Pub Date : 2024-11-13DOI: 10.1186/s13065-024-01342-9
Omkulthom Al Kamaly, Amel S. Younes, Marwa F. Harras, Rehab Sabour, Aisha A. Alsfouk, Mona H. Ibrahim
A set of innovative N-amino-5-cyano-6-pyridones derivatives was developed and produced using one-pot three-component procedures. The evaluated molecules were examined for their antimicrobial efficacy. Based on the acquired findings, most of the investigated compounds had promising antimicrobial properties. Out of these derivatives of 3-cyanopyridine, compounds 3d and 3e exhibited minimum inhibitory concentrations (MIC) of 3.91 µg/mL against E.coli. In vitro evaluation of DNA gyrase A displayed that molecule 3d exhibited promising potency as an inhibitor, with an IC50 value of 1.68 µg/mL compared to ciprofloxacin (IC50 = 0.45 µg/mL). Furthermore, it was observed that molecule 3e exhibited a moderate inhibitory effect, as indicated by its IC50 value of 3.77 µg/mL. A kinetics study conducted to assess the time required to kill E. coli bacteria demonstrated that gentamycin and compounds 3d and 3e exhibited bactericidal effects within a time frame of 90–120 min. Based on the ADME predictions, compounds 3d and 3e are expected to have favorable oral bioavailability and are unlikely to penetrate the blood-brain barrier. Computational mutagenicity and tumorigenicity studies were conducted on compounds 3d and 3e. The molecular docking investigation has conclusively demonstrated the binding of compounds 3d and 3e to the target DNA gyrase A enzyme, further reinforcing the existing data.
采用三组份一锅法开发并生产了一组创新的 N-氨基-5-氰基-6-吡啶酮衍生物。对所评估的分子进行了抗菌功效检测。根据获得的研究结果,大多数研究化合物都具有良好的抗菌性能。在这些 3-氰基吡啶衍生物中,化合物 3d 和 3e 对大肠杆菌的最低抑制浓度 (MIC) 为 3.91 µg/mL。DNA 回旋酶 A 的体外评估显示,分子 3d 具有良好的抑制作用,与环丙沙星(IC50 = 0.45 µg/mL)相比,IC50 值为 1.68 µg/mL。此外,还观察到分子 3e 显示出中等程度的抑制作用,其 IC50 值为 3.77 微克/毫升。为评估杀死大肠杆菌所需的时间而进行的动力学研究表明,庆大霉素、化合物 3d 和 3e 在 90-120 分钟的时间范围内表现出杀菌效果。根据 ADME 预测,化合物 3d 和 3e 预计具有良好的口服生物利用度,不太可能穿透血脑屏障。对化合物 3d 和 3e 进行了诱变性和致瘤性计算研究。分子对接研究确证了化合物 3d 和 3e 与目标 DNA 回旋酶 A 的结合,进一步巩固了现有数据。
{"title":"New N-amino-5-cyano-6-pyridones as antimicrobial small molecules endowed with DNA gyrase a inhibitory activity: design, one-pot synthesis, biological assessment and in silico insights","authors":"Omkulthom Al Kamaly, Amel S. Younes, Marwa F. Harras, Rehab Sabour, Aisha A. Alsfouk, Mona H. Ibrahim","doi":"10.1186/s13065-024-01342-9","DOIUrl":"10.1186/s13065-024-01342-9","url":null,"abstract":"<div><p>A set of innovative <i>N</i>-amino-5-cyano-6-pyridones derivatives was developed and produced using one-pot three-component procedures. The evaluated molecules were examined for their antimicrobial efficacy. Based on the acquired findings, most of the investigated compounds had promising antimicrobial properties. Out of these derivatives of 3-cyanopyridine, compounds <b>3d</b> and <b>3e</b> exhibited minimum inhibitory concentrations (MIC) of 3.91 µg/mL against <i>E.coli</i>. In vitro evaluation of DNA gyrase A displayed that molecule <b>3d</b> exhibited promising potency as an inhibitor, with an IC<sub>50</sub> value of 1.68 µg/mL compared to ciprofloxacin (IC<sub>50</sub> = 0.45 µg/mL). Furthermore, it was observed that molecule <b>3e</b> exhibited a moderate inhibitory effect, as indicated by its IC<sub>50</sub> value of 3.77 µg/mL. A kinetics study conducted to assess the time required to kill <i>E. coli</i> bacteria demonstrated that gentamycin and compounds <b>3d</b> and <b>3e</b> exhibited bactericidal effects within a time frame of 90–120 min. Based on the ADME predictions, compounds <b>3d</b> and <b>3e</b> are expected to have favorable oral bioavailability and are unlikely to penetrate the blood-brain barrier. Computational mutagenicity and tumorigenicity studies were conducted on compounds <b>3d</b> and <b>3e</b>. The molecular docking investigation has conclusively demonstrated the binding of compounds <b>3d</b> and <b>3e</b> to the target DNA gyrase A enzyme, further reinforcing the existing data.</p></div>","PeriodicalId":496,"journal":{"name":"BMC Chemistry","volume":"18 1","pages":""},"PeriodicalIF":4.3,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://bmcchem.biomedcentral.com/counter/pdf/10.1186/s13065-024-01342-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142611872","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-11DOI: 10.1186/s13065-024-01341-w
Hilya N. Iman, Henry Susilo, Adhi Satriyatama, Ignatius D. M. Budi, Kiki A. Kurnia, I. G. Wenten, K. Khoiruddin
This research explores the enhancement of polyethersulfone (PES) membranes through the incorporation of chitosan derived from the lignicolous fungus Ganoderma sp. Utilizing wet phase inversion and solution casting techniques, chitosan was successfully integrated into the PES matrix, as confirmed by Fourier Transform Infrared Spectroscopy (FT-IR), which indicated a high deacetylation degree of 75.7%. The incorporation of chitosan significantly increased the membrane hydrophilicity, as evidenced by a reduction in the water contact angle and a substantial improvement in pure water permeability, from 17.9 L m-2 h-1 bar-1 to 27.3 L m-2 h-1 bar-1. The membrane anti-fouling properties were also notably enhanced, with the Flux Recovery Ratio (FRR) increasing from approximately 60–80%. Moreover, the chitosan-modified PES/CS membrane, particularly at a 5% chitosan concentration, demonstrated exceptional efficacy in pollutant removal, achieving over 90% elimination of total suspended solids, cadmium (Cd), and lead (Pb), alongside a 79% reduction in color during the treatment of textile wastewater.
{"title":"Separation properties and fouling resistance of polyethersulfone membrane modified by fungal chitosan","authors":"Hilya N. Iman, Henry Susilo, Adhi Satriyatama, Ignatius D. M. Budi, Kiki A. Kurnia, I. G. Wenten, K. Khoiruddin","doi":"10.1186/s13065-024-01341-w","DOIUrl":"10.1186/s13065-024-01341-w","url":null,"abstract":"<div><p>This research explores the enhancement of polyethersulfone (PES) membranes through the incorporation of chitosan derived from the lignicolous fungus <i>Ganoderma sp</i>. Utilizing wet phase inversion and solution casting techniques, chitosan was successfully integrated into the PES matrix, as confirmed by Fourier Transform Infrared Spectroscopy (FT-IR), which indicated a high deacetylation degree of 75.7%. The incorporation of chitosan significantly increased the membrane hydrophilicity, as evidenced by a reduction in the water contact angle and a substantial improvement in pure water permeability, from 17.9 L m<sup>-2</sup> h<sup>-1</sup> bar<sup>-1</sup> to 27.3 L m<sup>-2</sup> h<sup>-1</sup> bar<sup>-1</sup>. The membrane anti-fouling properties were also notably enhanced, with the Flux Recovery Ratio (FRR) increasing from approximately 60–80%. Moreover, the chitosan-modified PES/CS membrane, particularly at a 5% chitosan concentration, demonstrated exceptional efficacy in pollutant removal, achieving over 90% elimination of total suspended solids, cadmium (Cd), and lead (Pb), alongside a 79% reduction in color during the treatment of textile wastewater.</p></div>","PeriodicalId":496,"journal":{"name":"BMC Chemistry","volume":"18 1","pages":""},"PeriodicalIF":4.3,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://bmcchem.biomedcentral.com/counter/pdf/10.1186/s13065-024-01341-w","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142600567","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-11DOI: 10.1186/s13065-024-01328-7
Huda E. Abdelwahab, Mohammed Elhag, Mohamed M. El Sadek
Elevated Arsenic and Chromium levels in surface and ground waters are a significant health concern in several parts of the world. Chitosan quinoxaline Schiff base (CsQ) and cross-linked chitosan quinoxaline Schiff base (CsQG) were prepared to adsorb both Arsenate [As(V)] and Chromium [Cr(VI)] ions. The thermo-gravimetric analysis (TGA), X-ray diffraction analysis (XRD), and Fourier-transform infrared spectroscopy (FTIR) were used to investigate the prepared Schiff bases (CsQ) and (CsQG). The UV–VIS spectra showed a shift in the wavelength area of the modified polymer, indicating the reaction occurrence, besides the variation of the shape and intensity of the peaks. The XRD patterns showed the incensement of the amorphous characteristic. On the other hand, the thermal stability of the modified polymers is better according to TGA studies; also, the morphology of the modified chitosan was investigated before and after crosslinking (CsQ and CsQG) using a scanning electron microscope (SEM) where the surface was fall of wrinkles and pores, which then were decreased after cross-linking. Contact time, temperature, pH, and initial metal ion concentration were all studied as factors influencing metal ion uptake behavior. The Langmuir, Temkin, Dubinin–Radushkevich, and Freundlich isotherm models were used to describe the equilibrium data using metal concentrations of 10–1000 mg/L at pH = 7 and 1 g of adsorbent. The pseudo-first-order and pseudo-second-order kinetic parameters were evaluated. The experimental data revealed that the adsorption kinetics follow the mechanism of the pseudo-second-order equation with R2 values (0.9969, 0.9061) in case of using CsQ and R2 values (0.9989, 0.9999) in case of using CsQG, demonstrating chemical sorption is the rate-limiting step of the adsorption mechanism. Comparing the adsorption efficiency of the synthesized Schiff base and the cross-linked one, it was found that CsQ is a better adsorbent than CsQG in both cases of As(V) and Cr(VI) removal. This means that cross-linking doesn’t enhance the efficiency as expected, but on the contrary, in some cases, it decreases the removal. In addition, the newly modified chitosan polymers work better in As(V) removal than Cr(VI); the removal is 22.33% for Cr(VI) and 98.36% for As(V) using CsQ polymer, whereas using CsQG, the values are 6.20% and 91.75% respectively. On the other hand, the maximum adsorption capacity (Qm) for As(V) and Cr(VI) are 8.811 and 3.003 mg/g, respectively, using CsQ, while in the case of using CsQG, the Qm value reaches 31.95 mg/g for As(V), and 103.09 mg/g for Cr(VI).
{"title":"Removal of As(V) and Cr(VI) using quinoxaline chitosan schiff base: synthesis, characterization and adsorption mechanism","authors":"Huda E. Abdelwahab, Mohammed Elhag, Mohamed M. El Sadek","doi":"10.1186/s13065-024-01328-7","DOIUrl":"10.1186/s13065-024-01328-7","url":null,"abstract":"<div><p>Elevated Arsenic and Chromium levels in surface and ground waters are a significant health concern in several parts of the world. Chitosan quinoxaline Schiff base (CsQ) and cross-linked chitosan quinoxaline Schiff base (CsQG) were prepared to adsorb both Arsenate [As(V)] and Chromium [Cr(VI)] ions. The thermo-gravimetric analysis (TGA), X-ray diffraction analysis (XRD), and Fourier-transform infrared spectroscopy (FTIR) were used to investigate the prepared Schiff bases (CsQ) and (CsQG). The UV–VIS spectra showed a shift in the wavelength area of the modified polymer, indicating the reaction occurrence, besides the variation of the shape and intensity of the peaks. The XRD patterns showed the incensement of the amorphous characteristic. On the other hand, the thermal stability of the modified polymers is better according to TGA studies; also, the morphology of the modified chitosan was investigated before and after crosslinking (CsQ and CsQG) using a scanning electron microscope (SEM) where the surface was fall of wrinkles and pores, which then were decreased after cross-linking. Contact time, temperature, pH, and initial metal ion concentration were all studied as factors influencing metal ion uptake behavior. The Langmuir, Temkin, Dubinin–Radushkevich, and Freundlich isotherm models were used to describe the equilibrium data using metal concentrations of 10–1000 mg/L at pH = 7 and 1 g of adsorbent. The pseudo-first-order and pseudo-second-order kinetic parameters were evaluated. The experimental data revealed that the adsorption kinetics follow the mechanism of the pseudo-second-order equation with R<sup>2</sup> values (0.9969, 0.9061) in case of using CsQ and R<sup>2</sup> values (0.9989, 0.9999) in case of using CsQG, demonstrating chemical sorption is the rate-limiting step of the adsorption mechanism. Comparing the adsorption efficiency of the synthesized Schiff base and the cross-linked one, it was found that CsQ is a better adsorbent than CsQG in both cases of As(V) and Cr(VI) removal. This means that cross-linking doesn’t enhance the efficiency as expected, but on the contrary, in some cases, it decreases the removal. In addition, the newly modified chitosan polymers work better in As(V) removal than Cr(VI); the removal is 22.33% for Cr(VI) and 98.36% for As(V) using CsQ polymer, whereas using CsQG, the values are 6.20% and 91.75% respectively. On the other hand, the maximum adsorption capacity (Qm) for As(V) and Cr(VI) are 8.811 and 3.003 mg/g, respectively, using CsQ, while in the case of using CsQG, the Qm value reaches 31.95 mg/g for As(V), and 103.09 mg/g for Cr(VI).</p></div>","PeriodicalId":496,"journal":{"name":"BMC Chemistry","volume":"18 1","pages":""},"PeriodicalIF":4.3,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://bmcchem.biomedcentral.com/counter/pdf/10.1186/s13065-024-01328-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142600568","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-09DOI: 10.1186/s13065-024-01340-x
Shoaib Khan, Tayyiaba Iqbal, Muhammad Bilal Khan, Rafaqat Hussain, Yousaf Khan, Hany W. Darwish
As a springboard to explore novel potent inhibitors of cholinesterase enzymes (AChE and BChE) responsible for causing Alzheimer disorder, the current study was conducted to synthesize pyrrole derived triazole based Schiff base scaffolds by facile synthetic route. These compounds were validated by 1HNMR, 13CNMR and HREI-MS. All these scaffolds (1–16) were examined for their inhibitory activity against AChE and BChE in contrast to Donepezil (10.20 ± 0.10 and 10.80 ± 0.20 µM) and Allanzanthone (12.40 ± 0.10 and 13.10 ± 0.10 µM). All pyrrole derived triazole based Schiff base scaffolds (1–16) showed varied range of inhibitory potentials against acetylcholinesterase and butyrylcholinesterase enzymes with lowest inhibition concentration values ranging from 5.10 ± 0.40–27.10 ± 0.10 µM (for AChE) and 5.60 ± 0.30–28.40 ± 0.30 µM (for BChE). SAR analysis of these derivatives revealed analog 7 as lead molecule against targeted enzyme, while analog 6 and 11 were ranked as second and third most potent scaffolds. Binding affinity and selectivity of potent molecules against targeted enzymes were examined by molecular docking and obtained results showed that potent molecule have versatile significant binding interactions with stated enzymes. Furthermore, safety profiles of potent analogues were predicted via ADMET protocols.