Pub Date : 2024-11-05DOI: 10.1016/j.molstruc.2024.140607
Zhuo-Hao Jiao , Shuo Sun , Hua Li , Xiao-Na Gao , Zi-Qian Li , Yu-Heng Liu , Yan Fu , Lei Nie , Lei Wang
Efficient utilization of CO2 and its conversion into high-value-added products contribute to mitigating environmental issues such as the greenhouse effect. Among these methods, the carboxylation cyclization of CO2 with propargylic amine represents a green and atom-economical approach. Developing cost-effective catalyst that can promote this reaction under mild condition is desirable but challenging. Herein, a unique two-dimensional (2D) metal–organic framework (MOF) {[Cu(QCA)2]∙0.5DMF∙0.5H2O}n (1) (QCA =6-quinolinecarboxylic acid, DMF = N,N-dimethylformamide) have been synthesized and thoroughly characterized. Compound 1 was constructed from paddle-wheel dinuclear copper clusters [Cu2(COO)4] and carboxylate ligands, presenting a two-dimensional framework with new topology. Stability tests indicate that compound 1 undergoes reversible structural changes in different solvents and exhibits good thermal stability. 1 as heterogeneous catalyst enabled the transformation of CO2 and propargylic amine into oxazolidinones under mild conditions with broad substrate generality. In addition, 1 could maintain its catalytic performance with five continuous reactions. This work presents an infrequent example of a 2D noble metal free MOF-based catalyst that shows high catalytic efficiency under mild conditions.
{"title":"Efficient paddle-wheel copper cluster-based metal-organic framework for catalytic conversion of CO2 to oxazolidinones under mild conditions","authors":"Zhuo-Hao Jiao , Shuo Sun , Hua Li , Xiao-Na Gao , Zi-Qian Li , Yu-Heng Liu , Yan Fu , Lei Nie , Lei Wang","doi":"10.1016/j.molstruc.2024.140607","DOIUrl":"10.1016/j.molstruc.2024.140607","url":null,"abstract":"<div><div>Efficient utilization of CO<sub>2</sub> and its conversion into high-value-added products contribute to mitigating environmental issues such as the greenhouse effect. Among these methods, the carboxylation cyclization of CO<sub>2</sub> with propargylic amine represents a green and atom-economical approach. Developing cost-effective catalyst that can promote this reaction under mild condition is desirable but challenging. Herein, a unique two-dimensional (2D) metal–organic framework (MOF) {[Cu(QCA)<sub>2</sub>]∙0.5DMF∙0.5H<sub>2</sub>O}<em><sub>n</sub></em> (<strong>1</strong>) (QCA =6-quinolinecarboxylic acid, DMF = <em>N</em>,N-dimethylformamide) have been synthesized and thoroughly characterized. Compound <strong>1</strong> was constructed from paddle-wheel dinuclear copper clusters [Cu<sub>2</sub>(COO)<sub>4</sub>] and carboxylate ligands, presenting a two-dimensional framework with new topology. Stability tests indicate that compound <strong>1</strong> undergoes reversible structural changes in different solvents and exhibits good thermal stability. <strong>1</strong> as heterogeneous catalyst enabled the transformation of CO<sub>2</sub> and propargylic amine into oxazolidinones under mild conditions with broad substrate generality. In addition, <strong>1</strong> could maintain its catalytic performance with five continuous reactions. This work presents an infrequent example of a 2D noble metal free MOF-based catalyst that shows high catalytic efficiency under mild conditions.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140607"},"PeriodicalIF":4.0,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this study, the aqueous leaf extract of Hyoscyamus muticus L Plant leaf was prepared using three methods: maceration (MAC), microwave-assisted extraction (MAE), and ultrasonic-assisted extraction (UAE). Then, the extracts were used to synthesize silver nanoparticles (Ag NPs) in an environmentally friendly approach. The characterization of the synthesized Ag NPs was carried out by various techniques. The XRD results confirmed the successful synthesis of nano-sized Ag crystals with spherical structure. The SEM images showed the formation of Ag NPs, which were smaller than 75 nm. The UV–Vis studies showed an obvious absorption peak for Ag NPs between 400 and 500 nm, with a clear peak around 450 nm for all samples. The elemental analysis using the EDS technique confirmed the presence of silver in the synthesized Ag NPs. Furthermore, the effect of different concentrations of Ag NPs was investigated on hatching and second-stage juvenile (J2s) mortality of Meloidogyne javanica, under controlled conditions. The results showed that increasing concentrations of Ag NPs led to higher percentages of inhibition of egg hatching and J2s mortality. Additionally, the Ag NPs synthesized by ultrasonic-assisted extraction with lower lethal concentration were found to be more toxic to M. javanica than the extract prepared by soaking. According to the results, Ag NPs showed a stronger inhibitory effect on M. javanica egg hatching and J2s mortality compared to the total extracts and chemically synthesized Ag NPs. Also, the lowest LC50 was observed for the Ag NPs synthesized using the plant extract as: UAE > MAE (180 w) > MAE (90 w) > MAC methods. The highest inhibition of egg hatch occurred at 0.5% v/v of Ag NPs after 72 h and remained consistent after 120 h.
本研究采用浸渍法（MAC）、微波辅助萃取法（MAE）和超声辅助萃取法（UAE）三种方法制备了植物叶 Hyoscyamus muticus L 的水性叶提取物。然后，利用提取物以环境友好的方法合成银纳米粒子（Ag NPs）。合成的银纳米粒子采用了多种技术进行表征。XRD 结果证实成功合成了具有球形结构的纳米级银晶体。扫描电镜图像显示形成了小于 75 纳米的 Ag NPs。紫外可见光研究表明，Ag NPs 在 400 至 500 纳米之间有一个明显的吸收峰，所有样品在 450 纳米附近都有一个清晰的吸收峰。利用 EDS 技术进行的元素分析证实了合成的 Ag NPs 中含有银。此外，在受控条件下，研究了不同浓度的银纳米粒子对爪螨孵化和第二阶段幼虫（J2s）死亡率的影响。结果表明，Ag NPs 浓度越高，对卵孵化和 J2s 死亡率的抑制率越高。此外，与浸泡提取物相比，通过超声波辅助提取合成的致死浓度较低的银氧化物对爪螨的毒性更大。结果表明，与总提取物和化学合成的 Ag NPs 相比，Ag NPs 对爪哇蝇卵孵化和 J2s 死亡率有更强的抑制作用。此外，使用植物提取物合成的 Ag NPs LC50 最低：UAE > MAE (180 w) > MAE (90 w) > MAC 方法。72 小时后，0.5% v/v 的 Ag NPs 对卵孵化的抑制率最高，120 小时后仍保持不变。
{"title":"Green synthesis of silver nanoparticle by Hyoscyamus muticus L. extract and study of its effect on tomato infected with Meloidogyne javanica","authors":"Seyyed Maryam Mousavi Kordsholie , Hamid Reza Rajabi , Habiballah Chadegani","doi":"10.1016/j.molstruc.2024.140605","DOIUrl":"10.1016/j.molstruc.2024.140605","url":null,"abstract":"<div><div>In this study, the aqueous leaf extract of <em>Hyoscyamus muticus L</em> Plant leaf was prepared using three methods: maceration (MAC), microwave-assisted extraction (MAE), and ultrasonic-assisted extraction (UAE). Then, the extracts were used to synthesize silver nanoparticles (Ag NPs) in an environmentally friendly approach. The characterization of the synthesized Ag NPs was carried out by various techniques. The XRD results confirmed the successful synthesis of nano-sized Ag crystals with spherical structure. The SEM images showed the formation of Ag NPs, which were smaller than 75 nm. The UV–Vis studies showed an obvious absorption peak for Ag NPs between 400 and 500 nm, with a clear peak around 450 nm for all samples. The elemental analysis using the EDS technique confirmed the presence of silver in the synthesized Ag NPs. Furthermore, the effect of different concentrations of Ag NPs was investigated on hatching and second-stage juvenile (J2s) mortality of <em>Meloidogyne javanica</em>, under controlled conditions. The results showed that increasing concentrations of Ag NPs led to higher percentages of inhibition of egg hatching and J2s mortality. Additionally, the Ag NPs synthesized by ultrasonic-assisted extraction with lower lethal concentration were found to be more toxic to <em>M. javanica</em> than the extract prepared by soaking. According to the results, Ag NPs showed a stronger inhibitory effect on <em>M. javanica</em> egg hatching and J2s mortality compared to the total extracts and chemically synthesized Ag NPs. Also, the lowest LC50 was observed for the Ag NPs synthesized using the plant extract as: UAE > MAE (180 w) > MAE (90 w) > MAC methods. The highest inhibition of egg hatch occurred at 0.5% v/v of Ag NPs after 72 h and remained consistent after 120 h.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140605"},"PeriodicalIF":4.0,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142651680","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-05DOI: 10.1016/j.molstruc.2024.140603
N. Dinesh kumar , G. Thirunarayanan , R. Elancheran , P. Suppuraj , L. Guganathan , R. Sivasakthikumaran , S. Ramkumar , M. Swaminathan
This research examines the green synthesis of bis-Schiff bases with benzyl substitutions at 3,4-dimethoxy and 3,4,5-trimethoxy positions through solvent-free microwave-assisted condensation between para-phenylenediamine and 3,4-dimethoxybenzaldehyde (I) and 3,4,5-trimethoxybenzaldehyde (II), using sulfated-TiO2 as a solid acid catalyst. The structures were confirmed through various physicochemical and spectroscopic techniques, including IR, ¹H NMR, ¹³C NMR, and SC-XRD. The compound II crystallized in the monoclinic system (space group of P-21/c). The primary objective was to explore the geometry using both experimental methods and density functional theory (DFT) with the B3LYP/6–311 G (d,p) level. A comparison of experimental (FT-IR, NMR, SC-XRD) and simulated data showed strong agreement. Additionally, Hirshfeld analysis, ELF, LOL, and RDG topological studies were performed. Docking simulations on the 2V54 monkeypox target protein revealed binding affinities, with compounds I and II. The target protein had a binding energy of 4.83 and −4.98 kcal/mol with I and II. ADMET predictions further demonstrated the pharmacological profile of the synthesized compounds.
本研究以硫酸化二氧化钛为固体酸催化剂，通过无溶剂微波辅助对苯二胺与 3,4- 二甲氧基苯甲醛（I）和 3,4,5- 三甲氧基苯甲醛（II）缩合，研究了在 3,4- 二甲氧基和 3,4,5- 三甲氧基位置上具有苄基取代的双席夫碱的绿色合成。通过各种理化和光谱技术（包括红外光谱、¹H NMR、¹³C NMR 和 SC-XRD）确认了化合物的结构。化合物 II 在单斜系统中结晶（空间群为 P-21/c）。主要目的是利用实验方法和密度泛函理论（DFT）（B3LYP/6-311 G (d,p)水平）探索其几何结构。实验数据（傅立叶变换红外光谱、核磁共振、SC-XRD）与模拟数据的比较结果表明两者非常吻合。此外，还进行了 Hirshfeld 分析、ELF、LOL 和 RDG 拓扑研究。对 2V54 猴痘目标蛋白的对接模拟显示了化合物 I 和 II 的结合亲和力。目标蛋白与 I 和 II 的结合能分别为 4.83 和 -4.98 kcal/mol。ADMET 预测进一步证明了合成化合物的药理特性。
{"title":"Solid acid-catalyzed green synthesis of bis-Schiff bases: Spectroscopic, DFT, molecular docking, and ADMET studies","authors":"N. Dinesh kumar , G. Thirunarayanan , R. Elancheran , P. Suppuraj , L. Guganathan , R. Sivasakthikumaran , S. Ramkumar , M. Swaminathan","doi":"10.1016/j.molstruc.2024.140603","DOIUrl":"10.1016/j.molstruc.2024.140603","url":null,"abstract":"<div><div>This research examines the green synthesis of bis-Schiff bases with benzyl substitutions at 3,4-dimethoxy and 3,4,5-trimethoxy positions through solvent-free microwave-assisted condensation between para-phenylenediamine and 3,4-dimethoxybenzaldehyde (I) and 3,4,5-trimethoxybenzaldehyde (II), using sulfated-TiO<sub>2</sub> as a solid acid catalyst. The structures were confirmed through various physicochemical and spectroscopic techniques, including IR, ¹H NMR, ¹³C NMR, and SC-XRD. The compound <strong>II</strong> crystallized in the monoclinic system (space group of P-2<sub>1</sub>/<em>c</em>). The primary objective was to explore the geometry using both experimental methods and density functional theory (DFT) with the B3LYP/6–311 G (d,p) level. A comparison of experimental (FT-IR, NMR, SC-XRD) and simulated data showed strong agreement. Additionally, Hirshfeld analysis, ELF, LOL, and RDG topological studies were performed. Docking simulations on the 2V54 monkeypox target protein revealed binding affinities, with compounds <strong>I</strong> and <strong>II</strong>. The target protein had a binding energy of 4.83 and −4.98 kcal/mol with I and II. ADMET predictions further demonstrated the pharmacological profile of the synthesized compounds.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140603"},"PeriodicalIF":4.0,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657627","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-05DOI: 10.1016/j.molstruc.2024.140602
Hany M. Abd El-Lateef , Mai M. Khalaf , Mohamed Gouda , Tamer Mohamed Abdelghani Ibrahim , Amer A. Amer , Nawaf I Alsenani , Antar A. Abdelhamid , Aly Abdou
This study presents the synthesis and characterization of two novel metal complexes derived from the symmetrical Schiff base N,N'-benzene-1,2-diylbis[1-(2-chloroquinolin-3-yl)methanimine] (OBCQ), coordinated with Nickel(II) (NiOBCQ) and Copper(II) (CuOBCQ). The structural elucidation of these complexes was achieved through a comprehensive suite of analytical techniques, including elemental analysis, UV–visible spectroscopy, mass spectrometry, infrared spectroscopy, magnetic susceptibility, conductivity measurements, and thermal analysis. The data confirm that both NiOBCQ and CuOBCQ adopt octahedral geometries, formulated as [Ni(OBCQ)(H₂O)₂(Cl)₂] and [Cu(OBCQ)(H₂O)₂(Cl)₂], respectively. Density Functional Theory (DFT) calculations were employed to validate the molecular structures and explore the quantum chemical parameters of OBCQ and its metal complexes. Additionally, in vitro assessments of anti-inflammatory and antioxidant activities revealed enhanced bioactivity for the metal complexes compared to the free OBCQ ligand. Molecular docking studies against key proteins (5IKT for Human Cyclooxygenase-2 and 5IJT for Human Peroxiredoxin 2) highlighted strong binding affinities and molecular interactions, suggesting that OBCQ and its metal complexes hold significant promise as novel therapeutic agents with multifaceted biological activities.
{"title":"Design, characterization, and bioactivity evaluation of novel symmetrical N,N'-benzene-1,2-diylbis[1-(2-chloroquinolin-3-yl)methanimine] based metal complexes","authors":"Hany M. Abd El-Lateef , Mai M. Khalaf , Mohamed Gouda , Tamer Mohamed Abdelghani Ibrahim , Amer A. Amer , Nawaf I Alsenani , Antar A. Abdelhamid , Aly Abdou","doi":"10.1016/j.molstruc.2024.140602","DOIUrl":"10.1016/j.molstruc.2024.140602","url":null,"abstract":"<div><div>This study presents the synthesis and characterization of two novel metal complexes derived from the symmetrical Schiff base N,N'-benzene-1,2-diylbis[1-(2-chloroquinolin-3-yl)methanimine] (OBCQ), coordinated with Nickel(II) (NiOBCQ) and Copper(II) (CuOBCQ). The structural elucidation of these complexes was achieved through a comprehensive suite of analytical techniques, including elemental analysis, UV–visible spectroscopy, mass spectrometry, infrared spectroscopy, magnetic susceptibility, conductivity measurements, and thermal analysis. The data confirm that both NiOBCQ and CuOBCQ adopt octahedral geometries, formulated as [Ni(OBCQ)(H₂O)₂(Cl)₂] and [Cu(OBCQ)(H₂O)₂(Cl)₂], respectively. Density Functional Theory (DFT) calculations were employed to validate the molecular structures and explore the quantum chemical parameters of OBCQ and its metal complexes. Additionally, in vitro assessments of anti-inflammatory and antioxidant activities revealed enhanced bioactivity for the metal complexes compared to the free OBCQ ligand. Molecular docking studies against key proteins (5IKT for Human Cyclooxygenase-2 and 5IJT for Human Peroxiredoxin 2) highlighted strong binding affinities and molecular interactions, suggesting that OBCQ and its metal complexes hold significant promise as novel therapeutic agents with multifaceted biological activities.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140602"},"PeriodicalIF":4.0,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657626","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-05DOI: 10.1016/j.molstruc.2024.140552
Nkechinyere N. Ukwueze , Chigozie J. Ezeorah , Ebuka L. Onyeyilim , Chiamaka P. Uzoewulu , Uchechukwu C. Okoro , Pius O. Ukoha , Nnaemeka Nnaji , Chigozie J.O. Anarado , Necmi Dege , Nnamdi L. Obasi , Albert O. Ugwu , Ngozi M. Onyeisi , Kevin Lobb , Oguejiofo T. Ujam
A coupling precursor, 4-hexanoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1 synthesized by the reaction of 3-methyl-1-phenyl-1H-pyrazol-5-one with hexanoyl chloride was reacted with 2-aminophenol to synthesize (E)-4-(1-((2-hydroxyphenyl)imino)hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1a. The compounds were characterized by conventional spectroscopic techniques, 1H and 13C NMR, UV–Visible, FTIR spectroscopy and single crystal X-ray crystallograpic structural determinations and computational techniques. To augment the experimental data, DFT calculations were carried. Molecular dockings were used to predict the interactions between, 1a with some biological targets. The binding free energies in the Plasmepsin II active sites indicated anti−malarial activity against P. falciparum in epidermal growth factor receptor (EGFR) inhibition, anti-inflammatory properties against human peroxiredoxin 5, and anticancer properties. With binding energies less than −5.00 kcal/mol, the results indicate that 1a is a potential drug target for anti-inflammatory, anti-malarial and anti-cancer properties.
{"title":"Synthesis, characterization and computational studies on (E)-4-(1-((2-hydroxyphenyl)imi no) hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one","authors":"Nkechinyere N. Ukwueze , Chigozie J. Ezeorah , Ebuka L. Onyeyilim , Chiamaka P. Uzoewulu , Uchechukwu C. Okoro , Pius O. Ukoha , Nnaemeka Nnaji , Chigozie J.O. Anarado , Necmi Dege , Nnamdi L. Obasi , Albert O. Ugwu , Ngozi M. Onyeisi , Kevin Lobb , Oguejiofo T. Ujam","doi":"10.1016/j.molstruc.2024.140552","DOIUrl":"10.1016/j.molstruc.2024.140552","url":null,"abstract":"<div><div>A coupling precursor, 4-hexanoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, <strong>1</strong> synthesized by the reaction of 3-methyl-1-phenyl-1H-pyrazol-5-one with hexanoyl chloride was reacted with 2-aminophenol to synthesize (E)-4-(1-((2-hydroxyphenyl)imino)hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, <strong>1a</strong>. The compounds were characterized by conventional spectroscopic techniques, <sup>1</sup>H and <sup>13</sup>C NMR, UV–Visible, FTIR spectroscopy and single crystal X-ray crystallograpic structural determinations and computational techniques. To augment the experimental data, DFT calculations were carried. Molecular dockings were used to predict the interactions between, <strong>1a</strong> with some biological targets. The binding free energies in the Plasmepsin II active sites indicated anti−malarial activity against <em>P. falciparum</em> in epidermal growth factor receptor (EGFR) inhibition, anti-inflammatory properties against human peroxiredoxin 5, and anticancer properties. With binding energies less than −5.00 kcal/mol, the results indicate that <strong>1a</strong> is a potential drug target for anti-inflammatory, anti-malarial and anti-cancer properties.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140552"},"PeriodicalIF":4.0,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142651789","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-04DOI: 10.1016/j.molstruc.2024.140600
Pei Huang , Meng-Qi Tuo , Guo Xin-Yu , Sheng-Rui Zhang , Jiu-Fu Lu , Dong Wang
The development of multifunctional and structurally unique metal−organic frameworks (MOFs) presents a highly attractive yet challenging endeavor for chemists. In this study, we employ a dual-ligand strategy to synthesize two isomorphic Co/Zn MOFs, {[Co4(BMIP)3(MIP)4]·3DMF·H2O}n (SNUT-35-Co) and {[Zn4(BMIP)3(MIP)4]·2DMF·2H2O}n (SNUT-35-Zn). The photocatalytic performance of SNUT-35-Co and SNUT-35-Zn was evaluated using methylene blue (MB). Under UV/visible-light irradiation, the photocatalytic decolorization rates of MB for SNUT-35-Co and SNUT-35-Zn reached 95 % within 140 min and 120 min, respectively, indicating their superior degradation. Notably, SNUT-35-Zn demonstrated exceptional detection capabilities for aromatic compounds, such as aniline and nitrobenzene, at lower concentration range without interference from other components. The detection limits for these two small molecules were found to be 0.430 and 0.431 μM, respectively. Additionally, both MOFs exhibited large transient photocurrent and low impedance in electrochemical measurement. The results suggested that the photocatalytic activities of MOFs are influenced by their three-dimensional structures, which facilitate electrons passing due to the inherent semiconductor properties.
{"title":"Construction of two isomorphic multifunctional MOFs via a dual-ligand strategy for aromatic compounds detection and photocatalytic degradation performance","authors":"Pei Huang , Meng-Qi Tuo , Guo Xin-Yu , Sheng-Rui Zhang , Jiu-Fu Lu , Dong Wang","doi":"10.1016/j.molstruc.2024.140600","DOIUrl":"10.1016/j.molstruc.2024.140600","url":null,"abstract":"<div><div>The development of multifunctional and structurally unique metal−organic frameworks (MOFs) presents a highly attractive yet challenging endeavor for chemists. In this study, we employ a dual-ligand strategy to synthesize two isomorphic Co/Zn MOFs, {[Co<sub>4</sub>(BMIP)<sub>3</sub>(MIP)<sub>4</sub>]·3DMF·H<sub>2</sub>O}<sub>n</sub> (<strong>SNUT-35-Co</strong>) and {[Zn<sub>4</sub>(BMIP)<sub>3</sub>(MIP)<sub>4</sub>]·2DMF·2H<sub>2</sub>O}<sub>n</sub> (<strong>SNUT-35-Zn</strong>). The photocatalytic performance of <strong>SNUT-35-Co</strong> and <strong>SNUT-35-Zn</strong> was evaluated using methylene blue (MB). Under UV/visible-light irradiation, the photocatalytic decolorization rates of MB for <strong>SNUT-35-Co</strong> and <strong>SNUT-35-Zn</strong> reached 95 % within 140 min and 120 min, respectively, indicating their superior degradation. Notably, <strong>SNUT-35-Zn</strong> demonstrated exceptional detection capabilities for aromatic compounds, such as aniline and nitrobenzene, at lower concentration range without interference from other components. The detection limits for these two small molecules were found to be 0.430 and 0.431 μM, respectively. Additionally, both MOFs exhibited large transient photocurrent and low impedance in electrochemical measurement. The results suggested that the photocatalytic activities of MOFs are influenced by their three-dimensional structures, which facilitate electrons passing due to the inherent semiconductor properties.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140600"},"PeriodicalIF":4.0,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656969","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Polyphenols are known to form complexes with various organic compounds. This ability can may change the chemical or physical properties of the compounds involved and may even affect their efficacy in the case of drugs. Our research revealed that mixing solutions of the polyphenol rosmarinic acid (RA) and berberine (Ber), a widely used and pharmacologically important isoquinoline alkaloid, resulted in the formation of a precipitate of the RA–Ber complex at a molar ratio of 1:1. This was confirmed using 1H NMR and Fourier Transform Infrared Spectroscopy. To elucidate the formation mechanism of the precipitate, the behavior of RA and Ber in an aqueous solution was examined using 1H NMR, indicating the formation of the RA–Ber complex at a molar ratio of 1:1, consistent with the results of precipitation. Additionally, we investigated the steric structure of the RA–Ber complex in an aqueous solution using molecular modeling calculations. These calculations suggested the existence of seven types different steric structures of the RA–Ber complex, primarily stabilized by π–π interactions. Based on these results, we concluded that mixing RA and Ber solutions in an aqueous environment results in the formation of RA–Ber complexes with seven types different steric structures at a molar ratio of 1:1. The precipitate forms because these complexes are less water-soluble than either RA or Ber alone.
众所周知，多酚可以与各种有机化合物形成复合物。这种能力可能会改变相关化合物的化学或物理特性，甚至可能影响药物的疗效。我们的研究发现，将多酚类化合物迷迭香酸（RA）和小檗碱（Ber）（一种广泛使用且具有重要药理作用的异喹啉生物碱）的溶液混合，会形成摩尔比为 1:1 的 RA-Ber 复合物沉淀。1H NMR 和傅立叶变换红外光谱法证实了这一点。为了阐明沉淀的形成机制，我们使用 1H NMR 对 RA 和 Ber 在水溶液中的行为进行了检测，结果表明 RA-Ber 复合物的摩尔比为 1:1，与沉淀结果一致。此外，我们还利用分子模型计算研究了水溶液中 RA-Ber 复合物的立体结构。这些计算表明 RA-Ber 复合物存在七种不同的立体结构，主要由 π-π 相互作用稳定。基于这些结果，我们得出结论：在水环境中将 RA 和 Ber 溶液混合，会形成摩尔比为 1:1 的 RA-Ber 复合物，其立体结构有七种不同类型。形成沉淀的原因是这些复合物的水溶性低于 RA 或 Ber 本身。
{"title":"Elucidation of complexation mechanism of rosmarinic acid and berberine","authors":"Hiroyuki Tsutsumi, Yoshiyuki Akita, Tomonori Ohata, Rie Nakashima, Hirohito Ikeda","doi":"10.1016/j.molstruc.2024.140601","DOIUrl":"10.1016/j.molstruc.2024.140601","url":null,"abstract":"<div><div>Polyphenols are known to form complexes with various organic compounds. This ability can may change the chemical or physical properties of the compounds involved and may even affect their efficacy in the case of drugs. Our research revealed that mixing solutions of the polyphenol rosmarinic acid (RA) and berberine (Ber), a widely used and pharmacologically important isoquinoline alkaloid, resulted in the formation of a precipitate of the RA–Ber complex at a molar ratio of 1:1. This was confirmed using <sup>1</sup>H NMR and Fourier Transform Infrared Spectroscopy. To elucidate the formation mechanism of the precipitate, the behavior of RA and Ber in an aqueous solution was examined using <sup>1</sup>H NMR, indicating the formation of the RA–Ber complex at a molar ratio of 1:1, consistent with the results of precipitation. Additionally, we investigated the steric structure of the RA–Ber complex in an aqueous solution using molecular modeling calculations. These calculations suggested the existence of seven types different steric structures of the RA–Ber complex, primarily stabilized by π–π interactions. Based on these results, we concluded that mixing RA and Ber solutions in an aqueous environment results in the formation of RA–Ber complexes with seven types different steric structures at a molar ratio of 1:1. The precipitate forms because these complexes are less water-soluble than either RA or Ber alone.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140601"},"PeriodicalIF":4.0,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657890","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this study, a series of antipyrine-based Schiff bases (1–10) was designed, synthesized, and evaluated as potential inhibitors of various metabolic enzymes, including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human erythrocyte carbonic anhydrase I and II (hCA I and hCA II). The target molecules were characterized by UV–vis, FT-IR, 1H NMR, 13CNMR, LC-HRMS, and elemental analysis. All tested derivatives demonstrated low nanomolar inhibition with Ki values of in the range of 20.58 ± 0.35 to 53.11 ± 1.02 nM against AChE, 21.84 ± 0.40 to 54.41 ± 1.05 nM against BChE, 27.45 ± 0.41 to 48.22 ± 0.91 nM against cytosolic hCA I isoform associated with epilepsy, and 6.02 ± 0.11 to 29.32 ± 0.54 nM against cytosolic hCA II isoform associated with glaucoma. In general, most these molecules, except for a few, inhibited these enzymes more than acetazolamide (AZA) and neostigmine. Among them, compounds 5, 7, 8, and 9 showed the best inhibitory activities against AChE, BChE, hCA I, and hCA II, respectively. Docking results were calculated for the compounds that showed the best inhibitory activity against these enzymes and for reference compounds. Based on the molecular docking results, they were determined to have high binding energies, including hydrogen bonds, electrostatic interactions, and hydrophobic interactions. Absorption, distribution, metabolism, and excretion (ADME) parameters determined that all the synthesized pyrazolone ring-bearing Schif base derivatives (1–10) have the expected physicochemical properties in terms of drug-likeness and can be evaluated as orally active potential. Properties such as the electrophilicity index and chemical hardness were also investigated by density functional theory (DFT) at the B3LYP/6–311G** level of theory.
本研究设计、合成了一系列基于抗吡啶的希夫碱（1-10），并将其评估为各种代谢酶的潜在抑制剂，包括乙酰胆碱酯酶（AChE）、丁酰胆碱酯酶（BChE）以及人红细胞碳酸酐酶 I 和 II（hCA I 和 hCA II）。通过紫外-可见光、傅立叶变换红外光谱、1H NMR、13CNMR、LC-HRMS 和元素分析对目标分子进行了表征。所有测试的衍生物都表现出低纳摩尔的抑制作用，对 AChE 的 Ki 值范围为 20.58 ± 0.35 至 53.11 ± 1.02 nM，对 BChE 的 Ki 值范围为 21.84 ± 0.40 至 54.41 ± 1.05 nM，对 AChE 的 Ki 值范围为 27.45 ± 0.41 至 48.22 ± 0.91 nM，以及 6.02 ± 0.11 至 29.32 ± 0.54 nM，分别针对与癫痫相关的细胞膜 hCA I 异构体和与青光眼相关的细胞膜 hCA II 异构体。一般来说，除少数化合物外，大多数化合物对这些酶的抑制作用都强于乙酰唑胺（AZA）和新斯的明。其中，化合物 5、7、8 和 9 对 AChE、BChE、hCA I 和 hCA II 的抑制活性分别最好。计算了对这些酶具有最佳抑制活性的化合物和参考化合物的对接结果。根据分子对接结果，确定这些化合物具有较高的结合能，包括氢键、静电相互作用和疏水相互作用。吸收、分布、代谢和排泄（ADME）参数表明，所有合成的吡唑酮环希夫碱衍生物（1-10）都具有药物相似性方面的预期理化性质，可以被评估为具有口服活性的潜在化合物。此外，还通过密度泛函理论（DFT）在 B3LYP/6-311G** 理论水平上对亲电指数和化学硬度等性质进行了研究。
{"title":"Design, synthesis of antipyrine-based Schiff bases and investigation of their cholinesterase and carbonic anhydrase activities by in vitro and in silico approaches","authors":"Reşit Çakmak , Eyüp Başaran , Burçin Türkmenoğlu , Murat Şentürk","doi":"10.1016/j.molstruc.2024.140599","DOIUrl":"10.1016/j.molstruc.2024.140599","url":null,"abstract":"<div><div>In this study, a series of antipyrine-based Schiff bases (<strong>1</strong>–<strong>10</strong>) was designed, synthesized, and evaluated as potential inhibitors of various metabolic enzymes, including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human erythrocyte carbonic anhydrase I and II (hCA I and hCA II). The target molecules were characterized by UV–vis, FT-IR, <sup>1</sup>H NMR, <sup>13</sup>CNMR, LC-HRMS, and elemental analysis. All tested derivatives demonstrated low nanomolar inhibition with <em>K</em><sub>i</sub> values of in the range of 20.58 ± 0.35 to 53.11 ± 1.02 nM against AChE, 21.84 ± 0.40 to 54.41 ± 1.05 nM against BChE, 27.45 ± 0.41 to 48.22 ± 0.91 nM against cytosolic hCA I isoform associated with epilepsy, and 6.02 ± 0.11 to 29.32 ± 0.54 nM against cytosolic hCA II isoform associated with glaucoma. In general, most these molecules, except for a few, inhibited these enzymes more than acetazolamide (AZA) and neostigmine. Among them, compounds <strong>5, 7, 8</strong>, and <strong>9</strong> showed the best inhibitory activities against AChE, BChE, hCA I, and hCA II, respectively. Docking results were calculated for the compounds that showed the best inhibitory activity against these enzymes and for reference compounds. Based on the molecular docking results, they were determined to have high binding energies, including hydrogen bonds, electrostatic interactions, and hydrophobic interactions. Absorption, distribution, metabolism, and excretion (ADME) parameters determined that all the synthesized pyrazolone ring-bearing Schif base derivatives (<strong>1</strong>–<strong>10</strong>) have the expected physicochemical properties in terms of drug-likeness and can be evaluated as orally active potential. Properties such as the electrophilicity index and chemical hardness were also investigated by density functional theory (DFT) at the B3LYP/6–311G** level of theory.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140599"},"PeriodicalIF":4.0,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656924","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-04DOI: 10.1016/j.molstruc.2024.140598
Hong-Wei Huang , Yue-Bo He , Zhao-Hui Xin , Qian-Yong Cao
Four pyrene functionalized triazolium salts with different lengths of alkyl tail from C4 to C16, i.e., PYTAZ-C4, PYTAZ-C8, PYTAZ-C12 and PYTAZ-C16, have been designed and synthesized for ATP recognition. It was revealed that the longer alkyl tail anchored receptors PYTAZ-C12 and PYTAZ-C16 exhibit low CMC values, and self-assemble nanoaggregation at low concentration in aqueous solution, which show a pyrene-based excimer emission at 496 nm. However, the shorter alkyl anchored receptors PYTAZ-C4 and PYTAZ-C8 give only the pyrene-based monomer emission at 380 nm at the test concentration of 10 μM in aqueous solution. Importantly, PYTAZ-C12 and PYTAZ-C16 exhibit a good fluorescence turn-on response toward polyphosphate anions, especially ATP, with the detection limits of 2.5 μM and 0.77 μM, respectively. Furthermore, probe PYTAZ-C16 was successfully used for fluorescence imaging of intracellular ATP in living cells.
{"title":"Amphiphilic pyrene-functionalized triazoliums for ATP recognition","authors":"Hong-Wei Huang , Yue-Bo He , Zhao-Hui Xin , Qian-Yong Cao","doi":"10.1016/j.molstruc.2024.140598","DOIUrl":"10.1016/j.molstruc.2024.140598","url":null,"abstract":"<div><div>Four pyrene functionalized triazolium salts with different lengths of alkyl tail from C4 to C16, i.e., <strong>PYTAZ-C4, PYTAZ-C8, PYTAZ-C12</strong> and <strong>PYTAZ-C16</strong>, have been designed and synthesized for ATP recognition. It was revealed that the longer alkyl tail anchored receptors <strong>PYTAZ-C12</strong> and <strong>PYTAZ-C16</strong> exhibit low CMC values, and self-assemble nanoaggregation at low concentration in aqueous solution, which show a pyrene-based excimer emission at 496 nm. However, the shorter alkyl anchored receptors <strong>PYTAZ-C4</strong> and <strong>PYTAZ-C8</strong> give only the pyrene-based monomer emission at 380 nm at the test concentration of 10 μM in aqueous solution. Importantly, <strong>PYTAZ-C12</strong> and <strong>PYTAZ-C16</strong> exhibit a good fluorescence turn-on response toward polyphosphate anions, especially ATP, with the detection limits of 2.5 μM and 0.77 μM, respectively. Furthermore, probe <strong>PYTAZ-C16</strong> was successfully used for fluorescence imaging of intracellular ATP in living cells.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140598"},"PeriodicalIF":4.0,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657224","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-03DOI: 10.1016/j.molstruc.2024.140595
Abdallah E. Abdallah , Hazem Elkady , Alaa Elwan , Mahmoud Rashed , Ali Hammad , Mohamed A. Elkady , Elsayed G.E. Elsakka , Mohamed S. Alesawy
In our attempts to improve pharmacokinetics and pharmacodynamics characters of vatalanib, four strategies of the drug design were applied to design and synthesis new quinoxaline based vatalanib analogs. Antiproliferative activities of the synthesized compounds were investigated against two tumor cell lines (HepG2 and HCT‐116) using vatalanib as a positive control. The new candidates showed promising anticancer activity against two tested cancer cell lines with IC50 values ranging from 6.04 ± 0.19 to 100.15 ± 3.26 µM, in particular compounds 11b and 11c which were more potent than vatalanib. The most potent was the 4-benzoylquinoxaline derivative 11b (IC50 = 6.04 ± 0.19 µM and 15.58 ± 0.58 µM) compared to vatalanib (IC50 of 25.27 ± 0.84 µM and 43.91 ± 1.64 µM) against HepG2 and HCT116, respectively. The selectivity indices of 11b were found to be approximately 14 and 5 towards HepG2 and HCT116, respectively. While vatalanib showed selectivity indices of about 5 and 3 towards HepG2 and HCT116, respectively. The most promising compound 11b was further investigated in HepG‐2 cells for its apoptotic effect, cell cycle arrest and in vitro VEGFR-2 inhibitory activity as the main mechanisms of cell death. It was found that 11b can induce apoptosis and arrest the cell cycle at the at G1 phase in addition to, compound 11b showed effective inhibition of VEGFR-2 with IC50 of 0.918 ± 0.033 µM compared to vatalanib (IC50 of 0.265 ± 0.009 µM). Deep computational studies were created for the designed compounds including molecular docking, physicochemical properties, profiling pharmacokinetics, ADMET studies, and toxicity predictions to evaluate the prospective drug candidates. The results of the docking study were consistent with biological testing, furthermore, in silico ADMET study revealed the superior pharmacokinetics characters of the new candidates over vatalanib. So, the current work suggests that the 4-benzoylquinoxaline-1-yl-acetamide derivatives, especially 11b, can serve as lead molecules for development of new effective anticancer drugs.
{"title":"New vatalanib analogs: Design, synthesis, in silico study and biological evaluation for anticancer activity","authors":"Abdallah E. Abdallah , Hazem Elkady , Alaa Elwan , Mahmoud Rashed , Ali Hammad , Mohamed A. Elkady , Elsayed G.E. Elsakka , Mohamed S. Alesawy","doi":"10.1016/j.molstruc.2024.140595","DOIUrl":"10.1016/j.molstruc.2024.140595","url":null,"abstract":"<div><div>In our attempts to improve pharmacokinetics and pharmacodynamics characters of vatalanib, four strategies of the drug design were applied to design and synthesis new quinoxaline based vatalanib analogs. Antiproliferative activities of the synthesized compounds were investigated against two tumor cell lines (HepG2 and HCT‐116) using vatalanib as a positive control. The new candidates showed promising anticancer activity against two tested cancer cell lines with IC<sub>50</sub> values ranging from 6.04 ± 0.19 to 100.15 ± 3.26 µM, in particular compounds <strong>11b</strong> and <strong>11c</strong> which were more potent than vatalanib. The most potent was the 4-benzoylquinoxaline derivative <strong>11b (</strong>IC<sub>50</sub> = 6.04 ± 0.19 µM and 15.58 ± 0.58 µM) compared to vatalanib (IC<sub>50</sub> of 25.27 ± 0.84 µM and 43.91 ± 1.64 µM) against HepG2 and HCT116, respectively. The selectivity indices of <strong>11b</strong> were found to be approximately 14 and 5 towards HepG2 and HCT116, respectively. While vatalanib showed selectivity indices of about 5 and 3 towards HepG2 and HCT116, respectively. The most promising compound <strong>11b</strong> was further investigated in HepG‐2 cells for its apoptotic effect, cell cycle arrest and in vitro VEGFR-2 inhibitory activity as the main mechanisms of cell death. It was found that <strong>11b</strong> can induce apoptosis and arrest the cell cycle at the at G1 phase in addition to, compound <strong>11b</strong> showed effective inhibition of VEGFR-2 with IC<sub>50</sub> of 0.918 ± 0.033 µM compared to vatalanib (IC<sub>50</sub> of 0.265 ± 0.009 µM). Deep computational studies were created for the designed compounds including molecular docking, physicochemical properties, profiling pharmacokinetics, ADMET studies, and toxicity predictions to evaluate the prospective drug candidates. The results of the docking study were consistent with biological testing, furthermore, <em>in silico</em> ADMET study revealed the superior pharmacokinetics characters of the new candidates over vatalanib. So, the current work suggests that the 4-benzoylquinoxaline-1-yl-acetamide derivatives, especially <strong>11b,</strong> can serve as lead molecules for development of new effective anticancer drugs.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140595"},"PeriodicalIF":4.0,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657216","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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