Search Results (4)

Thiol antioxidants play important roles in cell and body defense against oxidative stress. In body fluid, albumin is the richest source of thiol antioxidants. One recent study showed that the reductive modification of thiol residues in albumin potentiated its antioxidative activity. Given that whey protein (WP) contains albumin and other thiol-active proteins, this property of WP could be exploited to develop novel thiol antioxidants. The aim of this study was to address this possibility. WP was reductively modified with dithiothreitol (DTT). The modified protein exhibited significantly elevated free sulfhydryl groups (-SH) and thiol antioxidative activity. It detoxified H₂O₂ and prevented H₂O₂-initiated protein oxidation and cell death in a -SH group-dependent way in vitro. In addition, it reacted with GSH/GSSG and altered the GSH/GSSG ratio via thiol–disulfide exchange. In vivo, oral administration of the reductively modified WP prevented oxidative stress and renal damage in a mouse model of renal injury caused by ischemia reperfusion. It significantly improved renal function, oxidation, inflammation, and cell injury. These protective effects were not observed in the WP control and were lost after blocking the -SH groups with maleimide. Furthermore, albumin, one of the ingredients of WP, also exhibited similar protective effects when reductively modified. In conclusion, the reductive modification of thiol residues in WP transformed it into a potent thiol antioxidant that protected kidneys from ischemia reperfusion injury. Given that oxidative stress underlies many life-threatening diseases, the reductively modified dietary protein could be used for the prevention and treatment of many oxidative-stress-related conditions, such as cardiovascular diseases, cancer, and aging. Full article

Mercury is a highly toxic pollutant of major public health concern, and human exposure is mainly related to the aqueous phase, where its dominant form is methyl-mercury (MeHg). In the current work, two carbon-based adsorbents, i.e., a commercial activated carbon and a sunflower seeds’ biochar, were modified by the introduction of thiol-active groups onto their surfaces for the MeHg removal from natural-like water in ppb concentration levels. The examined thiol-functionalization was a two-step process, since the raw materials were initially treated with nitric acid (6 N), which is a reagent that favors the formation of surface carboxyl groups, and subsequently by the thiol surface bonding groups through an esterification reaction in methanol matrix. The adsorbents’ capacity was evaluated toward the Hg_total legislative regulation limit (1 μg/L) in drinking water (denoted as Q₁). The respective isothermal adsorption results revealed an increased affinity between MeHg and thiol-functionalized materials, where the commercial carbon showed slightly higher capacity (0.116 μg Hg/mg) compared with the biochar (0.108 μg Hg/mg). This variation can be attributed to the respective higher surface area, resulting, also, to higher thiol groups loading. Regarding the proposed mechanism, it was proved that the S-Hg bond was formed, based on the characterization of the best performed saturated adsorbent. Full article

In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean S_N2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially available benzyl (S)-lactate in 76%, 94% ee (2 steps). Deprotection of the acetyl group using N,N-dimethylethylenediamine afforded benzyl (R)-2-sulfanylpropanoate in 93% yield with 90% ee. These two sulfur-containing benzyl esters were sufficiently odorless to be purified by column chromatography. Direct HPLC analysis was applied to determine the enantiomeric excess without thiazolidin-4-one derivatizations. A complementary debenzylation of benzyl (R)-2-(acetylthio)propanoate was also performed using HBr/AcOH to afford (R)-2-(acetylthio)propanoic acid without critical racemization in 92% yield with 92% ee. Full article

Reaction of 3-(2-methylbenzimidazol-1-yl)propanoic acid hydrazide (1) with CS₂/KOH gave oxadiazole 2 which underwent Mannich reaction to give 3. Compound 2 was treated with hydrazine hydrate to give triazole 4 which was treated with both aldehydes and acetic anhydride to give 5 and 6, respectively. Carbohydrazide 1 was reacted with ethyl acetoacetate, acetylacetone and aldehydes to give 7, 8 and 9, respectively. Cyclocondensation of 9 with thioglycolic and thiolactic acids gave 10 and 11, respectively. Some of these compounds showed potential antimicrobial activities. Full article