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CARBOHYDRATE POLYMERS · 2018 · IF 5.158

Disulfide bond reconstruction: A novel approach for grafting of thiolated chitosan onto wool

Pan Zhang,Nan Zhang,Qiang Wang,Ping Wang,Jiugang Yuan,Jinsong Shen,Xuerong Fan

Chitosan, a natural biopolymer, is used as a multifunctional agent for modification of wool either through chemical crosslinking or physical coating. For the first time, wool fabric has been modified with chitosan through disulfide bond breaking and reforming reactions. The chitosan was thiolated and then grafted onto the reduced wool fibers through disulfide bonds. In order to understand the mechanism of the grafting of thiolated chitosan onto wool, glutathione was used as a model compound for wool in the research. The structures of thiolated chitosan reacted with glutathione and wool fabrics grafted with thiolated chitosan were investigated by FTIR, 13 CNMR, XPS, XRD, SEM. The dyeability, shrink-resistance and biocompatibility were also tested. The results suggested that glutathione reacted with thiolated chitosan and formed disulfide bond. The thiolated chitosan-grafted wool fabric had good shrink-resistance and dyeability. Hydrophilicity and antibacterial properties were also improved compared with untreated wool fabric. The results provide a novel approach for modification of wool through fiber-intrinsic groups like disulfide bonds.

CAS / MDL: 616-91-1 70-18-8
研究领域: 材料科学 · 纺织工程 · 生物化学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2019 · IF 4.784

The thiolated chitosan: Synthesis, gelling and antibacterial capability

Qiang Luo,Qianqian Han,Ying Wang,Hongmei Zhang,Zhenghao Fei,Yanqing Wang

Chitosan-1-(mercaptomethyl)-cyclopropane acetic acid (CS-MCA) copolymer was synthesized by amino linkage. The obtained copolymer was characterized by FTIR, 1 H NMR, XRD, TGA and SEM. Porous and reticulate morphologies were found on the CS-MCA surface. The effects of pH on the rheological properties of CS-MCA were investigated. On the one hand, the apparent viscosity of CS-MCA indicated a shear-thinning behavior. The graft of MCA enhanced the moduli and the maximum elastic properties were observed at pH = 7.00. The addition of dithiothreitol reduced the viscosity and modulus of CS-MCA hydrogel, and the gelation time, temperature and frequency were obtained in dynamic oscillatory tests. The antibacterial effect of CS-MCA against E . coli was investigated for the inhibition zone and bacterial growth curve. These results showed that CS-MCA had better antibacterial ability than chitosan without modification. Therefore, the rheological behavior and functional activities can be applied for the hydrocolloid gels in food and pharmaceutical applications .

研究领域: 食品科学 · 药学 · 材料科学
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Innovative Food Science & Emerging Technologies · 2022 · IF 7.104

Preparation and characterization of a novel antibacterial hydrogel based on thiolated ovalbumin/gelatin with silver ions

Yue Chen,Ning Qiu,Bin Ma,Gan Hu,Deog-Hwan Oh,Xing Fu

Hydrogels synthesized from natural proteins have better biocompatibility than polymer hydrogels. In this paper, the hydrogels (referred to as tOVA/ [email protected] ) was developed using coordinative crosslinking of thiolated ovalbumin (tOVA) and thiolated gelatin (tGel) with silver nitrate . After thiolation with Traut's reagent, the free sulfhydryl group content of ovalbumin increased from 1.5 μmol/g to 68.6 μmol/g, and the molecular weight (MW) increased from 44.5 kDa to around 50 kDa. Then, the physicochemical and rheological properties of hydrogels with different tOVA/tGel ratios (10:0, 7:3, 5:5, 3:7, and 0:10) were analyzed. With the decrease in the proportion of tOVA/tGel, the scanning electron microscope (SEM) showed that the network structure of hydrogel became more uniform and denser. Meanwhile, microrheological analysis displayed that the gel properties had been improved, which coincidently confirmed a better water-holding performance. During the antibacterial experiment, the diameter of the bacteriostatic ring of tOVA/ [email protected] hydrogels against Escherichia coli ( E. coli ) and Staphylococcus aureus ( S. aureus ) could reach 10.8 mm and 10.3 mm respectively, indicating their significant antibacterial properties . In summary, hydrogel prepared with thiolated proteins exhibited a good three-dimensional (3D) network structure with the help of silver ions, which was expected to play an important role in the field of food and medicine as antibacterial materials.

CAS / MDL: 4781-83-3
研究领域: 材料科学 · 生物材料 · 生物医学工程 · 药学
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NEW JOURNAL OF CHEMISTRY · 2019 ·Vol. 43 ·期 39 ·15700-15705 · IF 3.069

Condensation of 9-fluorenone and phenol using an ionic liquid and a mercapto compound synergistic catalyst

Yan Lei,Limei Yu,Maochang Shen,Shikang Luo,Zhanxian Gao

A series of ionic liquids (ILs) were synthesized and their Hammett acidities (H0) were determined using 4-nitroaniline as the indicator. The relationship among IL's structure, the acid strength, and the catalytic performance in the condensation reaction of 9-fluorenone with phenol was discussed. The effective H0 range of ionic liquids that can catalyse the condensation reaction was obtained. Moreover, the catalysis of the mercapto compound co-catalyst was also systematically studied. According to the analysis of how the structure of the sulfydryl co-catalyst affects the percent conversion of 9-fluorenone and the selectivity of BHPF, a mechanism for the reaction in the IL–thiol cooperative catalytic system was proposed. The present work gave a clear clue to design novel IL catalysts for the synthesis of BHPF.

研究领域: 有机化学 · 催化化学
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ACS Applied Bio Materials · 2024 · IF 4.6

Mucoadhesive Thiolated Hyaluronic Acid/Pluronic F127 Nanogel Formation via Thiol–Maleimide Click Reaction for Intravesical Drug Delivery

Fayang Li,Xianhuang Chen,Yuanqiao He,Zhiping Peng

The development of nanocarriers to prolong the residence time and enhance the permeability of chemotherapeutic drugs on bladder mucosa is important in the postsurgery treatment of superficial bladder cancers (BCs). Here, the mucoadhesive HA-SH/PF127 nanogels composed of a temperature-sensitive Pluronic F127 (PF127) core and thiolated hyaluronic acid (HA-SH) shell were prepared by the emulsification/solvent evaporation method. The nanogels were constructed through the thiol-maleimide click reaction in the HA-SH aqueous side of the oil–water interface and self-oxidized cross-linking thiols between HA-SH. The HA-SH/PF127 nanogels prepared at different thiol-to-maleimide group molar ratios, water-to-oil volume ratios, and cross-linking reaction times were characterized regarding hydrodynamic diameter (Dh) and zeta potential (ζ), and the optimal formulation was obtained. The excellent mucoadhesive properties of the HA-SH/PF127 nanogels were evaluated by using the mucin particle method. Doxorubicin (DOX) was encapsulated in the PF127 core of DOX@HA-SH/PF127 nanogels with a high loading efficiency (87.5%) and sustained release from the nanogels in artificial urine. Ex vivo studies on porcine bladder mucosa showed that the DOX@HA-SH/PF127 nanogels enhanced the penetration of the DOX into the bladder mucosa without disrupting the mucus structure or the bladder tissue. A significant dose-dependent cytotoxic effect of DOX@HA-SH/PF127 nanogels on both T24 and MB49 cells was observed. The present study demonstrates that the mucoadhesive HA-SH/PF127 nanogels are a promising intravesical drug delivery system for superficial BC therapy.

研究领域: 药剂学 · 肿瘤学 · 生物材料
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ORGANIC & BIOMOLECULAR CHEMISTRY · 2015 ·Vol. 13 ·期 26 ·7323-7330 · IF 3.562

Catalyst-free direct decarboxylative coupling of α-keto acids with thiols: a facile access to thioesters

Kelu Yan,Daoshan Yang,Wei Wei,Jing Zhao,Yuanyuan Shuai,Laijin Tian,Hua Wang

A novel, efficient, and catalyst-free strategy has been initially developed for the construction of thioesters via the direct radical oxidative decarboxylation of α-keto acids with thiols, and the corresponding target products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse thioesters.

CAS / MDL: 7727-21-1
研究领域: 有机化学 · 合成化学
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PLANT AND SOIL · 2025 · IF 4.1

Hydrogen sulfide enhances Cd tolerance through persulfidation of SlGSTU24 in Solanum lycopersicum L

Yi Yuying,Li Wenhui,Wang Jinzhao,Sun Guozhi,Ma Ying,Li Fali,Shi Wei,Hu Yanfeng,Jia Honglei,Li Jisheng

Aims Hydrogen sulfide (H₂S), a gaseous signaling molecule, plays a pivotal role in facilitating plant resistance to cadmium (Cd) stress. Glutathione S-transferases (GSTs) are critical enzymes to tolerate Cd stress in plants. However, the regulatory interplay between H₂S and GSTs activity remains elusive. Here, we identified the persulfidation of SlGSTU24 as a previously uncharacterized mechanism regulating Cd detoxification. Methods To investigate the effect of H₂S on the growth of tomato seedlings under Cd stress, 1, 3, and 5 mg/L CdCl 2 and 200 μM NaHS (an H₂S donor) were used to treat three-week-old seedlings for 7 days in this study. Morphological characteristics, malondialdehyde (MDA) content, non-protein thiol (NPT) levels, metallothioneins (MTs) and protein content of treated seedlings were analyzed. GSTs activity were assessed, and persulfidation proteomics was conducted on GSTs. Mass spectrometry and the modified biotin switch method (MBSM) identified persulfidated residues in SlGSTU24. Cys132 was mutated to alanine for functional analysis. Results Cd exposure inhibited the growth of tomato seedlings, while treatment with NaHS alleviated growth inhibition, decreased malondialdehyde (MDA) content and electrolyte leakage (EL) under Cd stress. The application of NaHS increased non-protein thiols glutathione (GSH) and phytochelatins (PCs) contents, and protein thiols metallothionein (MTs) content. The endogenous activity of GSTs was enhanced by NaHS. Cys132 in SlGSTU24 was identified as a persulfidated residue. Persulfidation of Cys132 increased the SlGSTU24 wild type (WT) activity. When Cys132 was mutated to alanine, H₂S-induced SlGSTU24 activity were compromised in SlGSTU24 Cys(C)132 Ala(A) . Conclusions H₂S-mediated persulfidation of Cys132 in SlGSTU24 enhances its activity and improves tomato resistance to Cd stress.

研究领域: 植物学 · 环境科学 · 分子生物学
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Frontiers in Plant Science · 2018 · IF 3.677

Ethylene-Induced Hydrogen Sulfide Negatively Regulates Ethylene Biosynthesis by Persulfidation of ACO in Tomato Under Osmotic Stress

Jia Honglei,Chen Sisi,Liu Dan,Liesche Johannes,Shi Cong,Wang Juan,Ren Meijuan,Wang Xiaofeng,Yang Jun,Shi Wei,Li Jisheng

A number of recent studies identified hydrogen sulfide (H2S) as an important signal in plant development and adaptation to environmental stress. H2S has been proven to participate in ethylene-induced stomatal closure, but how the signaling pathways of H2S and ethylene interact is still unclear. Here, we reveal how H2S controls the feedback-regulation of ethylene biosynthesis in tomato (Solanum lycopersicum) under osmotic stress. We found that ethylene induced the production of H2S in guard cells. The supply of hypotaurine (HT; a H2S scavenger) or DL-pro-pargylglycine (PAG; a synthetic inhibitor of H2S) removed the effect of ethylene or osmotic stress on stomatal closure. This suggests that ethylene-induced H2S is a downstream component of osmotic stress signaling, which is required for ethylene-induced stomatal closure under osmotic stress. We further found that H2S inhibited ethylene synthesis through inhibiting the activity of 1-aminocyclopropane-1-carboxylic acid (ACC) oxidases (ACOs) by persulfidation. A modified biotin-switch method (MBST) showed that H2S can induce persulfidation of LeACO1 and LeACO2 in a dose-dependent manner, and that persulfidation inhibits the activity of LeACO1 and LeACO2. We also found that LeACO1 is persulfidated at cysteine 60. These data suggested that ethylene-induced H2S negatively regulates ethylene biosynthesis by persulfidation of LeACOs. In addition, H2S was also found to inhibit the expression of LeACO genes. The results provide insight on the general mode of action of H2S and contribute to a better understanding of a plant’s response to osmotic stress.

研究领域: 植物生理学 · 胁迫生物学 · 分子生物学
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FUEL PROCESSING TECHNOLOGY · 2023 · IF 7.5

Experimental study on removal of mercaptans from gas streams by 1-butyl-3-methyl-imidazolyl alanine

Luoming Kang,Airong Li,Yuan Lu,Yuling Ma,Cheng Wang

Mercaptans as volatile organic sulfur compounds would cause environmental pollution. Researches are focused on the removal of mercaptans by solvent absorption method. In this work, a new efficient absorbent of 1-butyl-3-methylimidazolyl alanine ([Bmim]Ala) was prepared and evaluated by the removal of mercaptans from the model gas containing methyl mercaptan (MeSH, 307.6 mg/m 3 ), ethyl mercaptan (EtSH, 201.1 mg/m 3 ) and propyl mercaptan (PrSH, 149.9 mg/m 3 ) in nitrogen. The results showed that the removal rate of MeSH, EtSH and PrSH was 97.77, 98.12 and 100.00%, respectively, at a temperature of 35 °C and a pressure of 1.00 bar for 2 min. After 6 recycling times, [Bmim]Ala remained a good performance for the removal of mercaptans. The desulfurization mechanism was proposed that the absorption sites were mainly on the alanine anion (Ala − ) and Ala − could be replaced by the thiol anion (RS − ) to form a new ionic liquid 1-butyl-3-methylimidazolyl thiolate ([Bmim] + RS − ). Meanwhile, since the electrostatic interaction between -COO − in Ala − and H -g on the imidazolium cation could be destroyed by the -SH group, the -COO − group would interact with mercaptans to form a strong H-bond. The amino in Ala − and the -SH group could form Lewis acid-base compounds.

研究领域: 环境科学 · 化学工程
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JOURNAL OF ORGANIC CHEMISTRY · 2024 · IF 3.3

Regioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials

Yang Zhu,Guisheng Deng

The Cu(MeCN)4PF6-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with aryl/alkyl mercaptan and subsequent treatment with K2CO3 only offered 3-(alkylthio)benzofurans, whereas the stoichiometric-exceeding CuI-mediated reaction and subsequent treatment with DIPEA furnished 2-(alkylthiomethyl)benzofurans with high selectivity. The amount of Cu(I) salts plays a key role in selective formation. This unique protocol for the selective construction of the two series of benzofurans containing alkylthio group proved to be suitable for broad substrates 1 and 2 except for aliphatic alkynyl alcohols.

研究领域: 有机化学 · 药物化学
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Natural Product Communications · 2020 · IF 0.468

Synthesis of HA-SS-MP: A Prodrug With High Specificity for Cancer Cells

Bo Tao,Zong-ning Yin

Thiolated hyaluronic acid was synthesized, and a quantification method was established to determine the content of the thiol group. Three thiol compounds, 2-nitro-5-mercapto-benzoic acid (TNB), 2- mercaptonicotinic acid (2-MNA), and mercaptopyridine (MPD), were tested for their efficiency in forming adducts with hyaluronic acid (HA) through disulfide bonds. Our results showed that MPD exhibited the highest disulfide exchange efficiency when the reaction was conducted at the optimal pH value. The synthesized hyaluronic acid-SS-mercaptopurine (HA-SS-MP) was characterized by 1H-nuclear magnetic resonance spectroscopy. The HA-SS-MP micelle showed a particle size of 264.4 nm in aqueous solution. An in vitro release experiment demonstrated that the releasing rate of 6-MP from HA-SS-MP in the release medium containing glutathione (GSH) was much higher than that in the release medium without GSH. Cell uptake experiments demonstrated the CD44 targeting of hyaluronic acid. Cytotoxicity tests in mouse melanoma cells (B16F10) showed that HA-SS-MP can kill melanoma cells effectively and with lower cytotoxicity, compared with the active ingredient, 6-MP.

研究领域: 药学 · 肿瘤学 · 生物化学
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TETRAHEDRON · 2016 · IF 2.645

A rational designed thiols fluorescence probe: the positional isomer in PET

Xinyue Zhu,Hong Gao,Wenyan Zan,Yan Li,Jianjian Zhang,Xiaoyan Liu,Xuan Wei,Fengchao Qi,Xiaojun Yao,Haixia Zhang

It was reported here a devised and synthesized thiol fluorescent probes ortho -Z3 , meta -Z3 and para -Z3 based on photoinduced electron transfer (PET) pathway utilizing fluorophore naphthalimide as the electron donor and responsive group maleimide as the electron acceptor . The fluorescence intensity of these probes varied significantly depending on the position of the maleimide toward the naphthalimide fluorophore. Comparing to the meta and para isomers, the ortho isomer displayed the best fluorescence response performances upon addition of thiols. The results indicated that relative position of the electron acceptor played key role in the PET process, and probe ortho -Z3 could detect endogenous biothiols in serum samples and live cells successfully.

研究领域: 生物化学 · 分析化学
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