Aleksandar Mijatovic, Angelina Cakovic, Aleksandar Lolic, Snezana Sretenovic, Marko Zivanovic, Dragana Seklic, Jovana Bogojeski, Biljana Petrovic
Three Schiff base Cu(II) complexes, (N,N?-bis(acetylacetone)- propylenediimine)copper(II) complex, [Cu(acac2pn)] (1), (N,N'-bis- (benzoylacetone)propylenediimine)copper(II) complex, [Cu(phacac2pn)] (2) and (N,N?-bis-(trifluoroacetylacetone)propylenediimine)copper(II) complex, [Cu(tfacac2pn)] (3), were used to investigate the interactions with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) using the electronic absorption and spectroscopic fluorescence methods. UV-Vis absorption studies showed that studied complexes interact with DNA molecule and exhibit moderate binding affinity. Fluorescence studies of complexes 1-3 also showed a possibility for DNA intercalation as well as a relatively high binding ability toward BSA. Among the tested complexes, the highest affinity for DNA and BSA molecules was shown by complex 1. Cytotoxic analyses, performed on human colorectal carcinoma HCT-116 and healthy lung fibroblast MRC-5 cell lines, showed that complex 2 exhibited activity on both cell lines, while complexes 1 and 3 did not show any activity.
{"title":"DNA/BSA interactions and cytotoxic studies of tetradentate N,N,O,O Schiff base copper(II) complexes","authors":"Aleksandar Mijatovic, Angelina Cakovic, Aleksandar Lolic, Snezana Sretenovic, Marko Zivanovic, Dragana Seklic, Jovana Bogojeski, Biljana Petrovic","doi":"10.2298/jsc230614063m","DOIUrl":"https://doi.org/10.2298/jsc230614063m","url":null,"abstract":"Three Schiff base Cu(II) complexes, (N,N?-bis(acetylacetone)- propylenediimine)copper(II) complex, [Cu(acac2pn)] (1), (N,N'-bis- (benzoylacetone)propylenediimine)copper(II) complex, [Cu(phacac2pn)] (2) and (N,N?-bis-(trifluoroacetylacetone)propylenediimine)copper(II) complex, [Cu(tfacac2pn)] (3), were used to investigate the interactions with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) using the electronic absorption and spectroscopic fluorescence methods. UV-Vis absorption studies showed that studied complexes interact with DNA molecule and exhibit moderate binding affinity. Fluorescence studies of complexes 1-3 also showed a possibility for DNA intercalation as well as a relatively high binding ability toward BSA. Among the tested complexes, the highest affinity for DNA and BSA molecules was shown by complex 1. Cytotoxic analyses, performed on human colorectal carcinoma HCT-116 and healthy lung fibroblast MRC-5 cell lines, showed that complex 2 exhibited activity on both cell lines, while complexes 1 and 3 did not show any activity.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135557155","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Stefan Richter, Peter Lönnecke, Dijana Bovan, Sanja Mijatovic, Danijela Maksimovic-Ivanic, Goran Kaludjerovic, Evamarie Hey-Hawkins
The coordination behavior of three ligand precursors 2-[(2- pyridinylmethyl)amino]acetic acid hydrochloride, 4-[(2- pyridinylmethyl)amino]benzoic acid hydrochloride and 4-{[2-(pyridin-2- ylmethylamino)ethylamino]methyl}benzoic acid hydrochloride, HL1?HCl- HL3?HCl, respectively, in copper(II) complexes is described. The complexes were characterized by elemental analysis, ESI mass spectrometry and IR spectroscopy, as well as X-ray structural analysis. The reaction of copper(II) with HL1?HCl in methanol afforded the polymeric complex [{Cu(?-Cl)2(MeL1- ?2N,N?)}n] (1) featuring the methyl ester of L1 (MeL1). With HL2?HCl or HL3?HCl, the dimeric complex [{CuCl(?-Cl)(HL2-?2N,N?)}2] (2) or the mononuclear complex [CuCl2(HL3-?3N,N?,N??)] (3) were obtained. All complexes exhibited square-pyramidal geometries. In 1, polymeric chains are formed through bridging chlorido ligands without typical hydrogen bonding interaction. Contrarily, the COOH group in 2 is participating in the formation of intermolecular hydrogen bonding forming a supramolecular structure. In 3, intermolecular hydrogen bonding (Cl?O) leads to a 1-D polymeric structure. The copper(II) complex 2 diminished viability of human 8505C, MCF-7, 518A2 and SW480 cell lines. The tumoricidal effect of 2 was realized mainly through caspase-mediated apoptosis.
{"title":"Square-pyramidal mononuclear, dinuclear and polymeric copper(II) complexes with (2-pyridinylmethyl)amino derivatives","authors":"Stefan Richter, Peter Lönnecke, Dijana Bovan, Sanja Mijatovic, Danijela Maksimovic-Ivanic, Goran Kaludjerovic, Evamarie Hey-Hawkins","doi":"10.2298/jsc230818072r","DOIUrl":"https://doi.org/10.2298/jsc230818072r","url":null,"abstract":"The coordination behavior of three ligand precursors 2-[(2- pyridinylmethyl)amino]acetic acid hydrochloride, 4-[(2- pyridinylmethyl)amino]benzoic acid hydrochloride and 4-{[2-(pyridin-2- ylmethylamino)ethylamino]methyl}benzoic acid hydrochloride, HL1?HCl- HL3?HCl, respectively, in copper(II) complexes is described. The complexes were characterized by elemental analysis, ESI mass spectrometry and IR spectroscopy, as well as X-ray structural analysis. The reaction of copper(II) with HL1?HCl in methanol afforded the polymeric complex [{Cu(?-Cl)2(MeL1- ?2N,N?)}n] (1) featuring the methyl ester of L1 (MeL1). With HL2?HCl or HL3?HCl, the dimeric complex [{CuCl(?-Cl)(HL2-?2N,N?)}2] (2) or the mononuclear complex [CuCl2(HL3-?3N,N?,N??)] (3) were obtained. All complexes exhibited square-pyramidal geometries. In 1, polymeric chains are formed through bridging chlorido ligands without typical hydrogen bonding interaction. Contrarily, the COOH group in 2 is participating in the formation of intermolecular hydrogen bonding forming a supramolecular structure. In 3, intermolecular hydrogen bonding (Cl?O) leads to a 1-D polymeric structure. The copper(II) complex 2 diminished viability of human 8505C, MCF-7, 518A2 and SW480 cell lines. The tumoricidal effect of 2 was realized mainly through caspase-mediated apoptosis.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135748626","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Palygorskite is a magnesium-rich aluminosilicate clay mineral with a unique chain-layered structure. This structure gives palygorskite a large specific surface area and interesting physical properties. Many researchers have investigated the applications of palygorskite in various fields, including heavy metal adsorption, petroleum and chemical industries, building materials, medicine, and agriculture. In this study, molecular dynamics simulations were used to explore the heavy metal adsorption ability of palygorskite. The results showed that polyacrylic acid (PAA) had a heavy metal adsorption ability. In terms of the ability of the substrate to adsorb Pb2+, Ni2+, and Cr3+, palygorskite (attapulgite, ATP) was more effective than SiO2 or clay. Based on this study, the same phenomenon reported in the literature was confirmed, and it was demonstrated that molecular dynamics could properly simulate the filtration of heavy metal ions in water using novel materials. Moreover, H+ ions were found to play an essential role in assisting PAA/ATP in capturing heavy metal ions. Using this method, we were able to observe the details of heavy-ion adsorption.
{"title":"Study of the metal ion adsorption capacity of palygorskite by computer simulation","authors":"Chuan-Wen Liu, Min-Hsien Liu, To-Mai Wang, Cheng-Lung Chen","doi":"10.2298/jsc230708082l","DOIUrl":"https://doi.org/10.2298/jsc230708082l","url":null,"abstract":"Palygorskite is a magnesium-rich aluminosilicate clay mineral with a unique chain-layered structure. This structure gives palygorskite a large specific surface area and interesting physical properties. Many researchers have investigated the applications of palygorskite in various fields, including heavy metal adsorption, petroleum and chemical industries, building materials, medicine, and agriculture. In this study, molecular dynamics simulations were used to explore the heavy metal adsorption ability of palygorskite. The results showed that polyacrylic acid (PAA) had a heavy metal adsorption ability. In terms of the ability of the substrate to adsorb Pb2+, Ni2+, and Cr3+, palygorskite (attapulgite, ATP) was more effective than SiO2 or clay. Based on this study, the same phenomenon reported in the literature was confirmed, and it was demonstrated that molecular dynamics could properly simulate the filtration of heavy metal ions in water using novel materials. Moreover, H+ ions were found to play an essential role in assisting PAA/ATP in capturing heavy metal ions. Using this method, we were able to observe the details of heavy-ion adsorption.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135211083","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Deana Andric, Sladjana Dukic-Stefanovic, Mihajlo Krunic, Ivana Jevtic, Jelena Penjisevic, Vladimir Sukalovic, Sladjana Kostic-Rajacic
Serotonin, or 5-hydroxytryptamine (5-HT), is a biogenic amine most noted as a neurotransmitter, an activator of the utmost subtype family of G-protein-coupled receptors (GPCR). Drugs targeting 5-HT1A and other 5-HT receptors treat central nervous system diseases such as schizophrenia and depression. Recent advances in serotonin receptor structure research gave us several crystal 5-HT1A receptor structures, most notably 5-HT1A bound to the antipsychotic drug aripiprazole (Abilify?). This discovery prompted us to evaluate a series of newly synthesized ligands for serotonergic activity since those arylpiperazine derivatives share minimal general structure with aripiprazole. The results of molecular docking analysis of unsubstituted starting substances encouraged us to propound further modifications of the tail and head parts of the parent molecules to maximize receptor binding affinity. Intrigued by the results of molecular analysis, all foreseen derivatives were synthesized. The pharmacological activity of all nine (5a and 6a are synthesised previously) compounds was assessed by the in vitro tests, and in silico pharmacokinetics predictions for the most promising candidates. All tested ligands have improved affinity compering to parent compounds (10a and 11a), 8b and 9b expressed the best pharmacological profile with an improved binding affinity toward serotonin 5-HT1A receptors (Ki 12.1 and 4.8 nM, respectively.
{"title":"Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides","authors":"Deana Andric, Sladjana Dukic-Stefanovic, Mihajlo Krunic, Ivana Jevtic, Jelena Penjisevic, Vladimir Sukalovic, Sladjana Kostic-Rajacic","doi":"10.2298/jsc230906076a","DOIUrl":"https://doi.org/10.2298/jsc230906076a","url":null,"abstract":"Serotonin, or 5-hydroxytryptamine (5-HT), is a biogenic amine most noted as a neurotransmitter, an activator of the utmost subtype family of G-protein-coupled receptors (GPCR). Drugs targeting 5-HT1A and other 5-HT receptors treat central nervous system diseases such as schizophrenia and depression. Recent advances in serotonin receptor structure research gave us several crystal 5-HT1A receptor structures, most notably 5-HT1A bound to the antipsychotic drug aripiprazole (Abilify?). This discovery prompted us to evaluate a series of newly synthesized ligands for serotonergic activity since those arylpiperazine derivatives share minimal general structure with aripiprazole. The results of molecular docking analysis of unsubstituted starting substances encouraged us to propound further modifications of the tail and head parts of the parent molecules to maximize receptor binding affinity. Intrigued by the results of molecular analysis, all foreseen derivatives were synthesized. The pharmacological activity of all nine (5a and 6a are synthesised previously) compounds was assessed by the in vitro tests, and in silico pharmacokinetics predictions for the most promising candidates. All tested ligands have improved affinity compering to parent compounds (10a and 11a), 8b and 9b expressed the best pharmacological profile with an improved binding affinity toward serotonin 5-HT1A receptors (Ki 12.1 and 4.8 nM, respectively.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136302322","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Andrei Bitang, Viorel Bitang, Vlad Grosu, Alecu Ciorsac, Adriana Isvoran
There is control over the use and marketing of steroids, and new compounds that mimic their effects, steroid derivatives, are being synthesized. They are frequently produced as dietary supplements intended to improve physical activity, and usually no information is provided regarding their ingredients, dosages, and efficacy or safety. In this study, a computational approach was used to evaluate the absorption, distribution, metabolism, excretion and toxicity (ADMET) profiles of several steroid derivatives: methasterone, methyl-1-testosterone, 4-hydroxytestosterone, methyldienolone, methyltrienolone, 19-nor-5-androstenedione. The following computational prediction tools were applied: admetSAR2.0, ADMETLab2.0, Endocrine Disruptome, PredSkin3.0. All investigated compounds showed good human intestinal absorption, are not able to penetrate the blood-brain barrier and inhibit cytochrome P450 enzymes involved in the metabolism of xenobiotics. These compounds have potential for skin sensitisation, induce reproductive toxicity and endocrine disruption, and have a low potential for hepatotoxicity and respiratory toxicity. The results of the study are important to be known by those who are exposed at workplaces where these compounds are produced and packed and by consumers. These predictions can also guide the experimental evaluation of the possible toxicity of the investigated compounds, the results of which can be further used for purposes of regulating the use of these steroid derivatives.
{"title":"Admet profiles of selected anabolic steroid derivatives","authors":"Andrei Bitang, Viorel Bitang, Vlad Grosu, Alecu Ciorsac, Adriana Isvoran","doi":"10.2298/jsc230803086b","DOIUrl":"https://doi.org/10.2298/jsc230803086b","url":null,"abstract":"There is control over the use and marketing of steroids, and new compounds that mimic their effects, steroid derivatives, are being synthesized. They are frequently produced as dietary supplements intended to improve physical activity, and usually no information is provided regarding their ingredients, dosages, and efficacy or safety. In this study, a computational approach was used to evaluate the absorption, distribution, metabolism, excretion and toxicity (ADMET) profiles of several steroid derivatives: methasterone, methyl-1-testosterone, 4-hydroxytestosterone, methyldienolone, methyltrienolone, 19-nor-5-androstenedione. The following computational prediction tools were applied: admetSAR2.0, ADMETLab2.0, Endocrine Disruptome, PredSkin3.0. All investigated compounds showed good human intestinal absorption, are not able to penetrate the blood-brain barrier and inhibit cytochrome P450 enzymes involved in the metabolism of xenobiotics. These compounds have potential for skin sensitisation, induce reproductive toxicity and endocrine disruption, and have a low potential for hepatotoxicity and respiratory toxicity. The results of the study are important to be known by those who are exposed at workplaces where these compounds are produced and packed and by consumers. These predictions can also guide the experimental evaluation of the possible toxicity of the investigated compounds, the results of which can be further used for purposes of regulating the use of these steroid derivatives.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135447646","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The synthesis, structural analysis and spectroscopic characterisation of three new 7-azaindole ligands is reported, alongside a novel 7-azaindole derived coordination polymer, with the aim of identifying new bridging ligands containing inner-sphere hydrogen bond donor functionality. Structural characterisation shows that the 7-azaindole hydrogen bond donor ability is significantly stronger in the hydrazone and imine species 1 and 2 compared to the amine 3, with the opposite trend evident in their hydrogen bond acceptor character. These findings are mirrored by the fluorescence spectroscopy results which show bimodal emission, characteristic of multiple emissive species related by proton transfer, is only evident in the amine species and not the more acidic imines. The polymeric copper(II) complex of the hydrazone ligand 1 shows the anticipated inner-sphere hydrogen bonding with a similar donor strength to that observed in the free ligand, which leads to deformation in the remainder of the coordination sphere. These results show the untapped versatility of the 7-azaindole functional group as a building block for ligands in coordination polymers and other multinuclear assemblies, with the potential for both stabilisation through hydrogen bonding and interesting photophysical properties.
{"title":"Ligands containing 7-azaindole functionality for inner-sphere hydrogen bonding: structural and photophysical investigations","authors":"Alec Coles, Oskar Wood, Chris Hawes","doi":"10.2298/jsc230623061c","DOIUrl":"https://doi.org/10.2298/jsc230623061c","url":null,"abstract":"The synthesis, structural analysis and spectroscopic characterisation of three new 7-azaindole ligands is reported, alongside a novel 7-azaindole derived coordination polymer, with the aim of identifying new bridging ligands containing inner-sphere hydrogen bond donor functionality. Structural characterisation shows that the 7-azaindole hydrogen bond donor ability is significantly stronger in the hydrazone and imine species 1 and 2 compared to the amine 3, with the opposite trend evident in their hydrogen bond acceptor character. These findings are mirrored by the fluorescence spectroscopy results which show bimodal emission, characteristic of multiple emissive species related by proton transfer, is only evident in the amine species and not the more acidic imines. The polymeric copper(II) complex of the hydrazone ligand 1 shows the anticipated inner-sphere hydrogen bonding with a similar donor strength to that observed in the free ligand, which leads to deformation in the remainder of the coordination sphere. These results show the untapped versatility of the 7-azaindole functional group as a building block for ligands in coordination polymers and other multinuclear assemblies, with the potential for both stabilisation through hydrogen bonding and interesting photophysical properties.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135557160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This study is the first work that focuses on unconventional ionic liquids hydrodistillation (IL-HD) extraction of the essential oil of Heliotropium europaeum L. using ionic liquids (ILs) as additives. Two ILs based on 1-butyl- 3-methylimidazolium were used by switching the anions (Cl- and PF6-). The effect of mass percent adding ILs on its yield and composition was evaluated. Compared to conventional hydrodistillation (HD), ILs-HD gives a higher yield of essential oils (0.10-0.36%). Particularly, with [C4mim] [PF6], observation of morphological changes using scanning electron microscopy (SEM) confirmed the effectiveness of the ionic liquid in this distillation process. The GC-MS analysis of essential oils (EOs) revealed the presence of sixty-six compounds in HD, ILs-HD methods. GC-MS analyze of the EOs revealed predominance of Eugenol (1.70-72.35%), Butylated hydroxytoluene (8.95-65.39%) and Phytol (18.20%). The new distillation methods of H. europaeum with ILs identifies more compounds (50 compounds in ILs-HD [C4mim] [PF6]; 22 compounds in ILs-HD [C4mim] [Cl]) than conventional hydrodistillation (25 compounds in HD). Therefore, the ILs-based hydrodistillation approach is superior in improving the production of EOs. It is important to emphasize that the data presented in this study are not yet available for any of this Algerian Heliotropium species of genus and reveal in literature the great potential of this medicinal plant as a source of novel bioactive extracts with potential therapeutic uses.
{"title":"Co-detection of eugenol and butylated hydroxyltoluene by green and selective hydrodistillation of Heliotropium europaeum L. using ionic liquids as additives","authors":"Sara Bendjelloul, Choukry Bendeddouche, Souhila Bendeddouche, Madani Sarri, Feriha Bensafiddine, Nadia Kambouche, Ludovic Paquin, Mohamed Yousfi, Mohamed Harrat","doi":"10.2298/jsc230713075b","DOIUrl":"https://doi.org/10.2298/jsc230713075b","url":null,"abstract":"This study is the first work that focuses on unconventional ionic liquids hydrodistillation (IL-HD) extraction of the essential oil of Heliotropium europaeum L. using ionic liquids (ILs) as additives. Two ILs based on 1-butyl- 3-methylimidazolium were used by switching the anions (Cl- and PF6-). The effect of mass percent adding ILs on its yield and composition was evaluated. Compared to conventional hydrodistillation (HD), ILs-HD gives a higher yield of essential oils (0.10-0.36%). Particularly, with [C4mim] [PF6], observation of morphological changes using scanning electron microscopy (SEM) confirmed the effectiveness of the ionic liquid in this distillation process. The GC-MS analysis of essential oils (EOs) revealed the presence of sixty-six compounds in HD, ILs-HD methods. GC-MS analyze of the EOs revealed predominance of Eugenol (1.70-72.35%), Butylated hydroxytoluene (8.95-65.39%) and Phytol (18.20%). The new distillation methods of H. europaeum with ILs identifies more compounds (50 compounds in ILs-HD [C4mim] [PF6]; 22 compounds in ILs-HD [C4mim] [Cl]) than conventional hydrodistillation (25 compounds in HD). Therefore, the ILs-based hydrodistillation approach is superior in improving the production of EOs. It is important to emphasize that the data presented in this study are not yet available for any of this Algerian Heliotropium species of genus and reveal in literature the great potential of this medicinal plant as a source of novel bioactive extracts with potential therapeutic uses.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136301950","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
O. Babatunde, S. Hameed, Kingsley A. Mbachu, F. Saleem, S. Chigurupati, A. Wadood, Rehman Ur, V. Venugopal, Khalid M Khan, M. Taha, O. Ekundayo, M. Khan
In search of potent inhibitors of cholinesterase enzymes and antioxidant agents, synthetic derivatives dihydroquinazolin-4(1H)-one 1-38 were evaluated as potential anti-Alzheimer agents through in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitions and radical (DPPH and ABTS) scavenging activities. The (SAR) was mainly based on the different substituents at the aryl part which showed a significant effect on the inhibitory potential of enzymes and radical scavenging activities. The kinetic studies of most active compounds showed a noncompetitive mode of inhibition for AChE and a competitive mode of inhibition for the BChE enzyme. Additionally, molecular modeling studies were carried out to investigate the possible binding interactions of quinazolinone derivatives with the active site of both enzymes.
{"title":"Evaluation of derivatives of 2,3-dihydroquinazolin-4(1H)-one as inhibitors of cholinesterases and their antioxidant activity: In vitro, in silico, and kinetics studies","authors":"O. Babatunde, S. Hameed, Kingsley A. Mbachu, F. Saleem, S. Chigurupati, A. Wadood, Rehman Ur, V. Venugopal, Khalid M Khan, M. Taha, O. Ekundayo, M. Khan","doi":"10.2298/jsc211106005b","DOIUrl":"https://doi.org/10.2298/jsc211106005b","url":null,"abstract":"In search of potent inhibitors of cholinesterase enzymes and antioxidant agents, synthetic derivatives dihydroquinazolin-4(1H)-one 1-38 were evaluated as potential anti-Alzheimer agents through in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitions and radical (DPPH and ABTS) scavenging activities. The (SAR) was mainly based on the different substituents at the aryl part which showed a significant effect on the inhibitory potential of enzymes and radical scavenging activities. The kinetic studies of most active compounds showed a noncompetitive mode of inhibition for AChE and a competitive mode of inhibition for the BChE enzyme. Additionally, molecular modeling studies were carried out to investigate the possible binding interactions of quinazolinone derivatives with the active site of both enzymes.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"68510713","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this study, an NMR spectral analysis of the mixture of diastereomeric acetals, synthesized from 2,3-dihydrofurane and a racemic mixture of citronellol, was performed. 1H NMR full spin analysis was achieved by manually adjusting ?H and J values (previously calculated using the Spartan software) to fit the experimentally available values, followed by further optimization using MestreNova software. The simulated 1H- and 13C-NMR spectra of individual diastereomers, as well as their superimposed and summed spectra, were compared with the obtained experimental spectra. Spin simulation of proton signals was particularly useful for the assignment of the diastereotopic protons of tetrahydrofuranyl moiety and diastereomer discrimination. The NMR spectral data of individual diastereomers - chemical shifts, coupling constants, HMBC, and NOESY interactions were systematized in appropriate tables and schemes. To the best of our knowledge, this is for the first time that the complete assignment of tetrahydrofuranyl moiety was performed, and the data obtained herein may be of great importance for the utilization of this protecting group in the future.
{"title":"Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation","authors":"Milan Nešić, M. Nesic, N. Radulović","doi":"10.2298/jsc230614054n","DOIUrl":"https://doi.org/10.2298/jsc230614054n","url":null,"abstract":"In this study, an NMR spectral analysis of the mixture of diastereomeric acetals, synthesized from 2,3-dihydrofurane and a racemic mixture of citronellol, was performed. 1H NMR full spin analysis was achieved by manually adjusting ?H and J values (previously calculated using the Spartan software) to fit the experimentally available values, followed by further optimization using MestreNova software. The simulated 1H- and 13C-NMR spectra of individual diastereomers, as well as their superimposed and summed spectra, were compared with the obtained experimental spectra. Spin simulation of proton signals was particularly useful for the assignment of the diastereotopic protons of tetrahydrofuranyl moiety and diastereomer discrimination. The NMR spectral data of individual diastereomers - chemical shifts, coupling constants, HMBC, and NOESY interactions were systematized in appropriate tables and schemes. To the best of our knowledge, this is for the first time that the complete assignment of tetrahydrofuranyl moiety was performed, and the data obtained herein may be of great importance for the utilization of this protecting group in the future.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"68517777","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sandra Stamenkovic-Stojanovic, Ivana T. Karabegović, B. Danilović, Stojan Mančić, M. Lazić
Bacillus subtilis is a non-pathogenic, sporulating, gram-positive bacteria with pronounced antimicrobial and metabolic activity and great potential for wide application in various fields. The aim of this paper was to determine the optimum B. subtilis NCIM 2063 growth conditions and to scale up biomass production from shake flasks to a bioreactor level. The critical growth parameters and their interaction effects were studied using Box-Bekhen experimental design and response surface methodology. Developed model equations were statistically significant with good prediction capability. It was found that during shake flask cultivation glucose should be added in concentration up to 5 g l-1 in DSM medium, OTR at 10 mol m-3h-1 and temperature of 33 ?C, to achieve the maximum number of viable cells and spores. To scale up the process from shake flasks to the bioreactor level kLa was used as a main criterion. Scale up effect was evaluated by comparing the growth kinetics in the shake flasks and in a laboratory bioreactor. The total number of cells obtained in the bioreactor was 4.57?109 CFU ml-1 which is 1.41 times higher than the number of cells in the shake flasks (3.24?109 CFU ml-1), proving that the scale-up procedure was conducted successfully.
枯草芽孢杆菌是一种非致病性、产孢子的革兰氏阳性菌，具有显著的抗菌和代谢活性，在各个领域具有广泛的应用潜力。本文的目的是确定最佳枯草芽孢杆菌NCIM 2063的生长条件，并将生物质生产从摇瓶扩大到生物反应器水平。采用Box-Bekhen试验设计和响应面法研究了关键生长参数及其交互效应。所建立的模型方程具有统计学显著性，预测能力较好。在摇瓶培养过程中，在DSM培养基中添加浓度为5 g l-1的葡萄糖，在10 mol m-3h-1的OTR和33℃的温度下，可以达到最大的活细胞和孢子数量。为了将工艺从摇瓶放大到生物反应器水平，kLa被用作主要标准。通过比较摇瓶和实验室生物反应器中的生长动力学来评估放大效应。在生物反应器中获得的细胞总数为4.57?109 CFU ml-1，比摇瓶中的细胞数(3.24?109 CFU ml-1)，证明放大过程成功进行。
{"title":"High cell density cultivation of Bacillus subtilis NCIM 2063: Modeling, optimization and a scale-up procedure","authors":"Sandra Stamenkovic-Stojanovic, Ivana T. Karabegović, B. Danilović, Stojan Mančić, M. Lazić","doi":"10.2298/jsc230407036s","DOIUrl":"https://doi.org/10.2298/jsc230407036s","url":null,"abstract":"Bacillus subtilis is a non-pathogenic, sporulating, gram-positive bacteria with pronounced antimicrobial and metabolic activity and great potential for wide application in various fields. The aim of this paper was to determine the optimum B. subtilis NCIM 2063 growth conditions and to scale up biomass production from shake flasks to a bioreactor level. The critical growth parameters and their interaction effects were studied using Box-Bekhen experimental design and response surface methodology. Developed model equations were statistically significant with good prediction capability. It was found that during shake flask cultivation glucose should be added in concentration up to 5 g l-1 in DSM medium, OTR at 10 mol m-3h-1 and temperature of 33 ?C, to achieve the maximum number of viable cells and spores. To scale up the process from shake flasks to the bioreactor level kLa was used as a main criterion. Scale up effect was evaluated by comparing the growth kinetics in the shake flasks and in a laboratory bioreactor. The total number of cells obtained in the bioreactor was 4.57?109 CFU ml-1 which is 1.41 times higher than the number of cells in the shake flasks (3.24?109 CFU ml-1), proving that the scale-up procedure was conducted successfully.","PeriodicalId":17489,"journal":{"name":"Journal of The Serbian Chemical Society","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"68517784","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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