A review on the degradation of acetaminophen by advanced oxidation process: pathway, by-products, biotoxicity, and density functional theory calculation

Qutob, Mohammad; Hussein, Mahmoud A.; Alamry, Khalid A.; Rafatullah, Mohd

doi:10.1039/d2ra02469a

Cited by 32 publications

(17 citation statements)

References 130 publications

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“…In AOPs, decomposition by oxidants such as hydroxyl radicals, sulfate radicals, and superoxide radicals are the dominant oxidation pathways. 36 From the perspective of molecular structure, the radicals prefer to attack the highest occupied molecular orbital (HOMO) site on the target compound, which makes the radical-attacked preferred sites predictable. The Fukui index representing electrophilic attack ( f − ) and radical attack ( f 0 ) are considered based on the density functional theory (DFT).…”

Section: Resultsmentioning

confidence: 99%

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Mechanistic explanation and influence of molecular structure on chemical degradation and toxicity reduction by hydroxyl radicals

Lee,

Cheng,

Fan

2024

RSC Adv.

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Section: Resultsmentioning

confidence: 99%

“…, C6 position in Fig. 4A ), and release hydroquinone and acetamide as degradation byproducts 36 ( Fig. 3A ).…”

Section: Resultsmentioning

confidence: 99%

Mechanistic explanation and influence of molecular structure on chemical degradation and toxicity reduction by hydroxyl radicals

Lee,

Cheng,

Fan

2024

RSC Adv.

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“…The hyperglycemia and the experimentally provoked diabetes induced an elevated oxidative stress, which was followed by there being high levels of free radicals and the simultaneous decline of the antioxidant defense mechanisms [ 51 ]. The non-enzymatic oxidative processes can produce hydroquinone, p-benzoquinone, p-aminophenol, p-nitrophenol, and benzaldehydes from paracetamol, and these derivatives interact with the cellular glutathione and cysteine [ 52 ]. When it is viewed as a whole, the overall status of the thiol redox system can reflect important information on the condition and reserve pool of the antioxidant defense mechanisms.…”

Section: Discussionmentioning

confidence: 99%

Investigation of Intestinal Absorption and Excretion of Paracetamol in Streptozotocin-Induced Hyperglycemia

Mészáros

Kovács

Kulcsár

et al. 2022

IJMS

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The phenolic drug molecules can be metabolized, among others, by the small intestine’s enterocytes. The conjugation reactions (glucuronidation and sulfation) show great importance in these transformations, although the oxidation reactions can be significant. These processes are dependent on the substituents of the phenolic compounds or the reacting functional groups (hydroxyl or carboxyl). Pathologic conditions, e.g., permanent hyperglycemia and diabetes, can alter the activities of the conjugative and possibly the oxidative enzymes, thus forming a change in the metabolic pattern and eventually provoking oxidative stress. A rat intestinal perfusion model was used to investigate the way in which experimental hyperglycemia affects the paracetamol’s intestinal elimination and metabolism. Hyperglycemia was induced by the administration of streptozotocin. Two hundred and fifty µM paracetamol was used in the intestinal perfusion solution. For the quantitation of the paracetamol and its major metabolites in the intestinal perfusate, an isocratic high-performance liquid chromatography method with UV-Vis detection was developed. The results revealed that quantities of all of the measured metabolites (glucuronide, sulfate, cysteine, and mercapturic acid conjugates) increased as the effect of the streptozotocin-induced hyperglycemia also did. In the small intestine’s homogenate, the glutathione levels showed that there was a decrease in the hyperglycemia levels after the paracetamol administration. In contrast, the tissue levels of the cysteine were lower in the streptozotocin-induced hyperglycemia and increased after the administration of the paracetamol. The changes in the activity of the intestinal CYP 3A4, CYP 2E1, and cyclooxygenase (COX) enzymes were determined in the control and the hyperglycemic cases. Still, there was a significant observable enzyme activity elevation in the intestinal COX enzymes, but there was a decrease in the amount of activity of the intestinal CYP3A4 enzymes, and the CYP2E1 enzyme activity was practically changeless. The results on the cysteine levels in the intestinal homogenate, at least partly, can be explained by the regulation function of the cysteine during the occurrence of oxidative stress.

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“…On the jnl > hand, acetaminophen is a well-known pain reliever and fever reducer that has been around for a long time. [5] Acetaminophen is the most widely used pain reliever in the United States, with millions of individuals using it on a daily basis to relieve pain and reduce temperature. Acetaminophen, unlike jnl > pain medications, lacks anti-inflammatory characteristics, making it less effective at reducing edema and inflammation.…”

Section: Introductionmentioning

confidence: 99%

“…As a result, standard cancer drugs such as thiotepa, tioguanine, and arsenic trioxide are heavily used in this study to investigate COF delivery capability. On the jnl> hand, acetaminophen is a well‐known pain reliever and fever reducer that has been around for a long time [5] . Acetaminophen is the most widely used pain reliever in the United States, with millions of individuals using it on a daily basis to relieve pain and reduce temperature.…”

Section: Introductionmentioning

confidence: 99%

Therapeutic Delivery Potential of Covalent Organic Framework (COF): Intuition from Theoretical Calculations

Mohammadi,

Louis,

Benjamin

et al. 2024

ChemistrySelect

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Regardless of the benefits, pharmaceutical companies are reticent to engage further in covalent organic framework‐based drug development and drug delivery systems, preferring rather to explore preexisting chemical compound libraries for drug delivery. As such, this study aims to account for the efficacy of covalent organic frameworks (COFs) in the delivery of seven conventional drugs: Acetaminophen, Clodronic Acid, Hydroxyurea, Mercaptoporine, Thiotepa, Tioguanine, and Arsenic trioxide. Herein, Gaussian 16 software package is employed for the purpose of optimizing the systems at the DFT/ωB97XD/def2svp level of theory. Substantially, the nature of the inter‐ and intra‐ molecular interactions between the COF and each of the drugs utilized resulted in the re‐adjustment of the molecular orbitals and yielded a distinct set of results for the most reactive and least stable and vice versa as deducible from the magnitudes of the highest occupied molecular orbital and lowest unoccupied molecular orbital (HOMO‐LUMO) gaps. Furthermore, the natural bond orbital (NBO) study indicates that the interacting molecules exhibit similar stability and reactivity, as evidenced by the proximity of their mean stabilization energies. Additionally, the topological analysis revealed that the most positive interaction occurred in Acetaminophen_COF, Clodronic acid_COF, Hydroxyurea_COF, and Tioguanine_COF. Also, the adsorption studies demonstrate that the above‐mentioned drugs have weak interaction kinetics when they interact with the investigated COF. Strong adsorbing contacts were detected in the interactions of Arsenic trioxide, Hydroxyurea, and Tioguanine with the COF in the order Arsenic trioxide_COF < Hydroxyurea_COF < Tiog_COF, with corresponding values of −9.413 kcal/mol, −12.550 kcal/mol, and −17.570 kcal/mol, respectively. Overall, the study hypothesizes that when delivering the various drugs studied through the COF to biological systems, Acetaminophen, Hydroxyurea, Tioguanine, and Mercaptopurine have high reactivity with the COF and would be better adsorbed on it, as well as a longer recovery time of desorption due to their high adsorption on the COF surface.

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A review on the degradation of acetaminophen by advanced oxidation process: pathway, by-products, biotoxicity, and density functional theory calculation

Abstract: Researchers use advanced oxidation processes because of water scarcity and environmental recalcitrance. State-of-the-art studies on ACT by-products and their biotoxicity, proposed degradation pathways, have been collected, organized, and summarized.

Cited by 32 publications

References 130 publications

Mechanistic explanation and influence of molecular structure on chemical degradation and toxicity reduction by hydroxyl radicals

Mechanistic explanation and influence of molecular structure on chemical degradation and toxicity reduction by hydroxyl radicals

Investigation of Intestinal Absorption and Excretion of Paracetamol in Streptozotocin-Induced Hyperglycemia

Therapeutic Delivery Potential of Covalent Organic Framework (COF): Intuition from Theoretical Calculations

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