ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY
·
2023
·
IF 6.8
Han Lu,Shaowei Wang,Jingyi Zheng,Yang Zhu,Yiyan Wang,Huitao Li,Ren-shan Ge
Bisphenol A (BPA) analogues are developed to replace BPA usage. However, their effects on 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1) are largely unknown. The inhibitory effects of BPA and 10 BPA analogues with the substituents on the bridge moiety on human and rat 11β-HSD1 were explored in human and rat liver microsomes. The strength of inhibiting human 11β-HSD1 was bisphenol FL (IC 50 , 3.87 μM) > bisphenol Z (6.86 μM) > bisphenol AF (9.42 μM) > bisphenol C (16.14 μM) > bisphenol AP (32.14 μM) = bisphenol B (32.34 μM) > 4,4′-thiodiphenol (67.35 μM) > BPA (297.35 μM) > other BPA analogues (ineffective at 100 μM). The strength of inhibiting rat 11β-HSD1 was bisphenol Z (IC 50 , 14.44 μM) > 4,4′-thiodiphenol (19.01 μM) > bisphenol B (20.13 μM) > bisphenol F (22.10 μM) > bisphenol E (33.04 μM) > bisphenol AF (49.67 μM) > bisphenol C > (56.97 μM) > bisphenol AP (62.71 μM) >bisphenol FL (96.31 μM) > other BPA analogues (ineffective at 100 μM). Bisphenol A, AF, AP, B, C, F, FL, Z, and 4,4′-thiodiphenol bind to the active sites of human and rat 11β-HSD1. Regression of LogP and molecular weight with IC 50 values revealed distinct inhibitory pattern (negative correlation for human 11β-HSD1 vs. positive correlation for rat enzyme). Regression of the lowest binding energy with IC 50 values revealed a significant positive regression. 3D QSAR pharmacophore analysis showed one hydrogen bond acceptor and two hydrogen bond donors for human 11β-HSD1. In conclusion, most BPA analogues are more potent inhibitors of human and rat 11β-HSD1 enzymes and there is structure-dependent and species-dependent inhibition.
研究领域:
药理学
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毒理学
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计算生物学
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SCIENCE OF THE TOTAL ENVIRONMENT
·
2024
·
IF 8.2
Fan Li,Lei Lei,Yuxi Zhou,Xiaochen Wang,Yindan Zhang,Jianghuan Hua,Jian Han,Lihua Yang,Bingsheng Zhou
The novel brominated flame retardants (NBFRs) have received wide concerns due to their ubiquitous occurrence in the environment and their potential risks to ecosystems and human health. However, the toxicity data of NBFRs are still lacking, especially their toxicity comparison data, and toxicity predictions for untested NBFRs are extremely limited. In this study, eight commonly used NBFRs and decabromodiphenyl ether (BDE209) were selected to compare their toxicity at concentrations between 0.03 and 3.69 μM, by exposing zebrafish embryos until 120 h post-fertilization (hpf) and evaluating 18 toxicity indicators including basic development indicators and a series of behavioral indicators. The toxicity potency of the tested compounds ranked by the total number of significantly affected endpoints were pentabromobenzene (PBB) ≈ 2,4,6-tribromophenol (TBP) > BDE209 ≈ bis(2-ethylhexyl) tetrabromophthalate (TBPH) > pentabromotoluene (PBT) ≈ 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (EHTBB) > 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) > hexabromobenzene (HBB) > decabromodiphenyl ethane (DBDPE). Almost all the tested compounds affected the locomotor behavior of zebrafish larvae, suggesting that the refined behavioral indicators were sensitive endpoints. Furthermore, the quantitative structure-activity relationship (QSAR) model we developed suggested that molecular surface area (MSA) might be the critical factor for determining the developmental neurotoxicity of NBFRs to zebrafish larvae, except for congeners with larger molecules (e.g. DBDPE, BTBPE). These findings would contribute to elucidating the toxicity differences among various NBFRs and provide important references for their toxicity prediction.
研究领域:
环境科学
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毒理学
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计算生物学
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PubMed
高影响因子
MOLECULES
·
2026
·Vol. 31
·期 7
·1078
·
IF 5.1
Yao Chen,Yu-Cheng Cui,You-Qiong Bi,Zhang-Li Guo,Xian-Li Ma,Wen-Gui Duan,Gui-Shan Lin
In order to find green fungicides derived from natural products, 22 unreported anethole-based thiazolinone-hydrazone compounds were designed and synthesized, and their structures were characterized by FT-IR,1H NMR,13C NMR, and HRMS. At a concentration of 50 mg/L, the preliminary antifungal activity of the target compounds against eight plant pathogens was evaluated. The results showed that5q(R =m-OH C6H4) exhibited the best inhibitory activity against most of the tested plant pathogenic fungi, demonstrating that this compound had certain broad-spectrum antifungal activity. In addition, a reasonable and effective 3D-QSAR model (r2= 0.994,q2= 0.529) was established using the comparative molecular field analysis (CoMFA) method to study the relationship between the structures of the target compounds and their antifungal activity againstPhysalospora piricola. Meanwhile, the results of electrostatic potential calculation of the compounds indicated that the electronic effect caused by different substituents on the benzene ring might be one of the factors affecting antifungal activity. In addition, frontier molecular orbital calculations implied that the anethole moiety and the thiazolinone-hydrazone-benzene structure in the target compounds might play an important role in antifungal activity. The potential binding mode between the target compound5q(R =m-OH C6H4) and the homology-modeled succinic dehydrogenase was explored by molecular docking.
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FOOD CHEMISTRY
·
2025
·
IF 9.8
Meng-Qi Liu,Zai-Xi Zhou,Hong-Fu Zhao,Ying-Hua Zhang
Emulsifiers maintain the stability of emulsions, and milk protein-formed emulsions are unstable. Hence, efficient ways to screen food-derived compounds need to be identified. This study combined molecular descriptors with machine learning algorithms to construct quantitative structure-activity relationship models for screening emulsifying compounds. The candidate compound was added to different milk protein emulsions to assess their stability. The results indicated that the model built with the molecular operating environment descriptor combined with the random forest algorithm had the optimal prediction ability (area under the curve: 0.9947; accuracy: 93.33 %). Glycyrrhizin has excellent emulsifying ability, and the emulsion droplets prepared by combining glycyrrhizin and milk protein have a smaller particle size and potential (102.64 nm and − 36.64 mV, respectively), better physical stability, improved foaming properties by 39.59 %, and higher viscosity. Glycyrrhizin significantly improved the physical stability of milk protein emulsions, providing new perspectives for the food industry.
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高影响因子
MOLECULES
·
2018
·Vol. 23
·期 2
·356
·
IF 3.098
Yanqing Gao,Jingjing Li,Jian Li,Zhanqian Song,Shibin Shang,Xiaoping Rao
Turpentine is a volatile component of resin, which is an abundant forest resource in Southern China. As one of the most important components, the integrated application of β-pinene has been studied. The broad-spectrum evaluation of β-pinene and its analogues has, therefore, been necessary. In an attempt to expand the scope of agro-activity trials, the preparation and the evaluation of the herbicidal activity of a series of β-pinene analogues against three agricultural herbs were carried out. In accordance with the overall herbicidal activity, it is noteworthy that compounds6k,6l, and6mdemonstrated extreme activity with IC50values of 0.065, 0.065, and 0.052 mol active ingredients/hectare againstE. crus-galli. The preliminary structure–activity relationship (SAR) was analyzed and the compounds with the appropriate volatility and substituent type that had beneficial herbicidal activity were analyzed. Simultaneously, the quantitative structure–activity relationship (QSAR) model was built and the most important structural features were indicated, which was, to a certain extent, in line with the SAR study. The study aimed to study the application of the forest resource turpentine in agriculture as a potential and alternative approach for comprehensive utilization.Keywords:turpentine;herbicidal activity;SAR;QSAR
研究领域:
农学
·
化学
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JOURNAL OF HAZARDOUS MATERIALS
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2014
·
IF 4.331
Hao Jin,Chao Wang,Jiaqi Shi,Lei Chen
The individual IC 50 (the concentrations causing a 50% inhibition of bioluminescence after 15 min exposure) of cadmium ion (Cd) and nine chlorinated anilines to Photobacterium phosphoreum ( P. phosphoreum ) were determined. In order to evaluate the combined effects of the nine chlorinated anilines and Cd, the toxicities of chlorinated anilines combined with different concentrations of Cd were determined, respectively. The results showed that the number of chlorinated anilines manifesting synergy with Cd decreased with the increasing Cd concentration, and the number manifesting antagonism decreased firstly and then increased. The joint toxicity of mixtures at low Cd concentration was weaker than that of most binary mixtures when combined with Cd at medium and high concentrations as indicated by TU Total . QSAR analysis showed that the single toxicity of chlorinated anilines was related to the energy of the lowest unoccupied molecular orbital ( E LUMO ). When combined with different concentrations of Cd, the toxicity was related to the energy difference ( E HOMO − E LUMO ) with different coefficients. Van der Waals’ force or the complexation between chlorinated anilines and Cd had an impact on the toxicity of combined systems, which could account for QSAR models with different physico-chemical descriptors.
研究领域:
环境科学
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毒理学
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RSC Advances
·
2016
·Vol. 6
·期 56
·50837-50845
·
IF 3.289
Bin Liu,Ji-Mei Ma,Hang-Wei Chen,Zi-Long Li,Lin-Hao Sun,Zhen Zeng,Hong Jiang
α-Glucosidase inhibitors can effectively control postprandial hyperglycemia. In this study, a series of phenolic acids with the L-amino acid moiety were synthesized and their inhibitory activities against α-glucosidase from Saccharomyces cerevisiae (EC 3.2.1.20) were evaluated. The results suggested that all these compounds showed strong α-glucosidase inhibitory activities. In particular, N-(4-hydroxyl-phenylpropenoyl)-L-alanine (c2) and N-(4-hydroxyl-phenylpropenoyl)-L-methionine (c8) exhibited much higher potency (IC50 values 0.04 mM) than the positive control, acarbose (IC50 values 1.70 mM). Three-dimensional quantitative structure–activity relationship (3D-QSAR) model for comparative molecular field analysis (CoMFA) was generated and the result showed that bulk groups and high electron density groups on the amino acid residues were a benefit to their activities. Moreover, the substituents with low electron density and little steric hindrance on the para position of the benzene ring were helpful in improving the activities. Kinetic analysis indicated that compound (c2) acted as a mixed-type inhibitor with a Ki value of 0.0124 mM. Docking analysis showed that they could bind to α-glucosidase at the catalytic site via hydrogen bonds and a π–π stacking.
研究领域:
药理学
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生物化学
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计算化学
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FOOD CHEMISTRY
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2026
·
IF 10.4
Sheng Geng,Guoyang Liu,Lu Bai,Chunyan Wang,Wei Yang,Yangyang Jia,Huan Liu,Benguo Liu
This research elucidates the mechanisms of non-covalent interactions between flavonoids and lysozyme. Binding constants were determined via fluorescence spectroscopy, and a Topomer CoMFA 3D-QSAR model was developed, effectively explaining the binding behavior. Detailed studies on rutin, naringenin, and hesperetin showed binding occurred via a static quenching mechanism with a 1:1 stoichiometry, and hydrogen bonding and van der Waals forces were indicated as the primary drivers. Synchronous fluorescence revealed flavonoid binding disrupted the tryptophan microenvironment but left tyrosine relatively stable. IGM analysis of rutin glycosylation revealed a rigid intramolecular hydrogen-bond network, whereas the aglycones were less stable. Intermolecularly, rutin formed multiple hydrogen bonds and extensive hydrophobic interactions, while aglycone binding was simpler. MD simulations and free energy calculations yielded the following binding affinity: hesperetin > naringenin > rutin, underscoring the importance of solvation effects. This work provides molecular-level insights into the structure-activity relationship, aiding the design of flavonoid delivery systems.
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Desalination and Water Treatment
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2024
·
IF 1
Pingru Su,Wenchao Ji,Zhemin Shen,Jianda Zhang,Weimin Guo
Nascent state manganese dioxide exhibits promising adsorptive capacity as it has large surface area with many water molecules and hydroxyls on. Therefore it has been applied as a treatment of organic pollution. The experimental removal rates (R exp ) under 3 different pH conditions and 18 quantum descriptors of 29 organic contaminants were used to construct quantitative structure-activity relationship (QSAR) models to predict the removal rate at a certain pH. The optimum models at pH 3, 7, 10 are listed as follows respectively, R re = 1 .437 – 5.627f(+) x + 1.018q(C – ) x + 0.099E HOMO (R 2 = 0.9273, pH = 3); R pre = –4.153 + 2.632BO x + 0.688B p O n – 0.696q(C – ) n (R 2 = 0.7459, pH = 7); R pre = –0.057 + 0.031μ + 0.243BO n + 4.976f(0) n – 3.938f(+) x (R 2 = 0.9213, pH = 10). All of the optimum models show satisfactory stability, evident reliability and powerful predicability. Furthermore, they have no possibility of chance correlation. The results presented that affinity with solvent, charge distribution and stability of a molecule were main molecular characters influencing removal effect.
研究领域:
环境化学
·
材料科学
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污染控制
·
计算化学
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高影响因子
FOOD RESEARCH INTERNATIONAL
·
2022
·
IF 7.425
Yuandong Yu,Guizhao Liang,Huabin Wang
Tartary buckwheat bran protein (TBBP) is a valuable by-product of Tartary buckwheat processing. Current studies have indicated that TBBP is a desirable carrier and protector of flavonoids. However, the quantitative structure-affinity relationship of flavonoids with TBBP still remains to be elucidated. Here, by using the fluorescence spectroscopy method to measure the binding constants of 16 flavonoids with TBBP, we employ a combination of the atom-based three dimensional-quantitative structure-affinity relationships (3D-QSAR) and quantum-chemical calculation to explore the underlying binding mechanisms. We show that flavonoids can cause the intrinsic fluorescence quenching and form non-covalent complexes with TBBP driven by hydrogen bonding and van der Waal forces. The atom-based 3D-QSAR model reveals that the rutoside group at the C-7 position of flavones is favorable to enhance the binding constants of flavonoids with TBBP. Quantum-chemical calculations consistently disclose that the rutoside group can intensify interaction forces of flavonoids, thereby strengthening the binding. This work provides theoretical evidence that TBBP has the potential application to be raw materials for develop functional food, and be the delivery carriers of flavonoids.
研究领域:
食品科学
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分子营养学
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生物物理化学
·
功能食品
·
药物传递
·
天然产物化学
·
蛋白质-配体相互作用
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高影响因子
Food Chemistry-X
·
2023
·
IF 6.1
Chengyun He,Lu Bai,Daqun Liu,Benguo Liu
The binding capacity of 10 flavonoids with okra seed protein (OSP) was studied by fluorescence spectroscopy. The structure of flavonoids had an obvious impact on binding performance. The binding ability of flavanone was lower than that of flavone, isoflavone and dihydrochalcone. The binding capacity of flavonoid glycoside was superior to that of the corresponding flavonoid aglycone. The binding ability was positively correlated with the number of phenolic hydroxyl groups on the B ring. The steric field and electrostatic field model constructed by 3D-QSAR method could well explain the above interaction behavior. Thermodynamic analysis suggested that the quenching mechanism of OSP caused by flavonoids was static quenching, and the binding-site number was 1. In addition, hydrogen bonding and van der Waals force dominated this interaction. The 3D and synchronous fluorescence spectra showed that there was no significant change in the polarity of the environment around tryptophan and tyrosine residues during binding.
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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
·
2017
·
IF 4.519
Jiabing Wang,Di Yun,Jiali Yao,Weitao Fu,Fangyan Huang,Liping Chen,Tao Wei,Cuijuan Yu,Haineng Xu,Xiaoou Zhou,Yanqing Huang,Jianzhang Wu,Peihong Qiu,Wulan Li
Molecular hybridization is considered as an effective tactic to develop drugs for the treatment of cancer. A series of novel hybrid compounds of isatin and Michael acceptor were designed and synthesized on the basis of association principle. These hybrid compounds were tested for cytotoxic potential against human cancer cell lines namely, BGC-823, SGC-7901 and NCI-H460 by MTT assay. Most compounds showed good anti-growth activities in all tested human cancer cells. SAR and QSAR analysis may provide vital information for the future development of novel anti-cancer inhibitors. Notably, compound 6a showed potent growth inhibition on BGC-823, SGC-7901 and NCI-H460 with the IC 50 values of 3.6 ± 0.6, 5.7 ± 1.2, 3.2 ± 0.7 μM, respectively. Besides, colony formation assays, wound healing assays and flow cytometry analysis indicated 6a exhibited a potent anti-growth and anti-migration ability in a concentration-dependence manner through arrested cells in the G2/M phase of cell cycle. Moreover, 6a significantly repressed tumor growth in a NCI-H460 xenograft mouse model. Overall, our findings suggested isatin analogues inspired Michael acceptor may provide promising lead compounds for the development of cancer chemotherapeutics.
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