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JOURNAL OF MEMBRANE SCIENCE · 2024 · IF 8.4

Aza-crown ether-coupled polyamide nanofiltration membrane for efficient Li+/Mg2+ separation

Zhiyuan Zha,Tingyu Li,Ismail Hussein,Ying Wang,Song Zhao

The scarcity of lithium can be effectively addressed by extracting it from salt-lake brines. In this work, aza-crown ether (diazo-18-crown-6, DA18C6) was coupled into a polyamide (PA) network interfacial polymerized by trimesoyl chloride and polyethyleneimine (PEI) for efficient Li + /Mg 2+ separation. The embedment of DA18C6 molecule into PA network was confirmed by structural characterization and density functional theory simulation, which enhanced crosslinking degree and reduced average pore size of PA selective layer. In addition, the strong interaction between DA18C6 and Li + was proven through molecular dynamics simulation. The resulting PEI@DA18C6-PA membrane displayed a high pure water permeance of 10.4 L⋅m − 2 ⋅h − 1 ⋅bar − 1 and an excellent Li + /Mg 2+ separation factor ( S Li,Mg ) of 11.2, which was comparable with most reported Li + /Mg 2+ separation membranes . Furthermore, the PEI@DA18C6-PA membrane was employed in a three-stage NF treatment process to filtrate simulated brines containing a high Mg 2+ /Li + ratio of 57. The results demonstrated that Li + can be effectively concentrated and extracted through the membrane to obtain a permeate with an ultralow Mg 2+ /Li + ratio of only 0.03, suggesting that PEI@DA18C6-PA membrane has great application potential in lithium extraction from salt-lake brines.

CAS / MDL: 4422-95-1
研究领域: 材料科学 · 环境工程
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JOURNAL OF CHEMICAL RESEARCH · 2012 · IF 0.633

Facile Aza-Michael Additions of Uracil Derivatives to Acrylates

Shuguang Zhou,Mingxia Xu,Siyu Ye,Dashuai Li,Jing Xu,Pei Mao,Jing Xiong

24 Aza-Michael adducts were synthesised in moderate to excellent yields by the addition of 5-substituted uracils to acrylates with ethylamine as a catalyst. Many of the adducts were obtained in almost quantitive yield without column chromatography. The procedure provideded an efficient approach to the synthesis of N-1 uracil adducts using acrylates as acceptors. The structures of the compounds were determined by 1H NMR, 13C NMR, mass spectra and X-ray crystallography analyses. The uracil unit is present in DNA and related natural products and has a broad spectrum of biological activity.

研究领域: 有机化学 · 药物化学 · 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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RADIOCHIMICA ACTA · 2022 ·Vol. 111 ·期 1 ·63-71 · IF 2.083

1-aza-18-crown-6 ether tailored graphene oxide for Cs(I) removal from wastewater

Peng Liu,Zhuang Shen,Jiaxian Cheng,Zhen Han,Wenda Xu,Mingbo Ji,Fuqiu Ma

Due to the relative abundance, long half-life and high mobility of radioactive cesium (Cs), new adsorbents are urgently needed to treat Cs to ensure public health. In this study, a graphene oxide (GO) based adsorbent for Cs(I) adsorption was prepared by 1-aza-18-crown-6 ether modification. XRD, FT-IR, XPS and SEM results showed that the properties of 1-aza-18-crown 6 ether modified GO (18C6-GO) changed dramatically compared with that of raw graphite. The adsorption properties of 18C6-GO for Cs(I) were studied by batch static adsorption experiments. The results showed that the adsorption equilibrium time of 18C6-GO was 20 h. Kinetic study revealed that the adsorption rate of Cs(I) conformed to pseudo-second-order kinetic model. Langmuir adsorption isotherm simulation indicated that the adsorption arises at homogeneous adsorption sites on 18C6-GO. Therefore, crown ether modified GO may have implications for the treatment of wastewater.

研究领域: 环境科学 · 材料科学 · 化学工程
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Future Medicinal Chemistry · 2019 ·Vol. 11 ·期 10 · IF 3.617

Synthesis and biological evaluation of aza-crown ether–squaramide conjugates as anion/cation symporters

Xi-Hui Yu,Xiong-Jie Cai,Xiao-Qiao Hong,Kin Yip Tam,Kun Zhang,Wen-Hua Chen

Aim: Anion/cation symport across cellular membranes may lead to cell apoptosis and be developed as a strategy for new anticancer drug discovery. Methodology: Four aza-crown ether–squaramide conjugates were synthesized and characterized. Their anion recognition, anion/cation symport, cytotoxicity and probable mechanism of action were investigated in details. Conclusion: These conjugates are able to form ion-pairing complexes with chloride anions and facilitate the transmembrane transport of anions via an anion/cation symport process. They can disrupt the cellular homeostasis of chloride anions and sodium cations and induce the basification of acidic organelles in live cells. These conjugates exhibit moderate cytotoxicity toward the tested cancer cells and trigger cell apoptosis by mediating the influx of chloride anions and sodium cations into live cells. Graphical abstract

CAS / MDL: 162558-52-3
研究领域: 药理学 · 生物化学 · 肿瘤学
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Materials Today Chemistry · 2024 · IF 6.7

Organic nanoparticles based on aza-boron dipyrromethene derivatives for combined photothermal and photodynamic cancer therapy

Huishuang Zhang,Qilong Sha,Guojing Li,Liwei Xiong,Ming Luo,Fengshou Wu

Cancer is one of the major diseases that threaten human being's health and life. Recently, phototherapy has gained great attention due to the advantages of high selectivity and low toxicity. Nonetheless, the development a single photosensitizer capable of simultaneously achieving photothermal and photodynamic effects remains a great challenge. Aza-boron-dipyrromethene (aza-BODIPY) dyes have been widely studied in biomedical area for their significant absorption in the near infrared region and high fluorescence quantum yield . In this contribution, three aza-BODIPY molecules (TAS-BP, TES-BP and TESO-BP) that conjugated with triphenylamine (TPA) or tetraphenylethylene (TPE) were designed and synthesized. The presence of donor-acceptor-donor pairs within compounds enables the intermolecular electron transfer , leading to the augmentation of near-infrared (NIR) absorbance and the generation of non-radiative heat. The nanoparticles were prepared via the assembly of the related organic compounds with amphiphilic polymer (DSPE-PEG 2000 ), which were named as TAS-BP NPs, TES-BP NPs and TESO-BP NPs, respectively. Importantly, three nanoparticles can generate heat and reactive oxygen species (ROS) simultaneously induced by a single laser (808 nm). The photothermal conversion efficiency of TAS-BP NPs, TES-BP NPs and TESO-BP NPs were determined to be 64.5%, 65.7%, and 53.6%, respectively. Furthermore, the cellular experiments demonstrated the good biocompatibility and outstanding photocytotoxicity of three nanoparticles , and the TES-BP NPs exhibited the highest photodynamic/photothermal synergistic effect. Thus, the as-prepared organic nanomaterials were demonstrated as potential candidates for cancer treatment through phototherapy.

研究领域: 生物医学 · 肿瘤学 · 材料科学
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JOURNAL OF MATERIALS SCIENCE · 2022 ·Vol. 57 ·期 45 ·21206-21218 · IF 4.682

Aza-BODIPY nanoparticles for near-infrared triggered synergistic photothermal and photodynamic antibacterial therapy

Song Shuang,Xu Guochao,Yang Na,Shahzad Sohail Anjum,Lv Junying,Shen Xiande,Yu Cong

Wound healing is a complicated process that can be susceptible toward infection caused by bacteria. The surging drug resistance has become one of the biggest challenges to the treatment of these infections in public health. Herein, a new asymmetrical aza-boron-dipyrromethene (ABDP) probe is prepared and encapsulated with cholesterol-modified polyethylene glycol polymer (Chol-PEG 2000 -NH 2 ) to construct a PTT/PDT dual-modality antibacterial agent (the ABDP NPs) and provide a new material for the treatment of MRSA-based infections. The ABDP NPs show remarkable wide UV–Vis absorption at 300–850 nm and superior bactericidal effects against Staphylococcus aureus ( S. aureus ), Escherichia coli ( E. coli ), and Methicillin-resistant S. aureus (MRSA), which can be controlled by a phototheranostic antibacterial switch (808 nm laser). Histological analysis indicates that wounds treated by the ABDP NPs plus NIR laser irradiation exhibit more complete re-epithelialization, abundant collagen fibers, and higher hair follicle numbers than the vancomycin-treated group. This study provides a promising perspective using aza-BODIPY dye for the treatment of multidrug-resistant bacteria-based infections and clinical applications in the future.

研究领域: 生物医学工程 · 药学 · 微生物学
✓ 已验证 DOI 高影响因子
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CHINESE CHEMICAL LETTERS · 2016 · IF 1.947

Enzyme-catalyzed direct three-component aza-Diels–Alder reaction using lipase from Candida sp. 99–125

Dong-Hang Yin,Wei Liu,Zhi-Xiang Wang,Xin Huang,Jing Zhang,De-Chun Huang

The direct three-component aza-Diels–Alder reaction was conducted with lipase as a catalyst for the first time. Under the optimized conditions, the aza-Diels–Alder reaction catalyzed by lipase from Candida sp. 99–125 provided the products in moderate to excellent yields. Meanwhile, the endo / exo ratio reached up to 88:12.

研究领域: 生物化学 · 有机合成 · 酶学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

Micelle-mediated chemiluminescence of 6-aza-2-thiothymine-protected gold nanoclusters for carbazochrome sodium sulfonate detection

Zhen Lin,Chuangui Cai,Wei Chen,Qian Deng,Jialin Yang,Kaiyuan Huang,Haohua Deng,Xinhua Lin,Wei Chen,Wensong Yao

Chemiluminescence (CL) intensity of luminol-H 2 O 2 system was dramatically enhanced by cetyltrimethylammonium bromide (CTAB) micelle-mediated 6-aza-2-thiothymine-protected gold nanoclusters (ATT-AuNCs). It is proved that spherical micelles of CTAB in aqueous solution improved the dispersity of ATT-AuNCs, thus enhancing their catalytic activity, which brought in the increased CL intensity of luminol-H 2 O 2 system. Carbazochrome sodium sulfonate (CSS) with a hemostatic containing tetrahydroindole structure broke the spherical micelles and notably quenched the CL intensity of luminol-H 2 O 2 -CTAB-ATT AuNCs system. Based on these results, a simple, fast, and sensitive CL method has been developed for the detection of CSS with a linear range of 0.25–25 μM and a detection limit of 0.11 μM. The method has also been successfully applied to the determination of CSS in serum with satisfied recoveries in the range of 89.6 % to 103.7 %. This study not only provides an effective approach for CSS detection but also paves the way for AuNCs-based CL applications.

研究领域: 分析化学 · 纳米生物学 · 药物检测
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Catalysts · 2022 ·Vol. 12 ·期 12 ·1658 · IF 4.501

Microfluidics Biocatalysis System Applied for the Synthesis of N-Substituted Benzimidazole Derivatives by Aza-Michael Addition

Rong-Kuan Jiang,Yue Pan,Li-Hua Du,Ling-Yan Zheng,Zhi-Kai Sheng,Shi-Yi Zhang,Hang Lin,Ao-Ying Zhang,Han-Jia Xie,Zhi-Kai Yang,Xi-Ping Luo

Benzimidazole scaffolds became an attractive subject due to their broad spectrum of pharmacological activities. In this work, a methodology was developed for the synthesis of N-substituted benzimidazole derivatives from benzimidazoles and α, β-unsaturated compounds (acrylonitriles, acrylate esters, phenyl vinyl sulfone) catalyzed by lipase TL IM fromThermomyces lanuginosusin continuous-flow microreactors. Investigations were conducted on reaction parameters such as solvent, substrate ratio, reaction temperature, reactant donor/acceptor structures, and reaction time. The transformation is promoted by inexpensive and readily available lipase in methanol at 45 °C for 35 min. A wide range of β-amino sulfone, β-amino nitrile, and β-amino carbonyl compounds were efficiently and selectively synthesized in high yields (76–97%). All in all, a microfluidic biocatalysis system was applied to the synthesis of N-substituted benzimidazole derivatives, and could serve as a promising fast synthesis strategy for further research to develop novel and highly potent active drugs.Keywords:enzymatic synthesis;benzimidazole derivatives;continuous-flow reaction technology;continuous-flow microreactor;aza-Michael addition

研究领域: 有机化学 · 生物催化 · 药物化学
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TALANTA · 2016 · IF 4.035

A simple naphthalene-based fluorescent probe for high selective detection of formaldehyde in toffees and HeLa cells via aza-Cope reaction

Junchao Xu,Yue Zhang,Lintao Zeng,Jinbiao Liu,Joseph M. Kinsella,Ruilong Sheng

A simple naphthalene-based fluorescent probe ( AENO ) for formaldehyde (FA) was successfully synthesized, which exhibited a significant fluorescence turn-on response towards FA in aqueous solution. The probe could quantitatively determine the concentration of FA (0–1.0   mM) with excellent selectivity, high sensitivity and low limit of detection (0.57   µM). The sensing mechanism was proposed as 2-aza-Cope rearrangement for AENO after reaction with FA, which was confirmed by 1 H NMR, HR-MS, FT-IR, UV–vis and fluorescence spectra . The probe has been employed to determine the FA contents in several commercially available toffee samples with satisfactory performance. Thus, AENO might be used as a promising tool for quantitative detection of FA in food. Furthermore, fluorescence imaging of HeLa cells indicated that the probe was cell membrane permeable and could be used for visualizing/imaging the FA trace/transportation in cancer cells.

研究领域: 分析化学 · 生物医学 · 食品科学
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CytoJournal · 2024 · IF 2.5

Effect of 5-Aza-2’-deoxycytidine on T-cell acute lymphoblastic leukemia cell biological behaviors and PTEN expression

Yan Li,Zhenwei Jia,Xiaoyang Kong,Hongbo Zhao,Xiaoyan Liu,Guirong Cui,Jianmin Luo

Objective: We currently face a sharp increase of T-cell acute lymphoblastic leukemia (T-ALL) incidence and a challenge of unmasking its complex etiology. The deoxycytidine analog 5-Aza-2’-deoxycytidine (5-Aza-dC) is currently the most common nucleoside methyltransferase inhibitor. The objective of this study was to clarify the role of 5-Aza-dC in T-ALL cell biological behaviors and phosphatase and tensin homolog deleted on chromosome ten (PTEN) expression. Material and Methods: T-ALL cell lines were divided into the experimental group with 5-Aza-dC solution treatment, and the control group without treatment. PTEN methylation was detected using methylation-specific polymerase chain reaction (MS-PCR). Following the measurement of cell proliferation, viability, apoptosis, invasion, migration, etc., quantitative reverse transcription-polymerase chain reaction (PCR) was conducted to detect PTEN, DNA methyl-transferases (DNMT1), DNMT3a, MBD2, and MeCP2 expressions; Western blot to detect PTEN, PI3K, AKT, and mTOR protein expressions. In addition, rescue experiments to inhibit and restore the expression of PTEN in different groups were performed for further identification of the results in the former parts. Results: MS-PCR results showed that in Jurkat cells, the target band was amplified using methylated primers for the PTEN gene promoter region; moreover, at 10 μmol/L of 5-Aza-dC for 24 h, PTEN methylation was completely removed without any un-methylated band observed. The experimental group had significantly lower cell proliferation and viability rates, higher apoptosis rates, decreased cell proportion in S phase, reduced invasion and migration; increased PTEN expression, decreased DNMT1, DNMT3a, MBD2, and MeCP2 mRNA expressions; and decreased PI3K, AKT, and mTOR protein expressions than those in the control group (all P < 0.05). Furthermore, according to the rescue experiment, silenced PTEN expression weakened the beneficial roles of 5-Aza-dC treatment, and resulted in significantly higher cell proliferation and viability rates, lower apoptosis rates, increased cell proportion in S phase, increased cell invasion and migration; decreased PTEN expression, elevated DNMT1, DNMT3a, MBD2, and MeCP2 mRNA expressions, and higher PI3K, AKT, and mTOR protein expressions (all P < 0.05). While restored PTEN expression enhanced functions of 5-Aza-dC treatment, leading to obviously lower cell proliferation and viability rates, higher apoptosis rates, increased cell proportion in G1 phase, and reduced cell invasion and migration; as well as increased PTEN expression, decreased DNMT1, DNMT3a, MBD2, and MeCP2 mRNA expressions, and lower PI3K, AKT, and mTOR protein expressions (all P < 0.05). Conclusion: Demethylation treatment with 5-Aza-dC can inhibit T-ALL cell malignant biological behaviors and enhance the sensitivity to chemotherapy agents possibly, which may be related to the inhibited expressions of DNMT1, DNMT3a, MBD2, and MeCP2, and restored expression activity of PTEN to negatively regulate the PI3K/AKT signal transduction. Our silencing and restoration of PTEN expressions further support our findings, highlighting that demethylation with 5-Aza-dC to restore the anti-tumor activity of the tumor suppressor gene PTEN may be a promising therapeutic option for treating T-ALL. Keywords: 5-Aza-2’-deoxycytidine, T-cell acute lymphoblastic leukemia, PTEN, Tumor cell biological behaviors, Demethylation

CAS / MDL: 8004-87-3
研究领域: 肿瘤学 · 分子生物学 · 血液学
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