D. D. Thiaré, P. A. Diaw, O. Mbaye, Diégane Sarr, M. D. Gaye-Seye, S. Ruellan, P. Giamarchi, F. Delattre, A. Coly, J. Aaron
{"title":"Photodegradation study of the fenvalerate insecticide by 1H NMR, 13C NMR, and GC-MS and structural elucidation of its transformation products","authors":"D. D. Thiaré, P. A. Diaw, O. Mbaye, Diégane Sarr, M. D. Gaye-Seye, S. Ruellan, P. Giamarchi, F. Delattre, A. Coly, J. Aaron","doi":"10.20450/mjcce.2022.2571","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2571","url":null,"abstract":"The photolysis of fenvalerate, a pyrethroid insecticide, was studied in acetonitrile by 1H nuclear magnetic resonance (NMR) and 13C NMR to identify the site of bond cleavage and gas chromatography-mass spectrometry (GC-MS) to establish the chemical structure of fenvalerate photoproducts. Ultraviolet (UV) irradiation of fenvalerate solutions was performed for 18 h with a solar light simulator, and the photolysis reaction obeyed first-order kinetics. Photolysis half-life time (t1/2) values ranged between 15.25 and 21.63 h (mean photodegradation percentage = 51.7 %) for 1H NMR and between 4.55 and 8.06 h (mean photodegradation percentage > 80 %) for 13C NMR. We observed five sites of bond cleavage, namely carbonyl-tertiary carbon, tertiary carbon-tertiary carbon, carbonyl-oxygen, carboxyl-tertiary carbon, and aromatic carbon-tertiary carbon, yielding photoproducts formation. GC-MS was associated with 1H NMR and 13C NMR to obtain a complete photodegradation mechanism. Before UV irradiation, two chromatogram peaks were obtained, due to the two fenvalerate isomers. Under irradiation, both peaks decreased, and new peaks appeared, corresponding to photoproduct formation. After a 12- to 13-h irradiation, 99.39 % of fenvalerate was degraded with a mean rate constant of 0.305 h–1. The chemical structure of the formed photoproducts was identified, either by using the National Institute of Standards and Technology (NIST) mass spectral database or by interpreting the mass spectra. Finally, a detailed mechanism was proposed for fenvalerate photodegradation.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46353682","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}
{"title":"Effects of Flavobacterium psychrophilum extracellular products and lipopolysaccharide antigens on the antioxidant enzyme system activity of rainbow trout (Oncorhynchus mykiss) fry","authors":"M. Kırıcı, M. Kırıcı, M. R. Taysı, U. Ispir","doi":"10.20450/mjcce.2022.2482","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2482","url":null,"abstract":"The aim of this study was to investigate the response of different doses of lipopolysaccharide (LPS) and extracellular product (ECP) antigens (25, 50, 100, 250, and 500 µg) obtained from Flavobacterium psychrophilum to changes in oxidative stress parameters (catalase [CAT], superoxide dismutase [SOD], glutathione peroxidase [GPx], glucose 6-phosphate dehydrogenase [G6PD], glutathione reductase [GR], and malondialdehyde [MDA]) in juvenile rainbow trout. For this purpose, 6 different doses of F. psychrophilum (102–106) were applied to the fish, and the lethal dose 50 % (LD50) value was determined as 1.33·104. Changes in MDA levels and antioxidant enzymes were determined by applying 25 % of the LD50 value to fish for 14 days. Accordingly, while F. psychrophilum increased GR, G6PD, GPx, and SOD activity, it decreased MDA levels and CAT activity. Initially, 25, 50, 100, 250, and 500 µg doses of ECP and LPS were applied to the fish; after 21 days, a 25 % dose of LD50 was applied to these fish. Fourteen days later, the fish were taken, and the changes in MDA levels and antioxidant enzymes were examined. As a result, it was determined that while ECP and LPS application decreased GR, G6PD, GPx, and SOD activity, there was an increase in MDA levels and CAT activity.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45743237","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}
{"title":"Comparative analysis of chemical composition and antioxidant activity of essential oil and hydrolate from black pepper fruit (Piper nigrum L.)","authors":"A. Milenković, J. Stanojević, L. Stanojević","doi":"10.20450/mjcce.2022.2608","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2608","url":null,"abstract":"The objective of this study was to analyze the chemical composition of the essential oil (EO) and hydrolate of black pepper fruit, as well as their antioxidant activity. The EO was obtained by Clevenger-type hydrodistillation with hydromodule 1:10 m/v for 240 minutes, and the hydrolate was collected after the hydrodistillation process. The qualitative composition of EO was determined by GC/MS and quantitative by GC/FID method, while the qualitative composition of a hydrolate was determined by HS-SPME-GC/MS and quantitative composition by HS-SPME-GC/FID method. The antioxidant activity was investigated by DPPH assay. Fifty-five compounds were identified from black pepper EO, where the most abundant compounds were (E)-caryophyllene (41.6 %), limonene (9.7 %), and sabinene (8.6 %). Twelve compounds were identified from black pepper hydrolate, where the most abundant compounds were α-terpineol (34.7 %), borneol (17.3 %), and terpinen-4-ol (13.9 %). The hydrolate showed higher antioxidant activity after 20 minutes of incubation with an EC50 value of 0.993 ± 0.011 mg/cm3 compared to the EO with an EC50 value of 67.72 ± 1.871 mg/cm3.\u0000According to the results obtained in this study, both the EO and hydrolate are good sources of natural antioxidants with potential uses in the food, organic agriculture, pharmaceutical, and cosmetic industries as a safer alternative to synthetic additives. Furthermore, the possibility of wider uses of the hydrolate should be investigated in more detail. Although researchers interested in hydrolate investigation focus mostly on their antioxidant activity, these \"aromatic wastes\" could also present promising cosmetic activities.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43030222","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}
{"title":"Surface catalytic mechanism-theoretical study under conditions of differential square-wave voltammetry","authors":"R. Gulaboski, V. Mirčeski","doi":"10.20450/mjcce.2022.2404","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2404","url":null,"abstract":"Differential square-wave voltammetry (DSWV) is the most recent modification of square-wave voltammetry (SWV) developed for advancing the performances of the technique for both analytical and kinetics applications. The differential current-measuring protocol in DSWV leads to improved voltammetric features of the forward and backward current components, in particular when slow i.e., quasireversible or irreversible electrode reactions are studied. In the present theoretical work catalytic electrode mechanism of surface bounded redox species (surface EC’ mechanism) is studied under conditions of the new technique, where E denotes the electrode reaction and C’ refers to the irreversible follow-up regenerative chemical reaction. Presented theoretical data provides a general overview of the EC’ reaction scheme, implying some specific voltammetric features which can be exploited for estimation of relevant physical parameters of the electrode reaction E and the regenerative chemical reaction C’.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45200551","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}
S. Kawsar, M. Ouassaf, Samir CHTITA, Aishi Barua Jui, S. Belaidi
{"title":"PASS prediction, molecular docking and pharmacokinetic studies of acyl substituted bioactive galactopyranoside esters as antibacterial agents","authors":"S. Kawsar, M. Ouassaf, Samir CHTITA, Aishi Barua Jui, S. Belaidi","doi":"10.20450/mjcce.2022.2403","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2403","url":null,"abstract":"Currently, methyl-β-D-galactopyranoside (MDG) esters have become a focus of attention due to their promising biological and pharmacokinetic properties and could be a good choice in unraveling the global issue of pathogenic multidrug resistance. Structural modification of MDG can improve its mode of biological activity. In line with these efforts, a series of previously synthesized MDG esters were designed and evaluated by Prediction of Activity Spectra for Substances (PASS), molecular docking simulation, and pharmacokinetic depiction. Encouraging PASS activity was observed for several aliphatic and aromatic MDG esters, and antibacterial efficacy was more promising than other features. In support, molecular docking studies were performed against the macrolide phosphotransferase enzyme MPH to identify a potential allosteric binding site for these esters. Molecular docking indicated that the shape of the MDG esters and their ability to form multiple electrostatic and hydrogen bonds with the active site corresponds to the binding modes of other minor-groove binders. Pharmacokinetic predictions were also performed to evaluate the absorption, metabolism, and toxic properties of MDG esters. These findings demonstrate that MDG esters are promising for use as biocompatible antibacterial agents in the future.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43194676","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}
V. Petrushevski, K. Béres, P. Bombicz, A. Farkas, L. Kótai, L. Bereczki
{"title":"Structural and Raman spectroscopic characterization of tetrapyridinesilver(I) perrhenate, [Agpy4]ReO4","authors":"V. Petrushevski, K. Béres, P. Bombicz, A. Farkas, L. Kótai, L. Bereczki","doi":"10.20450/mjcce.2022.2490","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2490","url":null,"abstract":"Tetrapyridinesilver(I) perrhenate [Agpy4]ReO4 was synthesized, and its crystal structure and Raman spectra were elucidated at low temperatures. The crystal lattice is constructed from isolated tetrahedral cations and anions having no argentophilic interactions. Weak hydrogen bonds are formed between the oxygens of the disordered perrhenate anions and the ortho-hydrogens of the pyridine ligands. No parallel π…π stacking interactions are observed, but C-H…π interactions of the pyridine ligands within columns of cations and between the columns appeared. Correlation analysis for Ag+, pyridine ligands, and perrhenate ions was performed, and the perrhenate ion and some of the AgN4 skeleton vibrational modes and pyridine ligand modes in the Raman spectrum of [Agpy4]ReO4 were assigned.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41909051","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}
{"title":"Determination of naproxen by using differential pulse voltammetry with poly (aniline-2-sulfonic acid) modified boron doped diamond electrode","authors":"Öznur Güngör","doi":"10.20450/mjcce.2022.2381","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2381","url":null,"abstract":"In this study, an electrochemical sensor based on a boron doped diamond electrode (BDDE) was developed for the determination of naproxen (NAP) using a poly(aniline-2-sulfonic acid)/boron doped diamond electrode, p(A2SA/BDDE). Polymerization of A2SA was conducted in a water/acetonitrile (1:1) mixture containing 0.1 M sodium perchlorate (NaClO4) on bare BDDE and the electrochemical properties studied by cyclic voltammetry in ferricyanide/KNO3 solution. The prepared p(A2SA/BDDE) was used for detection of NAP. Effects of parameters such as monomer type and concentration, the number of cycles, and scan rate were investigated using differential pulse voltammetry (DPV) in phosphate buffer containing 0.75 mM NAP. The effect of electrolyte type and pH on DPV responses to NAP were also studied. The oxidative current peak stem from NAP concentration observed at 1.1 V potential. A linear calibration curve was obtained in the range of 0.05–1.00 mM NAP concentration. Correlation coefficient (R2), detection limit, and quantification limit were calculated as 0.9944, 0.0328 mM, and 0.1093 mM, respectively. In conclusion, it may be claimed that the modified electrode constructed in this work can be used successfully as a naproxen-selective membrane due to its ease of preparation, high R2 value, and good reproducibility.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42865015","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}
{"title":"Preparation of a polyurethane membrane testosterone sensor and its application using square-wave stripping voltammetry","authors":"Cemre Zeynep Harman, Öznur Güngör","doi":"10.20450/mjcce.2022.2493","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2493","url":null,"abstract":"A novel electrochemical sensor for testosterone detection has been prepared by the chemical modification of a gold electrode (AuE). For the electrode modification, specific polyurethane (PU) films were synthesized from hexamethylene diisocyanate, olivetol, polyethylene glycol-100 (PEG100) and β-cyclodextrin. The synthesized PUs were investigated as selective films, and were used to coat a AuE surface at different concentrations and thicknesses. The testosterone responses of the modified electrodes were investigated by square-wave voltammetry (SWV). One separated cathodic SWV peak was obtained for testosterone at –0.390 V, with the prepared PU-modified AuE in 0.1 M phosphate buffer (PB) (pH 7.2). The linearity of testosterone responses of the prepared PU modified electrode was obtained over a concentration range of 0.1–1.0 µM (R2 = 0.995). It was observed that the response of the electrode increased regularly and sensitively with increasing testosterone amount. The detection limit, relative standard deviation and sensitivity of modified electrode were found to be approximately 5.69 nM, 1.669 % and 98.331 %, respectively. The PU-modified AuE exhibited good selectivity and a low response time for testosterone. Therefore, the prepared testosterone sensor offers a good alternative for fast and practical testosterone determination in clinical or biomedical studies.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44939496","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}
Elena Trajchova Kovachovska, J. Acevska, K. Brezovska, Stefan Trajkovic, Ivana Mitrevska, S. Ugarkovic, A. Dimitrovska
{"title":"Development of a stability-indicating method for evaluation of impurity profile of Atorvastatin film-coated tablets using cyano column based on core-shell technology","authors":"Elena Trajchova Kovachovska, J. Acevska, K. Brezovska, Stefan Trajkovic, Ivana Mitrevska, S. Ugarkovic, A. Dimitrovska","doi":"10.20450/mjcce.2022.2478","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2478","url":null,"abstract":"This research highlights the specificity of the new stability-indicating method developed to evaluate the impurity profile of Atorvastatin film-coated tablets. The proposed method has the ability to capture any possible changes that may occur during the stability studies over time and under different stress factors, and is selective enough to enable quality control of finished product from different suppliers of active pharmaceutical ingredient (API)/excipients. \u0000Satisfactory critical peak resolution between specified and unspecified impurities was achieved using the fused-core shell technology and extensively endcapped diisopropyl-cyanopropylsilane stationary phase (Halo ES-CN 150 mm × 4.6 mm, 2.7 µm), with a 10 mM ammonium formate buffer pH 3.5 and acetonitrile as mobile phase. A potential worse case impurity profile was assumed by using retained samples combined with the data obtained for samples manufactured with APIs from different suppliers exposed to the forced degradation study. The mass balance for stressed samples demonstrated the stability-indicating capability of the proposed method.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41618748","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}
B. Stojanovska Dimzoska, Zehra Hajrulai Musliu, Risto Uzunov, A. Angeleska, K. Blagoevska, Radmila Crceva Nikolovska, G. Ilievska, Elizabeta Dimitrieska Stojkovic
{"title":"Application of reliable cost-effective strategy for analysis of mycotoxins in corn-based foods with HPLC-FLD after multi-toxin immunoaffinity clean-up","authors":"B. Stojanovska Dimzoska, Zehra Hajrulai Musliu, Risto Uzunov, A. Angeleska, K. Blagoevska, Radmila Crceva Nikolovska, G. Ilievska, Elizabeta Dimitrieska Stojkovic","doi":"10.20450/mjcce.2022.2422","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2422","url":null,"abstract":"A different, reliable, and cost-effective strategy for the analysis of aflatoxins, ochratoxin A, and zearalenone in corn-based foods was proposed, including one multi-toxin immunoaffinity column (IAC) sample preparation and three different high-performance liquid chromatography fluorescence detection methods. The analytical procedures were tested and verified, keeping in mind their occurrence at trace levels in corn-based foods. With the validation of the proposed multi-toxin IAC methodology and comparison of the performance characteristics with methods using a single-toxin IAC, we confirmed the reliability of the multi-toxin IAC procedure versus the single-toxin IAC. The methods were validated by revealing satisfactory performance characteristics; for example, the obtained values of limit of detection were significantly lower than the maximum limits for all mycotoxins of concern. In addition, the recovery values were between 70.9 % and 106.1 % for all mycotoxins of interest, with precision values lower than 10.5 %.\u0000 ","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2022-06-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43387257","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}