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INTRODUCTION: Tert-butylphenol (TBP) derivatives, antioxidants in adhesives and diabetes devices, may provoke allergic contact dermatitis (ACD). OBJECTIVES: The objective of this study is to report sensitization to TBP derivatives in medical devices and to highlight that tert-butylhydroquinone (BHQ) and tert-butylcatechol (TBC) are potential screeners in this regard. METHODS: Fifteen patients with ACD from adhesives and diabetes devices were patch tested to different TBPs: BHQ 1% pet., TBC 0.25% pet., BHA 2% pet., BHT 2% pet., 4-tert-butylphenol (TBP) 1% pet. and 2,4-di-tert-butylphenol (di TBP) 1% pet. The culprit devices (medical adhesives, sanitary pads, diabetes devices) and TBP patch preparations were analysed using gas chromatography-mass spectrometry (GC-MS). RESULTS: BHQ (9/13), TBC (7/13), and to a lesser extent BHT (3/15), BHA (2/15) and TBP (2/13) gave positive reactions. Seven patients had developed ACD from adhesives and diabetes devices, respectively, and one patient from sanitary pads. GC-MS analyses of the medical devices and patch test materials confirmed the presence of the patch-test positive TBPs, or chemically related derivatives, or, interestingly, tert-butylbenzoquinones (BBQ) were found, that is, spontaneously formed, highly reactive TBP metabolites, likely (pseudo-) cross reacting with the patch tested TBPs. CONCLUSION: TBPs might be overlooked sensitizers in medical devices, and BHQ and TBC are potential screeners in this regard.

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This study employs electrochemical and Density Functional Theory (DFT) calculation approaches to investigate the potential of a novel analogue of trimetozine (TMZ) antioxidant profile. The correlation between oxidative stress and psychological disorders indicates that antioxidants may be an effective alternative treatment option. Butylatedhydroxytoluene (BHT) is a synthetic antioxidant widely used in industry. The BHT-TMZ compound derived from molecular hybridization, known as LQFM289, has shown promising results in early trials, and this study aims to elucidate its electrochemical properties to further support its potential as a therapeutic agent. The electrochemical behavior of LQFM289 was investigated using voltammetry and a mechanism for the redox process was proposed based on the compound's behavior. LQFM289 exhibits two distinct oxidation peaks: the first peak, Ep1a ≈ 0.49, corresponds to the oxidation of the phenolic fraction (BHT), and the second peak, Ep2a ≈ 1.2 V (vs. Ag/AgCl/KClsat), denotes the oxidation of the amino group from morpholine. Electroanalysis was used to identify the redox potentials of the compound, providing insight into its reactivity and stability in different environments. A redox mechanism was proposed based on the resulting peak potentials. The DFT calculation elucidates the electronic structure of LQFM289, resembling the precursors of molecular hybridization (BHT and TMZ), which may also dictate the pharmacophoric performance.

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Recent studies have indicated the critical importance of mitochondria in the induction and progression of ferroptosis. There is evidence indicating that tert-butyl hydroperoxide (TBH), a lipid-soluble organic peroxide, is capable of inducing ferroptosis-type cell death. We investigated the effect of TBH on the induction of nonspecific membrane permeability measured by mitochondrial swelling and on oxidative phosphorylation and NADH oxidation assessed by NADH fluo rescence. TBH and iron, as well as their combinations, induced, with a respective decrease in the lag phase, the swelling of mitochondria, inhibited oxidative phosphorylation and stimulated NADH oxidation. The lipid radical scavenger butylhydroxytoluene (BHT), the inhibitor of mitochondrial phospholipase iPLA2γ bromoenol lactone (BEL), and the inhibitor of the mitochondrial permeability transition pore (MPTP) opening cyclosporine A (CsA) were equally effective in protecting these mitochondrial functions. The radical-trapping antioxidant ferrostatin-1, a known indicator of ferroptotic alteration, restricted the swelling but was less effective than BHT. ADP and oligomycin significantly decelerated iron- and TBH-induced swelling, confirming the involvement of MPTP opening in mitochondrial dysfunction. Thus, our data showed the participation of phospholipase activation, lipid peroxidation, and the MPTP opening in the mitochondria-dependent ferroptosis. Presumably, their involvement took place at different stages of membrane damage initiated by ferroptotic stimuli.

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BACKGROUND: Traditional production of dry salted shrimp enhances cholesterol oxidation and astaxanthin degradation in the product. The aim of this study was to evaluate the effect of addition of the antioxidants butylhydroxytoluene (BHT) and tert-butylhydroquinone (TBHQ) to cooked shrimp on the formation of cholesterol oxidation products (COPs) and astaxanthin degradation during solar drying of shrimp. RESULTS: The added antioxidants significantly inhibited COPs formation after the product was boiled in brine. Smaller amounts of COPs were formed in antioxidant-treated shrimps (~-23%) as compared to untreated samples. The antioxidants continued to significantly inhibit COPs formation (~-39%) during sun drying. Similarly, TBHQ and BHT reduced by 51.3% and 37.2%, respectively, the degradation rate of astaxanthin, favoring a higher retention of this carotenoid in the final product. CONCLUSION: The use of the antioxidants BHT and TBHQ in the preparation of dry salted shrimp significantly inhibited the formation of COPs after cooking raw shrimp and during direct solar drying. They also protected astaxanthin contained in the cooked shrimp from photodegradation. These results are technologically relevant because it is possible to prepare a product with a higher content of astaxanthin and lower the presence of hazardous COPs. © 2022 Society of Chemical Industry.

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BACKGROUND: The disadvantages associated with the use of synthetic additives in animal production could threaten human and animal health, and the safety of animal-derived foods. This study assessed the growth performance, blood chemistry, immune indices, selected caeca bacterial population, muscle antioxidant enzyme activities, and meat quality in broiler chickens fed diet supplemented with antibiotic (70% oxytetracycline +30% neomycin), tert-butylhydroxytoluene or onion leaf powder (OLP). One day old Ross 308 chicks (n = 240) were assigned randomly to either D-1, control diet (CD) without additives; D-2, CD + 0.3 g kg-1 antibiotic +0.15 g kg-1 tert-butylhydroxytoluene; D-3, CD + 2.5 g kg-1 OLP; or D-4, CD + 5 g kg-1 OLP for 42 days. RESULTS: The D-2 and D-4 diets improved (P < 0.05) bodyweight gain and feed efficiency in broilers. Platelet and cecal Lactobacillus spp. counts were higher (P < 0.05) whereas muscle cholesterol was lower (P < 0.05) in the OLP-supplemented birds. Supplemented birds had higher (P < 0.01) splenic interleukin-10 and lower (P < 0.01) splenic tumor necrosis factor-α, immunoglobulin A, cecal E. coli and C. perfringens counts compared with the D-1 birds. The D-4 birds had the least (P < 0.05) splenic interleukin-1ß. Dietary supplements increased (P < 0.05) catalase, glutathione peroxidase, and total antioxidant capacity, and lowered (P < 0.05) drip loss, malondialdehyde and carbonyl content in breast meat. CONCLUSION: Dietary supplementation of 5 g kg-1 OLP exerted antimicrobial, immunomodulatory, and antioxidant effects that were comparable to those of antibiotics and tert-butylhydroxytoluene in broiler chickens. © 2021 Society of Chemical Industry.

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The addition of antioxidants to the cryopreservation medium has been shown to exert a positive effect on the quality of frozen-thawed sperm in different species. The objective of the present study was to evaluate the effects of supplementing the freezing medium with butylhydroxytoluene (BHT) and melatonin (MEL) in frozen-thawed pig spermatozoa. With this purpose, six ejaculates coming from six separate boars were cryopreserved in traditional freezing medium (i.e. lactose/egg-yolk/glycerol; Control) supplemented with 1.0 mM BHT (BHT-1), 2.0 mM BHT (BHT-2), 0.01 µM MEL (MEL-1) and 1.0 µM MEL (MEL-2). We evaluated sperm viability, membrane lipid disorder, acrosome integrity, mitochondrial membrane potential, lipid peroxidation, oxidation of thiol groups, and levels of total reactive oxygen species (ROS), peroxynitrite and superoxide anion (·O2-). We also analysed total (TM) and progressive sperm motilities (PM), and kinetic parameters at post-thaw (T0, T30 and T60). The BHT-2 and MEL-2 groups presented higher viability and acrosome integrity, and lower levels of peroxynitrite, ·O2- and lipid peroxidation than the control (P < 0.05), whereas MEL-2 diminished the levels of total ROS (P < 0.05). TM and PM were not affected by the treatment, while, LIN and STR shows differences between experimental groups. In conclusion, the addition of BHT and MEL to cryopreservation medium diminishes oxidative and nitrosative stress markers, which has repercussions for the integrity of plasma and acrosomal membranes of frozen-thawed spermatozoa.

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AIM: The study is aimed at examining of action of iron, DOX, and their complex on the Mitochondrial Permeability Transition Pore (MPTP) opening and detecting of possible protectors of MPTP in the conditions close to mitochondria-dependent ferroptosis. BACKGROUND: The Toxicity of Doxorubicin (DOX) is mainly associated with free iron accumulation and mitochondrial dysfunction. DOX can provoke ferroptosis, iron-dependent cell death driven by membrane damage. The Mitochondrial Permeability Transition Pore (MPTP) is considered as a common pathway leading to the development of apoptosis, necrosis, and, possibly, ferroptosis. The influence of DOX on the Ca2+ -induced MPTP opening in the presence of iron has not yet been studied. OBJECTIVE: The study was conducted on isolated liver and heart mitochondria. MPTP and succinate- ubiquinone oxidoreductase were studied as targets of DOX in mitochondria-dependent ferroptosis. The iron chelator deferoxamine (DFO), the lipid radical scavenger butyl-hydroxytoluene (BHT), and rutenium red (Rr), as a possible inhibitor of ferrous ions uptake in mitochondria, were tested as MPTP protectors. The role of medium alkalization was also examined. METHODS: Changes of threshold calcium concentrations required for MPTP opening were measured by a Ca2+ selective electrode, mitochondrial membrane potential was registered by tetraphenylphosphonium (TPP+)-selective electrode, and mitochondrial swelling was recorded as a decrease in absorbance at 540 nm. The activity of Succinate Dehydrogenase (SDH) was determined by the reduction of the electron acceptor DCPIP. CONCLUSION: MPTP and the respiratory complex II are identified as the main targets of the iron-dependent action of DOX on the isolated mitochondria. All MPTP protectors tested abolished or weakened the effect of iron and a complex of iron with DOX on Ca2+ -induced MPTP opening, acting in different stages of MPTP activation. These data open new approaches to the modulation of the toxic influence of DOX on mitochondria with the aim to reduce their dysfunction.

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The effect of supercritical fluid extract of tomato pomace (TP) and essential oil of organic peppermint (PM) on pH, color, residual nitrite content, lipid oxidation (TBARS value) and total plate count (TPC) of cooked pork sausages produced with 50 mg/kg of sodium nitrite was investigated. Five batches were produced: T1: 100 mg/kg of sodium nitrite; T2: 50 mg of sodium nitrite; T3: 50 mg of sodium nitrite and 0.150 µL/g TP; T4: 50 mg of sodium nitrite, 0.075 µL/g TP and 0.075 µL/g PM; T5: 50 mg of sodium nitrite and 0.150 µL/g PM. The lowest residual nitrite content and TBARS value were observed in treatment T4. The inclusion of TP increased redness of cooked pork sausages. TPC was the lowest in treatment T5. The results of this study showed that the addition of TP and PM enhanced quality of cooked sausages produced with reduced level of sodium nitrite.

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The effect of coriander essential oil (CEO) at concentrations of 0.075-0.150 µL/g on pH, color, lipid oxidation (TBARS), residual nitrite concentration and microbial growth of cooked pork sausages produced with different levels of sodium nitrite (0, 50 and 100 mg/kg) was investigated. Artificial neural networks modeling and the multi-response optimization were used to determine the optimal combinations of process parameters and storage time. Reduced concentration of sodium nitrite (60 mg/kg) in combination with 0.12 µL/g of CEO resulted in satisfying redness (a* approx. 11.1) and improved oxidative (TBARS approx. 0.12 mg MDA/kg) and microbial stability (total plate count - TPC approx. 2.50 Log CFU/g) of cooked pork sausages during refrigerated storage. Therefore, the results of this paper revealed significant antioxidative and antimicrobial activity of CEO, and consequently its high potential of utilization in processing of cooked pork sausages with enhanced quality and shelf-life.

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The effect of winter savory (Satureja montana L.) essential oil (SEO) and supercritical extracts (SE1; SE2) at concentrations of 0.075 and 0.150 µL/g on pH, lipid oxidation (TBARS), microbial growth and sensory quality of fresh pork sausages during storage were investigated. SEO, SE1 and SE2 improved oxidative and microbial stability of fresh pork sausages. The addition of SEO and SE1 at concentration of 0.150 µL/g affected the reduction of total Enterobacteriaeceae count to under 3 log cfu/g. Sausages produced with SE1 and SE2 had a higher scores for odor, flavor and overall acceptance compared to sausages treated with SEO and control sample. Therefore, the results of this paper revealed significant antioxidative and antimicrobial activity of SE1 and SE2, and consequently its high potential of utilization in processing of fresh pork sausages.

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Rat liver mitochondria (1.5-2.1mg protein·mL-1) supplemented with either 25 and 100µM Cu2+ or 100 and 500µM Fe3+ show inhibition of active respiration (O2 consumption in state 3) and increased phospholipid peroxidation . Liver mitochondria were supplemented with the antioxidants reduced glutathione, N-acetylcysteine or butylated hydroxitoluene, to evaluate their effects on the above-mentioned alterations. Although the mitochondrial dysfunction is clearly associated to phospholipid peroxidation, the different responses to antioxidant supplementation indicate that the metal ions have differences in their mechanisms of toxicity. Mitochondrial phospholipid peroxidation through the formation of hydroxyl radical by a Fenton/Haber-Weiss mechanism seems to precede the respiratory inhibition and to be the main fact in Fe-induced mitochondrial dysfunction. In the case of Cu2+, it seems that the ion oxidizes glutathione, and low molecular weight protein thiol groups in a direct reaction, as part of its intracellular redox cycling. The processes involving phospholipid peroxidation, protein oxidation and mitochondrial respiratory inhibition characterize a redox dyshomeostatic situation that ultimately leads to cell death. However, Cu2+ exposure involves an additional, yet unidentified, toxic event as previous reduction of the metal with N-acetylcysteine has only a minor effect in preventing the mitochondrial damage.

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Butylhydroxytoluene (BHT), a synthetic analogue of vitamin E, shows antioxidant and antiviral properties and has been successfully used for mammalian sperm cryopreservation. In this study, BHT was included in a vitrification solution to determine its cryoprotective effect on human spermatozoa. Spermatozoa were selected by swim-up and vitrified in close sealed straw using either a combination of human tubal fluid (HTF), sucrose and BHT 1 mm (VMBHT), or only HTF and sucrose (VM). The optimal concentration of BHT was determined by the observation of preserved progressive sperm motility (PSM) after warming and detection of plasma membrane (PMI), membrane mitochondrial potential (ΔΨm) and DNA integrity. The presence of reactive oxygen species (ROS) was also detected. The PSM was significantly higher in the VMBHT group (80.86 ± 5.41%) compared with the VM group (68.9 ± 3.67%) (P < 0.05). Butylhydroxytoluene significantly preserved DNA integrity (4.0 ± 0.1% versus 6.1 ± 1.6%; P < 0.05) and reduced ROS production (5.5 ± 2.2 versus 8.6 ± 1.8%; P < 0.05). Plasma membrane and ΔΨm showed no statistical differences. One millimolar BHT effectively maintained cell function and due to its antioxidant and antiviral properties could be used in semen cryopreservation of patients with viral infections transmitted by seminal plasma.

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The development of a convenient mathematical application for testing the antioxidant and pro-oxidant capacity is essential in order to investigate potential sources of new agents and processes. In this regard, authors use the standardized values of the area under the curve of a kinetic profile of a dose-response agent, as a way to bypass the complex process of analyzing the kinetic variations of agents. In general, linear approaches are used, but such patterns frequently lead to unreliable results and misinterpretations, making it extremely difficult to compare the results from different assays. In this work, we have demonstrated the non-linearity of the dose-response area under the curve assessment criteria by means of simulations. A simple non-linear dose-response model was developed to describe the accurate response. As a case study, experimental data of extracts of unroasted coffee beans from five different country-climate locations for the two most common coffee varieties (Robusta and Arabica) were obtained using the ß-carotene and crocin bleaching in vitro assays. Their antioxidant capacity was analyzed in detail and compared with commercial standards. The results show that the antioxidant capacity was greater than some of the commercial standards in terms of its maximum capacity, while when the analyses are based on rate parameters, the coffee extracts show between 6 and 40 times lower values than the standard antioxidants. In addition, to illustrate the advantages of using the standardized area units and the mathematical model developed, other more complex scenarios were recreated. We believe that the model application developed provides a simple alternative to summarize meaningful parameters that characterize the response, facilitates rigorous comparisons among the effects of different compounds and experimental approaches and helps to comprehend multi-variable scenarios.

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The sydnone SYD-1 (3-[4-chloro-3-nitrophenyl]-1,2,3-oxadiazolium-5-olate] possesses important antitumor activity against Sarcoma 180 and Ehrlich tumors. We previously showed that SYD-1 depresses mitochondrial phosphorylation efficiency, which could be involved in its antitumoral activity. Considering the important role of mitochondria in the generation of reactive oxygen species (ROS) and the involvement of ROS in cell death mechanisms, we evaluated the effects of SYD-1 on oxidative stress parameters in rat liver mitochondria. SYD-1 (0.5 and 0.75µmolmg(-1) protein) inhibited the lipoperoxidation induced by Fe(3+)/ADP-oxoglutarate by approximately 75% and promoted total inhibition at the highest concentration tested (1.0µmolmg(-1) protein). However, SYD-1 did not affect lipoperoxidation started by peroxyl radicals generated by α-α'-azodiisobutyramidine dihydrochloride. The mesoionic compound (0.25-1.0µmolmg(-1) protein) demonstrated an ability to scavenge superoxide radicals, decreasing their levels by 9-19%. The activities of catalase and superoxide dismutase did not change in the presence of SYD-1 (0.25-1.0µmolmg(-1) protein). SYD-1 inhibited mitochondrial swelling dependent on the formation/opening of the permeability transition pore induced by Ca(2+)/phosphate by approximately 30% (1.0µmolmg(-1) protein). When Ca(2+)/H2O2 were used as inducers, SYD-1 inhibited swelling only by approximately 12% at the same concentration. NADPH oxidation was also inhibited by SYD-1 (1.0µmolmg(-1) of protein) by approximately 48%. These results show that SYD-1 is able to prevent oxidative stress in isolated mitochondria and suggest that the antitumoral activity of SYD-1 is not mediated by the increasing generation of ROS.

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