Pub Date : 2024-04-13DOI: 10.2174/0113852728295467240219051245
Mohd Jahir Khan, Abrar Ahmad
: In the present study, an immobilization support, Polyaniline tin oxide nanocomposite (PANI-SnO2- NC) was synthesized by in situ polymerization of aniline and ammonium peroxydisulphate. The prepared nanocomposite was characterized by various state-of-the-art techniques. The average size of native SnO2-NPs and PANI-SnO2-NC was 65±19 nm and 93±15 nm, respectively. An important industrial enzyme, α-amylase from Aspergillus oryzae was immobilized on PANI-SnO2-NC, which retained 87% enzyme activity. The improved stability of the immobilized enzyme was noticed against pH and temperature, as it retained 65% activity at 60 °C while the free enzyme exhibited 41% activity under similar experimental conditions. Moreover, PANI-SnO2- NC-immobilized α-amylase produced starch (26.42 mg mL–1) more efficiently than free enzyme (20.90 mg mL– 1) after 8 h in batch hydrolysis. PANI-SnO2-NC-bound α-amylase exhibited 54% activity after eight repeated uses. Molecular docking analysis of α-amylase with PANI suggested the ligand binding site to be located quite far away from the active site of the enzyme.
{"title":"Improved Stability of Aspergillus oryzae α-Amylase Immobilized on Polyaniline Tin Oxide Nanocomposites","authors":"Mohd Jahir Khan, Abrar Ahmad","doi":"10.2174/0113852728295467240219051245","DOIUrl":"https://doi.org/10.2174/0113852728295467240219051245","url":null,"abstract":": In the present study, an immobilization support, Polyaniline tin oxide nanocomposite (PANI-SnO2- NC) was synthesized by in situ polymerization of aniline and ammonium peroxydisulphate. The prepared nanocomposite was characterized by various state-of-the-art techniques. The average size of native SnO2-NPs and PANI-SnO2-NC was 65±19 nm and 93±15 nm, respectively. An important industrial enzyme, α-amylase from Aspergillus oryzae was immobilized on PANI-SnO2-NC, which retained 87% enzyme activity. The improved stability of the immobilized enzyme was noticed against pH and temperature, as it retained 65% activity at 60 °C while the free enzyme exhibited 41% activity under similar experimental conditions. Moreover, PANI-SnO2- NC-immobilized α-amylase produced starch (26.42 mg mL–1) more efficiently than free enzyme (20.90 mg mL– 1) after 8 h in batch hydrolysis. PANI-SnO2-NC-bound α-amylase exhibited 54% activity after eight repeated uses. Molecular docking analysis of α-amylase with PANI suggested the ligand binding site to be located quite far away from the active site of the enzyme.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140581316","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-04-09DOI: 10.2174/0113852728292818240301052024
Jacek E. Nycz, Nataliya Karaush-Karmazin, Boris Minaev, Valentina Minaeva, Jan G. Małecki, Maria Książek, Daniel Swoboda, Joachim Kusz
: The quinoline derivatives arouse interest due to their broad spectrum of activity. The phosphorus compounds under investigation, quinolinylphosphonic and -phosphinic acids and aminophenylphosphonic and -phosphinic acids, possess potent bioactive properties, mimicking amino acids, phosphate esters, anhydrides, or carboxylate groups in enzymes. Despite its potential value, there is no reported example of quinolinylphosphonic or - phosphinic acids with phosphonic or phosphinic functional groups connected directly to the benzene ring in quinoline constitution. The selected quinoline derivatives have been synthesized by adopting the Skraup-Doebner-Von Miller reaction. To this end, the syntheses of aminophenylphosphonic and -phosphinic acids were conducted and afforded the target products with high yield. All structures have been proven by the combination of NMR, IR, MS, and HRMS techniques and were rationalized based on DFT calculation. The structures of triphenylphosphane oxide (TPO), diphenylphosphosphinic acid (1c), (tert-butyl)phenylphosphinic acid (1d) and bis(3-nitrophenyl)phosphinic acid (2c) were determined by single-crystal X-ray diffraction measurements. The Hirshfeld surface analyses for 1c, 1d and 2c were performed to analyze the intermolecular interactions in their crystal structures. Rephrase: According to our findings, the presence of numerous intermolecular PO•••H, NO•••H, and CH•••O contacts stabilizes the crystal structures. The NO•••H interactions manifest in the IR spectrum of 2c crystal as a narrow band with a maximum at 3088 cm-1. The PO•••H intermolecular interactions are attributed to a weak experimental band at 1288 cm-1. background: The quinoline derivatives arouse interest due to their broad spectrum of activity. The phosphorus compounds under investigation, such as quinolinylphosphonic or quinolinylphosphinic acids, aminophenylphosphonic or aminophenylphosphinic acids aminophenylphosphonic or aminophenylphosphinic acids, possess potent properties bioactive properties, mimicking amino acids, phosphate esters, anhydrides, or carboxylate groups in enzymes. Despite its potential value, there is no reported example of quinolinylphosphonic and quinolinylphosphinic acids with phosphonic and phosphinic functional groups directly connected to the benzene ring in quinoline constitution to the best of our knowledge, according to literature data. objective: Syntheses and spectroscopic characterization of selected methyl quinolinylphosphonic and quinolinylphosphinic acids, rationalized based on DFT calculation method: All the structures have been proven by the combination of NMR, IR, MS, and HRMS and rationalized based on DFT calculation. The structures of triphenylphosphane oxide (TPO), diphenylphosphosphinic acid (1c), (tert-butyl)phenylphosphinic acid (1d) and bis(3-nitrophenyl)phosphinic acid (2c) were determined by single-crystal X-ray diffraction measurements.
{"title":"Syntheses and Spectroscopic Characterization of Selected Methyl Quinolinylphosphonic and Quinolinylphosphinic Acids; Rationalized Based on DFT calculation","authors":"Jacek E. Nycz, Nataliya Karaush-Karmazin, Boris Minaev, Valentina Minaeva, Jan G. Małecki, Maria Książek, Daniel Swoboda, Joachim Kusz","doi":"10.2174/0113852728292818240301052024","DOIUrl":"https://doi.org/10.2174/0113852728292818240301052024","url":null,"abstract":": The quinoline derivatives arouse interest due to their broad spectrum of activity. The phosphorus compounds under investigation, quinolinylphosphonic and -phosphinic acids and aminophenylphosphonic and -phosphinic acids, possess potent bioactive properties, mimicking amino acids, phosphate esters, anhydrides, or carboxylate groups in enzymes. Despite its potential value, there is no reported example of quinolinylphosphonic or - phosphinic acids with phosphonic or phosphinic functional groups connected directly to the benzene ring in quinoline constitution. The selected quinoline derivatives have been synthesized by adopting the Skraup-Doebner-Von Miller reaction. To this end, the syntheses of aminophenylphosphonic and -phosphinic acids were conducted and afforded the target products with high yield. All structures have been proven by the combination of NMR, IR, MS, and HRMS techniques and were rationalized based on DFT calculation. The structures of triphenylphosphane oxide (TPO), diphenylphosphosphinic acid (1c), (tert-butyl)phenylphosphinic acid (1d) and bis(3-nitrophenyl)phosphinic acid (2c) were determined by single-crystal X-ray diffraction measurements. The Hirshfeld surface analyses for 1c, 1d and 2c were performed to analyze the intermolecular interactions in their crystal structures. Rephrase: According to our findings, the presence of numerous intermolecular PO•••H, NO•••H, and CH•••O contacts stabilizes the crystal structures. The NO•••H interactions manifest in the IR spectrum of 2c crystal as a narrow band with a maximum at 3088 cm-1. The PO•••H intermolecular interactions are attributed to a weak experimental band at 1288 cm-1. background: The quinoline derivatives arouse interest due to their broad spectrum of activity. The phosphorus compounds under investigation, such as quinolinylphosphonic or quinolinylphosphinic acids, aminophenylphosphonic or aminophenylphosphinic acids aminophenylphosphonic or aminophenylphosphinic acids, possess potent properties bioactive properties, mimicking amino acids, phosphate esters, anhydrides, or carboxylate groups in enzymes. Despite its potential value, there is no reported example of quinolinylphosphonic and quinolinylphosphinic acids with phosphonic and phosphinic functional groups directly connected to the benzene ring in quinoline constitution to the best of our knowledge, according to literature data. objective: Syntheses and spectroscopic characterization of selected methyl quinolinylphosphonic and quinolinylphosphinic acids, rationalized based on DFT calculation method: All the structures have been proven by the combination of NMR, IR, MS, and HRMS and rationalized based on DFT calculation. The structures of triphenylphosphane oxide (TPO), diphenylphosphosphinic acid (1c), (tert-butyl)phenylphosphinic acid (1d) and bis(3-nitrophenyl)phosphinic acid (2c) were determined by single-crystal X-ray diffraction measurements.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140581531","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-04-09DOI: 10.2174/0113852728295396240314054651
Irina V. Sterkhova, Lidiya N. Parshina, Lyudmila A. Grishchenko, Tatyana N. Borodina, Lyudmila A. Belovezhets, Valentin A. Semenov
: Complexes of cobalt(II) chloride with 1-propargylimidazole, 1-propargyl-2-methylimidazole, and 1- propargylbenzimidazole ligands were synthesized and studied by FTIR spectroscopy and X-ray analysis. According to the X-ray analysis, the crystal molecules of compounds were connected by non-covalent interactions, such as halogen bonds and π-stacking. The nature and energy of coordination metal-ligand and noncovalent bonds for structures under study were estimated in the frame of QTAIM (Quantum Theory “Atoms In Molecules”). The antimicrobial activity of obtained cobalt(II) chloride complexes was evaluated in relation to microorganisms, E. durans, B. subtilis, and E. coli. Complexes of 1-propargyl-2-methylimidazole and 1- propargylbenzimidazole with cobalt(II) chloride demonstrated high activity against E. coli and E. durans relatively and could be recommended as antimicrobial drugs.
:合成了氯化钴(II)与 1-丙炔基咪唑、1-丙炔基-2-甲基咪唑和 1-丙炔基苯并咪唑配体的配合物,并通过傅立叶变换红外光谱和 X 射线分析进行了研究。根据 X 射线分析,化合物的晶体分子通过卤素键和π堆叠等非共价相互作用连接在一起。在 QTAIM("原子在分子中 "量子理论)的框架内,对所研究结构的金属配位键和非共价键的性质和能量进行了估算。对所获得的氯化钴(II)络合物的抗菌活性进行了评估,这些络合物与微生物(杜氏大肠杆菌、枯草杆菌和大肠杆菌)有关。1- 丙炔基-2-甲基咪唑和 1- 丙炔基苯并咪唑与氯化钴(II)的络合物对大肠杆菌和杜兰氏菌表现出较高的活性,可推荐用作抗菌药物。
{"title":"Synthesis, Structure, and Antimicrobial Properties of New Cobalt(II) Complexes with 1-Propargylimidazoles","authors":"Irina V. Sterkhova, Lidiya N. Parshina, Lyudmila A. Grishchenko, Tatyana N. Borodina, Lyudmila A. Belovezhets, Valentin A. Semenov","doi":"10.2174/0113852728295396240314054651","DOIUrl":"https://doi.org/10.2174/0113852728295396240314054651","url":null,"abstract":": Complexes of cobalt(II) chloride with 1-propargylimidazole, 1-propargyl-2-methylimidazole, and 1- propargylbenzimidazole ligands were synthesized and studied by FTIR spectroscopy and X-ray analysis. According to the X-ray analysis, the crystal molecules of compounds were connected by non-covalent interactions, such as halogen bonds and π-stacking. The nature and energy of coordination metal-ligand and noncovalent bonds for structures under study were estimated in the frame of QTAIM (Quantum Theory “Atoms In Molecules”). The antimicrobial activity of obtained cobalt(II) chloride complexes was evaluated in relation to microorganisms, E. durans, B. subtilis, and E. coli. Complexes of 1-propargyl-2-methylimidazole and 1- propargylbenzimidazole with cobalt(II) chloride demonstrated high activity against E. coli and E. durans relatively and could be recommended as antimicrobial drugs.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140581030","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-04-09DOI: 10.2174/0113852728295939240315040152
Reema Abu Khalaf, Lama Jaradat, Maha Habash
: Cardiovascular disease is one of the primary causes of death. Atherosclerosis produces artery constriction or obstruction, which can lead to a heart attack or stroke. Cholesteryl Ester Transfer Protein (CETP) is a protein that aids in reverse cholesterol transport. It promotes cholesteryl ester transfer from HDL to LDL and VLDL. So, inhibition of CETP by drugs limits cardiovascular disease by decreasing LDL and increasing HDL cholesterol. In this study, ten ortho-fluoro substituted benzenesulfonamides 6a-6j were prepared, and their structure was fully determined using 1H NMR, 13C NMR, HR-MS, and IR. In vitro biological evaluation showed that compound 6d has the highest inhibitory activity with 100% inhibition, while compounds 6a-6c and 6e-6j had activities ranged from 29% - 83% at 10 μM concentration. Interestingly, para-substituted derivatives (6d, 6g, and 6j) were observed to have greater CETP inhibitory activities than their ortho- and meta- analogues irrespective to the nature of substituent, i.e., CH3, Cl, or NO2. Ligandfit docking experiment revealed the difference in the binding mode among the synthesized compounds, which is reflected in their CETP inhibitory activity. background: Cardiovascular disease is one of the primary causes of death. Atherosclerosis produces artery constriction or obstruction, which can lead to a heart attack or stroke. Cholesteryl ester transfer protein (CETP) is a protein that aids in reverse cholesterol transport. It promotes cholesteryl ester transfer from HDL to LDL and VLDL. So, inhibition of CETP by drugs limits cardiovascular disease by decreasing LDL and increasing HDL cholesterol. method: and their structure was fully determined using 1H-NMR, 13C-NMR, HR-MS, and IR. conclusion: Ligandfit docking experiment revealed the difference in the binding mode among the synthesized compounds which is reflected on their CETP inhibitory activity.
{"title":"Synthesis and In-Silico Studies of Ortho-Fluorinated Benzenesulfonamides as Putative Anti-CETP Agents","authors":"Reema Abu Khalaf, Lama Jaradat, Maha Habash","doi":"10.2174/0113852728295939240315040152","DOIUrl":"https://doi.org/10.2174/0113852728295939240315040152","url":null,"abstract":": Cardiovascular disease is one of the primary causes of death. Atherosclerosis produces artery constriction or obstruction, which can lead to a heart attack or stroke. Cholesteryl Ester Transfer Protein (CETP) is a protein that aids in reverse cholesterol transport. It promotes cholesteryl ester transfer from HDL to LDL and VLDL. So, inhibition of CETP by drugs limits cardiovascular disease by decreasing LDL and increasing HDL cholesterol. In this study, ten ortho-fluoro substituted benzenesulfonamides 6a-6j were prepared, and their structure was fully determined using 1H NMR, 13C NMR, HR-MS, and IR. In vitro biological evaluation showed that compound 6d has the highest inhibitory activity with 100% inhibition, while compounds 6a-6c and 6e-6j had activities ranged from 29% - 83% at 10 μM concentration. Interestingly, para-substituted derivatives (6d, 6g, and 6j) were observed to have greater CETP inhibitory activities than their ortho- and meta- analogues irrespective to the nature of substituent, i.e., CH3, Cl, or NO2. Ligandfit docking experiment revealed the difference in the binding mode among the synthesized compounds, which is reflected in their CETP inhibitory activity. background: Cardiovascular disease is one of the primary causes of death. Atherosclerosis produces artery constriction or obstruction, which can lead to a heart attack or stroke. Cholesteryl ester transfer protein (CETP) is a protein that aids in reverse cholesterol transport. It promotes cholesteryl ester transfer from HDL to LDL and VLDL. So, inhibition of CETP by drugs limits cardiovascular disease by decreasing LDL and increasing HDL cholesterol. method: and their structure was fully determined using 1H-NMR, 13C-NMR, HR-MS, and IR. conclusion: Ligandfit docking experiment revealed the difference in the binding mode among the synthesized compounds which is reflected on their CETP inhibitory activity.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140581351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}