Institut für Pharmazie und Lebensmittelchemie
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Institute
- Institut für Pharmazie und Lebensmittelchemie (396)
- Institut für Pharmakologie und Toxikologie (11)
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Sonstige beteiligte Institutionen
- Universität Belgrad, Serbien (2)
- ACC GmbH Analytical Clinical Concepts (1)
- Apotheke, Universitätsklinikum Würzburg (1)
- Bayer AG, Research & Development, Pharmaceuticals, Investigational Toxicology (1)
- Bundesinstitut für Arzneimittel und Medizinprodukte (1)
- Friedrich-Schiller-Universität Jena (1)
- Helmholtz Institute for RNA-based Infection Biology (HIRI), Josef-Schneider-Straße 2/D15, DE-9708 Wuerzburg, Germany (1)
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- Johns Hopkins School of Medicine (1)
EU-Project number / Contract (GA) number
- 26230120009 (1)
- 296679 (1)
- 314911 (1)
- 701983 (1)
Red fruit oil (RFO) can be extracted from fruits of Pandanus conoideus, Lam., an endogenous plant of Papua, Indonesia. It is a commonly used essential original traditional medicine. By applying a newly developed quantitative \(^1\)H NMR (qNMR) spectroscopy method for quality assessment, a simultaneous determination of the saponification value (SV), acid value (AV), ester value (EV), and iodine value (IV) in RFO was possible. Dimethyl sulfone (DMSO\(_2\)) was used as an internal standard. Optimization of NMR parameters, such as NMR pulse sequence, relaxation delay time, and receiver gain, finally established the \(^1\)H NMR-based quantification approach. Diagnostic signals of the internal standard at δ = 2.98 ppm, SV at δ = 2.37–2.20 ppm, AV at δ = 2.27–2.20 ppm, EV at δ = 2.37–2.27 ppm, and IV at δ = 5.37–5.27 ppm, respectively, were used for quantitative analysis. The method was validated concerning linearity (R\(^2\) = 0.999), precision (less than 0.83%), and repeatability in the range 99.17–101.17%. Furthermore, this method was successfully applied to crude RFO, crude RFO with palmitic and oleic acid addition, and nine commercial products. The qNMR results for the respective fat values are in accordance with the results of standard methods, as can be seen from the F- and t-test (< 1.65 and < 1.66, respectively). The fundamental advantages of qNMR, such as its rapidity and simplicity, make it a feasible and existing alternative to titration for the quality control of RFO.
Capillary electrophoresis was chosen as cost-effective and robust method to separate ketamine enantiomers. For the method development, first different native and modified cyclodextrins were tested. The most promising chiral selector was α-cyclodextrin. A design of experiments (DoE) was carried out, which started with the screening of relevant factors. Based on these results, the method was optimized according to the significant factors (buffer, cyclodextrin concentration, pH value, voltage, temperature) of the screening based on the response resolution and migration time of the later migrating enantiomer. The optimized conditions consisted of a background electrolyte with 275 mM TRIS, adjusted with 85% phosphoric acid to a pH of 2.50, and 50 mM α-cyclodextrin, at a temperature of 15 °C, an applied voltage of 30 kV and an injection pressure of 1.0 psi for 10 s. A fused-silica capillary with a total length of 70 cm and an effective length to the detector of 60 cm was used. The method was validated according to ICH guideline Q2 R(1). The limit of quantification was 3.51 µg mL\(^{−1}\) for S-ketamine and 3.98 µg mL\(^{−1}\)for R-ketamine. The method showed good linearity for racemic ketamine with R\(^2\) of 0.9995 for S-ketamine and 0.9994 for R-ketamine. The lowest quantifiable content of S-ketamine found in R-ketamine was 0.45%.
An alternative to the time-consuming and error-prone pharmacopoeial gas chromatography method for the analysis of fatty acids (FAs) is urgently needed. The objective was therefore to propose a robust liquid chromatography method with charged aerosol detection for the analysis of polysorbate 80 (PS80) and magnesium stearate. FAs with different numbers of carbon atoms in the chain necessitated the use of a gradient method with a Hypersil Gold C\(_{18}\) column and acetonitrile as organic modifier. The risk-based Analytical Quality by Design approach was applied to define the Method Operable Design Region (MODR). Formic acid concentration, initial and final percentages of acetonitrile, gradient elution time, column temperature, and mobile phase flow rate were identified as critical method parameters (CMPs). The initial and final percentages of acetonitrile were fixed while the remaining CMPs were fine-tuned using response surface methodology. Critical method attributes included the baseline separation of adjacent peaks (α-linolenic and myristic acid, and oleic and petroselinic acid) and the retention factor of the last compound eluted, stearic acid. The MODR was calculated by Monte Carlo simulations with a probability equal or greater than 90%. Finally, the column temperature was set at 33 °C, the flow rate was 0.575 mL/min, and acetonitrile linearly increased from 70 to 80% (v/v) within 14.2 min.
In the last few years, fluorescence resonance energy transfer (FRET) receptor sensors have contributed to the understanding of GPCR ligand binding and functional activation. FRET sensors based on muscarinic acetylcholine receptors (mAChRs) have been employed to study dual-steric ligands, allowing for the detection of different kinetics and distinguishing between partial, full, and super agonism. Herein, we report the synthesis of the two series of bitopic ligands, 12-Cn and 13-Cn, and their pharmacological investigation at the M\(_1\), M\(_2\), M\(_4\), and M\(_5\) FRET-based receptor sensors. The hybrids were prepared by merging the pharmacophoric moieties of the M\(_1\)/M\(_4\)-preferring orthosteric agonist Xanomeline 10 and the M\(_1\)-selective positive allosteric modulator 77-LH-28-1 (1-[3-(4-butyl-1-piperidinyl)propyl]-3,4-dihydro-2(1H)-quinolinone) 11. The two pharmacophores were connected through alkylene chains of different lengths (C3, C5, C7, and C9). Analyzing the FRET responses, the tertiary amine compounds 12-C5, 12-C7, and 12-C9 evidenced a selective activation of M\(_1\) mAChRs, while the methyl tetrahydropyridinium salts 13-C5, 13-C7, and 13-C9 showed a degree of selectivity for M\(_1\) and M\(_4\) mAChRs. Moreover, whereas hybrids 12-Cn showed an almost linear response at the M\(_1\) subtype, hybrids 13-Cn evidenced a bell-shaped activation response. This different activation pattern suggests that the positive charge anchoring the compound 13-Cn to the orthosteric site ensues a degree of receptor activation depending on the linker length, which induces a graded conformational interference with the binding pocket closure. These bitopic derivatives represent novel pharmacological tools for a better understanding of ligand-receptor interactions at a molecular level.
Poor or variable oral bioavailability is of major concern regarding safety and efficacy for the treatment of patients with poorly water-soluble drugs (PWSDs). The problem statement of this work involves a pharmaceutical development perspective, the physicochemical basis of the absorption process and physiological / biopharmaceutical aspects. A methodology was developed aiming at closing the gap between drug liberation and dissolution on the one hand and the appearance of drug in the blood on the other. Considering what is out of control from a formulation development perspective, a clear differentiation between bioavailability and bioaccessibility was necessary. Focusing on the absorption process, bioaccessibility of a model compound, a poorly soluble but well permeable weak base, was characterized by means of flux across artificial biomimetic membranes. Such setups can be considered to reasonably mimic relevant oral absorption resistances in vitro in terms of diffusion through an unstirred water layer (UWL) and a lipidic barrier. Mechanistic understanding of the driving force for permeation was gained by differentiating drug species and subsequently linking them to the observed transfer rates using a bioaccessibility concept. The three key species that need to be differentiated are molecularly dissolved drug, drug associated in solution with other components (liquid reservoir) and undissolved drug (solid reservoir). An innovative approach to differentiate molecularly dissolved drug from the liquid reservoir using ultracentrifugation in combination with dynamic light scattering as control is presented. A guidance for rational formulation development of PWSDs is elaborated based on the employed model compound. It is structured into five guiding questions to help drug formulation scientists in selecting drug form, excipients and eventually the formulation principle. Overall, the relevance but also limitations of characterizing bioaccessibility were outlined with respect to practical application e.g. in early drug formulation development.
Even though the international combat against Neglected Tropical Diseases such as schistosomiasis or soil-transmitted helminthiases depends on reliable therapeutics, anthelminthic pharmacovigilance has been neglected on many national African drug markets. Therefore, quality and composition of 88 different batches of Albendazole, Mebendazole and Praziquantel locally collected from randomly selected facilities in Western Burkina Faso, Southeast Côte d’Ivoire, Southwest Ghana and Northwest Tanzania were analysed.
Visual examination of both packaging and samples was performed according to the WHO ‘Be Aware’ tool. Products were then screened with the GPHF Minilab, consisting of tests of mass uniformity, disintegration times and thin-layer chromatography (TLC). Confirmatory tests were performed according to international pharmacopoeiae, applying assays for dissolution profiles and high-performance liquid chromatography (HPLC).
Despite minor irregularities, appearance of the products did not hint at falsified medicines. However, 19.6 % of the brands collected in Ghana and Tanzania were not officially licensed for sale. Mass uniformity was confirmed in 53 out of 58 brands of tablets. 41 out of 56 products passed disintegration times; 10 out of the 15 failing products did not disintegrate at all.
TLC results did not reveal any falsifications or pronounced dosing errors. HPLC findings confirmed the TLC results despite shifted specification limits: ten of the 83 tested batches contained less than 90 %, none more than 110 % label claim. However, no more than 46.3 % (31 / 67) of the tablet batches assayed passed the respective criteria for dissolution.
In the four study countries, no falsified anthelminthic medicine was encountered. The active pharmaceutical ingredient was not found to either exceed or distinctively fall below specification limits. Galenic characteristics as most critical criteria however, especially dissolution profiles, revealed substantial deficits.
Objectives
Mechanisms of wound healing are often impaired in patients with osteonecrosis of the jaw (ONJ). According to the guidelines for the treatment of this disease, early surgical intervention is indicated. However, surgery often faces complications such as wound healing disorders. The application of platelet-rich fibrin (PRF) after necrosectomy between bone and mucosa may constitute a promising approach to improve surgical results. An aspect that was not investigated until now is that PRF acts as a “bio-carrier” for antibiotics previously applied intravenously.
Materials and methods
We investigated the antimicrobial properties of PRF in 24 patients presenting ONJ undergoing systemic antibiosis with ampicillin/sulbactam. We measured the concentration of ampicillin/sulbactam in plasma and PRF and performed agar diffusion tests. Ampicillin/sulbactam was applied intravenously to the patient 10 minutes for blood sampling for PRF. No further incorporation of patients’ blood or PRF product with antibiotic drugs was obtained. Four healthy patients served as controls.
Results
Our results revealed that PRF is highly enriched with ampicillin/sulbactam that is released to the environment. The antibiotic concentration in PRF was comparable to the plasma concentration of ampicillin/sulbactam. The inhibition zone (IZ) of PRF was comparable to the standard ampicillin/sulbactam discs used in sensitivity testing.
Conclusions
The results of our study demonstrated that PRF is a reliable bio-carrier for systemic applied antibiotics and exhibits a large antimicrobial effect.
Clinical relevance
We describe a clinically useful feature of PRF as a bio-carrier for antibiotics. Especially when applied to poorly perfused tissues and bone such as in ONJ, the local release of antibiotics can reduce wound healing disorders like infections.
Für Kinder und Jugendliche stellt die Blutentnahme im Rahmen des Therapeutischen Drug Monitorings (TDM) aufgrund der Invasivität häufig eine große physische sowie psychische Belastung dar. Diese Stresssituation kann durch Speichelsammlung aufgrund des nicht invasiven Prozederes vermieden und zusätzlich der Material-, Personal- und Zeitaufwand im Vergleich zu einer Blutentnahme minimiert werden. Da die therapeutischen Referenzbereiche in der AGNP Konsensus-Leitlinie zum TDM von Psychopharmaka nur für Serum und Plasma validiert sind, sind vergleichende Untersuchungen von alternativen Matrizes mit Serum oder Plasma sowie eine klinische Validierung essenziell für die Implementierung in die klinische Praxis.
Die Zielsetzung dieser Arbeit war es daher, den Zusammenhang zwischen Speichel- und Serumkonzentrationen von Amphetamin und Guanfacin zu untersuchen, um zukünftig das Prozedere der Probenahme für TDM bei Kinder und Jugendliche unter ADHS-Pharmakotherapie durch ein nicht invasives Verfahren zu erleichtern. Zur quantitativen Bestimmung wurden zwei unterschiedliche Methoden aus der Literatur weiterentwickelt. So war es möglich, aus Speichel- und Serumproben Amphetamin mittels HPLC-FL Analytik sowie Guanfacin mittels LC-MS/MS Analytik zu quantifizieren. Die chromatographischen Methoden wurden in Anlehnung an die Richtlinien der Gesellschaft für toxikologische und forensische Chemie (GTFCh) erfolgreich validiert.
Zur Untersuchung des Zusammenhangs zwischen Speichel- und Serumkonzentrationen von Amphetamin und Guanfacin bei Kinder und Jugendlichen wurde eine klinische Studie in der Klinik und Poliklinik für Kinder- und Jugendpsychiatrie, Psychosomatik und Psychotherapie des Universitätsklinikum Würzburgs initiiert. Von 34 Probanden, die mit Lisdexamphetamin und/oder Guanfacin behandelt wurden, konnte jeweils eine korrespondierende Speichel- und Serumprobe gewonnen und quantifiziert werden. Für Amphetamin wurde belegt, dass der Speichel-pH-Wert einen erheblichen Einfluss auf die Wirkstoffverteilung, den Quotienten aus Speichel- und Serumkonzentration, hat (ρ = -0,712; P < 0,001). Dadurch konnte erstmalig unter Berücksichtigung des Speichel-pH-Wertes eine Berechnung der theoretischen Serumkonzentration aus der Speichelkonzentration durchgeführt werden. Es wurde zwar gezeigt, dass sich sowohl der Mittelwert der Differenzen durch die Berechnung theoretischen Serumkonzentration von -343 auf 12 ng/mL als auch die Anzahl der Messwert innerhalb des Akzeptanzintervalls von 20 % verbessern, jedoch war auch nach der Umrechnung die Differenz der Messwerte zu groß, sodass eine klinische Validierung für Amphetamin nicht möglich war. In dieser Studie wurde auch erstmals Guanfacin im Speichel nachgewiesen und quantifiziert, die Konzentrationen lagen zwischen 0,45 und 5,55 ng/mL und waren im Mittel dreifach niedriger als im Serum (2,36 ng/mL vs. 7,47 ng/mL; t (8) = 5,94; P < 0,001).
Die Speichelguanfacinkonzentration wies einen starken Zusammenhang mit der korrespondierenden Serumkonzentration auf (r = 0,758; P = 0,018). Obwohl ein nicht signifikanter Trend für den Einfluss des Speichel-pH-Wertes auf den Quotienten aus Speichel- und Serumkonzentration zu erkennen war, scheint dieser weniger stark ausgeprägt zu sein als bei Amphetamin und anderen basischen Arzneistoffen (r = -0,574; P = 0,106).
Mit der vorliegenden Arbeit konnte zum einen gezeigt werden, dass sich die Speichelbestimmung von Amphetamin nur zum qualitativen Nachweis für TDM eignet. Zum anderen konnte gezeigt werden, dass der Speichel-pH-Wert einen geringeren Einfluss auf die Speichelkonzentration von Guanfacin zu haben scheint, als es bei Amphetamin der Fall ist, und sich Guanfacin somit potenziell für TDM in Speichel eignet. Zukünftig könnten Speichelproben zur Kontrolle der Adhärenz sowohl von Amphetamin als auch von Guanfacin verwendet werden und die Probenahme für die Patienten vereinfachen.
Most medicines are taken orally. To enter the systemic circulation, they dissolve in the intestinal fluid, cross the epithelial barrier, and pass through the liver. Intestinal absorption is driven by the unique features of the gastrointestinal tract, including the bile colloids formed in the lumen and the mucus layer covering the intestinal epithelium. Neglecting this multifaceted environment can lead to poor drug development decisions, especially for poorly water-soluble drugs that interact with bile and mucus. However, there is a lack of a rationale nexus of molecular interactions between oral medicines and gastrointestinal components with drug bioavailability. Against this background, this thesis aims to develop biopharmaceutical strategies to optimize the presentation of oral therapeutics to the intestinal epithelial barrier.
In Chapter 1, the dynamics of bile colloids upon solubilization of the poorly-water soluble drug Perphenazine was studied. Perphenazine impacted molecular arrangement, structure, binding thermodynamics, and induced a morphological transition from vesicles to worm-like micelles. Despite these dynamics, the bile colloids ensured stable relative amounts of free drug substance. The chapter was published in Langmuir.
Chapter 2 examined the impact of pharmaceutical polymeric excipients on bile-mediated drug solubilization. Perphenazine and Imatinib were introduced as model compounds interacting with bile, whereas Metoprolol did not. Some polymers altered the arrangement and geometry of bile colloids, thereby affecting the molecularly soluble amount of those drugs interacting with bile. These insights into the bile-drug-excipient interplay provide a blueprint to optimizing formulations leveraging bile solubilization. The chapter was published in Journal of Controlled Release.
Chapter 3 deals with the impact of bile on porcine intestinal mucus. Mucus exposed to bile solution changed transiently, it stiffened, and the overall diffusion rate increased. The bile-induced changes eased the transport of the bile-interacting drug substance Fluphenazine, whereas Metoprolol was unaffected. This dichotomous pattern was linked to bioavailability in rats and generalized based on two previously published data sets. The outcomes point to a bile-mucus interaction relevant to drug delivery. The chapter is submitted.
The Appendix provides a guide for biopharmaceutical characterization of drug substances by nuclear magnetic resonance spectroscopy aiming at establishing a predictive algorithm.
In summary, this thesis deciphers bile-driven mechanisms shaping intestinal drug absorption. Based on these molecular insights, pharmaceuticals can be developed along a biopharmaceutical optimization, ultimately leading to better oral drugs of tomorrow.
In this thesis, a new approach of a qNMR method has been investigated to demonstrate the reliability and importance of this method as an alternative solution for analyzing oil quality parameters, especially in RFO, which has particular characteristics (red color). This study also includes the chemometric evaluation of spectral data for authentication, visual grouping, and prediction of RFO quality based on the degree of unsaturation, FFA value, and unsaturated fatty acid content.
The analytical measurement procedure of NMR spectroscopy begins with optimization of the analytical acquisition parameters, including effect of solvent, effect of sample concentration, selection of appropriate internal standards, determination of T1, and method validation. Furthermore, the results of the method development were interpreted to RFO samples evaluation, which began with determining the assignment of signal spectra for the determination of AV, SV, EV, and IV simultaneously with: the hydrolysis approach and standard addition of palmitic acid.