Molecular modelling of antioxidant agent by QSAR study of caffeic acid derivatives

Abstract

Molecular modeling using Quantitative Structure and Activity Relationship (QSAR) has been performed on caffeic acid derivatives which is previously studied as an effective antioxidant agent. This research focuses on a set of experimentally IC50 value data of 4 caffeic acid derivatives. The mathematical method (i.e., multilinear regression calculation) was used to build the QSAR model. QSAR analysis was employed on fitting subset using log (1/IC50) as a dependent variable and atomic net charges aromatic carbons, dipole moment and partition coefficient in n-octanol/water as independent variables. The PM3 method was used to calculate the quantum chemical descriptors, chosen to represent the electronic descriptors of molecular structures. The relationship between log (1/IC50) and the descriptors was described by resulted in the QSAR model. The resulted QSAR model for caffeic acid derivatives as an antioxidant is presented below: -7.858+1.149dipol+0.485logP-61.68C5 R=1; R2=0.999; SE=0.008; F=342 QSAR model for caffeic acid derivatives showed the enhancement of antioxidant activity due to the decrease of electronic properties (derived from the dipole moment value and C5 atomic charge), Log P representing hydrophobicity did not show a significant effect on antioxidant activity while increasing the chain length of antioxidant molecules indicate an increase in steric hindrance causes a decrease in antioxidant activity. The calculated PRESS (Predicted Residual Error Sum of Square) value was 6.69E-05, which indicates the calculated log (1/IC50) using QSAR Hansch Model of caffeic acid derivatives is similar with experimental data.

Kombucha as a Potential Active Ingredient in Cosmetics—An Ex Vivo Skin Permeation Study

“…The high hydrophilic properties of caffeine (log P = −0.07) [35] are probably the reason for the low penetration through the skin layer, which is lipophilic. A similar tendency was also observed in the case of other compounds characterized by high hydrophilicity, such as gallic acid (log P = −0.7) [36] or caffeic acid (log P = −0.66) [37].…”

QSAR of antioxidant activity of some novel sulfonamide derivatives.

“…It shows the convergence between the two values and the presence of a slight difference that can be neglected. [32] Table4. Shown the experimental (IC50) and calculated (IC50) The compounds 2g and 2j showed the lowest values of IC50 (calculated IC50 =0.33578 and 0.3412), respectively, which proves and confirms the success of the mathematical model, where the lower the value of (IC50) meaning the least amount of the compound gives the highest effectiveness.…”

Quantitative Structure-Activity Relationship Study of Ester-Based Ferulic Acid Derivatives Against Cervical Cancer Cell (Hela)

“…The calculations for electronic descriptors are performed using computational chemistry modeling with the geometry optimization procedure of each compound structure. E as described previously [23]. Each compound was created into a 2D structure model using the ChemDraw Ultra 8.0 and equipped with hydrogen atoms to form a 3D structure.…”

“…The QSAR equation was optimized by fitting six ferulic acid derivatives and the influence of the dependent and independent variables to the QSAR equation. The variables were determined as described previously in Rahmawati et al (2020). The following regression equation was expressed as the resul of QSAR approach:…”

“…Figure3shows the position of the carbon. The net atomic charge, the dipole moment, and the partition coefficient were determined as described in the previous report[23]. Then the most stable molecular geometry was optimized by minimizing the molecular energy using PM3 method, the convergence limit was 0.001 kcal / Å.mol for ferulic acid derivatives, according to Polak-Ribiere algorithm.Table2.…”