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RSC Advances · 2016 ·Vol. 6 ·期 20 ·16467-16473 · IF 3.289

A “turn-on” fluorescent probe used for the specific recognition of intracellular GSH and its application in bioimaging

Lanfang Pang,Yanmei Zhou,Enze Wang,Fang Yu,Hua Zhou,Wenli Gao

We have designed and synthesized a carbazole-based fluorescent probe (CZ-Nm) for the specific recognition of GSH over Cys and Hcy. The probe is almost non-fluorescent owing to the photoinduced electron transfer (PET) process from the carbazole fluorophore to the nitroolefin moiety. Upon treatment with GSH, owing to the Michael addition of GSH to the double bond of the nitroolefin moiety, the probe shows a fluorescence enhancement and absorption change. The CZ-Nm probe displays desirable properties such as acting as a “naked eye” probe, a wide linear range of 0–0.01 M, high sensitivity, and strong anti-jamming capability. More importantly, the probe can also be successfully applied to the detection of intracellular GSH with a bright fluorescence signal, good cell permeability and bio-compatibility.

研究领域: 生物化学 · 细胞生物学 · 分析化学
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Biointerphases · 2019 ·Vol. 14 ·期 6 · IF 2.009

Preparation and characterization of DNA array slides via surface Michael addition

Cheng Fang,Ma Xiaochun,Feng Qiancheng,Wang Hanqi,Yin Meng,He Wei

The reliability and stability of array slides are a big concern for array vendors and end users. Herein, we report on a new type of array slide with high reactivity toward DNA probes and low side reaction. A one-step surface reaction via the Michael addition involved in preparing array slides was developed and characterized by x-ray photoelectron spectroscopy, contact angle, and fluorescence labeling. The effects of array fabrication and storage conditions, i.e., spotting solution p H, high humidity, and long-term storage on the reactivity of the slides were examined. The fabricated DNA arrays could realize good hybridization efficiency (38.2% for slides with 0.88 pmol/cm 2 ), low limit of detection (4 × 10 −14 M), as well as high mismatch selectivity.

研究领域: 分子生物学 · 生物化学
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JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY · 2012 ·Vol. 51 ·期 3 ·708-715 · IF 3.919

Facile synthesis of dendrimers combining aza-Michael addition with Thiol-yne click chemistry

Yong Shen,Yinan Ma,Zhibo Li

We report a highly efficient approach to prepare dendrimers by taking advantage of the orthogonal characteristic of aza-Michael addition and thiol-yne reactions. A fifth generation dendrimer was synthesized within five steps without protection/activation procedures. The reactions proceed under benign conditions without byproducts, and the target products can be easily purified via extraction or precipitation without chromatography. The structure of each generation dendrimer was characterized using NMR spectroscopy, size exclusion chromatography, and mass spectrometry. The obtained dendrimers can have peripheral amine or alkyne groups. We demonstrated that these groups can be used for selective and specific conjugation with various functional groups. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

CAS / MDL: 814-68-6 927-74-2
研究领域: 材料科学 · 有机化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2017 · IF 2.536

Enzyme-catalyzed Michael addition for the synthesis of warfarin and its determination via fluorescence quenching of l-tryptophan

Yusheng Yuan,Liu Yang,Shaopu Liu,Jidong Yang,Hui Zhang,Jingjing Yan,Xiaoli Hu

A sensitive fluorescence sensor for warfarin was proposed via quenching the fluorescence of l -tryptophan due to the interaction between warfarin and l -tryptophan. Warfarin, as one of the most effective anticoagulants , was designed and synthesized via lipase from porcine pancreas (PPL) as a biocatalyst to catalyze the Michael addition of 4-hydroxycoumarin to α, β-unsaturated enones in organic medium in the presence of water. Furthermore, the spectrofluorometry was used to detect the concentration of warfarin with a linear range and detection limit (3σ/k) of 0.04–12.0   μmol   L −   1 (R 2   =   0.994) and 0.01   μmol   L −   1 , respectively. Herein, this was the first application of bio-catalytic synthesis and fluorescence for the determination of warfarin. The proposed method was applied to determine warfarin of the drug in tablets with satisfactory results.

CAS / MDL: 1076-38-6
研究领域: 药物化学 · 分析化学 · 生物催化
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JOURNAL OF CHEMICAL RESEARCH · 2015 · IF 0.633

Synthesis of 10-Substituted 3,6-Diphenyl-9-Aryl-3,4,6,7,9,10-Hexahydroacridine-1,8(2H,5H)-Dione Derivatives

Fang-Ming Wang,Dan Bao,Bing-Xiang Hu,Ze-Yu Zhou,Deng-Deng Huang,Li-Zhuang Chen,Yuan-Yuan Dan

A series of novel 10-substituted 3,6-diphenyl-9-aryl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione derivatives synthesised by condensation of different amines with xanthenes, was prepared from 5-phenylcyclohexane-1,3-dione and aromatic aldehydes by a Knoevenagel and Michael reaction and cyclisation catalysed by a trace of l-proline at room temperature. In addition, the molecular structure of a xanthene was determined by single-crystal X-ray diffraction analysis.

研究领域: 有机化学 · 药物化学
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Polymer Chemistry · 2018 ·Vol. 9 ·期 38 ·4716-4723 · IF 4.927

Phosphazene-catalyzed oxa-Michael addition click polymerization

Hongjun Yang,YongKang Zuo,Jiadong Zhang,Yiye Song,Wenyan Huang,Xiaoqiang Xue,Qimin Jiang,Aibin Sun,Bibiao Jiang

This paper reports a new type of click chemistry via a phosphazene bases-catalyzed oxa-Michael addition of an alcohol to an acrylate. The studies on the reactions between small molecules showed that only 5 mol% phosphazene base, t-BuP2, could catalyze the reaction between the acrylate double bonds and a primary alcohol and drive the reaction to completion within a few minutes under solvent-free conditions at room temperature. Additionally, t-BuP2 was a particularly efficient catalyst for the oxa-Michael addition of secondary alcohols to acrylate double bonds under similar conditions. Moreover, applying this reaction to the synthesis of polymers could successfully afford degradable poly(ester-ether)s with excellent monomer conversions under mild conditions. Throughout the polymerization, transesterification reactions were unavoidable, which increased the randomness in the structures of the resulting polymers. Considering the remarkable features of this method, such as the ready availability of the alcohol substrates, this work provides a simple, easy, and versatile method for synthesizing degradable polymers from commercially available compounds and will be useful in polymer chemistry.

研究领域: 高分子化学 · 材料科学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2022 ·Vol. 139 ·期 32 ·e52747 · IF 3.057

Self-dispersible waterborne comb-like polyester with alkali resistance and pigment-dispersion capability

Hao Fu,Shu-ling Gong

Waterborne polyester is a common eco-friendly material in which ester bonds are easy to hydrolyze. Therefore, we synthesized a series of waterborne comb-like polyesters (WCPEs) with hydrophilic side chains through aza-Michael addition under green and mild conditions. The physicochemical structure of the polyesters was verified by 1 H NMR, FTIR, and GPC characterizations. The pH value of dispersions dropped by less than 0.7 after storage for 2 months. The dispersions remained stable after 6 months at room temperature. In addition, the WCPEs exhibited good wetting and dispersing ability for pigment particles as Tego 740 W, which is a mature pigment dispersant product for waterborne coatings. Moreover, the cross-linked WCPEs exhibited excellent chemical resistance, there was only 1.2% weight loss, and almost no mechanism properties decline for cross-linked transparent films even after treatment under an alkaline environment for 20 days. Thus, the synthesized WCPE has potential application as an alkali resistance eco-friendly material, and possesses excellent performance as pigment-dispersion resin.

研究领域: 材料科学 · 化学工程
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POLYMER · 2015 · IF 3.562

Low molecular weight PEI-based polycationic gene vectors via Michael addition polymerization with improved serum-tolerance

Miao-Miao Xun,Ya-Ping Xiao,Ji Zhang,Yan-Hong Liu,Qi Peng,Qian Guo,Wan-Xia Wu,Yong Xu,Xiao-Qi Yu

A series of polycationic gene delivery vectors were synthesized via Michael addition from low molecular weight PEI and linking compounds with various heteroatom compositions . Agarose gel electrophoresis results reveal that these polymers can well condense plasmid DNA and can protect DNA from degradation by nuclease. The formed polyplexes , which are stable toward serum, have uniform spherical nanoparticles with appropriate sizes around 200–350 nm and zeta-potentials about +40 mV. In vitro experiments show that these polymers have lower cytotoxicity and higher transfection efficiency than 25 KDa PEI. Furthermore, the title materials exhibit excellent serum tolerance. With the present of 10% serum, up to 19 times higher transfection efficiency than PEI was obtained, and no obvious decrease of TE was observed even the serum concentration was raised to >40%. Flow cytometry and confocal microscopy studies also demonstrate the good serum tolerance of the materials.

CAS / MDL: 9002-98-6
研究领域: 生物化学 · 分子生物学 · 基因治疗
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DESIGNED MONOMERS AND POLYMERS · 2017 · IF 1.139

Synthesis and characterization of hyperbranched poly(ester-amine) by Michael addition polymerization

Miao Sun,Chunxiao Yin,Yanan Gu,Yun Li,Zhirong Xin

A series of tertiary amine-based hyperbranched poly(amine-ester)s have been synthesized by Michael addition polymerization of trifunctional monomer, TMEA and difunctional monomer, diacylates in chloroform, and the resultant polymers were subsequently treated with mercaptoethenol or 1-dodecanethiol for improving stability in storage. The caption efficiency of mercaptoethanol is much better than that of 1-dodecanthiol. Kinetic study reveals that the thiol group is consumed faster than the acrylate group when the polymerization with feed molar ratio of diacrylate/TMEA = 2/1 was carried out. At initial polymerization, monomer conversion increases fast, but the molecular weights increase slowly and sharp increase of the molecular weight occurs at the final polymerization. The hyperbranched polymers were well characterized by 1H NMR spectra and TD-SEC, and DBs of the polymers obtained are between 0.6 and 0.82, as well as the molar ratios of diacrylate/TMEA in the hyperbranched polymers are between 1.60 and 1.82. The fluorescence efficiency and quantum yields of HypET20, HypHT24 and HypDT24 has the following sequence: HypET20 > HypHT24 > HypDT24.

CAS / MDL: 814-68-6
研究领域: 高分子化学 · 材料科学
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EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY · 2017 ·Vol. 119 ·期 12 ·1700243 · IF 2.145

Development of an Improved Method to Determine Saturated Aliphatic Aldehydes in Docosahexaenoic Acid-Rich Oil: A Supplement to p-Anisidine Value

Wenlu Zuo,Xuechao Hu,Yaqiong Yang,Ling Jiang,Lujing Ren,He Huang

p -Anisidine value (AV) is an important and commonly used index to determine the second oxidation statue of edible oils, but it sometimes cannot reflect the concentrations of all the secondary products, such as saturated aldehydes. An improved method for the determination of saturated aliphatic aldehydes (SAA) in docosahexaenoic acid (DHA)-rich oils is developed in this study. This method reduces the aldehyde 2,4-dinitrophenylhydrazone adducts (DNPhydrazones) using 2-picoline borane, which can eliminate the analytical error caused by the isomerism of DNPhydrazone derivatives. The changes of SAA content during the oxidation of DHA-rich oil is subsequently monitored. Acetaldehyde (168.8 µmol kg −1 ) and propionaldehyde (78.5 µmol kg −1 ) are the two main SAAs in fresh oil, and their concentrations increase to 824.8–811.9 µmol kg −1 , respectively, after oxidation for 50 h at 80 °C. Furthermore, a Michael addition reaction is found to significantly reduce the AV of oxidized oils, from 172.5 to 11.7. Moreover, the concentration of SAAs shows no significant difference and could clearly identify the low-quality oil. These results demonstrate that SAA content might be a potential index to identify oxidized oils, which could provide a good supplementary value to the traditional AV index. Practical Applications : The method that has been developed in this study makes it possible to quantify saturated aliphatic aldehydes as markers of oxidation of oils, especially when the panisidine value (AV) cannot correctly assess the levels of secondary products. It could serve as a supplement to the AV index and could be applied to oils, fats, and food products. This work provides quantitative data regarding the amounts of saturated aliphatic aldehydes that can be present in DHA-rich oils during the oxidation process. An improved method for determinig saturated aliphatic aldehydes (SAA) in docosahexaenoic acid (DHA)-rich oils is developed. The changes of SAA content during the oxidation of DHA-rich oil is monitored. Furthermore, a Michael addition reaction is found to significantly reduce the AV of oxidized oils, from 172.5 to 11.7. The concentration of SAAs does not display significant differences and can clearly identify the low-quality oil. These results demonstrate that the SAA content might be a potential index to identify oxidized oils, which could serve as a good supplement to the AV index.

研究领域: 食品科学 · 分析化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2017 · IF 5.401

Synthesis of fluorescent polydopamine nanoparticles by Michael addition reaction as an analysis platform to detect iron ions and pyrophosphate efficiently and construction of an IMPLICATION logic gate

Li Tang,Shi Mo,Shi Gang Liu,Liu Li Liao,Nian Bing Li,Hong Qun Luo

Unique water-soluble endogenous fluorescent polydopamine-glutathione nanoparticles (PDA-GNPs) with high fluorescence quantum yield were firstly prepared through Michael addition reaction of glutathione and polydopamine. The PDA-GNPs were prepared under mild conditions, and the preparation process was facile (one-pot reaction) and environmentally friendly. With the introduction of Fe 3+ , the fluorescence intensity of PDA-GNPs decreased sharply. Interestingly, the fluorescence can restore by adding PPi to the system of PDA-GNPs/Fe 3+ . Based on these phenomena, a probe for quantification of Fe 3+ and PPi was set up. With a wide linear range of 0.1–300   μM, the probe can be used to determine Fe 3+ in practical water samples because of its nanomolar magnitude detection limit and negligible influences of other interferences. As to the detection of PPi, the linear range was 2–12   μM and the detection limit was 0.6   μM. In addition, an IMPLICATION logic gate was built by utilizing Fe 3+ and PPi as inputs and the fluorescence signal of PDA-GNPs as output.

CAS / MDL: 70-18-8 77-86-1
研究领域: 分析化学 · 生物传感 · 材料科学
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ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS · 2017 · IF 3.165

2-methoxyethylacrylate modified polysulfone membrane and its blood compatibility

Xin Tian,Yun-Ren Qiu

Hydrophilic material 2-methoxyethylacrylate (MEA) was grafted onto polysulfone (PSF) membrane via Michael addition reaction . The 1 H nuclear magnetic resonance ( 1 H NMR), Attenuated total reflectance-Fourier transform infrared spectroscope (ATR-FTIR) and X-ray photoelectron spectroscopy (XPS) characterization of the modified membrane proved that MEA had been successfully grafted onto PSF membrane surface. The water contact angle of the membrane surface was tested. The results showed that the water contact angle changed from 76° to 59.5°, which means that the hydrophilicity of the modified membrane was improved. A series of blood compatibility tests including bovine serum protein adsorption , platelet adhesion , prothrombin time (PT), partial thromboplastin time (APTT) and thrombin time (TT) were carried out on PSF membrane and the modified PSF membrane with highest grafted density of MEA. All of the results indicate that MEA plays an important role in improving the blood compatibility of PSF membrane.

研究领域: 材料科学 · 生物医学工程
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