A computational prospect to aspirin side effects: Aspirin and COX-1 interaction analysis based on non-synonymous SNPs

Naeini, Marjan Mojtabavi; Tanha, Hamzeh Mesrian; Emamzadeh, Rahman; Vallian, Sadeq

doi:10.1016/j.compbiolchem.2014.05.002

Cited by 24 publications

(15 citation statements)

References 27 publications

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“…Acetylsalicylic acid, also known as aspirin is currently one of the most widely used drugs worldwide owing to its analgesic, antipyretic, anti-inflammatory and cardioprotective effects. 36 Aspirin irreversibly inhibits both isozymes of COX, but with a greater potency for COX-1, 36 which was demonstrated by our docking study as well. COX-1 is constitutively expressed in blood platelets and most tissues, particularly gastric mucosal cells, whereas COX-2 is an inducible form expressed during inflammation.…”

Section: Molecular Dockingsupporting

confidence: 69%

“…Therapeutic effects of acetylsalicylic acid are achieved by COX-2 inhibition, while inhibition of COX-1 is responsible for the side effects. 36 The risk of adverse effects, especially gastrointestinal mucosa damage, limits the benefit of aspirin use. 37 Lower affinity of salicin toward COX-1 might partially explain why willow bark extract does not damage the gastrointestinal mucosa in contrast to aspirin.…”

Section: Molecular Dockingmentioning

confidence: 99%

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Methodological Aspects of Extraction, Phytochemical Characterization and Molecular Docking Studies of Salix caprea L. Bark and Leaves

Gligorić¹,

Igić²,

Suvajdžić³

et al. 2019

ACSi

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Contents of twelve selected bioactive substances and antioxidant potential of Salix caprea L. extracts were compared in its two vegetative organs (bark and leaves) and in terms of different ethanol/water mixtures used for extraction (30-70% aq, ethanol) and extraction time (30 min; 24, 48 and 72 h). The extracts were characterized by High Pressure Liquid Chromatography (HPLC), and total phenolics and flavonoids were determined spectrophotometrically. All secondary metabolites identified in Salix caprea L. extracts (gallic, chlorogenic and vanillic acid, epicatechin, rutin, quercetin and naringenin) were found more accumulated in bark. Salicin and p-hydroxybenzoic acid were detected in bark and ferulic, trans-cinnamic and p-coumaric acid in leaves extracts only. Rutin was most abundant bioactive compound both in bark (1.71 g/100 g of de) and leaves extracts (0.434 g/100 g of de). Bark extract with highest bioactive substances contents was obtained with 70% aq. ethanol as most suitable solvent during extraction time of 48 h. Molecular docking showed salicin to have similar affinity toward COX-2 as acetylsalicylic acid, but lower toward COX-1.

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Section: Molecular Dockingsupporting

confidence: 69%

Section: Molecular Dockingmentioning

confidence: 99%

Methodological Aspects of Extraction, Phytochemical Characterization and Molecular Docking Studies of Salix caprea L. Bark and Leaves

Gligorić¹,

Igić²,

Suvajdžić³

et al. 2019

ACSi

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show abstract

“…Datt et al, 2012 investigated experimental and computational study of the loading and release of aspirin from zeolite HY [9]. Besides, Marjan et al, 2014 conducted a computational study to find the prospect of aspirin side effects [10]. Khan et al, 2015 reported a theoretical study of geometry, molecular properties and molecular docking study of aspirin [11].…”

Section: Introductionmentioning

confidence: 99%

Effects of Solvent Polarity on Solvation Free Energy, Dipole Moment, Polarizability, Hyperpolarizability and Molecular Reactivity of Aspirin

Khan

Rashid

Faruk

et al. 2017

Int J Pharm Pharm Sci

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Objective: 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.Methods: 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 n-octanol.Results: 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 n-octanol. The chemical potential, electronegativity and electrophilicity index of aspirin in n-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.Conclusion: 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.

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“…The NSAIDs exerts their therapeutic effects through inhibition of cyclooxygenase(COX)isoform 2 (COX-2), while the inhibition of COX-1 by ASA leads to apparent side effects (Marjan, et al, 2014). It probably act by inhibiting prastanoid synthesis by acetylation of fatty acid cyclooxygenase (Durand et al, 2002a).…”

Section: Introductionmentioning

confidence: 99%

Some Hematological and Biochemical Changes Associated with Aspirin Administration in Albino Rats = بعض التغيرات الدموية و البيوكيميائية المصاحبة لإعطاء الأسبرين في الجرذان البيضاء

Abdel-Aziz¹,

Elyazji²,

Ashour³

2015

JAU : SNS

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A computational prospect to aspirin side effects: Aspirin and COX-1 interaction analysis based on non-synonymous SNPs

Cited by 24 publications

References 27 publications

Methodological Aspects of Extraction, Phytochemical Characterization and Molecular Docking Studies of Salix caprea L. Bark and Leaves

Methodological Aspects of Extraction, Phytochemical Characterization and Molecular Docking Studies of Salix caprea L. Bark and Leaves

Effects of Solvent Polarity on Solvation Free Energy, Dipole Moment, Polarizability, Hyperpolarizability and Molecular Reactivity of Aspirin

Some Hematological and Biochemical Changes Associated with Aspirin Administration in Albino Rats = بعض التغيرات الدموية و البيوكيميائية المصاحبة لإعطاء الأسبرين في الجرذان البيضاء

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