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Serum-binding properties of isosteric ruthenium and osmium anticancer agents elucidated by SEC-ICP-MS. SEC-ICP-MS阐明了钌和锇抗癌剂的血清结合特性。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-08-25 DOI: 10.1007/s00706-018-2280-1
Matthias H M Klose, Anna Schöberl, Petra Heffeter, Walter Berger, Christian G Hartinger, Gunda Koellensperger, Samuel M Meier-Menches, Bernhard K Keppler
{"title":"Serum-binding properties of isosteric ruthenium and osmium anticancer agents elucidated by SEC-ICP-MS.","authors":"Matthias H M Klose,&nbsp;Anna Schöberl,&nbsp;Petra Heffeter,&nbsp;Walter Berger,&nbsp;Christian G Hartinger,&nbsp;Gunda Koellensperger,&nbsp;Samuel M Meier-Menches,&nbsp;Bernhard K Keppler","doi":"10.1007/s00706-018-2280-1","DOIUrl":"10.1007/s00706-018-2280-1","url":null,"abstract":"<p><strong>Abstract: </strong>Size-exclusion chromatography-inductively coupled plasma-mass spectrometry (SEC-ICP-MS) was used to study the serum-binding preferences of two metallodrugs with anticancer activities in vivo, namely the organoruthenium compound plecstatin-1 and its isosteric osmium analog. The complexes were administered intraperitoneally into mice bearing a CT-26 tumor. Comparing the total metal content of mouse whole blood and serum underlined that the metallodrugs are mainly located in serum and not in the cellular fraction of the blood samples. In mouse serum, both compounds were not only found to bind extensively to the serum albumin/transferrin fraction but also to immunoglobulins. Free drug was not observed in any of the samples indicating rapid protein binding of the metallodrugs. These findings were validated by spiking human serum with the respective compounds ex vivo. An NCI-60 screen is reported for the osmium analog, which revealed a relative selectivity for cancer cell lines of the ovary and the central nervous system with respect to plecstatin-1. Finally, a COMPARE 170 analysis revealed disruption of DNA synthesis as a possible treatment effect of the osmium-based drug candidate.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 10","pages":"1719-1726"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2280-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36510808","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}
引用次数: 22
Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety. 含有1,4-苯二氧杂环的反式二氢精氨酸衍生物的立体选择性合成。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-10-26 DOI: 10.1007/s00706-018-2287-7
Gábor Varró, Balázs Pogrányi, Alajos Grün, András Simon, László Hegedűs, István Kádas
{"title":"Stereoselective synthesis of <i>trans</i>-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.","authors":"Gábor Varró, Balázs Pogrányi, Alajos Grün, András Simon, László Hegedűs, István Kádas","doi":"10.1007/s00706-018-2287-7","DOIUrl":"10.1007/s00706-018-2287-7","url":null,"abstract":"<p><strong>Abstract: </strong>Some new <i>trans</i>-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety were stereoselectively synthesised using our feasible and efficient method developed recently. These new phenanthridone alkaloid analogues were obtained in both racemic and optically active forms. High enantioselectivities (up to 99% <i>ee</i>) were achieved by applying (8<i>S</i>,9<i>S</i>)-9-amino(9-deoxy)epiquinine as an organocatalyst. Due to a side reaction, various methoxyphenanthridine regioisomers were also prepared which afforded further synthetic <i>trans</i>-dihydronarciclasine analogues modified in the ring A of the phenanthridone scaffold.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 12","pages":"2265-2285"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2287-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37772620","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}
引用次数: 4
The evaluation of alternative method of ferrous ions assessment in pharmaceutical preparations. 药物制剂中亚铁离子评价替代方法的评价。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-02-13 DOI: 10.1007/s00706-018-2147-5
Anna Lisik, Anna Prescha, Levent E Cavlaz, Halina Grajeta, Witold Musiał
{"title":"The evaluation of alternative method of ferrous ions assessment in pharmaceutical preparations.","authors":"Anna Lisik, Anna Prescha, Levent E Cavlaz, Halina Grajeta, Witold Musiał","doi":"10.1007/s00706-018-2147-5","DOIUrl":"10.1007/s00706-018-2147-5","url":null,"abstract":"<p><strong>Abstract: </strong>The atomic absorption spectrometry (AAS) method is one of the most accessible procedures for ferrous ions testing in various compositions including pharmaceutical preparations. The aim of the study was to develop and partially validate analytical method which could be an excellent alternative to the routine procedure performed within dissolution studies. Electric conductivity is simple, fast, and hassle-free method. The samples during dissolution process were measured using conductivity probe in entire dissolution assessment protocol. The conductivity results were compared to data obtained from AAS. The dissolution studies were performed according to modified pharmacopoeial standards, in 900 cm<sup>3</sup> of purified water as an acceptor medium, at 37 °C, until the achievement of an equilibrium state for every tested composition. Validity study of the developed method confirmed acceptable linearity of obtained calibration plots (<i>r</i><sup>2</sup> > 0.9553). Linearity at 100% level was found to be 100.59, 97.49, and 94.82, respectively, for drug compositions A, B, and C. Precision results were 100.45, 95.97, and 95.73, respectively, for A, B, and C, with RSD below 2% between all samples in all above mentioned formulations. The drug composition D hindered the proper validation of the method due to the high variability between samples. The method has acceptable performance features for evaluation of three of four solid drug composition containing ferrous ions.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 5","pages":"931-937"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2147-5","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36064556","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}
引用次数: 1
Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloaddition. 硝基甲基取代的3-苯基-4,5-二氢异恶唑的区域特异性形成 + 2] 环加成。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-08-20 DOI: 10.1007/s00706-018-2227-6
Barbara Mirosław, Dmytro Babyuk, Agnieszka Łapczuk-Krygier, Agnieszka Kącka-Zych, Oleg M Demchuk, Radomir Jasiński
{"title":"Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloaddition.","authors":"Barbara Mirosław,&nbsp;Dmytro Babyuk,&nbsp;Agnieszka Łapczuk-Krygier,&nbsp;Agnieszka Kącka-Zych,&nbsp;Oleg M Demchuk,&nbsp;Radomir Jasiński","doi":"10.1007/s00706-018-2227-6","DOIUrl":"10.1007/s00706-018-2227-6","url":null,"abstract":"<p><strong>Abstract: </strong>5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 + 2] cycloaddition reaction of in situ-generated benzonitrile <i>N</i>-oxide and 3-nitroprop-1-ene. For the first time, the regiochemistry of this reaction was unambiguously proven by X-ray structural analysis. The quantum-chemical calculation performed at the M06-2X/6-31G(d) (PCM) theoretical level affords a basis for explaining the course of reaction as well as the nature of transition states. Next, further DFT calculations together with spectral data shed light on structural aspects of the product.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 10","pages":"1877-1884"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2227-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36510810","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}
引用次数: 19
Modifications of quinolones and fluoroquinolones: hybrid compounds and dual-action molecules. 喹诺酮类和氟喹诺酮类药物的修饰：杂化化合物和双作用分子。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-06-07 DOI: 10.1007/s00706-018-2215-x
Joanna Fedorowicz, Jarosław Sączewski
{"title":"Modifications of quinolones and fluoroquinolones: hybrid compounds and dual-action molecules.","authors":"Joanna Fedorowicz, Jarosław Sączewski","doi":"10.1007/s00706-018-2215-x","DOIUrl":"10.1007/s00706-018-2215-x","url":null,"abstract":"<p><strong>Abstract: </strong>This review is aimed to provide extensive survey of quinolones and fluoroquinolones for a variety of applications ranging from metal complexes and nanoparticle development to hybrid conjugates with therapeutic uses. The review covers the literature from the past 10 years with emphasis placed on new applications and mechanisms of pharmacological action of quinolone derivatives. The following are considered: metal complexes, nanoparticles and nanodrugs, polymers, proteins and peptides, NO donors and analogs, anionic compounds, siderophores, phosphonates, and prodrugs with enhanced lipophilicity, phototherapeutics, fluorescent compounds, triazoles, hybrid drugs, bis-quinolones, and other modifications. This review provides a comprehensive resource, summarizing a broad range of important quinolone applications with great utility as a resource concerning both chemical modifications and also novel hybrid bifunctional therapeutic agents.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 7","pages":"1199-1245"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6006264/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36293485","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}
引用次数: 0
Progress in the synthesis of δ-sultones. δ-硫酮的合成研究进展。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2017-07-15 DOI: 10.1007/s00706-017-2010-0
Christina Gaunersdorfer, Mario Waser
{"title":"Progress in the synthesis of δ-sultones.","authors":"Christina Gaunersdorfer,&nbsp;Mario Waser","doi":"10.1007/s00706-017-2010-0","DOIUrl":"https://doi.org/10.1007/s00706-017-2010-0","url":null,"abstract":"<p><strong>Abstract: </strong>Sultones, the cyclic esters of hydroxyl sulfonic acids, are a fascinating class of heterocycles and the recent years have witnessed an increasing interest in these molecules, especially in six-ring δ-sultones. The importance of these compounds is either because of their biological properties themselves or due to their versatility as intermediates in more complex target syntheses. Accordingly, the development of new synthesis methods to access δ-sultones is an important and rewarding task which we wish to highlight in this review.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"701-714"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2010-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031580","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}
引用次数: 3
Novel naphthylpyridines from cobalt-catalyzed cyclotrimerization of a chiral diyne. 由钴催化手性二炔环三聚反应合成的新型萘基吡啶。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2017-11-28 DOI: 10.1007/s00706-017-2083-9
Volkmar Trommer, Fabian Fischer, Marko Hapke
{"title":"Novel naphthylpyridines from cobalt-catalyzed cyclotrimerization of a chiral diyne.","authors":"Volkmar Trommer,&nbsp;Fabian Fischer,&nbsp;Marko Hapke","doi":"10.1007/s00706-017-2083-9","DOIUrl":"https://doi.org/10.1007/s00706-017-2083-9","url":null,"abstract":"<p><strong>Abstract: </strong>The concise synthesis of a novel chiral diyne substrate for the assembly of chiral naphthylpyridines was described and different conditions for the cobalt-catalyzed co-cyclotrimerization with nitriles investigated. The products are novel naphthylpyridines possessing configurationally stable biaryl axes.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"755-763"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2083-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031582","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}
引用次数: 6
Palladium complexes containing imino phenoxide ligands: synthesis, luminescence, and their use as catalysts for the ring-opening polymerization of rac-lactide. 含有亚氨基苯氧配体的钯配合物：合成、发光及其用作 rac-内酰胺开环聚合的催化剂。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2017-12-12 DOI: 10.1007/s00706-017-2119-1
Mrinmay Mandal, Manuela List, Ian Teasdale, Günther Redhammer, Debashis Chakraborty, Uwe Monkowius
{"title":"Palladium complexes containing imino phenoxide ligands: synthesis, luminescence, and their use as catalysts for the ring-opening polymerization of <i>rac</i>-lactide.","authors":"Mrinmay Mandal, Manuela List, Ian Teasdale, Günther Redhammer, Debashis Chakraborty, Uwe Monkowius","doi":"10.1007/s00706-017-2119-1","DOIUrl":"10.1007/s00706-017-2119-1","url":null,"abstract":"<p><strong>Abstract: </strong>The preparation, structural characterization, luminescence, and catalytic activity of three palladium(II) complexes bearing imino phenoxide ligands are reported. The X-ray studies revealed that the complexes are mononuclear with palladium centres coordinated in a square-planar coordination environment. Two of the complexes are emissive in solution at room temperature. The catalytic activities towards the ring-opening polymerization of <i>rac</i>-lactide (<i>rac</i>-LA) were tested. Polymers with moderate molecular weights and relatively broad dispersity (<i>Ð</i>) were obtained. Kinetic studies revealed that the polymerization followed first-order kinetics.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"783-790"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5906497/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031584","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}
引用次数: 0
Complementary use of GCxGC-TOF-MS and statistics for differentiation of variety in biosolid samples. 互补使用GCxGC-TOF-MS和统计学对生物固体样品的多样性进行鉴别。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-08-09 DOI: 10.1007/s00706-018-2221-z
Hubert Byliński, Tomasz Dymerski, Jacek Gębicki, Jacek Namieśnik
{"title":"Complementary use of GCxGC-TOF-MS and statistics for differentiation of variety in biosolid samples.","authors":"Hubert Byliński,&nbsp;Tomasz Dymerski,&nbsp;Jacek Gębicki,&nbsp;Jacek Namieśnik","doi":"10.1007/s00706-018-2221-z","DOIUrl":"https://doi.org/10.1007/s00706-018-2221-z","url":null,"abstract":"","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 9","pages":"1587-1594"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2221-z","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36455424","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}
引用次数: 12
Rapid assessment of the authenticity of limequat fruit using the electronic nose and gas chromatography coupled with mass spectrometry. 利用电子鼻和气相色谱-质谱联用技术快速鉴定枸杞果实的真伪。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-08-09 DOI: 10.1007/s00706-018-2242-7
Martyna Lubinska-Szczygeł, Dominika Pudlak, Tomasz Dymerski, Jacek Namieśnik
{"title":"Rapid assessment of the authenticity of limequat fruit using the electronic nose and gas chromatography coupled with mass spectrometry.","authors":"Martyna Lubinska-Szczygeł,&nbsp;Dominika Pudlak,&nbsp;Tomasz Dymerski,&nbsp;Jacek Namieśnik","doi":"10.1007/s00706-018-2242-7","DOIUrl":"https://doi.org/10.1007/s00706-018-2242-7","url":null,"abstract":"<p><strong>Abstract: </strong>Citrus fruits are very popular food products. There are many species and varieties of them. There are also documented cases of some citrus fruits causing a severe allergic reaction. Some species of the citrus fruits, especially hybrid ones show a reduced allergenic effect due to the lack of seeds. There is a need for rapid methods for evaluation of citrus' botanical origin. During research, the headspace of three citrus fruits <i>Citrus Aurantifolia, Citrus japonica</i>, and <i>Citrus </i>× <i>floridana</i> was analysed using electronic nose based on ultrafast gas chromatography and gas chromatography with mass spectrometry. In the paper, two approaches were compared. The usefulness of an electronic nose to control the quality of hybrids was demonstrated. The results obtained during ultrafast gas chromatography analyses were subjected to statistical analysis. Four chemometric methods namely: principal component analysis (PCA), discriminant function analysis (DFA), soft independent modeling of class analogies (SIMCA), statistical quality control (SQC) were used to distinguish between limequat and its parent fruits. Electronic nose combined with chemometrics is a novel analytical tool for hybrid fruits' classification due to their botanical origin. It can supplement established techniques by providing results in a short time and at a low cost.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 9","pages":"1605-1614"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2242-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36455426","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}
引用次数: 10
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