A Structure and Antioxidant Activity Study of Paracetamol and Salicylic Acid

Borges, Rosivaldo S.; Barros, Tainá G.; Pereira, Glaécia A. N.; Batista, João; Filho, Raimundo F. G. P. Beleza; Veiga, Andrex A. S.; Hamoy, Moisés; Mello, Vanessa Jóia de; Silva, Albérico Borges Ferreira da; Barros, Carlos A. L.

doi:10.4236/pp.2014.513130

Cited by 14 publications

(8 citation statements)

References 35 publications

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“…This antagonism could be by preventing Ca 2+ loading in to the erythrocyte and/or inhibiting calcium-induced K + loss from the cell 6 . Since there are no reports in the literature suggesting that paracetamol could inhibit Ca 2+ influx in the human erythrocyte, and since the present study showed that paracetamol doesn't prevent plasma recalcification (clotting) indicating no Ca 2+ binding to the drug, it seems that this antagonism could be due to the antioxidant activity of paracetamol that has been reported in human erythrocytes 16,17,18,19 , and also shown in the present study (Table 1), with consequent anti-lipidperoxidation activity that has been reported previously 16,18 , and also shown in the present study (Fig. 4).…”

Section: Discussionmentioning

confidence: 63%

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2016

IJPSR

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Human erythrocytes were pre-incubated in vitro with paracetamol and then erythrocyte's rheological properties of deformability, osmotic fragility and aggregation were evaluated after being compromised by various means. Paracetamol (1, 2, 4mg/ml) significantly prevented the loss of deformability through 5m diameter pores of erythrocytes dehydrated with hypertonic buffer or with calcium ionophore A23187 at 4 mg/ml. When the potassium ionophore valinomycin was used to induce cell dehydration, paracetamol (4mg/ml) also prevented partially the loss of deformability. Paracetamol (4mg/ml) also decreased significantly erythrocyte osmotic fragility induced by hypotonic saline, and prevented significantly the aggregation of erythrocytes induced by dextran 70. The antioxidant properties of paracetamol was studied by chemical assays and found to be as follows: total antioxidant capacity (88.9 µg AAE/mg), reducing power (A 0 at 700 nm= 1.0 compared to 3.0 for Vit. C), DPPH scavenging activity (IC 50 = 62.5 µg/ml compared to 5.8 for Vit. C), OH· scavenging activity (IC 50 = 40.2 µg/ml compared to <10 for catecholamin), iron chelating (IC 50 = 144.6 µg/ml compared to 17.3 for EDTA) and Paracetamol at 1, 2, 4, 5 mg/ml also prevented significantly lipid peroxidation in a concentration dependent manner of human erythrocytes incubated with H 2 O 2 . The observed rheological and anti-lipid-peroxidant effects of paracetamol could be explained by its antioxidant activity, thus protecting membrane integrity and deformability. The results suggest that paracetamol could have a rheologically useful role on erythrocytes, preventing dehydration, aggregation and lipid-peroxidation, that may contribute positively to its analgesic and antipyretic effects.

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Section: Discussionmentioning

confidence: 63%

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2016

IJPSR

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“…In fact, previous works for the antioxidant activity of these drugs have focused mainly on the general capacity of the paracetamol to decrease the malondialdehyde formation in the lipid peroxidation systems (Orhan and Sahin, 2001;Maharaj et al, 2004), whereas the salicylate working as scavenger of hydroxyl radical is very well known (Dinis et al, 1994;Sairam et al, 2003;Maharaj et al, 2006;Borges et al, 2014). Soon, hydroxyl radical can be formed via Fenton and Haber-Weiss reactions.…”

Section: Resultsmentioning

confidence: 99%

A computational study for the antioxidant capacity increases in hydroxy-derivatives of paracetamol and salicylic acid

et al. 2015

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Paracetamol is a more potent antioxidant than salicylic acid on the several oxidative stress-forced models. A possible mechanism of hydroxylation by the hydroxyl radicals and their antioxidant properties was performed by molecular modeling using quantum chemical calculations at the B3LYP level of theory. The calculation was made in gas phase and water using PCM method. The electron abstraction for hydroxylated paracetamol derivatives is more favored than hydroxylated salicylic acid derivatives. The increase in antioxidant capacity is more observed for hydroxylated derivatives of the paracetamol than salicylic acid. Some hydroxylated derivatives of paracetamol and salicylic acid were more reactive than trolox by hydrogen transfer. Their antioxidant capacity can be increased by number and position of the hydroxyl group.

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“…Numerous experimental works have been done on APAP to understand the structure, structural assignment and stability [11][12][13] , the mechanism of action [14][15] , photocatalytic degradation [16][17] , method validation for quantitative determination [18][19][20] , to improve analgesic and antipyretic activities and to reduce side effect 21 and applications in prevention of metal corrosion from acid rain 22 . Compared to experimental works, there is no so many computational research yet on APAP.…”

Section: Introductionmentioning

confidence: 99%

The Effect of Temperature and Solvents on the Thermodynamical and Electronic Properties of N-acetyl-para-aminophenol (APAP): A Computational Study

Alauddin

2022

Dhaka Univ. J. Sci.

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Effects of temperature and solvents on the thermodynamical and electronic properties of N-acetyl-para-aminophenol (APAP) have been investigated using density functional theory (DFT) and time dependent density functional theory (TD-DFT). Calculated results shows that thermodynamic properties such as enthalpy (H), entropy (S) and specific heat capacity (Cv) are increased by the raising of temperature (100 K-1200 K) because of enhancing the intensities of molecular vibration. On the contrary, change of Gibb’s free energy (ΔG) has been decreased with the increase of temperature. FMO energy gap is enlarged by solvation and therefore APAP becomes more stable in solution especially in polar solvents. Moreover, solvation increases the magnitude of ionization potential, electron affinity, electronegativity, chemical potential and global hardness. Two UV absorption maxima (λmax1 and λmax2) are found at 243.08 nm and 193.85 nm which are originated from phenyl and amide chromophore, respectively. The calculated λmax1 and λmax2 agree quite well with the available experimental data. On the other hand, calculated results reveal that solvation blueshifts the electronic absorption spectraas well as enhances the absorption intensity significantly. Dhaka Univ. J. Sci. 69(3): 125-132, 2022 (June)

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A Structure and Antioxidant Activity Study of Paracetamol and Salicylic Acid

Cited by 14 publications

References 35 publications

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Untitled

A computational study for the antioxidant capacity increases in hydroxy-derivatives of paracetamol and salicylic acid

The Effect of Temperature and Solvents on the Thermodynamical and Electronic Properties of N-acetyl-para-aminophenol (APAP): A Computational Study

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