018/46237

Cited by 3 publications

(8 citation statements)

References 16 publications

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“…Phenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine but withdrawn in 1983 by U.S. Food and Drug Administration due to severe side effects, including kidney disease and carcinogenicity [ 53 ]. Nevertheless, there has been reports of their continue use in physico- chemical research due to their crystallization properties [ 54 ]. Pactamycin is an antibiotic isolated from the bacteria Streptomycespactum as a potent antitumor drug with broad cytotoxicity [ 55 ].…”

Section: Discussionmentioning

confidence: 99%

Evaluating non-targeted analysis methods for chemical characterization of organic contaminants in different matrices to estimate children’s exposure

Cui

Cox

Mejias

et al. 2023

J Expo Sci Environ Epidemiol

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Background Children are vulnerable to environmental exposure of contaminants due to their small size, lack of judgement skills, as well as their proximity to dust, soil, and other environmental sources. A better understanding about the types of contaminants that children are exposed to or how their bodies retain or process these compounds is needed. Objective In this study, we have implemented and optimized a methodology based on non-targeted analysis (NTA) to characterize chemicals in dust, soil, urine, and in the diet (food and drinking water) of infant populations. Methods To evaluate potential toxicological concerns associated with chemical exposure, families with children between 6 months and 6 years of age from underrepresented groups were recruited in the greater Miami area. Samples of soil, indoor dust, food, water, and urine were provided by the caregivers, prepared by different techniques (involving online SPE, ASE, USE, QuEChERs), and analyzed by liquid chromatography-high resolution mass spectrometry (LC-HRMS). Data post-processing was performed using the small molecule structure identification software, Compound Discoverer (CD) 3.3, and identified features were plotted using Kendrick mass defect plot and Van Krevelen diagrams to show unique patterns in different samples and regions of anthropogenic compound classifications. Results The performance of the NTA workflow was evaluated using quality control standards in terms of accuracy, precision, selectivity, and sensitivity, with an average of 98.2%, 20.3%, 98.4% and 71.1%, respectively. Sample preparation was successfully optimized for soil, dust, water, food, and urine. A total of 30, 78, 103, 20 and 265 annotated features were frequently identified (detection frequency >80%) in the food, dust, soil, water, and urine samples, respectively. Common features detected in each matrix were prioritized and classified, providing insight on children’s exposure to organic contaminants of concern and their potential toxicities. Impact statement Current methods to assess the ingestion of chemicals by children have limitations and are generally restricted by specific classes of targeted organic contaminants of interest. This study offers an innovative approach using non-targeted analysis for the comprehensive screening of organic contaminants that children are exposed to through dust, soil, and diet (drinking water and food).

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Section: Discussionmentioning

confidence: 99%

Evaluating non-targeted analysis methods for chemical characterization of organic contaminants in different matrices to estimate children’s exposure

Cui

Cox

Mejias

et al. 2023

J Expo Sci Environ Epidemiol

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“…The structures of isolated phthalates were optimized through density functional theory (DFT) by 6-311G* basis set and this was carried out with B3LYP density functionals . Quantum mechanically calculated descriptors augmented by DFT offer the quantitative structure–activity relationship (QSAR) for isolated compounds.…”

Section: Methodsmentioning

confidence: 99%

“…The structures of isolated phthalates were optimized through density functional theory (DFT) by 6-311G* basis set and this was carried out with B3LYP density functionals. 32 and electronic and optical characteristics of compounds as this technique is organized and suggests an effectual balance among chemical precision, computational tariff, and biological activity. 31 2.6.1.…”

Section: Enzyme Inhibition Activitymentioning

confidence: 99%

“…56 A higher value of E Homo indicates the good electron-donating ability of the compound and favors better reactivity, however, a lower E LUMO value indicates the good electron-accepting ability of the compound and better reactivity. 32 The computed E HOMO values for the isolated phthalates from H. rosa-sinensis flowers range from −0.2677 eV for HR1 and HR5 to −0.2568 eV for The computed E LUMO values for the isolated phthalates range from −0.0707 eV for HR3 to −0.0592 eV for HR2 (Supporting Information, Figures S11−S15). Thus, the activity status of under-studied compounds with the increase in E LUMO value is as follows:…”

Section: Frontier Molecular Orbital Analysismentioning

confidence: 99%

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Plant-Based Bioactive Phthalates Derived fromHibiscus rosa-sinensis: As In Vitro and In Silico Enzyme Inhibition

Yasmin,

Nazli,

Shafiq

et al. 2023

ACS Omega

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Hibiscus rosa-sinensis is an attractive, ever-blossoming, and effortlessly available plant around the globe. The fabulous flowers of H. rosa-sinensis enjoy a significant status in folk medicine throughout the world and comprise a range of phyto constituents due to which this splendid flower owns numerous biological and pharmaceutical activities like antioxidant, antifungal, antimicrobial, anti-inflammatory, antipyretic, antidiabetic, and antifertility activity. Considering this, column chromatographic isolation of the phytoconstituents of ethyl acetate fraction of the flowers of H. rosa-sinensis was performed. A series of five phthalates including Di- n -octyl phthalate ( HR1 ), ditridecyl phthalate ( HR2 ), 1-allyl 2-ethyl phthalate ( HR3 ), diethyl phthalate ( HR4 ), and bis (6-methylheptyl) phthalate ( HR5 ) were isolated. The structures of the isolated phthalates were elucidated by gas chromatography–mass spectrometry, 1 H NMR, and 13 C NMR. In silico and in vitro antidiabetic and antioxidant potential and DFT studies of isolated phthalates were carried out. In our study, isolated ligands were explored as potent antidiabetic as well as antioxidant agents as they exhibited good binding affinity (in in vitro and in silico experiments) against all selected protein targets. Compounds HR1–HR5 showed that the binding affinity value ranged from −5.9 to −5.2 kcal/mol, −5.5 to −4.3 kcal/mol, and −5.0 to −4.1 kcal/mol for target proteins 1HNY , 2I3Y , and 5O40 , respectively. Among all isolated phthalates, HR5 can be a lead compound as it showed the best binding affinity with human pancreatic α-amylase (Δ G = −5.9 kcal/mol) and displayed a minimum inhibition concentration (IC 50 ) of 11.69 μM among all phthalates. Compound HR1 was the best docked and scored compound for inhibiting glutathione peroxidase; however, HR2 possessed the lowest binding score of −5.0 kcal/mol, thus indicating the highest potential among isolated phthalates for inhibiting the superoxide dismutase. Furthermore, the top-ranked docked ligand–protein complex for each protein was assessed for stability of protein and complex mobility by molecular dynamics simulation using the IMOD server.

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“…Due to its low cost, phenacetin is still being used for research into the physical and refractive properties of crystals [7]. Conventional methods are being used to remove pharmaceutical compounds from wastewater; some examples of which are chlorination, oxidation, biological treatment, electrochemical treatment, and adsorption.…”

Section: Introductionmentioning

confidence: 99%

Kinetic and Isotherm Studies of the Adsorption Phenacetin onto Two Copper Porous Coordination Compounds: Nonlinear Regression Analysis

Loris

Raoul

Atemkeng

et al. 2022

Journal of Chemistry

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Two coordination compounds, copper (II) fumarate (CuFum) and copper (II) tartrate (CuTart), synthesized from copper (II) with fumaric acid and tartaric acid as ligands and using the slow evaporation method have been applied to study the adsorption of phenacetin in aqueous solution. These compounds were characterized by elemental analysis, IR-FT spectroscopy, and X-ray powder diffraction. The melting points of the synthesized coordination compounds were found to be above 350°C. The influence of parameters such as the initial pH, the contact time, and the initial concentration on the adsorption of phenacetin in an aqueous solution has been studied. The studies showed that adsorption equilibrium was reached after 80 minutes for both coordination compounds; the adsorption capacity increased with increasing phenacetin concentration, and the maximum adsorption capacity was obtained in the acidic medium at pH 4. The adsorbed amount of phenacetin on copper (II) fumarate (CuFum) was 25.158 mg/g while that on copper (II) tartrate (CuTart) was 25.906 mg/g. Nonlinear regression analysis showed the best fit for the Freundlich model isotherm for CuTart with R2 of 0.963 and a Chi-square test (χ2) of 0.529 while for the CuFum material, it is the Redlich-Peterson model with R2 of 0.975 and Chi-square test (χ2) of 0.263. The kinetic study shows that the pseudo-second-order model better describes the adsorption of the two materials. The results show that physisorption and chemisorption participate in the adsorption of phenacetin and that these materials can be used for the elimination of phenacetin in solution.

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Theoretical Investigation on Biological Activity of Phenacetin and Its Derivatives via DFT and Docking Approach

Cited by 3 publications

References 16 publications

Evaluating non-targeted analysis methods for chemical characterization of organic contaminants in different matrices to estimate children’s exposure

Evaluating non-targeted analysis methods for chemical characterization of organic contaminants in different matrices to estimate children’s exposure

Plant-Based Bioactive Phthalates Derived fromHibiscus rosa-sinensis: As In Vitro and In Silico Enzyme Inhibition

Kinetic and Isotherm Studies of the Adsorption Phenacetin onto Two Copper Porous Coordination Compounds: Nonlinear Regression Analysis

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