soft electrophiles
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2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Melissa Faria ◽  
Eva Prats ◽  
Cristian Gómez-Canela ◽  
Chuan-Yu Hsu ◽  
Mark A. Arick ◽  
...  

Abstract Two essential key events in acrylamide (ACR) acute neurotoxicity are the formation of adducts with nucleophilic sulfhydryl groups on cysteine residues of selected proteins in the synaptic terminals and the depletion of the glutathione (GSx) stores in neural tissue. The use of N-acetylcysteine (NAC) has been recently proposed as a potential antidote against ACR neurotoxicity, as this chemical is not only a well-known precursor of the reduced form of glutathione (GSH), but also is an scavenger of soft electrophiles such as ACR. In this study, the suitability of 0.3 and 0.75 mM NAC to protect against the neurotoxic effect of 0.75 mM ACR has been tested in vivo in adult zebrafish. NAC provided only a mild to negligible protection against the changes induced by ACR in the motor function, behavior, transcriptome and proteome. The permeability of NAC to cross blood-brain barrier (BBB) was assessed, as well as the ACR-scavenging activity and the gamma-glutamyl-cysteine ligase (γ-GCL) and acylase I activities. The results show that ACR not only depletes GSx levels but also inhibits it synthesis from NAC/cysteine, having a dramatic effect over the glutathione system. Moreover, results indicate a very low NAC uptake to the brain, probably by a combination of low BBB permeability and high deacylation of NAC during the intestinal absorption. These results strongly suggest that the use of NAC is not indicated in ACR acute neurotoxicity treatment.


Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1970 ◽  
Author(s):  
Olivier Dangles ◽  
Julie-Anne Fenger

Owing to their specific pyrylium nucleus (C-ring), anthocyanins express a much richer chemical reactivity than the other flavonoid classes. For instance, anthocyanins are weak diacids, hard and soft electrophiles, nucleophiles, prone to developing π-stacking interactions, and bind hard metal ions. They also display the usual chemical properties of polyphenols, such as electron donation and affinity for proteins. In this review, these properties are revisited through a variety of examples and discussed in relation to their consequences in food and in nutrition with an emphasis on the transformations occurring upon storage or thermal treatment and on the catabolism of anthocyanins in humans, which is of critical importance for interpreting their effects on health.


2011 ◽  
Vol 61 (4) ◽  
pp. 547-557 ◽  
Author(s):  
D. A. Dawson ◽  
T. Mooneyham ◽  
J. Jeyaratnam ◽  
T. W. Schultz ◽  
G. Pöch

2010 ◽  
Vol 59 (4) ◽  
pp. 532-541 ◽  
Author(s):  
D. A. Dawson ◽  
J. Jeyaratnam ◽  
T. Mooneyham ◽  
G. Pöch ◽  
T. W. Schultz

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