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The title compound, C20H22O2, crystallizes with two independent molecules in the asymmetric unit. In each molecule, all the non-H atoms lie in a common plane (r.m.s. deviations of 0.098 and 0.079 Å). There is a [pi]-[pi] stacking interaction in the crystal structure. The central aromatic rings of the two molecules, which are stacked head-to-tail one above the other, are separated by centroid-to-centroid distances of 3.872 (13) and 3.999 (10) Å. Key indicators: single-crystal X-ray study; T = 173 K; mean σ(C–C) = 0.003 A° ; R factor = 0.044; wR factor = 0.101; data-to-parameter ratio = 14.6.
The title compound, C14H20O3, is a synthetic analogue with a long aliphatic side chain of the important food additive and flavoring agent, vanillin. There are two independent molecules in the asymmetric unit, each having an essentially planar conformation (r.m.s. deviations of 0.023 and 0.051Å for all non-H atoms of the two molecules in the asymmetric unit). Key indicators: single-crystal X-ray study; T = 173 K; mean σ(C–C) = 0.002 A°; R factor = 0.049; wR factor = 0.144; data-to-parameter ratio = 15.9.
Heute gewinnen pflanzliche Arzneimittel im Zeichen einer verstärkten Hinwendung zu natürlichen, relativ nebenwirkungsarmen Medikamenten zunehmend an Bedeutung, so auch die über Jahrtausende hinweg traditionell angewandte Ginsengwurzel (Panax ginseng) und der Indische Weihrauch (Boswellia serrata). Neben der Struktur- und Extraktanalytik konzentriert sich die Forschung in zunehmenden Maße darauf, die zahlreichen pharmakologisch untersuchten und klinisch beobachteten Wirkungen dieser beiden Arzneipflanzen einzelnen Inhaltsstoffen zuzuordnen. Bei der Ginsengwurzel gestaltet sich dies jedoch besonders schwierig. Dies ist begründet durch die große Anzahl strukturell ähnlicher Ginsenoside sowie durch deren unterschiedlicher Metabolismus. Zwar ist aus In-vitro-Experimenten bekannt, daß die Degradation über die stufenweise Deglukosylierung stattfindet, allerdings ist bislang nicht geklärt, ob intakte Ginsenoside überhaupt resorbiert werden und welche der vielen in vitro ermittelten Degradationsprodukte tatsächlich den systemischen Kreislauf erreichen. Anders als bei Ginseng, kann die therapeutische Wirkung des Indischen Weihrauches wohl definierten Inhaltsstoffen, AKBA und KBA, zugeschrieben werden. Dennoch mangelt es hier an verlässlichen pharmakokinetischen Daten, da bislang keine validierte bioanalytische Methode zur Verfügung stand. Im Rahmen der Bioanalytik von Ginsenosiden und Boswellliasäuren kamen in der vorliegenden Arbeit die Nano-ESI-MS(n)-Technik sowie die HPLC-Analytik zur Anwendung. Bereits bei der Strukturanalyse von Ginsenosiden erwies sich die Kombination der Nano-ESI-Technik mit MS(n)-Experimenten in einer Quadrupol-Ionenfalle als besonders vorteilhaft. Im Vergleich zu konventionellem ESI bietet Nano-ESI nicht nur den Vorzug, mit kleinsten Substanzmengen lange Messungen durchführen zu können, sondern auch den Vorteil einer effektiveren, weniger diskreminierenden Ionisation. Sowohl die hohe Sensitivität der Nano-Elektrosprayionisierung bei der Analyse von glykosidischen Verbindungen als auch die umfangreichen Strukturinformationen infolge mehrerer aufeinanderfolgender stoßinduzierter Fragmentierungen machen diese Technik zu einer attraktiven und effizienten Methode zur Analyse von Ginsenosiden. In MS(n)-Experimenten äußert sich das charakteristische Fragmentierungsverhalten der Ginsenoside in der sequentiellen Abspaltung der Zuckereinheiten in sukkzessiven Fragmentierungsschritten. Mit dieser Methode konnten die Zuckerketten an verschiedenen Positionen des Protopanaxadiol- bzw. Protopanaxatriolaglykons der Ginsenoside identifiziert, die glykosidischen Verknüpfungen innerhalb der einzelnen Zuckereinheiten durch spezifische Ringfragmente bestimmt und die genaue(n) Verknüpfungsposition(en) enzymatisch eingeführter Galaktose(n) lokalisiert werden. Bisher wurden allerdings Nano-ESI-MS/MS bzw. MS(n)-Untersuchungen primär an wässrigen oder organischen Lösungen von isolierten / aufgereinigten Stoffen oder Stoffgemischen durchgeführt. In dieser Arbeit wurde erstmals diese Technik in der Bioanalytik zur Identifizierung von Ginsenosiden und deren Degradationsprodukte in Humanplasma und -urin angewandt. Obwohl die optimale Analytkonzentration für die Nano-Elektrosprayionisierung im allgemeinen bei 10-5M liegt, ist es gelungen, die Ginsenoside anhand ihrer spezifischen Fragmentionen im MS/MS Modus bis zu einer Konzentration von 2 ng/mL (10-8M) in biologischen Matrices nachzuweisen. Auch wenn die Molekülionenpeaks bei diesen geringen Konzentrationen im Rauschen untergehen, können die Ginsenoside durch selektive Isolierung der gewünschten Vorläuferionen und deren anschließende Fragmentierung in der Quadrupol-Ionenfalle auf der Basis der Detektion spezifischer Fragmente identifiziert werden. Da bei der Fragmentierung der gleichen Vorläuferionenmasse in Leerplasma bzw. Urin keine charakteristischen Fragmentionen gebildet werden, handelt es sich somit um einen spezifischen Nachweis der Ginsenoside in biologischen Matrices. Vor dem Hintergrund dieser vielversprechenden Vorversuche wurde eine Pilotstudie zum qualitativen Screening von Ginsenosiden und deren Metaboliten in Humanplasma und –urin durchgeführt. Es konnte gezeigt werden, daß Protopanaxatriol-Ginsenoside sowohl im Magen hydrolysiert als auch intestinal degradiert werden. Schon in den ersten Stunden nach der einmaligen oralen Einnahme von Ginsana G115 Kapseln wurden die Hydrolyseprodukte G-Rh1 und hydratisiertes G-Rh1 in Humanplasma detektiert. Die schnelle Resorption dieser beiden Verbindungen aus dem oberen Gastrointestinaltrakt deutet auf die Hydrolyse des Ginsenosides Rg1 im Magen hin. Das spätere Auftreten eines weiteren monoglukosylierten Protopanaxatriols, des Degradationsproduktes G-F1, liefert den ersten In-Vivo-Hinweis auf einen intestinalen Metabolismus von Protopanaxatriol-Ginsenoside. Im Gegensatz zu den Protopanaxatriolginsenosiden passieren die Protopanaxadiol-Ginsenoside den Magen unverändert, wie aus der Abwesenheit jeglicher Protopanaxadiol-Degradationsprodukte im Plasma und Urin in den ersten Stunden nach der Applikation geschlossen werden kann. Erst im unteren Gastrointestinaltrakt werden Protopanaxadiol-Ginsenoside durch intestinale Bakterien zu „Compound-K“ abgebaut und anschließend resorbiert. Der Nachweis von Ginsenosid Rb1 im Plasma, sowie weiterer Ginsenoside im Urin eines Probanden zeigt, daß auch Ginsenoside in ihrer intakten Form resorbiert werden können. Dennoch sind weitere Studien hierzu notwendig, um zu klären, ob die Resorption intakter Ginsenoside die Regel oder eher eine Ausnahme darstellt. Mit der Identifizierung des Hydrolyseproduktes G-Rh1, der Degradationsprodukte G-F1 sowie „Compound-K“ in Humanplasma und -urin konnte schließlich die Frage geklärt werden, welche der zahlreichen in vitro bestimmten Degradationsprodukte tatsächlich den systemischen Kreislauf erreichen. Damit ist die Basis für eine spätere Quantifizierung dieser Verbindungen nach ihrer Isolierung bzw. Herstellung und Charakterisierung als Referenzsubstanzen geschaffen. Außerdem können diese neuen Erkenntnisse helfen, pharmakologische Ergebnisse aus In-vitro-Versuchen mit In-vivo-Daten besser zu korrelieren, da sie erste Hinweise geben, welche der in vitro getesteten Substanzen für die in vivo beobachteten Effekte verantwortlich sein könnten. Bisher wurde Nano-ESI-MS(n) in der Bioanalytik pflanzlicher Arzneistoffe nicht eingesetzt. In dieser Arbeit wurde diese Technik erstmals zum Screening von Ginsenosiden und deren Degradationsprodukte in Humanplasma und –urin benutzt. Darüber hinaus konnte gezeigt werden, daß Nano-ESI-MS(n) auch eine empfindliche und sensitive Methode zur Identifizierung und zum Nachweis anderer medizinisch relevanter glykosidischer Verbindungen in biologischen Matrices darstellt, woraus sich neue Perspektiven für den Einsatz dieser Technik in der Metabolitenforschung sowie in der Bioanalytik pflanzlicher Xenobiotika ergeben. In den letzten Jahren rückte auch der Indische Weihrauch immer mehr in den Mittelpunkt des wissenschaftlichen sowie therapeutischen Interesses. Aufgrund der selektiven Hemmung der 5-Lipoxygenase gewinnen AKBA und KBA, als neue entzündungshemmende Verbindungen, zunehmend an Bedeutung. Während die quantitative Analytik der Boswelliasäuren in Extrakten und in verschiedenen Fertigarzneimitteln erhebliche Fortschritte erzielen konnte, fehlten auf dem Gebiet der Bioanalytik bislang validierte analytische Methoden zur Durchführung pharmakokinetischer Studien. Vor diesem Hintergrund wurde eine HPLC-Methode zur Bestimmung von KBA in Humanplasma entwickelt und validiert. Die Methode ist durch eine einfache Probenvorbereitung gekennzeichnet, die sich auf eine Festphasenextraktion der KBA aus der komplex zusammengesetzten biologischen Matrix beschränkt. Im Anschluß an die chromatographische Trennung auf einer RP-C18 Säule erfolgt die Quantifizierung der KBA mittels UV-Detektion bei 250 nm. Um eine adäquate Bestimmung der KBA in Humanplasma zu gewährleisten, wurde eine umfassende Validierung durchgeführt. Alle ermittelten Validierungsparameter, wie Spezifität, Linearität, Präzision, Richtigkeit, Reproduzierbarkeit, untere Quantifizierungsgrenze und Stabilität lagen innerhalb der vorgegebenen Grenzen. Damit erfüllt die entwickelte HPLC-Methode die allgemein gültigen Anforderungen an die Validierung bioanalytischer Methoden. Mit der Erstellung einer Plasmakonzentrations-Zeit-Kurve im Rahmen einer ersten Pilotstudie konnte diese Methode zudem ihre praktische Anwendbarkeit unter Beweis stellen. Somit steht für zukünftige pharmakokinetische Studien eine validierte HPLC-Analytik zur Bestimmung von KBA, einer der Hauptwirkstoffe des Indischen Weihrauches, zur Verfügung, die sich durch hohe Spezifität, Reproduzierbarkeit und Präzision auszeichnet. Verlässliche Daten zur Pharmakokinetik am Menschen sind heute von besonderer Bedeutung, da sie helfen, die Dosierung zu optimieren, die biopharmazeutischen Eigenschaften von Präparaten zu verbessern und die Sicherheit bei der Anwendung zu erhöhen. Insbesondere im Hinblick auf bereits festgestellte Interaktionen von pflanzlichen Arzneimitteln mit Medikamenten reicht es nicht mehr aus, wenn sich pflanzliche Arzneimittel, wie beispielsweise Ginseng und Indischer Weihrauch, nur auf ihre langjährigen tradierten Anwendungserfahrungen berufen. So wird auch bei Phytopharmaka in verstärktem Maße eine wissenschaftliche Absicherung durch bioanalytische Forschung erwartet. Mit der Identifizierung der Ginsenoside und deren Degradationsprodukte im Menschen, der erstmaligen Anwendung von Nano-ESI-MS(n) in der Metabolitenforschung und der Entwicklung einer validierten bioanalytischen Methode zur Bestimmung der 11-Keto-Beta-Boswelliasäure in Humanplasma wurde diesen Erfordernissen Rechnung getragen.
The utilization of Ginkgo biloba in medicinal practice dates back to 1505 A.D. Ironically, the mechanisms of action of Ginkgo are not fully clarified till now. Nowadays, Ginkgo biloba leaf extracts are mainly indicated for mild to moderate cerebrovascular insufficiency and different forms of dementia. The fact that it is an herbal extract composed of several different components indeed adds to the intricacy of finding its mechanisms of actions. Indisputably, many scientists tried to elucidate the mechanisms of actions of Ginkgo. The first step to achieve this goal was to standardize the leaf extract. The standardized Ginkgo leaf extract contains 22-27 % flavonol glycosides, 2.8-3.4 % of ginkgolide A, B and C, as well as approximately 2.6-3.2 % bilobalide and below 5 ppm ginkgolic acids. A widespread standardized Ginkgo extract is the EGb 761, which was utilized in the current work. One of the earliest proposed mechanisms is the ability of the Ginkgo extract to act as an anti-oxidant, which could be explained by its high flavonoid contents. However, without doubt EGb 761 encompasses other characteristics which distinguish it from other herbal extracts that are also rich in flavonoids. Since free radicals and reactive oxygen species are highly associated with the mitochondrial functions, examination of the effect of EGb 761 on mitochondrial functions was lately addressed. Moreover, this was encouraged as the link between Alzheimer’s disease [AD] and the mitochondria started to emerge. Previously, our group observed mitochondrial protective actions of EGb 761 on cell culture in vitro. Furthermore, anti-apoptotic effects were previously described for EGb 761. However, only very few studies addressed the single constituents and their effect on mitochondrial functions. Flavonoids were studied in several other plant extracts and their radical scavenging activity is unquestionable, but EGb 761 has anti-apoptotic actions which may be attributed to its terpenoid fraction. Exclusively found in the Ginkgo plant, are the ginkgolides and therefore their actions are not yet fully elucidated. Moreover, those who attempted to address these constituents concentrated on one or two candidates, for example bilobalide or ginkgolide B and ignored the rest. Unfortunately, this led to incomplete results, and one couldn’t compare the relative activities of all EGb 761 components in order to state whether all the components are effective or not. ...
From theoretical considerations a dynamically distorted octahedron as a result of vibronic coupling between the ground state and the first excited state should exist for 14 electron AX6E systems like TeX62- . A high symmetry crystal field yielding at least a center of symmetry for the Te position stabilizes this fluctuating structure, otherwise statical distortion will be observed. From X-ray diffraction experiments on antifluorite type compounds A2TeX6 (A = Rb. Cs: X = Cl, Br) the averaged structure (m3̅m symmetry) of the anions was found even at very low temperatures. The thermal parameters are not significantly different from those of similar SnX62 compounds. Distortions therefore are very small and are evident from FTIR spectroscopic measurements only. Here very broad T1u-deformation vibration bands are observed down to temperatures <10 K without splitting: Astatically distorted species could not be frozen out. In contrast to XeF6 for TeX62- the energy gap between the threefold, fourfold or sixfold minima of the potential surface (according to the symmetry of one component of the T1u-vibration) is very small and shifted to temperatures lower than reached with the devices used for these experiments.
Over the past two decades the “one drug – one target – one disease” concept became the prevalent paradigm in drug discovery. The main idea of this approach is the identification of a single protein target whose inhibition leads to a successful treatment of the examined disease. The predominant assumption is that highly selective ligands would avoid unwanted side effects caused by binding to secondary non-therapeutic targets. In recent years the results of post-genomic and network biology showed that proteins rarely act in isolated systems but rather as a part of a highly connected network [1]. In addition this connectivity leads to more robust systems that cannot be interfered by the inhibition of a single target of that network and consequently might not lead to the desired therapeutic effect [2]. Furthermore studies prove that robust systems are rather affected by weak inhibitions of several parts than by a complete inhibition of a single selected element of that system [3]. Therefore there is an increasing interest in developing drugs that take effect on multiple targets simultaneously but is concurrently a great challenge for medicinal chemists. There has to be a sufficient activity on each target as well as an adequate pharmacokinetic profile [4]. Early design strategies tried to link the pharmacophors of known inhibitors, however these methods often lead to high molecular weight and low ligand efficacy. We present a new rational approach based on a retrosynthetic combinatorial analysis procedure [5] on approved ligands of multiple targets. These RECAP fragments are used to design a large combinatorial library containing molecules featuring chemical properties of each ligand class. The molecules are further validated by machine learning models, like random forests and self-organizing maps, regarding their activity on the targets of interest.
Ackermann, Hans ; Dubbers, Dirk ; Grupp, Michael ; Heitjans, Paul ; Stöckmann, Hans-Jürgen ; Wanczek, Karl-Peter ; Recker, Kurt ; Leckebusch, Rudolf
Nuclear magnetic resonance measurements were carried out on neutron activated 20F(T1/2=11s) nuclei in a single crystal of KZnF3. The quadrupolar splitted NMR spectrum, detected via the 20F β-radiation asymmetry, could be observed using a radio frequency modulation technique. The quadrupole coupling constant was determined to e2 q Q/h= + (12.0 ± 1.5) MHz at room temperature. The sign of e2 q Q was obtained from a simultaneous γ-ray anisotropy measurement on the succeeding 20Ne transition. Utilising a calculated field gradient of the fluorine atom, an fQ = 4.6% is determined. This value is compared with literature data of similar compounds.
Adatia, Karishma K. ; Halbritter, Thomas ; Reinfelds, Matiss ; Michele, Andre ; Tran, Michael ; Laschat, Sabine ; Heckel, Alexander ; Tovar, Günter E. M. ; Southan, Alexander
(Coumarin‐4‐yl)methyl (c4m) and p‐hydroxyphenacyl (pHP)‐based compounds are well known for their highly efficient photoreactions, but often show limited solubility in aqueous media. To circumvent this, we synthesized and characterized the two new c4m and pHP‐based photoacid generators (PAGs), 7‐[bis(carboxymethyl)amino]‐4‐(acetoxymethyl)coumarin (c4m‐ac) and p‐hydroxyphenacyl‐2,5,8,11‐tetraoxatridecan‐13‐oate (pHP‐t), and determined their solubilities, stabilities and photolysis in aqueous media. The two compounds showed high solubilities in water of 2.77 mmol L−1±0.07 mmol L−1 (c4m‐ac) and 124.66 mmol L−1±2.1 mmol L−1 (pHP‐t). In basic conditions at pH 9, solubility increased for c4m‐ac to 646.46 mmol L−1±0.63 mmol L−1, for pHP‐t it decreased to 34.68 mmol L−1±0.62 mmol L−1. Photochemical properties of the two PAGs, such as the absorption maxima, the maximum molar absorption coefficients and the quantum yields, were found to be strongly pH‐dependent. Both PAGs showed high stabilities s24h ≥95 % in water for 24 h, but decreasing stability with increasing pH value due to hydrolysis. The present study contributes to a clearer insight into the synthesis, solubilities, stabilities, and photolysis of c4m and pHP‐based PAGs for further photochemical applications when high PAG concentrations are required, such as in polymeric foaming.
Modelling protein flexibility and plasticity is computationally challenging but important for understanding the function of biological systems. Furthermore, it has great implications for the prediction of (macro) molecular complex formation. Recently, coarse-grained normal mode approaches have emerged as efficient alternatives for investigating large-scale conformational changes for which more accurate methods like MD simulation are limited due to their computational burden. We have developed a Normal Mode based Simulation (NMSim) approach for efficient conformation generation of macromolecules. Combinations of low energy normal modes are used to guide a simulation pathway, whereas an efficient constraints correction approach is applied to generate stereochemically allowed conformations. Non-covalent bonds like hydrogen bonds and hydrophobic tethers and phi-psi favourable regions are also modelled as constraints. Conformations from our approach were compared with a 10 ns MD trajectory of lysozyme. A 2-D RMSD plot shows a good overlap of conformational space, and rms fluctuations of residues show a correlation coefficient of 0.78 between the two sets of conformations. Furthermore, a comparison of NMSim simulations starting from apo structures of different proteins show that ligand-bound conformations can be sampled for those cases where conformational changes are mainly correlated, e.g., domain-like motion in adenylate kinase. Efforts are currently being made to also model localized but functionally important motions for protein binding pockets and protein-protein interfaces using relevant normal mode selection criteria and implicit rotamer basin creation.
C2-symmetric bisamidines : chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
(2008)
C2-symmetric bisamidines 8 have been tested as chiral Brønsted bases in the Diels- Alder reaction of anthrones and N-substituted maleimides. High yields of cycloadducts and significant asymmetric inductions up to 76% ee are accessible. The proposed mechanism involves proton transfer between anthrone and bisamidine, association of the resulting ions and finally a cycloaddition step stereoselectively controlled by the chiral ion pair.