Institut für Pharmazie und Lebensmittelchemie
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Insulin-like growth factor-I (IGF-I) is a 70-amino acid polypeptide with a molecular weight of approximately 7.6 kDa acting as an anabolic effector. It is essential for tissue growth and remodeling. Clinically, it is used for the treatment of growth disorders and has been proposed for various other applications including musculoskeletal diseases. Unlike insulin, IGF-I is complexed to at least six high-affinity binding proteins (IGFBPs) exerting homeostatic effects by modulating IGF-I availability to its receptor (IGF-IR) on most cells in the body as well as changing the distribution of the growth factor within the organism.1-3 Short half-lived IGF-I have been the driving forces for the design of localized IGF-I depot systems or protein modification with enhanced pharmacokinetic properties. In this thesis, we endeavor to present a versatile biologic into which galenical properties were engineered through chemical synthesis, e.g., by site-specific coupling of biomaterials or complex composites to IGF-I. For that, we redesigned the therapeutic via genetic codon expansion resulting in an alkyne introduced IGF-I, thereby becoming a substrate for biorthogonal click chemistries yielding a site-specific decoration.
In this approach, an orthogonal pyrrolysine tRNA synthetase (PylRS)/tRNAPyl CUA pair was employed to direct the co-translational incorporation of an unnatural amino acid—¬propargyl-L-lysine (plk)—bearing a clickable alkyne functional handle into IGF-I in response to the amber stop codon (UAG) introduced into the defined position in the gene of interest. We summarized the systematic optimization of upstream and downstream process alike with the ultimate goal to increase the yield of plk modified IGF-I therapeutic, from the construction of gene fusions resulting in (i) Trx-plk-IGF-I fusion variants, (ii) naturally occurring pro-IGF-I protein (IGF-I + Ea peptide) (plk-IGF-I Ea), over the subsequent bacterial cultivation and protein extraction to the final chromatographic purification. The opportunities and hurdles of all of the above strategies were discussed. Evidence was provided that the wild-type IGF-I yields were pure by exploiting the advantages of the pHisTrx expression vector system in concert with a thrombin enzyme with its highly specific proteolytic digestion site and multiple-chromatography steps. The alkyne functionality was successfully introduced into IGF-I by amber codon suppression. The proper folding of plk-IGF-I Ea was assessed by WST-1 proliferation assay and the detection of phosphorylated AKT in MG-63 cell lysate. The purity of plk-IGF-I Ea was monitored with RP-HPLC and SDS-PAGE analysis. This work also showed site-specific coupling an alkyne in plk-IGF-I Ea by copper (I)-catalyzed azide-alkyne cycloaddition (CuAAC) with potent activities in vitro. The site-specific immobilization of plk-IGF-I Ea to the model carrier (i.e., agarose beads) resulted in enhanced cell proliferation and adhesion surrounding the IGF-I-presenting particles. Cell proliferation and differentiation were enhanced in the accessibility of IGF-I decorated beads, reflecting the multivalence on cellular performance.
Next, we aimed at effectively showing the disease environment by co-delivery of fibroblast growth factor 2 (FGF2) and IGF-I, deploying localized matrix metalloproteinases (MMPs) upregulation as a surrogate marker driving the response of the drug delivery system. For this purpose, we genetically engineered FGF2 variant containing an (S)-2-amino-6-(((2-azidoethoxy)carbonyl)amino)hexanoic acid incorporated at its N-terminus, followed by an MMPs-cleavable linker (PCL) and FGF2 sequence, thereby allowing site-directed, specific decoration of the resultant azide-PCL-FGF2 with the previously mentioned plk-IGF-I Ea to generate defined protein-protein conjugates with a PCL in between. The click reaction between plk-IGF-I Ea and azide-PCL-FGF2 was systematically optimized to increase the yield of IGF-FGF conjugates, including reaction temperature, incubation duration, the addition of anionic detergent, and different ratios of the participating biopharmaceutics. The challenge here was that CuAAC reaction components or conditions might oxidize free cysteines of azide-PCL-FGF2 and future work needs to present the extent of activity retention after conjugation. Furthermore, our study provides potential options for dual-labeling of IGF-I either by the introduction of unnatural amino acids within two distinct positions of the protein of interest for parallel “double-click” labeling of the resultant plk-IGF-I Ea-plk or by using a combination of enzymatic-catalyzed and CuAAC bioorthogonal coupling strategies for sequentially dual-labeling of plk-IGF-I Ea.
In conclusion, genetic code expansion in combination with click-chemistry provides the fundament for novel IGF-I analogs allowing unprecedented site specificity for decoration. Considerable progress towards IGF-I based therapies with enhanced pharmacological properties was made by demonstrating the feasibility of the expression of plk incorporated IGF-I using E. coli and retained activity of unconjugated and conjugated IGF-I variant. Dual-labeling of IGF-I provides further insights into the functional requirements of IGF-I. Still, further investigation warrants to develop precise IGF-I therapy through unmatched temporal and spatial regulation of the pleiotropic IGF-I.
The International Symposium on Phytochemicals in Medicine and Food (ISPMF2015), organized by the Phytochemical Society of Europe (PSE) and the Phytochemical Society of Asia (PSA), was held June 26-29, 2015, in Shanghai of China. This was the first time that a PSE meeting has been held in Asia and a PSE-PSA joint symposium provided an opportunity for communication between scientists from Europe and Asia and other continents. ISPMF2015 has been jointly sponsored by Fujian Agriculture and Forestry University, Guizhou Medical University, Shanghai Normal University, Yancheng Institute of Technology, Beijing Normal University, and Fudan University. More than 270 scientists from 48 countries attended this meeting and presented their research and opinions on phytochemistry, phytomedicine and phytoneering. The international organizing committee and scientific advisory board of ISPMF 2015 comprised of outstanding scientists from around the globe. Dr. Jianbo Xiao was the chairman of the International Organizing Committee of ISPMF2015 and moderated the open address on June 26.
The organizing committee of ISPMF2015 assembled an exciting and diverse program, featuring 16 sessions including 12 plenary lectures, 20 invited talks, 55 short oral presentations, and more than 130 posters, which were dedicated to creating a podium for exchanging the latest research results in the phytochemicals for food and human health.
Ruxolitinib (RUX) is approved for the treatment of steroid-refractory acute and chronic graft versus host disease (GvHD). It is predominantly metabolized via cytochrome P450 (CYP) 3A4. As patients with GvHD have an increased risk of invasive fungal infections, RUX is frequently combined with posaconazole (POS), a strong CYP3A4 inhibitor. Knowledge of RUX exposure under concomitant POS treatment is scarce and recommendations on dose modifications are inconsistent. A physiologically based pharmacokinetic (PBPK) model was developed to investigate the drug–drug interaction (DDI) between POS and RUX. The predicted RUX exposure was compared to observed concentrations in patients with GvHD in the clinical routine. PBPK models for RUX and POS were independently set up using PK-Sim\(^®\) Version 11. Plasma concentration-time profiles were described successfully and all predicted area under the curve (AUC) values were within 2-fold of the observed values. The increase in RUX exposure was predicted with a DDI ratio of 1.21 (C\(_{max}\)) and 1.59 (AUC). Standard dosing in patients with GvHD led to higher RUX exposure than expected, suggesting further dose reduction if combined with POS. The developed model can serve as a starting point for further simulations of the implemented DDI and can be extended to further perpetrators of CYP-mediated PK-DDIs or disease-specific physiological changes.
Priority tasks of the present thesis were to generate various enantiopure C-3-substituted pyroglutamates as well as C-3-substituted glutamates, and furthermore to ameliorate the serious drawback of the bad atom-economy in the reaction sequence of previously published silylether-mediated procedures. To meet these requirements, the ortho ester functionality (OBO ester) developed by Corey was introduced. According to the plan of synthesis, the starting material, non-racemic (S)-pyroglutamic acid, was converted to the corresponding oxetane ester via a DCC-mediated esterification. The latter was N-protected to provide N-acceptor substituted pyroglutamic acid oxetane esters (Acceptor=Boc,Cbz,CO2Me). After rearrangement with boron trifluoride, the ortho ester derivatives (Acceptor=Cbz,CO2Me) were at hand and exclusively the N-Cbz derivative was converted to the corresponding alpha,beta-unsaturated lactam via a syn-elimination reaction. The formation of the C-3-substituted ortho ester compounds (R=methyl,ethyl,butyl,allyl,phenyl,4-chlorophenyl,biphenyl,naphthyl) was performed via a copper-mediated conjugate addition to the alpha,beta-enone system of the N-Cbz-alpha,beta-unsaturated lactam. The OBO functionality hence was envisaged to support perfect trans selectivity in this cuprate addition to the Michael system of the N-Cbz-alpha,beta-unsaturated lactam. Spectroscopic NMR-data, on the basis of 1H-, 13C- and DEPT spectra, proved the assumption that the C-3-substituted ortho ester derivatives exclusively are trans-configurated, i.e. the alkyl derivatives (R=methyl,ethyl,butyl,allyl) are (2S,3S)-configurated and the aryl derivatives (R=phenyl,4-chlorophenyl,biphenyl,naphthyl) are (2S,3R)-configurated). The C-3-substituted ortho ester derivatives were completely deprotected to yield the C-3-substituted pyroglutamates (R=ethyl,phenyl,4-chlorophenyl,naphthyl). Finally, ring opening reaction via route A-2 lead to the desired enantiopure C-3-substituted glutamates. Alternatively, latter preferably were reacted via route A-1 to yield the C-3-substituted glutamates (R=methyl,ethyl,butyl,phenyl,4-chlorophenyl,naphthyl). Their (2S,3R)-configuration (R=aryl) and (2S,3S)-configuration (R=alky), respectively, unambiguously was proved on the basis of available spectroscopic NMR-data. To ensure this assumption, diastereomeric (2S,3R)-3-methyl glutamic acid (i.e. cis-configurated) examplarily was synthesized via route A-3 and spectroscopic NMR-data was compared to that of (2S,3S)-3-methyl glutamic acid (i.e. trans-configurated). Conclusively, there can be recorded the fact that the serious drawback of the bad atom-economy in the reaction sequence previously used can be circumvented by the introduction of the OBO functionality, so the concept of an improved atom-economy is achieved. Additionally, in comparison to the silyl-ether-mediated synthesis, the OBO functionality provided crystalline ortho ester derivatives, which facilitated their purification as well as characterization.
Staphylococcus epidermidis, the common inhabitant of human skin and mucosal surfaces has emerged as an important pathogen in patients carrying surgical implants and medical devices. Entering the body via surgical sites and colonizing the medical devices through formation of multi-layered biofilms leads to refractory and persistent device-related infections (DRIs). Staphylococci organized in biofilms are more tolerant to antibiotics and immune responses, and thus are difficult-to-treat. The consequent morbidity and mortality, and economic losses in health care systems has strongly necessitated the need for development of new anti-bacterial and anti-biofilm-based therapeutics. In this study, we describe the biological activity of a marine sponge-derived Streptomyces sp. SBT348 extract in restraining staphylococcal growth and biofilm formation on polystyrene, glass, medically relevant titan metal, and silicone surfaces. A bioassay-guided fractionation was performed to isolate the active compound (SKC3) from the crude SBT348 extract. Our results demonstrated that SKC3 effectively inhibits the growth (MIC: 31.25 \(\mu\)g/ml) and biofilm formation (sub-MIC range: 1.95-<31.25 \(\mu\)g/ml) of S. epidermidis RP62A in vitro. Chemical characterization of SKC3 by heat and enzyme treatments, and mass spectrometry (HRMS) revealed its heat-stable and non-proteinaceous nature, and high molecular weight (1258.3 Da). Cytotoxicity profiling of SKC3 in vitro on mouse fibroblast (NIH/3T3) and macrophage (J774.1) cell lines, and in vivo on the greater wax moth larvae Galleria mellonella revealed its non-toxic nature at the effective dose. Transcriptome analysis of SKC3 treated S. epidermidis RP62A has further unmasked its negative effect on central metabolism such as carbon flux as well as, amino acid, lipid, and energy metabolism. Taken together, these findings suggest a potential of SKC3 as a putative drug to prevent staphylococcal DRIs.
A closer look at long-established drugs: enantioselective protein binding and stability studies
(2023)
The aim of this work was to investigate older, established drugs. The extent of the protein binding of chiral ephedra alkaloids to AGP and of ketamine to albumin was determined. Since enantiomers of these drugs are individual available, the focus was on possible enantioselective binding and structural moieties involved in the binding.
Previously published work suggested that ephedrine and pseudoephedrine can bind stereoselectively to proteins other than albumin in serum. For the determination of the extent of protein binding, the established ultrafiltration with subsequent chiral CE analysis was used. To determine the influence of basicity on binding, the drugs methylephedrine and norephedrine were also analyzed. Drug binding to AGP increased with increasing basicity as follows: norephedrine < methylephedrine < ephedrine < pseudoephedrine. pKaff was determined both graphically using the Klotz plot and mathematical indicating a low affinity of the ephedra alkaloids to AGP. Using STD-NMR spectroscopy experiments the aromatic protons and the C-CH3 side chain were shown to be most strongly involved in binding, which could be confirmed by molecular docking experiments in more detail. For all drugs, van der Waals-, π π , cationic interactions, hydrogen bonds, and a formation of a salt bridge were observed. The individual enantiomers showed no significant differences and thus the binding of ephedra alkaloids to AGP is not significant.
In contrast to the ephedra alkaloids, the possible enantioselective binding to albumin was investigated for R and S ketamine. Again, ultrafiltration followed by CE analysis was performed. The binding of ketamine to one main binding site could be identified. A non-linear fit was used for the determination of pKaff. Using the NMR methods STD-NMR, waterLOGSY-NMR, and CPMG-NMRspectroscopy: the aromatic protons as well as the protons of the NCH3 methyl group showed the largest signal intensity changes, while the cyclohexanone protons showed the smallest changes. pKaff was also determined by the change in the chemical shift at different drug-protein ratios. These obtained values confirm the values obtained from ultrafiltration. Based on this, ketamine is classified as a low-affinity ligand to albumin. There were no significant differences between the individual enantiomers and thus the binding of ketamine to albumin is not a stereoselective process.
Using statistical design of experiments an efficient chiral CE method for determining the extent of protein binding of R and S ketamine to albumin was developed and validated according to ICH Q2 (R1) guideline.
The stability of ketamine was also investigated because a yellowish discoloration of an aqueous solution of ketamine developed under heat. XRPD investigations showed the same crystal structure for all batches examined. An untargeted screening using LC HRMS as well as LC UV measurements showed no degradation of ketamine or the presence of impurities in stress and non-stressed ketamine solutions, confirming the stability of ketamine under the stress conditions investigated. The lower the quality of the water used in the stress tests, the more intense the yellow discoloration occurred. The impurity or the mechanism that causes the yellow discoloration could not be identified.
Alzheimer's disease (AD) is a multifactorial disease and the most common form of dementia. There are no treatments to cure, prevent or slow down the progression of the disease. Natural products hold considerable interest for the development of preventive neuroprotectants to treat neurodegenerative disorders like AD, due to their low toxicity and general beneficial effects on human health with their anti-inflammatory and antioxidant features. In this work we describe regioselective synthesis of 7-O-ester hybrids of the flavonoid taxifolin with the phenolic acids cinnamic and ferulic acid, namely 7-O-cinnamoyltaxifolin and 7-O-feruloyltaxifolin. The compounds show pronounced overadditive neuroprotective effects against oxytosis, ferroptosis and ATP depletion in the murine hippocampal neuron HT22 cell model. Furthermore, 7-O-cinnamoyltaxifolin and 7-O-feruloyltaxifolin reduced LPS-induced neuroinflammation in BV-2 microglia cells as assessed by effects on the levels of NO, IL6 and TNFα. In all in vitro assays the 7-O-esters of taxifolin and ferulic or cinnamic acid showed strong overadditive activity, significantly exceeding the effects of the individual components and the equimolar mixtures thereof, which were almost inactive in all of the assays at the tested concentrations. In vivo studies confirmed this overadditive effect. Treatment of an AD mouse model based on the injection of oligomerized Aβ\(_{25-35}\) peptide into the brain to cause neurotoxicity and subsequently memory deficits with 7-O-cinnamoyltaxifolin or 7-O-feruloyltaxifolin resulted in improved performance in an assay for short-term memory as compared to vehicle and mice treated with the respective equimolar mixtures. These results highlight the benefits of natural product hybrids as a novel compound class with potential use for drug discovery in neurodegenerative diseases due to their pharmacological profile that is distinct from the individual natural components.
Die vorliegende Arbeit beschäftigte sich mit der Entwicklung und Synthese von Inhibitoren der Deoxyhypusin-Hydroxylase (DOHH), die einen wichtigen Schritt in der Aktivierung des eukaryotischen Translationsinitiations-Faktors-5A (eIF-5A) katalysiert. Die Hemmung dieses Metalloenzyms durch kleine Moleküle, die mit dem katalytischen Eisenatom im aktiven Zentrum der DOHH einen Chelatkomplex bilden, hat einen antiproliferativen Effekt auf parasitäre Erreger, wie Plasmodien, Trypanosomen und Leishmanien zur Folge. Ausgehend von den antiplasmodial wirksamen Eisenkomplexbildnern und Pyridon-Derivaten Ciclopirox und Mimosin wurden besser wirksame 2,6-Diaryl-4-oxopiperidincarbonsäuremono- und -diester-Derivate abgeleitet, deren 4-Piperidon-Grundgerüst als Leitstruktur für die Entwicklung von antiplasmodialen und antitrypanosomalen Wirkstoffen fungierte. Entsprechend dieser Leitstrukturen gelang im Zuge dieser Arbeit durch verschiedene Modifikationen der Doppel-Mannich-Reaktion die Erstellung einer weitreichenden Bibliothek 52 strukturell diverser 4-Hydroxytetrahydropyridin-3,5-dicarbonsäurediester 1 – 6, darunter auch erstmals Derivate mit t-Butyl-esterfunktionen und 4-Hydroxytetrahydropyridin-3-carbonsäuremonoester 7 – 8. Dabei konnten vor allem Derivate mit der gewünschten nitroaromatischen Substitution in den Positionen 2 und 6 synthetisiert werden. Darüber hinaus wurden vielfältige Strukturabwandlungen dieser Substanzen in Form von verschiedenen 4-Piperidonderivaten ohne Esterfunktionen, deren Oximen sowie von 4-Hydroxychinoloncarbonsäureestern syn-thetisiert. Die hergestellten Derivate wurden In-vitro-Testungen an Plasmodium falciparum, Trypanosoma brucei brucei und Leishmania major unterzogen. Zusätzlich wurde die Zytotoxizität an der Makrophagen-Zelllinie J774.1 ermittelt.
Im Mittelpunkt dieser Arbeit stand die Substanzgruppe der 4-Chinolone, die zum einen über ein intrinsisches antiparasitäres Potenzial gegen Erreger wie Plasmodien, Trypanosomen oder Mykobakterien verfügt und zum anderen über gezielte Substitution auch die Möglichkeit zu strukturellen Modifikationen bietet. Vorrangiges Ziel dieser Arbeit war der Aufbau einer strukturell möglichst diversen Substanzbibliothek und deren sukzessive Testung innerhalb des SFB630. Auf diese Weise sollten neue antiparasitäre Leitstrukturen als Ausgangspunkt für weitere strukturelle Optimierungen erhalten werden. Der Chinolon-Grundkörper sollte hierzu gemäß Gould-Jacobs-Reaktion aufgebaut werden. Zur Synthese diverser Amid-Derivate wurden verschiedene Synthese-strategien verfolgt. Alternativ wurden, ebenfalls über eine nukleophile Substitution (Piperidin-Derivat), in 7-Position modifizierte Verbindungen generiert, die unter Verwendung des Kupplungs-reagenzes PyBOB (Benzotriazol-1-yloxytri-pyrrolidinophosphonium Hexafluorphosphat) in die entsprechenden 1-Alkyl-1,4-dihydro-7-piperidinyl-4-oxo-chinolin-3-carboxamide transformiert wurden. Die in dieser Arbeit generierte Substanzbibliothek wurde anschließend innerhalb des SFB630 getestet. Hierbei zeigte sich, dass die Amidierung der 3-Carbonsäurefunktion eine Steigerung der antimikrobiellen Wirkung gegen Trypanosoma brucei mit sich brachte. Es kristallisierten sich aktive Verbindungen heraus, die erstmals eine Aktivität derartiger Derivate gegen Trypanosomen belegen und so zukünftig als Leitstrukturen für weitere strukturelle Modifizierungen herangezogen werden können. Mit dem in dieser Arbeit angewandten Random-Chemistry-Verfahren sollte in die Suche nach neuen Leitstrukturen gezielt das Zufallsprinzip integriert werden bzw. es sollten neue aktive Verbindungen generiert werden, die über die klassischen kombinatorischen Syntheseschemata bzw. die gängigen Reaktionsmechanismen nur schwer zugänglich sind. Eine Reihe von Fluorchinolon-Derivaten wurden in verschiedenen Lösungsmitteln, meist DMSO mit Zusätzen von Methanol oder Chloroform, gelöst bzw. suspendiert und anschließend einer ionisierenden γ-Strahlung von 500 kGy ausgesetzt. Die Testung mittels HPLC / FCPC generierter Fraktionen ergab zum Teil höhere antitrypanosomale Aktivitäten als die der korrespondie¬renden Ausgangsverbindungen. Eine Aktivität gegen Makrophagen konnte nicht festgestellt werden. Darüber hinaus wurde im Rahmen dieser Arbeit in Kooperation mit Prof. Schneider-Schaulies an der Identifizierung viraler Fusionsinhibitoren ausgewählter Paramyxoviren (Masern-Virus, Nipah-Virus) gearbeitet. Aus einer Ähnlichkeitssuche, basierend auf dem literaturbekannten Masern-Fusionsinhibitor 2-(4-Chlorphenyl)-N-(2-hydroxy-4-nitrophenyl)acetamid (AM-2), konnte die Struktur eines Chinolinamides identifiziert werden, woraufhin die generierte Substanzbibliothek auf antiviral-aktive Verbindungen gescreent werden sollte. Die Kristallstruktur des Nipah-Virus-Fusionsproteins wurde im Jahre 2006 aufgeklärt. Mit diesen Informationen konnte mittels Molecular-Modelling eine Bindetasche innerhalb der HR1-Domäne des F-Proteins identifiziert werden, mit der die erzielten inhibitorischen Aktivitäten gut in Einklang gebracht werden konnten. Diese Bindetasche befindet sich in einem Bereich weitreichender Umstrukturierungsvorgängen: Durch die Einlagerung des Liganden 7-(4-Carbamoyl-piperidin-1-yl)-N-(2,4-dichlorbenzyl)-1-cyclopropyl-6-fluor-4-oxo-1,4-dihydro-chinolin-3-carboxamid, in diese hydrophobe Tasche werden Wechselwirkungen mit den korrespondierenden Aminosäuren in der HR2-Domäne und so auch dessen Anlagerung unterbunden. In 1 μmolarer Konzentration konnte die Fusionsaktivität um 42% reduziert werden, die verwendeten Referenzsubstanz (OX-1) erzielte in selbiger Konzentration keine Wirkung.