Monatshefte Fur Chemie最新文献

{"title":"Comparison of human cytochrome P450 1A1-catalysed oxidation of benzo[<i>a</i>]pyrene in prokaryotic and eukaryotic expression systems.","authors":"Marie Stiborová, Radek Indra, Michaela Moserová, Lucie Bořek-Dohalská, Petr Hodek, Eva Frei, Klaus Kopka, Heinz H Schmeiser, Volker M Arlt","doi":"10.1007/s00706-017-2002-0","DOIUrl":"10.1007/s00706-017-2002-0","url":null,"abstract":"<p><strong>Abstract: </strong>Cytochrome P450 (CYP) 1A1 is the most important enzyme activating and detoxifying the human carcinogen benzo[<i>a</i>]pyrene (BaP). In the previous studies, we had shown that not only the canonic NADPH:CYP oxidoreductase (POR) can act as electron donor but also cytochrome <i>b</i>₅ and its reductase, NADH:cytochrome <i>b</i>₅ reductase. Here, we studied the role of the expression system used on the metabolites generated and the levels of DNA adducts formed by activated BaP. We used an eukaryotic and a prokaryotic cellular system (Supersomes, microsomes isolated from insect cells, and Bactosomes, a membrane fraction of <i>Escherichia coli</i>, each transfected with <i>cDNA</i> of human CYP1A1 and POR). These were reconstituted with cytochrome <i>b</i>₅ with and without NADH:cytochrome <i>b</i>₅ reductase. We evaluated the effectiveness of each cofactor, NADPH and NADH, to mediate BaP metabolism. We found that both systems differ in catalysing the reactions activating and detoxifying BaP. Two BaP-derived DNA adducts were generated by the CYP1A1-Supersomes, both in the presence of NADPH and NADH, whereas NADPH but not NADH was able to support this reaction in the CYP1A1-Bactosomes. Seven BaP metabolites were found in Supersomes with NADPH or NADH, whereas NADPH but not NADH was able to generate five BaP metabolites in Bactosomes. Our study demonstrates different catalytic efficiencies of CYP1A1 expressed in prokaryotic and eukaryotic cells in BaP bioactivation indicating some limitations in the use of <i>E. coli</i> cells for such studies.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 11","pages":"1959-1969"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5653725/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35224587","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Cytochrome <i>b</i>₅ plays a dual role in the reaction cycle of cytochrome P450 3A4 during oxidation of the anticancer drug ellipticine.","authors":"Marie Stiborová,&nbsp;Radek Indra,&nbsp;Eva Frei,&nbsp;Kateřina Kopečková,&nbsp;Heinz H Schmeiser,&nbsp;Tomáš Eckschlager,&nbsp;Vojtěch Adam,&nbsp;Zbyněk Heger,&nbsp;Volker M Arlt,&nbsp;Václav Martínek","doi":"10.1007/s00706-017-1986-9","DOIUrl":"https://doi.org/10.1007/s00706-017-1986-9","url":null,"abstract":"<p><strong>Abstract: </strong>Ellipticine is an anticancer agent that forms covalent DNA adducts after enzymatic activation by cytochrome P450 (CYP) enzymes, mainly by CYP3A4. This process is one of the most important ellipticine DNA-damaging mechanisms for its antitumor action. Here, we investigated the efficiencies of human hepatic microsomes and human recombinant CYP3A4 expressed with its reductase, NADPH:CYP oxidoreductase (POR), NADH:cytochrome <i>b</i>₅ reductase and/or cytochrome <i>b</i>₅ in Supersomes™ to oxidize this drug. We also evaluated the effectiveness of coenzymes of two of the microsomal reductases, NADPH as a coenzyme of POR, and NADH as a coenzyme of NADH:cytochrome <i>b</i>₅ reductase, to mediate ellipticine oxidation in these enzyme systems. Using HPLC analysis we detected up to five ellipticine metabolites, which were formed by human hepatic microsomes and human CYP3A4 in the presence of NADPH or NADH. Among ellipticine metabolites, 9-hydroxy-, 12-hydroxy-, and 13-hydroxyellipticine were formed by hepatic microsomes as the major metabolites, while 7-hydroxyellipticine and the ellipticine <i>N</i>²-oxide were the minor ones. Human CYP3A4 in Supersomes™ generated only three metabolic products, 9-hydroxy-, 12-hydroxy-, and 13-hydroxyellipticine. Using the ³²P-postlabeling method two ellipticine-derived DNA adducts were generated by microsomes and the CYP3A4-Supersome system, both in the presence of NADPH and NADH. These adducts were derived from the reaction of 13-hydroxy- and 12-hydroxyellipticine with deoxyguanosine in DNA. In the presence of NADPH or NADH, cytochrome <i>b</i>₅ stimulated the CYP3A4-mediated oxidation of ellipticine, but the stimulation effect differed for individual ellipticine metabolites. This heme protein also stimulated the formation of both ellipticine-DNA adducts. The results demonstrate that cytochrome <i>b</i>₅ plays a dual role in the CYP3A4-catalyzed oxidation of ellipticine: (1) cytochrome <i>b</i>₅ mediates CYP3A4 catalytic activities by donating the first and second electron to this enzyme in its catalytic cycle, indicating that NADH:cytochrome <i>b</i>₅ reductase can substitute NADPH-dependent POR in this enzymatic reaction and (2) cytochrome <i>b</i>₅ can act as an allosteric modifier of the CYP3A4 oxygenase.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 11","pages":"1983-1991"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-1986-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35224589","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Improved electroanalytical characteristics for flumetralin determination in the presence of surface active compound.","authors":"Dariusz Guziejewski, Sylwia Smarzewska, Radovan Metelka, Agnieszka Nosal-Wiercińska, Witold Ciesielski","doi":"10.1007/s00706-017-1918-8","DOIUrl":"10.1007/s00706-017-1918-8","url":null,"abstract":"<p><strong>Abstract: </strong>The use of square wave voltammetry (SWV) and square wave adsorptive stripping voltammetry (SWAdSV) in conjunction with a cyclic renewable silver amalgam film electrode for the determination of flumetralin is presented. Poor separation of two overlapped reduction peaks is significantly improved when hexadecyltrimethylammonium bromide is used as a component of the supporting electrolyte solution (together with BR buffer pH 9.5). The SW technique parameters were investigated and found optimal as follows: frequency 50 Hz, amplitude 40 mV, and step potential 5 mV. Accumulation time and potential were studied to select the optimal conditions in adsorptive voltammetry. The analytical curve was linear for the flumetralin concentration range from 1.0 × 10^-6 to 1.0 × 10^-5 mol dm^-3 and from 5.0 × 10^-9 to 1.0 × 10^-7 mol dm^-3 for SWV and SWAdSV, respectively. Detection limit of 6.5 × 10^-10 mol dm^-3 was calculated for accumulation time 60 s at -0.2 V. The repeatability of the method was determined at a flumetralin concentration level equal to 5.0 × 10^-9 mol dm^-3 and expressed as %RSD = 5.0% (<i>n</i> = 6). The proposed method was applied and validated successfully by studying the recovery of herbicide content in spiked environmental samples.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 3","pages":"555-562"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5346150/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"34856867","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Poultry meat freshness evaluation using electronic nose technology and ultra-fast gas chromatography.","authors":"Wojciech Wojnowski, Tomasz Majchrzak, Tomasz Dymerski, Jacek Gębicki, Jacek Namieśnik","doi":"10.1007/s00706-017-1969-x","DOIUrl":"10.1007/s00706-017-1969-x","url":null,"abstract":"<p><strong>Abstract: </strong>To ensure that chicken meat products are safe to consume, it is important to be able to reliably determine its shelf-life. To assess the applicability of ultra-fast gas chromatography and electronic nose technology in evaluation of poultry, an analysis of the headspace of ground chicken meat samples refrigerated over a period of 7 days was performed. Chemometric techniques were used to mine additional information from a multiparametric data set. As a reference, sensory evaluation was also conducted, and several volatile chemical compounds that can potentially be used as poultry meat decomposition indicators were identified. The obtained results suggest the possibility of using both techniques to supplement the established methods of chicken meat quality assessment.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 9","pages":"1631-1637"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5541116/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35283998","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Determination of odour concentration by TD-GC×GC-TOF-MS and field olfactometry techniques.","authors":"Hubert Byliński, Paulina Kolasińska, Tomasz Dymerski, Jacek Gębicki, Jacek Namieśnik","doi":"10.1007/s00706-017-2023-8","DOIUrl":"10.1007/s00706-017-2023-8","url":null,"abstract":"<p><strong>Abstract: </strong>Field olfactometry is one of the sensory techniques used to determine odour concentration, in atmospheric air, directly in emission sources. A two-dimensional gas chromatography with time of flight mass spectrometer (GC×GC-TOF-MS) allows performing the chemical characterization of various groups of chemical compounds, even in complex mixtures. Application of these techniques enabled determination of odour concentration level in atmospheric air in a vicinity of the oil refinery and the neighbouring wastewater treatment plant. The atmospheric air samples were analysed during a time period extending from February to June 2016. Based on the GC×GC-TOF-MS analysis and odour threshold values, the theoretical odour concentrations were calculated and compared with the odour concentrations determined by field olfactometry technique. The investigations revealed that higher values of odour concentration were obtained with the field olfactometry technique where odour analysis was based on holistic measurement. It was observed that the measurement site or meteorological conditions had significant influence on odour concentration level. The paper also discusses the fundamental analytical instruments utilized in the analysis of odorous compounds and their mixtures.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 9","pages":"1651-1659"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5541126/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35284000","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Comparison of the oxidation of carcinogenic aristolochic acid I and II by microsomal cytochromes P450 in vitro: experimental and theoretical approaches.","authors":"Václav Martínek,&nbsp;František Bárta,&nbsp;Petr Hodek,&nbsp;Eva Frei,&nbsp;Heinz H Schmeiser,&nbsp;Volker M Arlt,&nbsp;Marie Stiborová","doi":"10.1007/s00706-017-2014-9","DOIUrl":"https://doi.org/10.1007/s00706-017-2014-9","url":null,"abstract":"<p><strong>Abstract: </strong>The herbal drug aristolochic acid, a natural mixture of 8-methoxy-6-nitrophenanthro[3,4-<i>d</i>]-1,3-dioxole-5-carboxylic acid (AAI) and 6-nitrophenanthro[3,4-<i>d</i>]-1,3-dioxole-5-carboxylic acid (AAII), is derived from <i>Aristolochia</i> species and is the cause of two nephropathies. Ingestion of aristolochic acid is associated with the development of urothelial tumors linked with aristolochic acid nephropathy and is implicated in the development of Balkan endemic nephropathy-associated urothelial tumors. The <i>O</i>-demethylated metabolite of AAI, 8-hydroxyaristolochic acid (AAIa), is the detoxification product of AAI generated by its oxidative metabolism. Whereas the formation of AAIa from AAI by cytochrome P450 (CYP) enzymes has been found in vitro and in vivo, this metabolite has not been found from AAII as yet. Therefore, the present study has been designed to compare the amenability of AAI and AAII to oxidation; experimental and theoretical approaches were used for such a study. In the case of experimental approaches, the enzyme (CYP)-mediated formation of AAIa from both carcinogens was investigated using CYP enzymes present in subcellular microsomal fractions and recombinant CYP enzymes. We found that in contrast to AAI, AAII is oxidized only by several CYP enzymatic systems and their efficiency is much lower for oxidation of AAII than AAI. Using the theoretical approaches, such as flexible <i>in silico</i> docking methods and ab initio calculations, contribution to explanation of these differences was established. Indeed, the results found by both used approaches determined the reasons why AAI is better oxidized than AAII; the key factor causing the differences in AAI and AAII oxidation is their different amenability to chemical oxidation.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 11","pages":"1971-1981"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2014-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35224588","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of a conjugated pyrrolopyridazinedione-benzodithiophene (PPD-BDT) copolymer and its application in organic and hybrid solar cells.","authors":"Astrid-Caroline Knall,&nbsp;Andrew O F Jones,&nbsp;Birgit Kunert,&nbsp;Roland Resel,&nbsp;David Reishofer,&nbsp;Peter W Zach,&nbsp;Mindaugas Kirkus,&nbsp;Iain McCulloch,&nbsp;Thomas Rath","doi":"10.1007/s00706-017-1949-1","DOIUrl":"https://doi.org/10.1007/s00706-017-1949-1","url":null,"abstract":"<p><strong>Abstract: </strong>Herein, we describe the synthesis and characterization of a conjugated donor-acceptor copolymer consisting of a pyrrolopyridazinedione (PPD) acceptor unit, and a benzodithiophene (BDT) donor unit. The polymerization was done via a Stille cross-coupling polycondensation. The resulting PPD-BDT copolymer revealed an optical bandgap of 1.8 eV and good processability from chlorobenzene solutions. In an organic solar cell in combination with PC₇₀BM, the polymer led to a power conversion efficiency of 4.5%. Moreover, the performance of the copolymer was evaluated in polymer/nanocrystal hybrid solar cells using non-toxic CuInS₂ nanocrystals as inorganic phase, which were prepared from precursors directly in the polymer matrix without using additional capping ligands. The PPD-BDT/CuInS₂ hybrid solar cells showed comparably high photovoltages and a power conversion efficiency of 2.2%.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 5","pages":"855-862"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-1949-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"34954714","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Unexpected course of reaction between (<i>E</i>)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?","authors":"Radomir Jasiński, Karolina Kula, Agnieszka Kącka, Barbara Mirosław","doi":"10.1007/s00706-016-1893-5","DOIUrl":"10.1007/s00706-016-1893-5","url":null,"abstract":"<p><strong>Abstract: </strong>Reactions between (<i>E</i>)-2-aryl-1-cyano-1-nitroethenes and diazafluorene lead to acyclic 2,3-diazabuta-1,3-diene derivatives, instead of the expected pyrazoline systems. DFT calculations suggest that this is a consequence of formation of zwitterionic structure in the first stage of the reaction. It must be noted that this is a specific property of the (<i>E</i>)-2-aryl-1-cyano-1-nitroethenes group, in contrast to most other conjugated nitroalkenes.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 5","pages":"909-915"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5387018/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"34954717","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Lead-rich carboxylate-substituted titanium-lead oxo clusters.","authors":"Christine Artner,&nbsp;Ulrich Schubert","doi":"10.1007/s00706-017-1972-2","DOIUrl":"https://doi.org/10.1007/s00706-017-1972-2","url":null,"abstract":"<p><strong>Abstract: </strong>The carboxylate-substituted mixed-metal oxo clusters Pb₆Ti₆O₉(acetate)(methacrylate)₁₇ and Pb₄Ti₈O₁₀(O<i>i</i>Pr)₁₈(acetate)₂ contain a higher number of lead atoms in the cluster core than previously reported compounds. The metal atoms in both clusters are arranged in three layers of different composition, which are connected through oxygen, propionate and/or carboxylate bridges.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 8","pages":"1371-1377"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-1972-2","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35205902","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Development and validation of an LC-MS/MS method for the determination of biogenic amines in wines and beers.","authors":"Katarzyna Nalazek-Rudnicka,&nbsp;Andrzej Wasik","doi":"10.1007/s00706-017-1992-y","DOIUrl":"https://doi.org/10.1007/s00706-017-1992-y","url":null,"abstract":"<p><strong>Abstract: </strong>Biogenic amines are group of organic, basic, nitrogenous compounds that naturally occur in plant, microorganism, and animal organisms. Biogenic amines are mainly produced through decarboxylation of amino acids. They are formed during manufacturing of some kind of food and beverages such as cheese, wine, or beer. Histamine, cadaverine, agmatine, tyramine, putrescine, and <i>β</i>-phenylethylamine are the most common biogenic amines found in wines and beers. This group of compounds can be toxic at high concentrations; therefore, their control is very important. Analysis of biogenic amines in alcoholic drinks (beers and wines) was carried out by HPLC-MS/MS after their derivatization with <i>p</i>-toluenesulfonyl chloride (tosyl chloride). The developed method has been applied for analysis of seventeen biogenic amines in twenty-eight samples of lager beers and in twelve samples of different homemade wines (white grape, red grape, strawberry, chokeberry, black currant, plum, apple, raspberry, and quince). The developed method is sensitive and repeatable for majority of the analytes. It is versatile and can be used for the determination of biogenic amines in various alcoholic beverages.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 9","pages":"1685-1696"},"PeriodicalIF":1.8,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-1992-y","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35284001","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}