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NEW JOURNAL OF CHEMISTRY · 2016 ·Vol. 40 ·期 10 ·8225-8228 · IF 3.277

Ruthenium-catalyzed synthesis of tri-substituted 1,3,5-triazines from alcohols and biguanides

Ming Zeng,Tao Wang,Dong-Mei Cui,Chen Zhang

An efficient ruthenium-catalyzed synthesis of tri-substituted 1,3,5-triazines from alcohols and biguanides under mild conditions has been developed. The reaction occurred in moderate to good yields and tolerated benzyl alcohol containing functionalities such as halogens. Monosubstituted to tetrasubstituted biguanidines also afforded the desired products.

CAS / MDL: 865-47-4
研究领域: 有机化学 · 催化反应
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Analytical Methods · 2023 ·Vol. 15 ·期 21 ·2685-2692 · IF 3.1

Sodium hexametaphosphate-treated halloysite based solid-phase extraction of biguanides from dietary supplements

Huanan Huang,Yihui Chen,Meilin Ni,Jing Du,Chunyan Hou,Xiaoqiang Qiao,Guozhou Cao,Tingting Wang

Raw halloysite was purified by using sodium hexametaphosphate and utilized as the solid-phase extraction sorbent for the determination of biguanides from dietary supplements. The purified halloysite was characterized using scanning electron microscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and X-ray diffraction. The purified halloysite interacted with biguanides through hydrophilic interaction and ion exchange on account of its abundant hydroxyl groups and negative charge. Compared with traditional extraction methods based on hydrophobic interaction and/or ion exchange, the purified halloysite adsorbed more biguanides due to hydrophilicity and ion exchange, with a sample loading volume of up to 100 mL at least. Excellent reproducibility of halloysite purification was achieved, with within-batch (n = 3) and batch-to-batch (n = 3) relative standard deviations in the ranges of 1.5–4.2% and 5.6–8.8%, respectively. Coupled with reversed-phase liquid chromatography-tandem mass spectrometry, a low limit of detection of 0.3 μg kg−1 was obtained. The intra- and inter-day mean recoveries of the biguanides spiked at three levels in dietary supplements were within the ranges of 88.5–107.2% and 86.4–102.0%, respectively. The intra- and inter-day precisions were within the ranges of 1.5–6.4% and 5.4–9.9%, respectively. These results indicated that the developed method is efficient for the determination of trace biguanides in dietary supplements.

研究领域: 分析化学 · 药物分析
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Acta Biomaterialia · 2023 · IF 9.7

Biguanide-anchored albumin-based nanoplatform inhibits epithelial-mesenchymal transition and reduces the stemness phenotype for metastatic cancer therapy

Tianze Jiang,Jiahao Wang,Laozhi Xie,Songlei Zhou,Yukun Huang,Yu Chen,Xiaoling Gao,Wenze Xiao,Jun Chen

In clinical chemotherapy, albumin-bound paclitaxel (Abraxane) can improve the tumor targeting property and therapeutic efficacy of paclitaxel (PTX) against orthotopic malignancies. However, patients with metastatic cancer have a poor prognosis, probably due to the instability, chemoresistance, and inability of albumin-bound paclitaxel to alter the tumor microenvironment. Here we propose a new biguanide-modified albumin-based nanoplatform that encapsulates paclitaxel for the effective treatment of metastatic cancer. The PTX is encapsulated in poly (lactic-co-glycolic acid) cores coated with biguanide-modified albumin (HSA-NH). The functionalized nanoparticles (HSA-NH NPs) exhibit a remarkable stable profile with low drug release ( P < 0.05 versus Abraxane), target tumor tissues, suppress epithelial-mesenchymal transition (EMT) events for anti-metastatic effects, and reduce the phenotype of cancer stem cells. As a result, HSA-NH NPs effectively prolong animal survival (55 days) by inhibiting not only primary tumor growth but also metastasis. This study provides proof of concept that the biguanide-anchored albumin-based nanoplatform encapsulating PTX is a powerful, safe, and clinically translational strategy for the treatment of metastatic cancer. Statement of significance Albumin-bound paclitaxel (Abraxane) can increase paclitaxel's tumor targeting and therapeutic efficacy in clinical cancer treatments such as breast cancer. However, the instability, chemoresistance, and lack of tumor microenvironment modulation of albumin-bound paclitaxel may lead to poor therapeutic efficacy in metastatic cancer patients. Here we develop biguanide-anchored albumin-based nanoplatforms that encapsulate paclitaxel (HSA-NH NPs) for metastatic cancer treatment. Poly(lactic-co-glycolic acid) (PLGA) cores encapsulating paclitaxel improve the stability of HSA-NH NPs. Based on the activities of metformin, biguanide-anchored albumin adsorbed on PLGA cores improves paclitaxel efficacy, inhibits various aberrant changes during epithelial-mesenchymal transition, and reduces tumor cell stemness. The biguanide-anchored albumin-based nanoplatform encapsulating PTX can serve as a potent, safe, and clinically translational approach for metastatic cancer therapies.

CAS / MDL: 7087-68-5
研究领域: 肿瘤学 · 药剂学 · 分子生物学
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ANALYTICAL CHEMISTRY · 2021 · IF 6.986

Multiplexed Analysis of Endogenous Guanidino Compounds via Isotope-Coded Doubly Charged Labeling: Application to Lung Cancer Tissues as a Case

Li Liu,Yan-Zhen Chen,Shu-Sheng Zhang,Xiu-Ping Chen,Guo-Qiang Lin,Hang Yin,Chen-Guo Feng,Fang Zhang

Endogenous guanidino compounds (GCs), nitrogen-containing metabolites, have very important physiological activities and participate in biochemical processes. Therefore, accurately characterizing the distribution of endogenous GCs and monitoring their concentration variations are of great significance. In this work, a new derivatization reagent, 4,4′-bis[3-(dimethylamino)propyl]benzyl (BDMAPB), with isotope-coded reagents was designed and synthesized for doubly charged labeling of GCs. BDMAPB-derivatized GCs not only promote the MS signal but also form multicharged quasimolecular ions and abundant fragment ions. With this reagent, an isotope-coded doubly charged labeling (ICDCL) strategy was developed for endogenous GCs with high-resolution liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF MS). The core of this methodology is a 4-fold multiplexed set of [d0]-/[d4]-/[d8]-/[d12]-BDMAPB that yields isotope-coded derivatized GCs. Following a methodological assessment, good linear responses in the range of 25 nM to 1 μM with correlation coefficients over 0.99 were achieved. The limit of detection and the limit of quantitation were below 5 and 25 nM, respectively. The intra- and interday precisions were less than 18%, and the accuracy was in the range of 77.3–122.0%. The percentage recovery in tissues was in the range of 85.1–113.7%. The results indicate that the developed method facilitates long-term testing and ensures accuracy and reliability. Finally, the method was applied for the simultaneous analysis of endogenous GCs in four types of lung tissues (solid adenocarcinoma, solid squamous-cell carcinoma, ground-glass carcinoma, and paracancerous tissues) for absolute quantification, nontargeted screening, and metabolic difference analysis. It is strongly believed that ICDCL combined with isotope-coded BDMAPB will benefit the analysis and study of endogenous GCs.

CAS / MDL: 74-79-3 156-86-5
研究领域: 代谢组学 · 分析化学 · 肿瘤学
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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2017 · IF 1.174

Glycerol carbonate synthesis from glycerol and dimethyl carbonate using guanidine ionic liquids

Xingxing Wang,Peng Zhang,Penglei Cui,Weiguo Cheng,Suojiang Zhang

A large number of surplus glycerol from the biodiesel production can be used as renewable feedstock to produce glycerol carbonate. In this paper, a series of guanidine-based ionic liquids were synthesized to catalyze the transesterification of glycerol and dimethyl carbonate. The tunable basicity and the anion–cation cooperative effect were responsible for the obtained results. The [TMG][TFE] showed the best activity (turnover frequency (TOF) of 1754.0   h −   1 , glycerol (GL) conversion of 91.8%, glycerol carbonate (GC) selectivity of 95.5%) at 80   °C with 0.1   mol% catalyst for 30   min. The reaction mechanism of the transesterification was also proposed.

研究领域: 化学工程 · 催化 · 可再生能源
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PROCESS BIOCHEMISTRY · 2019 · IF 2.883

Antityrosinase and antioxidant activities of guanidine compounds and effect of guanylthiourea on melanogenesis

Yu-Xia Wang,Wei-Chao Su,Qin Wang,Yu-Feng Lin,Yuan Zhou,Long-Fang Lin,Su Ren,Yan-Ting Li,Qing-Xi Chen,Yan Shi

In this study, the antityrosinase and antioxidant activities of four guanidine compounds (GCs), including guanylthiourea (GT), guanidine thiocyanate (GTC), phenylguanidine (PG), and phenethyldiguanide (PTDG), were investigated. The results showed that the GCs reduced the monophenolase and diphenolase activities of tyrosinase. The IC 50 values of GT, GTC, PG, and PTDG were 0.27, 3.53, 6.68, and 5.18 mM for monophenolase and 0.23, 3.24, 3.97 and 2.50 mM for diphenolase, respectively. The inhibition of diphenolase activity was reversible for the four GCs. The inhibition types of GT and PTDG were competitive, while those of GTC and PG were mixed. FRAP, ABTS, DPPH, and DNA damage protection assays revealed that only GT possessed significant antioxidant activity. Furthermore, GT was found to decrease the melanin content and expression of TYR, MITF and DCT in both B16F10 cells and zebrafish. Overall, our results indicated that GT can inhibit tyrosinase activity in vitro , which suggests that these GCs are potential candidates for novel small-molecule tyrosinase inhibitors and that GT could have broader application prospects.

CAS / MDL: 101311-04-0 98021-17-1
研究领域: 药理学 · 生物化学 · 细胞生物学 · 分子生物学
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CONSTRUCTION AND BUILDING MATERIALS · 2019 · IF 4.046

A comparison study of the performance of three electro-migrating corrosion inhibitors in improving the concrete durability and rehabilitating decayed reinforced concrete

Ling Shen,Hui Jiang,Jindong Cao,Mengjiao Zhang,Hui Zhang

Electro-migration (EM) treatment with injection of corrosion inhibitors is regarded as an efficient method to rehabilitate decayed reinforce concrete architectures and structures. In order to explore the advantages of different electrolytes used in this method, three reported nitrogenous electro-migrating inhibitors: guanidine, 1,6-hexamethylenediamine (HMDA) and 3-aminopropyltriethoxysilane (APS) were selected and their effectiveness on reinforced cement mortar durability were compared. APS and HMDA can more efficiently prevent the external aggressive factors (water, chloride and carbonation) rather than guanidine, while guanidine shows advantage in recovering the mortar alkalinity after EM treatment. To select the appropriate electro-migrating corrosion inhibitors, not only the inhibitive effect, but also their effectiveness on removing chloride and re-alkalization and enhancing the resistance to external aggressive factors should be taken into account.

CAS / MDL: 124-09-4
研究领域: 土木工程 · 材料科学
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Advanced Healthcare Materials · 2024 · IF 10

Platelet Membrane-Encapsulated Nanocomplexes Based on Profundity Scavenging ROS Strategy for Myocardial Infarction Therapy

Meng Sun,Nan Hu,Yangyang Gao,Nan Lv,Xiaohong Fu,Yafeng Li,Shaodong Zhai,Ruiping Zhang

Ischemia-induced myocardial injury has become a serious threat to human health, and its treatment remains a challenge. The occurrence of ischemic events leads to a burst release of reactive oxygen species (ROS), which triggers extensive oxidative damage and leads to dysfunctional autophagy, making it difficult for cells to maintain homeostasis. Antioxidants and modulation of autophagy have thus become promising strategies for the treatment of ischemic myocardial injury. This study proposes an antioxidant-activated autophagy therapeutic regimen based on combining melanin (Mel), an excellent antioxidant with metformin mimetic ploymetformin via electrostatic interactions, to obtain a nanocomplex (Met-Mel). The nanocomplex is finally encapsulated with platelet membranes (PMN) to construct a biomimetic nanoparticle (PMN@Met-Mel) capable of targeting injured myocardium. The prepared PMN@Met-Mel has good Mel loading capacity and optimal biosafety. It exhibits excellent antioxidant activity and autophagy activation, rapidly restoring mitochondrial function. Moreover, RNA sequencing (RNA-seq) analysis reveals that PMN@Met-Mel operates mechanistically by triggering the activation of the autophagy pathway. Subsequent in vivo experiments showcase promising cardioprotective effects of these nanoparticles. These discoveries present a newly devised nanoplatform with promising potential for the effective treatment of myocardial infarction.

CAS / MDL: 461-58-5 7647-01-0
研究领域: 心血管疾病 · 纳米医学 · 药学 · 分子生物学
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JOURNAL OF HAZARDOUS MATERIALS · 2021 · IF 10.588

Polyguanidine-modified adsorbent to enhance marine applicability for uranium recovery from seawater

Ningning He,Hao Li,Luyan Li,Chong Cheng,Xirui Lu,Jun Wen,Xiaolin Wang

The marine applicability of adsorbents intended for recovering uranium from seawater is crucial. For such applicability, the materials must exhibit anti-biofouling properties, seawater pH adaptability (pH~8), and salt tolerance. Extracting uranium from seawater is a long-term project; hence, biofouling, high salt concentrations, and weak alkaline environments negatively affect the adsorption of uranium and damage the recovered materials. Most studies on the extraction of uranium from seawater focus on increasing the adsorption capacity of the employed adsorbent, while its marine applicability is neglected. In the present study, three types of guanidine polymer (GP)-modified acrylic fibers were prepared to investigate the impact of the introduced structure on the marine applicability of the fibers. After screening, the introduction of polyhexamethylene biguanidine (PHMB) is observed to produce PAO-PHMB-A, characterized by excellent marine applicability. The enhanced properties include high antimicrobial activity (10 9 CFU/mL, 99.71%), good salt tolerance, and optimal adsorption at a pH of 8. Owing to the synergistic effect of its functional groups, the PAO-PHMB-A material exhibits excellent adsorption performance (525.89 mg/g), as well as high selectivity and durability. More importantly, long-term marine tests revealed that PAO-PHMB-A shows a remarkable uranium adsorption capacity (30 d, 3.19 mg/g) and excellent antibacterial activity. Considering its excellent marine applicability and good adsorption performance, the PAO-PHMB-A material developed in this work could serve as a potential adsorbent for engineering applications associated with uranium recovery from seawater.

研究领域: 材料科学 · 环境工程 · 化学工程 · 海洋科学
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