Irreversible inhibition of glucose-6-phosphate dehydrogenase by the coenzyme A conjugate of ketoprofen: A key to oxidative stress induced by non-steroidal anti-inflammatory drugs?

Asensio, Carine; Levoin, Nicolas; Guillaume, Cécile; Guerquin, Marie-Justine; Rouguieg, Koukeb; Chrétien, Françoise; Chapleur, Yves; Netter, Patrick; Minn, Alain; Lapicque, Françoise

doi:10.1016/j.bcp.2006.09.026

Cited by 32 publications

(16 citation statements)

References 43 publications

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“…Since NSAIDs-including D and ASA-affect the mitochondrion and consequently also oxidative phosphorylation, increased ROS production particularly of O • 2 − may occur, resulting in increased SOD activity and higher levels of hydrogen peroxide (Asensio et al 2007), as evident in the present study with exposure of H. azteca to these compounds.…”

Section: Antioxidant Activitymentioning

confidence: 76%

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Binary mixtures of diclofenac with paracetamol, ibuprofen, naproxen, and acetylsalicylic acid and these pharmaceuticals in isolated form induce oxidative stress on Hyalella azteca

Gómez-Oliván

Neri-Cruz

Galár-Martínez

et al. 2014

Environ Monit Assess

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Toxicity in natural ecosystems is usually not due to exposure to a single substance, but is rather the result of exposure to mixtures of toxic substances. Knowing the effects of contaminants as a mixture compared to their effects in isolated form is therefore important. This study aimed to evaluate the oxidative stress induced by binary mixtures of diclofenac with paracetamol, ibuprofen, naproxen, and acetylsalicylic acid and by these nonsteroidal anti-inflammatory drugs (NSAIDs) in isolated form, using Hyalella azteca as a bioindicator. The median lethal concentration (LC50) and the lowest observed adverse effect level (LOAEL) of each NSAID were obtained. Amphipods were exposed for 72 h to the latter value in isolated form and as binary mixtures. The following biomarkers were evaluated: lipid peroxidation (LPX), protein carbonyl content (PCC), and activity of the antioxidant enzymes: superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPx). Significant increases in LPX and PCC with respect to the control group (p ≤ 0.05) were induced by NSAIDs both in isolated form and as binary mixtures. Changes in SOD, CAT, and GPx activity likewise occurred with NSAIDs in isolated form and as binary mixtures. In conclusion, NSAIDs used in this study induce oxidative stress on H. azteca both in isolated form and as binary mixtures, and the interactions occurring between these pharmaceuticals are probably antagonistic in type.

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Section: Antioxidant Activitymentioning

confidence: 76%

“…Asensio et al (2007) note that inhibition of NSAID-induced G6PD elicits damage through protein thiol oxidation.…”

Section: Cellular Oxidation Indicatorsmentioning

confidence: 98%

Binary mixtures of diclofenac with paracetamol, ibuprofen, naproxen, and acetylsalicylic acid and these pharmaceuticals in isolated form induce oxidative stress on Hyalella azteca

Gómez-Oliván

Neri-Cruz

Galár-Martínez

et al. 2014

Environ Monit Assess

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“…52 , but not of that from L. mesenteroides 53,54 . However, additional TLC bioautography, in which glucose-6-phosphate was used instead of fructose-6-phosphate, was conducted as described in Materials and methods, bioautography assay, in order to confirm the lack of inhibition of glc-6P dehydrogenase from L. mesenteroides by PEP.…”

Section: Zymomonas Mobilismentioning

confidence: 86%

Establishment of an effective TLC bioautographic method for the detection ofMycobacterium tuberculosisH37Ra phosphoglucose isomerase inhibition by phosphoenolpyruvate

Paradowska

Polak

Chomicki

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A bioautographic assay based on thin layer chromatography was developed for phosphoenolpyruvate (PEP) detecting as a known but rarely studied inhibitor of phosphoglucose isomerase (PGI). The protocol with NADP + /NBT/PMS (b-nicotinamide adenine dinucleotide phosphate/nitrotetrazolium blue chloride/phenazine methosulfate) staining was capable of detecting Mycobacterium tuberculosis H 37 Ra PGI inhibition using PEP. According to this method, visibly brighter spots (zones) against purple background are observed in the area of inhibition of the above-mentioned enzyme activity. The detection limit for PEP as an inhibitor of Mycobacterium tuberculosis H 37 Ra PGI was 226 mg per spot/zone. Noteworthy is that we are the first authors to have successfully used a bioautographic assay to detect Mycobacterium tuberculosis H 37 Ra PGI inhibition by PEP.

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“…The lower inhibitory potency observed in the presence of cytosolic extracts than with purified GST is likely to be due to the buffering effect of additional proteins interacting with the two acyl metabolites of KPF. Various proteins such as albumin (Li et al, 2003b), sulfotransferases (Tulik et al, 2002), COX (Levoin et al, 2004), hepatocyte nuclear factor-4␣ (Hertz et al, 2001), and glucose-6-phosphate dehydrogenase (Asensio et al, 2007) have indeed been reported to interact with CoA thioester derivatives. It was found previously that long-chain saturated fatty acyl-CoAs and peroxisome proliferator-CoA thioesters exert high affinity toward GST (Silva et al, 1999).…”

Section: Osbild Et Almentioning

confidence: 99%

“…KPF, among other drugs, has been used as a model compound to study the possible reactivity of acyl metabolites with cellular proteins. Thus, it was previously observed that both of these KPF acyl derivatives are chemically reactive species that can trigger the formation of adducts with various proteins such as albumin (Presle et al, 1996), UDP-glucuronosyltransferases (Terrier et al, 1999), the cyclooxygenase COX-2 (Levoin et al, 2004), and glucose-6-phosphate dehydrogenase (Asensio et al, 2007).…”

mentioning

confidence: 99%

Interaction of the Electrophilic Ketoprofenyl-Glucuronide and Ketoprofenyl-Coenzyme A Conjugates with Cytosolic GlutathioneS-Transferases

Osbild¹,

Bour²,

Maunit³

et al. 2007

Drug Metab Dispos

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ABSTRACT:Carboxylic acid-containing drugs are metabolized mainly through the formation of glucuronide and coenzyme A esters. These conjugates have been suspected to be responsible for the toxicity of several nonsteroidal anti-inflammatory drugs because of the reactivity of the electrophilic ester bond. In the present study we investigated the reactivity of ketoprofenyl-acylglucuronide (KPF-OG) and ketoprofenyl-acyl-coenzyme A (KPF-SCoA) toward cytosolic rat liver glutathione S-transferases (GST). We observed that KPFSCoA, but not KPF-OG inhibited the conjugation of 1-chloro-2,4-dinitrobenzene and 4-nitroquinoline N-oxide catalyzed by both purified cytosolic rat liver GST and GST from FAO and H5-6 rat hepatoma cell lines. Photoaffinity labeling with KPF-SCoA suggested that the binding of this metabolite may overlap the binding site of 4-methylumbelliferone sulfate. Furthermore, high-performance liquid chromatography and mass spectrometry analysis showed that both hydrolysis and transacylation reactions were observed in the presence of GST and glutathione. The formation of ketoprofenyl-S-acyl-glutathione could be kinetically characterized (apparent K m ‫؍‬ 196.0 ؎ 70.6 M). It is concluded that KPF-SCoA is both a GST inhibitor and a substrate of a GST-dependent transacylation reaction. The reactivity and inhibitory potency of thioester CoA derivatives toward GST may have potential implications on the reported in vivo toxicity of some carboxylic acid-containing drugs.

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Irreversible inhibition of glucose-6-phosphate dehydrogenase by the coenzyme A conjugate of ketoprofen: A key to oxidative stress induced by non-steroidal anti-inflammatory drugs?

Cited by 32 publications

References 43 publications

Binary mixtures of diclofenac with paracetamol, ibuprofen, naproxen, and acetylsalicylic acid and these pharmaceuticals in isolated form induce oxidative stress on Hyalella azteca

Binary mixtures of diclofenac with paracetamol, ibuprofen, naproxen, and acetylsalicylic acid and these pharmaceuticals in isolated form induce oxidative stress on Hyalella azteca

Establishment of an effective TLC bioautographic method for the detection ofMycobacterium tuberculosisH37Ra phosphoglucose isomerase inhibition by phosphoenolpyruvate

Interaction of the Electrophilic Ketoprofenyl-Glucuronide and Ketoprofenyl-Coenzyme A Conjugates with Cytosolic GlutathioneS-Transferases

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