Insights into Ultrasound-Promoted Degradation of Naphthenic Acid Compounds in Oil Sands Process Affected Water. Part Ii: In Silico Quantum Screening of Hydroxyl Radical Initiated and Propagated Degradation of Benzoic Acid

2022 ◽  
Author(s):  
Deepak M. Kirpalani ◽  
Andy Nong ◽  
Rija Ansari
Keyword(s):  
Benzoic Acid ◽  
Hydroxyl Radical ◽  
In Silico ◽  
Oil Sands ◽  
Naphthenic Acid

2,4-Dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic Acid Derivatives: In Vitro Antidiabetic Activity, Molecular Modeling and In silico ADMET Screening

2019 ◽  
Vol 15 (2) ◽  
pp. 186-195 ◽  
Author(s):  
Samridhi Thakral ◽  
Vikramjeet Singh
Keyword(s):  
Molecular Docking ◽  
Benzoic Acid ◽  
Inhibitory Activity ◽  
In Silico ◽  
Computational Study ◽  
Antidiabetic Activity ◽  
Standard Drug ◽  
Benzoic Acid Derivatives ◽  
In Silico Admet ◽  
Inhibitory Potential

Background: Postprandial hyperglycemia can be reduced by inhibiting major carbohydrate hydrolyzing enzymes, such as α-glucosidase and α-amylase which is an effective approach in both preventing and treating diabetes. Objective: The aim of this study was to synthesize a series of 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl] benzoic acid derivatives and evaluate α-glucosidase and α-amylase inhibitory activity along with molecular docking and in silico ADMET property analysis. Method: Chlorosulfonation of 2,4-dichloro benzoic acid followed by reaction with corresponding anilines/amines yielded 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic acid derivatives. For evaluating their antidiabetic potential α-glucosidase and α-amylase inhibitory assays were carried out. In silico molecular docking studies of these compounds were performed with respect to these enzymes and a computational study was also carried out to predict the drug-likeness and ADMET properties of the title compounds. Results: Compound 3c (2,4-dichloro-5-[(2-nitrophenyl)sulfamoyl]benzoic acid) was found to be highly active having 3 fold inhibitory potential against α-amylase and 5 times inhibitory activity against α-glucosidase in comparison to standard drug acarbose. Conclusion: Most of the synthesized compounds were highly potent or equipotent to standard drug acarbose for inhibitory potential against α-glucosidase and α-amylase enzyme and hence this may indicate their antidiabetic activity. The docking study revealed that these compounds interact with active site of enzyme through hydrogen bonding and different pi interactions.

scholarly journals The Effects of Naphthenic Acids on Tryptophan Metabolism and Peripheral Serotonin Signalling

2021 ◽  
Vol 5 (Supplement_1) ◽  
pp. A493-A493
Author(s):  
Laiba Jamshed ◽  
Genevieve A Perono ◽  
Shanza Jamshed ◽  
Kim Ann Cheung ◽  
Philippe J Thomas ◽  
...  
Keyword(s):  
Oil Sands ◽  
Naphthenic Acid ◽  
Kynurenine Pathway ◽  
Naphthenic Acids ◽  
Tryptophan Metabolism ◽  
Lipid Homeostasis ◽  
Prostaglandin E ◽  
Serotonin Synthesis ◽  
Active Metabolites ◽  
Glucose And Lipid Homeostasis

Abstract Introduction: Serotonin produced in the periphery has been shown to affect glucose and lipid homeostasis. The availability of the amino acid tryptophan, the precursor of serotonin, affects serotonin availability. In addition, the metabolism of tryptophan via the kynurenine pathway produces physiologically active metabolites which have been shown to be altered under conditions of increased adiposity and dysglycemia. There is now evidence demonstrating some environmental xenobiotics, known to affect glucose and lipid homeostasis, can also alter serotonin production and key components of the kynurenine pathway. Recent evidence suggests that exposure to compounds present in petroleum and wastewaters from oil and gas extraction sites can impact endocrine signaling and result in aberrant lipid accumulation and altered glycemic control. However, whether any of these changes can be causally ascribed to altered serotonin synthesis/signaling or tryptophan metabolism remains unknown. The goal of this study was to determine the effects of exposure to naphthenic acid (NA), a key toxicant found in wastewater from bitumen (thick crude oil present in oil sands deposits) extraction on the enzymes involved in tryptophan metabolism and serotonin production. Methods: McA-RH7777 rat hepatoma cells, were exposed to a technical NA mixture for 48 hours at concentrations within the reported range of NA found in wastewaters from oil extraction. We assessed mRNA expression for key rate-limiting enzymes involved in tryptophan metabolism that lead to either serotonin [Tph1] and/or kynurenine [Ido2 and Tdo2] production, as well as downstream enzymes in the kynurenine pathway [Afmid, Kyat1, Aadat, Kyat3, Kmo, Haao, Acmsd, Qprt]. We also examined the effects of NA on prostaglandin synthesis [Ptgs1, Ptgs2, Ptges] and signalling [Ptger2, Ptger4] as prostaglandins have been shown to be induced by serotonin and are linked to hepatic fat accumulation. Results: NA treatment significantly increased Tph1 and Ido2 expression; this occurred in association with a significant increase in the expression of the inducible prostaglandin synthase Ptgs2 (COX-2), prostaglandin E synthase Ptges, and prostaglandin receptors Ptger2 and Ptger4. Acmsd was the only downstream enzyme in the kynurenine pathway that was significantly altered by NA treatment. Conclusion: These results provide proof-of-concept that compounds associated with oil sands extraction have the potential to perturb key components of serotonin synthesis (Tph1) and tryptophan metabolism (Ido2, Acmsd). Furthermore, we found that the increase in Tph1 expression paralleled expression of Ptgs2. As increased prostaglandin production has been reported in association with nonalcoholic steatohepatitis, these data provide a potential mechanism by which exposure to NA and other petroleum-based compounds may increase the risk of metabolic disease.

Investigating the toxicity of naphthenic acid fraction components from oil sands process-affected water to developing fathead minnow (Pimephales promelas)

2020 ◽  
Author(s):  
Brianna Jackson
Keyword(s):  
Oil Sands ◽  
Fathead Minnow ◽  
Pimephales Promelas ◽  
Naphthenic Acid ◽  
Natural Setting ◽  
Acid Fraction ◽  
Spinal Curvatures ◽  
Aquatic Life ◽  
Pericardial Edema ◽  
Embryo Heart

The extraction of bitumen from Alberta’s oil sands region generates large volumes of oil sands process-affected water (OSPW) that is stored in tailings ponds. Toxic constituents present in OSPW such as naphthenic acid fraction components (NAFCs) can cause adverse effects to aquatic life. Recent research has focused on the toxicity of NAFCs to highly vulnerable early life stages of fish. Here we examined the embryotoxicity of NAFCs (0-54 mg/L) extracted from OSPW to native fathead minnow (Pimephales promelas) from 1-day post-fertilization to hatch in a semi-natural setting at Queen’s University’s Biological Station. Embryo heart rate, mortality, prevalence and severity of malformations at hatch, post-hatch mass, and basal activity at hatch was examined. Embryo heart rates declined with increasing NAFC concentration, preceding pronounced exposure-response patterns of mortality and non-viable hatches. Visible malformations included cardiovascular (pericardial edema; present in 81.51% of non-viable hatches), craniofacial (reduced jaw and head size; 68.96%), myoskeletal (spinal curvatures; 60.90%), and peritoneal (yolk sac edema; 26.44%) malformations, that significantly increased in severity with increasing NAFC concentration. Fish that survived lethal concentrations displayed evidence of nervous system impairment including elevated patterns of erratic twitching. Post-hatch mass generally increased with increasing NAFC exposure, potentially as a compensatory-like response. Results of this work are the first to be reported in a semi-natural exposure setting and provide important toxicological information that will aid future policy directives for the management of OSPW in Alberta, Canada.

The Use of Carbon and Nitrogen Stable Isotope Analysis to Characterize Food Web Changes in Aquatic Systems for Reclamation of Oil Sands Process-Affected Materials

2009 ◽  
Vol 44 (4) ◽  
pp. 313-322 ◽  
Author(s):  
Monalisa Elshayeb ◽  
Michael D. MacKinnon ◽  
D. George Dixon ◽  
Michael Power
Keyword(s):  
Food Web ◽  
Oil Sands ◽  
Isotope Analysis ◽  
Naphthenic Acid ◽  
Carbon Sources ◽  
Nitrogen Isotope ◽  
Isotopic Signatures ◽  
Carbon And Nitrogen ◽  
Aquatic Food ◽  
Northern Alberta

Abstract One strategy for reclamation of oil sands leases in northern Alberta is the construction of lakes and wetlands by capping oil sands process-affected material (OSPM) with water. To assess this approach, experimental sites containing a range of OSPM have been constructed to monitor the evolution of the resulting aquatic habitats. Stable isotopes of carbon and nitrogen were used to assess the effects of OSPM on aquatic food webs. Carbon and nitrogen isotopic signatures of sediment, dissolved inorganic and organic carbon, particulate organic matter, periphyton, plants, plankton, aquatic invertebrates, and fish were used to assess differences related to the naphthenic acid (NA) concentration in OSPM and reference sites. NAs are a principal contaminant of concern in OSPM. Sites were grouped into low (0 to 4 mg/L), medium (4 to 15 mg/L), and high (>15 mg/L) NA concentrations. There were no significant differences in food web area or length among the three NA groupings. In most cases, carbon isotope analyses of samples from low, medium, and high NA concentration sites were not significantly different, suggesting that OSPM is not a significant contributor to food web carbon sources. Significant differences were found in nitrogen isotope signatures between low, medium, and high NA sites. Ammonia from OSPM is suggested as the main contributor to δ15N enrichment.

scholarly journals Culturing oil sands microbes as mixed species communities enhances ex situ model naphthenic acid degradation

2015 ◽  
Vol 6 ◽  
Author(s):  
Marc A. Demeter ◽  
Joseph A. Lemire ◽  
Gordon Yue ◽  
Howard Ceri ◽  
Raymond J. Turner
Keyword(s):  
Oil Sands ◽  
Naphthenic Acid ◽  
Ex Situ ◽  
Mixed Species ◽  
Acid Degradation

scholarly journals Developments in Molecular Level Characterization of Naphthenic Acid Fraction Compounds Degradation in a Constructed Wetland Treatment System

Environments ◽  
2020 ◽  
Vol 7 (10) ◽  
pp. 89
Author(s):  
Chukwuemeka Ajaero ◽  
Ian Vander Meulen ◽  
Monique C. Simair ◽  
Mignon le Roux ◽  
Joanne Parrott ◽  
...  
Keyword(s):  
High Resolution ◽  
Constructed Wetland ◽  
Analytical Methods ◽  
Oil Sands ◽  
Solid Phase ◽  
Aquatic Toxicity ◽  
Naphthenic Acid ◽  
Acid Fraction ◽  
Wetland Treatment ◽  
Spe Method

The reclamation of oil sands process-affected water (OSPW) is a matter of environmental importance because of the aquatic toxicity to biota. This study describes refinements in advanced analytical methods to assess the performance of biological treatment systems for OSPW, such as constructed wetland treatment systems (CWTSs). Assessment of treatment efficiency by measurement of the degradation of naphthenic acid fraction compounds (NAFCs) in OSPW is challenging in CWTS due to potentially interfering constituents such as humic acids, organic acids, salts, and hydrocarbons. Here we have applied a previous weak anion exchange (WAX) solid-phase extraction (SPE) method and high-resolution Orbitrap-mass spectrometry (MS) to remove major interferences from the NAFC analysis. The refinements in data processing employing principal component analysis (PCA) indicates that the relative abundance of NAFCs decreased with time in the treated OSPW relative to the untreated OSPW. The most saturated NAFCs with higher carbon numbers were relatively more degraded as compared to unsaturated NAFCs. The use of Kendrick plots and van Krevelen plots for assessment of the performance of the CWTS is shown to be well-suited to detailed monitoring of the complex composition of NAFCs as a function of degradation. The developments and application of analytical methods such as the WAX SPE method and high-resolution Orbitrap-MS are demonstrated as tools enabling the advancement of CWTS design and optimization, enabling passive or semi-passive water treatment systems to be a viable opportunity for OSPW treatment.

Hydroxyl radical scavenging and antipsoriatic activity of benzoic acid derivatives

1990 ◽  
Vol 9 (2) ◽  
pp. 111-115 ◽  
Author(s):  
Reiner F. Haseloff ◽  
Ingolf E. Blasig ◽  
Hans Meffert ◽  
Bernd Ebert
Keyword(s):  
Benzoic Acid ◽  
Hydroxyl Radical ◽  
Radical Scavenging ◽  
Benzoic Acid Derivatives

scholarly journals Transcriptome Analysis of Environmental Pseudomonas Isolates Reveals Mechanisms of Biodegradation of Naphthenic Acid Fraction Compounds (NAFCs) in Oil Sands Tailings

2021 ◽  
Vol 9 (10) ◽  
pp. 2124
Author(s):  
Parisa Chegounian ◽  
Stephane Flibotte ◽  
Kerry Peru ◽  
John Headley ◽  
Dena McMartin ◽  
...  
Keyword(s):  
Oil Sands ◽  
Naphthenic Acid ◽  
Gene Products ◽  
Acid Fraction ◽  
Microbial Cultures ◽  
New Directions ◽  
Pure Cultures ◽  
Biochemical Mechanisms ◽  
Oil Sands Tailings ◽  
Shed Light

Naphthenic acid fraction compounds (NAFCs) are highly recalcitrant constituents of oil sands tailings. Although some microorganisms in the tailings can individually and synergistically metabolize NAFCs, the biochemical mechanisms that underpin these processes are hitherto unknown. To this end, we isolated two microorganisms, Pseudomonas protegens and Pseudomonas putida, from oils sands tailings and analyzed their transcriptomes to shed light on the metabolic processes employed by them to degrade and detoxify NAFCs. We identified 1048, 521 and 1434 genes that are upregulated in P. protegens, P. putida and a 1:1 co-culture of the strains, respectively. We subsequently enumerated the biochemical activities of enriched genes and gene products to reveal the identities of the enzymes that are associated with NAFC degradation. Separately, we analyzed the NAFCs that are degraded by the two pseudomonads and their 1:1 co-culture and determined the composition of the molecules using mass spectrometry. We then compared these molecular formulas to those of the cognate substrates of the enriched enzymes to chart the metabolic network and understand the mechanisms of degradation that are employed by the microbial cultures. Not only does the consortium behave differently than the pure cultures, but our analysis also revealed the mechanisms responsible for accelerated rate of degradation of NAFCs by the co-culture. Our findings provide new directions for engineering or evolving microorganisms and their consortia for degrading NAFCs more stably and aggressively.

Effect of ozone pretreatment on naphthenic acid biodegradation and fouling behavior in a membrane bioreactor receiving oil sands process-affected water

2016 ◽  
Vol 2016 (5) ◽  
pp. 5953-5963
Author(s):  
Jinkai Xue ◽  
Yanyan Zhang ◽  
Hiroshi Noguchi ◽  
Yang Liu ◽  
Mohamed Gamal El-Din
Keyword(s):  
Oil Sands ◽  
Membrane Bioreactor ◽  
Naphthenic Acid ◽  
Ozone Pretreatment
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