POLYMER INTERNATIONAL
·
2012
·Vol. 62
·期 10
·1457-1464
·
IF 1.902
Youmei Bao,Jing He,Yuesheng Li
Hyperbranched polyesters with thioether linkages were facilely prepared from methyl 10-undecenoate, a castor oil-derived renewable chemical. The monomer was obtained in excellent yield through thiol–ene click chemistry in the presence of catalytic amounts of photoinitiator under UV irradiation. Subsequent bulk polycondensation via a transesterification process catalyzed by Ti(OBu) 4 , Sb 2 O 3 or Zn(OAc) 2 gave hyperbranched polyesters with high molecular weights and unusual crystalline properties. The degree of branching in the range 0.45 − 0.54 calculated from quantitative 13 C NMR spectroscopy and low inherent viscosities of 0.16 − 0.25 dL g −1 strongly confirmed the hyperbranched structures of the resultant polymers. © 2012 Society of Chemical Industry
研究领域:
材料化学
·
可再生资源化学
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DOI
高影响因子
POLYMER
·
2024
·
IF 4.1
Zichun Ding,Siying Wang,Runze Liu,Yuhang Wang,Jianing Guo,Xuedong Wu,Jiaming Wang,Xigao Jian,Lishuai Zong,Jinyan Wang
Phthalonitrile (PN) resin is renowned for its absence of small molecule release during curing, high processing stability, and exceptional thermal stability, positioning it favorably in the realm of high-temperature resin applications. However, its narrow processing window and high melting point present challenges to its development and practical use. To address these limitations, this work synthesized PN prepolymers 4,4′-bis (sulfonylbiphenyl) thiophtalonitrile (BSPS) and 4,4′-bis(carbonylbiphenyl) thiophtalonitrile (BSPC) by introducing thioether bonds as a substitute for ether bonds, aiming to expand the prepolymers' processing window. Meanwhile, building upon the oxidation process of thioether to sulfone observed in pharmaceutical production, the potential for in-situ oxidation of thioether bonds during the curing of phthalonitrile prepolymers was investigated. A comprehensive analysis of the curing behavior, viscosity changes, and thermal stability was conducted using differential scanning calorimetry (DSC), rheological analysis, and thermogravimetric analysis (TGA). The DSC and rheological test results reveal that the experimental group prepolymers BSPS and BSPC exhibit lower melting points (BSPS 179 °C; BSPC 180 °C) and broader processing windows (BSPS 52 °C; BSPC 79 °C) than blank. Additionally, the thermal performance of resins show improvement over the blank, with BSPS achieving a decomposition temperature of up to 530 °C ( T d5% ). XPS analysis of the curing process confirmed that the enhanced thermal stability is attributable to the partial oxidation of thioether bonds into stable sulfone groups. This innovative structural approach allows for satisfactory processing performance in the initial stage, followed by a spontaneous transformation into a more robust and thermo-resistant structure post-shaping. This finding carries significant implications for the development of a balanced phthalonitrile system that harmonizes processing ease with superior thermal endurance.
研究领域:
材料科学
·
化学工程
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DOI
高影响因子
BIOPOLYMERS
·
2018
·Vol. 110
·期 4
·e23243
·
IF 1.99
Xiaohui Fu,Jiliang Tian,Zheng Li,Jing Sun,Zhibo Li
A series of pegylated polypeptoids have been readily synthesized by a strategy combining ring-opening polymerization (ROP) and thiol-yne photoaddition. The polypeptoids simultaneously incorporated branched oligo(ethylene glycol) (OEG) units and thioether bonds in the side-chains. All the polypeptoids are readily soluble in aqueous solution and show reversible thermo-responsive properties. The cloud points (CPs) were demonstrated to be readily tunable in the range of ~25 °C-60 °C by varying the chemical composition, OEG chain length and the degree of polymerization. Attractively, the chemical compositions of the side chains are readily tunable via adjusting the molar ratios of a mixture of thiol terminated OEG molecules, which avoid synthesizing new monomers or copolymerization of different monomers. Further, the oxidation/reduction of thioether groups shows significant influence on the CPs, providing a second stimulus to tune the phase transition behaviors. Considering the biocompatibility and degradability, the dual-responsive polypeptoids are potential candidates for various biomedical or biotechnological applications. Graphical
研究领域:
生物材料学
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高分子化学
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生物医药工程
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DOI
PubMed
高影响因子
JOURNAL OF ORGANOMETALLIC CHEMISTRY
·
2013
·
IF 2
Lei Xue,Zhizhou Yang,Dengxu Wang,Yike Wang,Jie Zhang,Shengyu Feng
Novel hyperbranched organosilicon polymers were successfully prepared via step-growth thiol-ene click reaction using mercaptopropylmethyldiallylsilane (AB 2 ) and mercaptopropyltriallylsilane (AB 3 ) as hyperbranched monomers . The structures of the prepared polymers were characterized by Fourier transform infrared spectroscopy and nuclear magnetic resonance spectroscopy . The degree of branching (DB) of the polymers was determined using quantitative 29 Si NMR spectroscopy. The DB of the polymers from AB 2 and AB 3 was 0.60 and 0.22, respectively. The results of thermogravimetric analysis showed that the presence of thioether does not affect the thermal stability of the resulting silicon-containing hyperbranched polymers (Si-HBs). The resulting Si-HBs can be used as promising candidate materials for heavy metal adsorption because of the thioether bond.
研究领域:
材料科学
·
化学工程
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DOI
高影响因子
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS
·
2020
·
IF 3.99
Kaili Wang,Xian Li,Huili Wang,Hongyan Lu,Donghua Di,Qinfu Zhao,Siling Wang
Incorporation of degradable groups such as thioether bonds can make nanoparticles susceptible to be degraded by biological redox stimulus. Few studies have paid attention to effects of different surface properties of carriers on degradation behaviors between traditional mesoporous silica carriers and hybrid organosilica carriers, caused by inserted thioether groups. In this work, colloidal mesoporous silica (CMS) and hybrid colloidal mesoporous silica (HCMS) with different contents of doped thioether bonds are constructed to compare their physicochemical properties and degradability. With the increased amounts of doped thioether bonds, specific surface areas and Zeta potentials of HCMS nanoparticles decrease. Additionally, dynamic contact angle and the oil-water distribution coefficient are combined to characterize the hydrophobicity of CMS and HCMS nanoparticles. Therefore, after incorporating thioether bonds into the structure of carriers, the degradation behavior of HCMS nanoparticles in the medium were the result of weighing the advantages of degradable thioether bonds and disadvantages of decreased specific surface area and enhanced hydrophobicity of carriers. Experimental results displayed that, in the high concentration of reductive environment, HCMS carriers with doping proper proportion of thioether groups showed the fast degradation rate due to the cleaved thioether bonds as the dominant factor. The present work breaks the common views that all thioether bonds-bridged organosilica could become excellent biodegradable carriers, providing an objective perspective to evaluate the degradability of hybrid organosilica carriers.
研究领域:
材料科学
·
生物医学工程
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DOI
高影响因子
BIOMATERIALS
·
2019
·
IF 10.273
Yuejun Yao,Jie Ding,Zhaoyi Wang,Haolan Zhang,Jieqi Xie,Yingchao Wang,Liangjie Hong,Zhengwei Mao,Jianqing Gao,Changyou Gao
Reactive oxygen species (ROS) play an important role in the pathogenesis of numerous diseases including atherosclerosis, diabetes, inflammation and myocardial infarction (MI). In this study, a ROS-responsive biodegradable elastomeric polyurethane containing thioketal (PUTK) linkages was synthesized from polycaprolactone diol (PCL-diol ), 1,6-hexamethylene diisocyanate (HDI), and ROS-cleavable chain extender . The PUTK was electrospun into fibrous patches with the option to load glucocorticoid methylprednisolone (MP), which were then used to treat MI of rats in vivo . The fibrous patches exhibited suitable mechanical properties and high elasticity. The molecular weight of PUTK was decreased significantly after incubation in 1 mM H 2 O 2 solution for 2 weeks due to the degradation of thioketal bonds on the polymer backbone . Both the PUTK and PUTK/MP fibrous patches showed good antioxidant property in an oxidative environment in vitro . Implantation of the ROS-responsive polyurethane patches in MI of rats in vivo could better protect cardiomyocytes from death in the earlier stage (24 h) than the non ROS-responsive ones. Implantation of the PUTK/MP fibrous patches for 28 days could effectively improve the reconstruction of cardiac functions including increased ejection fraction , decreased infarction size, and enhanced revascularization of the infarct myocardium.
研究领域:
生物材料
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心脏病学
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药理学
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DOI
PubMed
高影响因子
RSC Advances
·
2023
·Vol. 13
·期 51
·35985-35991
·
IF 3.9
Congwei Wang,Dinglei Zhao,Yongjun Xie,Qiang Zhou,Haiyang Yang
Injectable self-healing hydrogels are being widely used in drug delivery, tissue engineering, and other fields. Because of their excellent biocompatibility and biodegradability, polypeptides are an ideal candidate for preparing injectable self-healing hydrogels. In this study, a polypeptide-based hydrogel with dual response to hydrogen peroxide and light was obtained by copolymerizing 4-arm PEG-amine, N-(p-nitrophenoxycarbonyl)-L-methionine, and N-(p-nitrophenoxycarbonyl)-γ-o-nitrobenzyl-L-glutamate. The hydrogel exhibits injectable self-healing behavior due to the hydrophobic interactions among peptide blocks, which also act as the reservoir of hydrophobic drug molecules. In the presence of hydrogen peroxide or under light irradiation, the thioether bond in methionine was oxidized to sulfoxide, whereas the o-nitro benzyl ester bond was broken to form glutamic acid. As a result, the corresponding hydrophobic blocks of polypeptide become hydrophilic, accelerating the release of drug molecules loaded in the polypeptide hydrophobic blocks. Using this technique, the controlled release of hydrophobic drug molecules was achieved. Our efforts could provide a new strategy for the preparation of self-healing hydrogels based on polypeptides with a dual response to hydrogen peroxide and light. In this view, the practical application of polypeptides in drug delivery, tissue engineering, and other fields, could be expanded and advanced.
研究领域:
材料科学
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药学
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生物医学工程
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DOI
PubMed
高影响因子
JOURNAL OF ANTIBIOTICS
·
2023
·Vol. 76
·期 5
·260-269
·
IF 3.3
Li Yanan,Dong Yuanzhen,Lu Jianguang,Zhang Jinhua,Feng Meiqing,Feng Jun
The escalating crisis of multidrug resistance is raising the fear of untreatable Gram-negative infections and killing a substantial number of patients. The underpopulated antibiotic drug development pipelines drive polymyxins (polymyxin B and colistin) as crucial therapeutic options. However, the cumbersome synthesis process and inefficient cyclization method limit the efficient preparation of polymyxin core scaffolds in the development of polymyxin derivatives. Here, we innovatively applied a substitution reaction between bromobenzene and sulfhydryl to cyclize colistin core scaffolds. The reaction was mild and efficient, improving the total yield of the compound from less than 10% to 55.90%. Nearly 30 novel derivatives with thioether bond-mediated cyclic scaffolds were designed and synthesized. Evaluation of antibacterial activities and biological properties revealed that many new compounds that are stable in mouse plasma possess high antimicrobial potency against Gram-negative bacteria and display no hemolytic toxicity. Our optimal peptide PE-2C-C8-DH eradicated Acinetobacter baumannii within 24 h in vitro, and had lower acute toxicity and significant therapeutic effects on mice infected with Pseudomonas aeruginosa , which deserves further development.
研究领域:
药物化学
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医药化学
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微生物学
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传染病学
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产品关联
DOI
PubMed
高影响因子
Carbohydrate Polymer Technologies and Applications
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2023
·
IF 5.5
Zi-Dan Wang,Hu-Hong Peng,Dong-Qiang Lin,Yi-Xin Guan
Curcumin is a BCPR inhibitor, antiproliferative agent and apoptotic inducer to cancer cells, which is poorly soluble in water. In order to broaden the application of curcumin, conjugations of quaternary ammonium substituted hydroxyethyl starch (QHES) with curcumin by thioether bond (QHES-2S-CUR), disulfide bond (QHES-SS-CUR), and carbon-carbon bond (QHES-CC-CUR) were implemented, respectively. The effect of above three linkers on the self-assembly behavior of QHES-curcumin prodrugs was evaluated. QHES-2S-CUR and QHES-SS-CUR could facilely self-assemble into spherical micelles in water, while QHES-CC-CUR was lack of conformational stability. In vitro drug release profiles of prodrug micelles were further investigated. Concretely, QHES-2S-CUR presented ROS-sensitive drug release, with 73.57 ± 4.22% of curcumin released under the addition of H 2 O 2 over 24 h. The release of curcumin from QHES-SS-CUR lasted for 54 h due to the slower oxidization of disulfide bonds, and QHES-CC-CUR was insensitive to ROS. In addition, QHES-2S-CUR prodrug micelles demonstrated superior cytotoxicity to murine colonic adenocarcinoma (CT-26) cells compared to QHES-SS-CUR and QHES-CC-CUR, which were internalized by CT-26 cells with high efficiency. These results reveal the potential of QHES-2S-CUR prodrug micelles as tumor microenvironment-responsive anticarcinogen.
研究领域:
药学
·
癌症研究
·
纳米技术
·
药物递送系统
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DOI
高影响因子
JOURNAL OF CONTROLLED RELEASE
·
2018
·
IF 7.877
Wei Wei,Cong Luo,Jincheng Yang,Bingjun Sun,Dongyang Zhao,Yan Liu,Yingli Wang,Wenqian Yang,Qiming Kan,Jin Sun,Zhonggui He
The anticancer efficacy of chemotherapy is greatly limited by short blood circulation and poor tumor selectivity. Thus, anticancer prodrugs with prolonged systemic circulation , tumor-specific distribution and bioactivation , could significantly strengthen the chemotherapy efficacy. Herein, we design two novel tumor cell reduction/oxidation-responsive docetaxel (DTX) prodrugs, DTX-maleimide conjugates with disulfide bond (DSSM) or thioether bond (DSM) linkages, to evaluate the roles of different sensitive linkages in drug release, pharmacokinetics and therapeutic efficacy. An ester bond-linkage prodrug (DM) is utilized as a non-sensitive control. DSSM and DSM show reduction- or oxidation-sensitive release behavior, respectively, and exhibit hyperselective bioactivation and cytotoxicities between cancerous and normal cells. They could instantly hitchhike blood circulating albumin after i.v. administration with albumin-binding half-lives as short as 1 min, resulting in prolonged systemic circulation, increased tumor accumulation. In response to the upregulated reduction/oxidation environment within tumor cells, DSSM and DSM exhibit selectively release capacity in tumor tissues, their TAI Tumor/Liver values are over 30-fold greater than DM. Combining the above delivery advantages into one, DSSM and DSM achieve enhanced antitumor efficacy of DTX. Such a uniquely developed strategy, integrating high albumin-binding capability and reduction/oxidation-sensitive drug superselective release in tumors, has great potential to be applied in clinical cancer therapy.
研究领域:
肿瘤学
·
药学
·
化疗
·
药物递送系统
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DOI
PubMed
高影响因子
Materials Today Bio
·
2022
·
IF 10.761
Chen Tan,Heng Fan,Jiahui Ding,Chaoqun Han,Yang Guan,Feng Zhu,Hui Wu,Yujin Liu,Wei Zhang,Xiaohua Hou,Songwei Tan,Qing Tang
Oxidative stress, caused by excessive production of reactive oxygen species (ROS), plays a crucial role in the occurrence and development of ulcerative colitis (UC). We developed ROS-responsive nanoparticles (NPs) as an efficacious nanomedicine against UC with oral administration. The NPs were fabricated with a d -α-tocopherol polyethylene glycol succinate-b-poly(β-thioester) copolymer (TPGS-PBTE) for ROS cleavage via the colitis-targeted delivery of luteolin (LUT), a natural flavonoid with good anti-inflammation and radical-scavenging activity. Owing to the thioether bond in the polymer main chain, the TPGS-PBTE NPs exhibited an ROS-responsive size change and drug release, which benefited the ROS-scavenging and selective accumulation of LUT in the inflamed colon. In a dextran sulfate sodium-induced acute colitis murine model, [email protected] NPs alleviated body weight loss, colon length shortening, and damage to the colonic tissues due to the suppression of ROS and proinflammatory cytokines (e.g., IL-17A, IL-6, interferon-γ, tumor necrosis factor-α), as well as upregulation of glutathione and anti-inflammatory factors (e.g., IL-10, IL-4). More importantly, [email protected] NPs regulated the inflammatory microenvironment by modulating the T helper (Th)1/Th2 and Th17/regulatory T cell (Treg) balance (i.e., increased numbers of Tregs and Th2 cells and decreased numbers of Th1 and Th17 cells), thus resolving inflammation and accelerating the healing of the intestinal mucosa. Additionally, the [email protected] NPs formulation enabled the reduction of the effective dose of LUT and showed excellent biosafety in the mouse model, demonstrating its potential as a targeted UC therapeutic oral preparation.
研究领域:
药学
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纳米技术
·
胃肠病学
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免疫学
·
药物递送系统
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）