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Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism.

ABSTRACT: To obtain novel structural antioxidants that have different antioxidant mechanisms, four 2-(alkylthio)-N-(4-(phenylamino)phenyl)acetamides 2a-d as dual functional antioxidants are designed, synthesized, and confirmed by ¹H-NMR, FTIR, MS, and elemental analysis. The antioxidant behavior of compounds 2a-d as additives of base oil triisodecyl trimellitate (TIDTM) is evaluated by non-isothermal and isothermal DSC analyses. The results showed all compounds can greatly increase the incipient oxidation temperature (IOT) and oxidation induction time (OIT) of TIDTM, especially, compound 2c exhibited an OIT value of 72.5 min at 230 °C, which is almost 28 times the length of TIDTM. Moreover, compounds 2a-d do not affect the tribological performance of TIDTM. The mechanism of antioxidants involved an intramolecular synergism are proposed. This work demonstrates compound 2c can be used as a novel potential antioxidant additive of TIDTM; in addition, it would inspire the emergence of highly potent antioxidants with different antioxidant mechanisms.

SUBMITTER: He JB

PROVIDER: S-EPMC6017979 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Design, synthesis and biological evaluation of sulfur-containing 1,1-bisphosphonic acids as antiparasitic agents.

Project description:As part of our efforts aimed at searching for new antiparasitic agents, 2-alkylmercaptoethyl-1,1-bisphosphonate derivatives were synthesized and evaluated against Trypanosoma cruzi, the etiologic agent of Chagas disease, and Toxoplasma gondii, the responsible agent for toxoplasmosis. Many of these sulfur-containing bisphosphonates were potent inhibitors against the intracellular form of T. cruzi, the clinically more relevant replicative form of this parasite, and tachyzoites of T. gondii targeting T. cruzi or T. gondii farnesyl diphosphate synthases (FPPSs), which constitute valid targets for the chemotherapy of these parasitic diseases. Interestingly, long chain length sulfur-containing bisphosphonates emerged as relevant antiparasitic agents. Taking compounds 37, 38, and 39 as representative members of this class of drugs, they exhibited ED(50) values of 15.8 ?M, 12.8 ?M, and 22.4 ?M, respectively, against amastigotes of T. cruzi. These cellular activities matched the inhibition of the enzymatic activity of the target enzyme (TcFPPS) having IC(50) values of 6.4 ?M, 1.7 ?M, and 0.097 ?M, respectively. In addition, these compounds were potent anti-Toxoplasma agents. They had ED(50) values of 2.6 ?M, 1.2 ?M, and 1.8 ?M, respectively, against T. gondii tachyzoites, while they exhibited a very potent inhibitory action against the target enzyme (TgFPPS) showing IC(50) values of 0.024 ?M, 0.025 ?M, and 0.021 ?M, respectively. Bisphosphonates bearing a sulfoxide unit at C-3 were also potent anti-Toxoplasma agents, particularly those bearing long aliphatic chains such as 43-45, which were also potent antiproliferative drugs against tachyzoites of T. gondii. These compounds inhibited the enzymatic activity of the target enzyme (TgFPPS) at the very low nanomolar range. These bisphosphonic acids have very good prospective not only as lead drugs but also as potential chemotherapeutic agents.

| S-EPMC3582829 | biostudies-literature

Synthesis of Cyanate Esters Based on Mono-O-Methylated Bisphenols with Sulfur-Containing Bridges.

Project description:We described a synthetic approach to bisphenol-based monocyanate esters based on mono-O-methylation of parental bisphenols followed by cyanation of the residual phenolic hydroxyl. Structures of the synthesized compounds were determined by the application of IR, NMR ¹H and 13C spectroscopies, EI and MALDI mass spectrometry, and purity of the final product was controlled by HPLC. We showed that stability of the cyanate esters depends on the nature of the bridging group. Temperature range of thermally initiated cyclotrimerization of synthesized monocyanate ester, as well as reaction enthalpy, was determined by differential scanning calorimetry (DSC).

| S-EPMC6337567 | biostudies-literature

A Multifunctional Coating on Sulfur-Containing Carbon-Based Anode for High-Performance Sodium-Ion Batteries.

Project description:A sulfur doping strategy has been frequently used to improve the sodium storage specific capacity and rate capacity of hard carbon. However, some hard carbon materials have difficulty in preventing the shuttling effect of electrochemical products of sulfur molecules stored in the porous structure of hard carbon, resulting in the poor cycling stability of electrode materials. Here, a multifunctional coating is introduced to comprehensively improve the sodium storage performance of a sulfur-containing carbon-based anode. The physical barrier effect and chemical anchoring effect contributed by the abundant C-S/C-N polarized covalent bond of the N, S-codoped coating (NSC) combine to protect SGCS@NSC from the shuttling effect of soluble polysulfide intermediates. Additionally, the NSC layer can encapsulate the highly dispersed carbon spheres inside a cross-linked three-dimensional conductive network, improving the electrochemical kinetic of the SGCS@NSC electrode. Benefiting from the multifunctional coating, SGCS@NSC exhibits a high capacity of 609 mAh g-1 at 0.1 A g-1 and 249 mAh g-1 at 6.4 A g-1. Furthermore, the capacity retention of SGCS@NSC is 17.6% higher than that of the uncoated one after 200 cycles at 0.5 A g-1.

| S-EPMC10142203 | biostudies-literature

Intramolecular synergism and proteolytic control of bacteriophage endolysin PlySK1249

Project description:Endolysins are peptidoglycan hydrolases produced at the end of the bacteriophage (phage) replication cycle to lyse the host cell. Gram-positive phages endolysins come in a variety of multi-modular forms that combine different catalytic domains and may have evolved to adapt to their bacterial hosts. However, the reason why phage can adopt endolysin with such complex multidomain architecture is for the moment not well understood. We used the Streptococcus dysgalactiae phage endolysin PlySK1249 as a model to study the implication of multi-domain architecture in phage-induced bacterial lysis and lysis regulation. The activity of the enzyme relied on a bacteriolytic amidase (Ami), a non-bacteriolytic L-Ala-D-Ala endopeptidase (CHAP) acting as a de-chaining enzyme and central LysM cell wall binding domain (CBD). Ami and CHAP synergized for peptidoglycan digestion and bacteriolysis in the native enzyme or when expressed individually and reunified in vitro. This cooperation could be modulated by bacterial cell wall-associated proteases, which specifically cleaved the two linkers connecting the different domains. While both catalytic domains were observed to act coordinately to optimize bacterial lysis, the CBD is expected to delay diffusion of the enzyme until proteolytic inactivation is achieved. As for certain autolysins, PlySK1249 cleavage by bacterial cell wall associated proteases might be an example of dual phage-bacterial regulation and mutual coevolution.

2021-04-15 | PXD024020 | Pride

8-Hydroxyquinoline Glycoconjugates Containing Sulfur at the Sugar Anomeric Position-Synthesis and Preliminary Evaluation of Their Cytotoxicity.

Project description:One of the main factors limiting the effectiveness of many drugs is the difficulty of their delivery to their target site in the cell and achieving the desired therapeutic dose. Moreover, the accumulation of the drug in healthy tissue can lead to serious side effects. The way to improve the selectivity of a drug to the cancer cells seems to be its conjugation with a sugar molecule, which should facilitate its selective transport through GLUT transporters (glucose transporters), whose overexpression is seen in some types of cancer. This was the idea behind the synthesis of 8-hydroxyquinoline (8-HQ) derivative glycoconjugates, for which 1-thiosugar derivatives were used as sugar moiety donors. It was expected that the introduction of a sulfur atom instead of an oxygen atom into the anomeric position of the sugar would increase the stability of the obtained glycoconjugates against untimely hydrolytic cleavage. The anticancer activity of new compounds was determined based on the results of the MTT cytotoxicity tests. Because of the assumption that the activity of this type of compounds was based on metal ion chelation, the effect of the addition of copper ions on cell proliferation was tested for some of them. It turned out that cancer cells treated with glycoconjugates in the presence of Cu2+ had a much slower growth rate compared to cells treated with free glycoconjugates in the absence of copper. The highest cytotoxic activity of the compounds was observed against the MCF-7 cell line.

| S-EPMC7570910 | biostudies-literature

Three-dimensional porous carbon composites containing high sulfur nanoparticle content for high-performance lithium-sulfur batteries.

Project description:Sulfur is a promising cathode material for lithium-sulfur batteries because of its high theoretical capacity (1,675?mA?h?g(-1)); however, its low electrical conductivity and the instability of sulfur-based electrodes limit its practical application. Here we report a facile in situ method for preparing three-dimensional porous graphitic carbon composites containing sulfur nanoparticles (3D S@PGC). With this strategy, the sulfur content of the composites can be tuned to a high level (up to 90?wt%). Because of the high sulfur content, the nanoscale distribution of the sulfur particles, and the covalent bonding between the sulfur and the PGC, the developed 3D S@PGC cathodes exhibit excellent performance, with a high sulfur utilization, high specific capacity (1,382, 1,242 and 1,115?mA?h?g(-1) at 0.5, 1 and 2 C, respectively), long cycling life (small capacity decay of 0.039% per cycle over 1,000 cycles at 2 C) and excellent rate capability at a high charge/discharge current.

| S-EPMC4740444 | biostudies-literature

Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration.

Project description:Complex mixtures were often observed when we attempted to synthesize 4-thio- and 2,4-dithio-glycoside derivatives by double parallel and double serial inversion, thus leading to no or low yields of target products. The reason was later found to be that many unexpected side products were produced when a nucleophile substituted the leaving group on the substrate containing the thioacetate group. We hypothesized that thioacetyl migration is prone to occur due to the labile thioacetate group even under weak basic conditions caused by the nucleophile, leading to this result. Therefore, we managed to inhibit the generation of thiol groups from thioacetate groups by the addition of an appropriate amount of conjugate acid/anhydride, successfully improving the synthesis of 4-thio- and 2,4-dithio-glycoside derivatives. The target products which were previously difficult to synthesize, were herein obtained in relatively high yields. Finally, 4-deoxy- and 2,4-dideoxy-glycoside derivatives were efficiently synthesized through the removal of thioacetate groups under UV light, starting from 4-thio- and 2,4-dithio-glycoside derivatives.

| S-EPMC7191076 | biostudies-literature

Synthesis and evaluation of nanosystem containing chondroitinase ABCI based on hydroxyapatite.

Project description:The bacterial enzyme chondroitinase ABCI (chABCI), which has been isolated from Proteus Vulgaris, is crucial in the treatment of spinal cord injuries. However, due to its short lifespan, the maintenance and clinical application of this enzyme are very constrained. In this study, the immobilization of this enzyme on hydroxyapatite has been carried out and assessed with the aim of enhancing the characteristics and efficiency of chABCI. Hydroxyapatite particles (HAPs) are a potential candidate for drug-delivery carriers because of their excellent biocompatibility, shape controllability, and high adsorption. The use of the nanometer scale allows efficient access to the enzyme's substrate. It demonstrates important biological application capabilities in this way. Field emission gun-scanning electron microscopy (FEG-SEM), X-ray diffraction (XRD), infrared spectroscopy (FT-IR), in vitro release study, and cytotoxicity test were used to characterize the drug nanosystem's properties. According to the findings, electrostatic bindings was formed between charged groups of the enzyme and hydroxyapatite nanoparticles. The results also demonstrated that immobilized chABCI on hydroxyapatite has beneficial properties, such as more manageable drug release, minimal toxicity and side effects, and a high potential to enhance the efficacy of drug delivery and decrease the need for repeated injections.

| S-EPMC10866842 | biostudies-literature

Synthesis and characterization of enzymatically degradable PEG-based peptide-containing hydrogels.

Project description:Biodegradable hydrogels were synthesized by the click reaction of 4-arm azido-terminated PEG differing in molecular weight (2,100 and 8,800) and two alkyne-terminated peptides: [alkyne]-GFLGK-[alkyne] and ([alkyne]-GFLG)(2)K. The physical properties of in situ formed hydrogels were examined. The hydrogels were highly elastic as determined by rheological and microrheological studies. Swelling degree and enzymatic degradation by papain were dependent on the molecular weight of the PEG, but not the peptide. For PEG8800-based hydrogels, time-course analysis of degradation showed that the molecular weight of the soluble fraction quickly reached the PEG precursor value. These findings may guide future design of hydrogels with controllable mechanical properties and enzymatic degradability.

| S-EPMC4608387 | biostudies-literature

Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.

Project description:Vinyl sulfides react rapidly and efficiently with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form ?,?-unsaturated thiocarbenium ions through oxidative carbon-hydrogen bond cleavage. These electrophiles couple with appended ?-nucleophiles to yield sulfur-containing heterocycles through carbon-carbon bond formation. Several nucleophiles are compatible with the procedure, and the reactions generally proceed through readily predictable transition states.

| S-EPMC3321134 | biostudies-literature

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