Abstract
<p><strong>Objective: </strong>The aim of the study is to explore the effects of solvent polarity on solvation free energy, dipole moment, polarizability, first order hyperpolarizability and different molecular properties like chemical hardness and softness, chemical potential, electronegativity, electrophilicity index of aspirin which may lead to better understand the reactivity and stability of aspirin in different solvent systems.</p><p><strong>Methods: </strong>Becke, 3-parameter, Lee-Yang-Parr (B3LYP) level of theory with 6-31G(d,p) basis set was employed to conduct all type of calculations for both in the gas phase and in solution. The solvation free energy, dipole moment and molecular properties were calculated by applying the Solvation Model on Density (SMD) in four solvent systems namely water, methanol, ethanol and <em>n</em>-octanol.</p><p><strong>Results: </strong>The solvation energies steadily increased as the dielectric constant was decreased i.e. free energy increases with decreasing polarity of the solvent. The dipole moment of aspirin was found to be increased when going from non-polar to polar solvents. The dipole moment of aspirin was higher in different solvents than that of the gas phase. The polarizability and first order hyperpolarizability were also increased with the increasing dielectric constant of the solvent. Moreover, ongoing from non-polar to polar solvent the chemical potential, electronegativity and electrophilicity index were increased except in <em>n</em>-octanol. The chemical potential, electronegativity and electrophilicity index of aspirin in <em>n</em>-octanol was higher than that of ethanol. On the other hand, chemical hardness was increased with decreasing polarity of the solvent and the inverse relation was found in the case of softness.</p><p><strong>Conclusion: </strong>The calculated solvation free energy, dipole moment, polarizability, first order hyperpolarizability and molecular properties found in this study may lead to the understanding of stability and reactivity of aspirin in different solvent systems.</p>
Highlights
Non-steroidal anti-inflammatory drugs (NSAIDs) are a class of compounds that block cyclooxygenase (COX) enzyme involved in the first step of the arachidonic acid cascade
And fig. 6, it is clear that HOMO-LUMO gap increases with decreasing polarity of the solvents suggesting a higher degree of interactions of aspiring with decreasing polarity of the medium
We report βtot for all the solvent systems listed in table 3
Summary
Non-steroidal anti-inflammatory drugs (NSAIDs) are a class of compounds that block cyclooxygenase (COX) enzyme involved in the first step of the arachidonic acid cascade. COX exists in two isoforms namely COX-1 and COX-2. COX-2 is inducible and plays a major role in prostaglandin biosynthesis in inflammatory cells [1]. 1) is a prototype NSAID and is used to treat pain, fever, and inflammation. It is a non-selective COX-2 inhibitor and inhibits both the isoforms of COX enzyme. The therapeutic effects of aspirin are obtained due to the inhibition of COX-2; on the other hand, inhibition of COX-1 leads to undesirable side effects on the gastrointestinal tract such as ulceration, bleeding and perforation of the gastrointestinal tract
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