On the mechanism of covalent binding of butylated hydroxytoluene to microsomal protein
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Stabilizing Polysorbate 20 and 80 Against Oxidative Degradation
2020, Journal of Pharmaceutical SciencesCitation Excerpt :Another consideration to be taken into account is the fact that the antioxidants on the one hand protect PS, as shown in our experiments, but on the other hand, their oxidation products might be a potential new source for the modification of the active proteins. It has been shown that some of the degradation products can modify proteins by covalent binding to, for example, sulfhydryl groups of cysteine residues.21 One of the highly reactive degradation products of BHT is its quinone methide.
Metabolic Activation and Toxicities of bis-Benzylisoquinoline Alkaloids
2017, Advances in Molecular ToxicologyCitation Excerpt :Adducts resulting from the attacks of QMs includes peptides, proteins, and nucleic acids [65,74,87,88,91–94]. The principal targets of QMs in general are cysteine-containing compounds including glutathione and proteins with accessible thiol residues [95–98]. Soft electrophiles, such as QMs, readily combine with soft nucleophiles, e.g., thiols and react more slowly with hard nucleophiles such as amino and hydroxyl groups [99].
Responses of tumorigenic and non-tumorigenic mouse lung epithelial cell lines to electrophilic metabolites of the tumor promoter butylated hydroxytoluene
2003, Chemico-Biological InteractionsCitation Excerpt :In addition, similar amounts of both BHT-SG (Table 2) and BHT-NAC were formed in the cell lines indicating that the differential toxicity of BHT-QM is not due to more efficient conjugation of the electrophile in neoplastic cells. This finding is consistent with an earlier conclusion that BHT-SG formation occurs non-enzymatically [34] and explains why conjugate levels are not elevated in cells that express higher GSH S-transferase activity (Fig. 4). Following exposure to BHT-QM, cells were oxidatively stressed as demonstrated by substantial increases in superoxide and lipid peroxidation products; similar increases were observed for each sibling pair (Tables 2 and 3).
Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: Studies utilizing amino acid and peptide models
1997, Chemico-Biological InteractionsRelationship of membrane fluidity, chemoprotection, and the intrinsic toxicity of butylated hydroxytoluene
1991, Biochemical Pharmacology