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Publikation

Edeler, D., Arlt, S., Petković, V., Ludwig, G., Drača, D., Maksimović-Ivanić, D., Mijatović, S. & Kaluđerović, G. N. Delivery of [Ru(η6-p-cymene)Cl2{Ph2P(CH2)3SPh-κP}] using unfunctionalized and mercapto functionalized SBA-15 mesoporous silica: Preparation, characterization and in vitro study. J Inorg Biochem. 180, 155-162, (2018) DOI: 10.1016/j.jinorgbio.2017.12.011

SBA-15 (Santa Barbara Amorphous 15) mesoporous silica and its functionalized form (with 3-mercaptopropyltriethoxysilane) SBA-15~SH were used as carriers for [Ru(η6-p-cymene)Cl2{Ph2P(CH2)3SPh-κP}] complex, denoted as [Ru]. Prepared mesoporous silica nanomaterials were characterized by traditional methods. Materials without [Ru] complex did not show any cytotoxic activity against melanoma B16 and B16-F10 cell lines. On the contrary, materials containing [Ru] such as SBA-15¦[Ru] and SBA-15~SH¦[Ru], exhibited very high activity against tested tumor cell lines, moreover with similar inhibitory potential. According to the loaded amount of the [Ru] in SBA-15¦[Ru] and SBA-15~SH¦[Ru] the IC50 values are 1–2 μM depending on the test used, thus in comparison to [Ru] alone the activity of nanomaterials containing [Ru] are elevated 3–6 times in vitro. However, the mechanism of apoptosis induction differs for these two mesoporous silica. Unlike reference [Ru] compound and SBA-15~SH¦[Ru], SBA-15¦[Ru] induces high caspase activation. Discrepancy in mechanism of drugs action at intracellular level points towards an influence of functionalization as well as availability of the drug. Moreover, both SBA-15¦[Ru] and SBA-15~SH¦[Ru] similarly to [Ru] are declining autophagy in B16 cell line.
Publikation

Knezevic, N. Z. & Kaluderovic, G. N. Silicon-based nanotheranostics.  Nanoscale 9, 12821-12829, (2017) DOI: 10.1039/C7NR04445C

With the rapid expansion of nanoscience and nanotechnology in interdisciplinary fields, multifunctional nanomaterials have attracted particular attention. Recent advances in nanotherapeutics for cancer applications provided diverse groups of synthetic particles with defined cellular and biological functions. The advance of nanotechnology significantly increased the number of possibilities for the construction of diverse biological tools. Such materials are destined to be of great importance because of the opportunity to combine the biotechnological potential of nanoparticles together with the recognition, sensitivity and modulation of cellular pathways or genes when applied to living organisms. In this mini review three main types of Si-based nanomaterials are highlighted in the area of their application for therapy and imaging: porous silicon nanoparticles (pSiNPs), mesoporous silica nanoparticles (MSNs), focusing on their nanoconstructs containing coordination compounds, and periodic mesoporous silica nanoparticles (PMONPs). Moreover, a critical discussion on the research efforts in the construction of nanotheranostics is presented.
Publikation

Kaluderovic, G. N., Abbas, M., Kautz, H. C., Wadaan, M. A. M., Lennicke, C., Seliger, B. & Wessjohann, L. A. Methionine and seleno-methionine type peptide and peptoid building blocks synthesized by five-component five-center reactions.  Chem Commun. 53, 3777-3780, (2017) DOI: 10.1039/C7CC00399D

A first example of 5-component 5-center reactions with isonitriles [Ugi-5CRs] is described. The extended Ugi type reactions involve selenoaldehydes as well as ammonia, both challenging reactants in multicomponent (MCR) systems, to generate methionine and Se-methionine moieties and derivatives as protected building blocks or for direct ligation in peptides or peptoids. The peptoid/peptide building blocks proved to be non-cytotoxic but increased the expression of genes encoding for stress protective selenoproteins (Gpx1).
Publikation

Farag, M. A., Ammar, N. M., Kholeif, T. E., , Metwally, N. S., El-Sheikh, N. M., Wessjohann, L. A. & Abdel-Hamid, A. Z. Rats' urinary metabolomes reveal the potential roles of functional foods and exercise in obesity management.  Food Funct. 8, 985-996, (2017) DOI: 10.1039/C6FO01753C

The complexity of the metabolic changes in obese individuals still presents a challenge for the understanding of obesity-related metabolic disruptions and for obesity management. In this study, a gas chromatography mass spectrometry (GC-MS) based metabolomics approach targeting urine metabolism has been applied to assess the potential roles of functional foods and exercise for obesity management in rats. Male albino rats diagnosed as obese via histopathology and biochemical assays were administered functional foods in common use for obesity management including pomegranate, grapefruit, and red cabbage juice extracts in parallel with swimming exercise. Urine samples were collected from these rats, and likewise from healthy control animals, for metabolite analysis using (GC-MS) coupled to multivariate data analysis. The results revealed a significant elevation in oxalate and phosphate levels in obese rat urine concurrent with lower lactate levels as compared to the control group. Furthermore, and to pinpoint the bioactive agents in the administered functional foods, ultra performance liquid chromatography (UPLC) coupled to high resolution time-of-flight mass spectrometry (TOF-MS) was employed for secondary metabolite profiling. The different phenolic classes found in the examined functional foods, viz. ellagitannins in pomegranate, flavanones in grapefruit and flavonols in red cabbage, are likely to mediate their anti-obesity effects. The results indicate that these functional foods and exercise were quite effective in reverting obesity-related metabolic disruptions back to normal status, as revealed by orthogonal partial least squares-discriminant analysis (OPLS-DA).
Publikation

El-Sayed, M. T., Wessjohann, L., Porzel, A. & Hilgeroth, A. Diazatruxenes from the condensation reaction of indoles with ninhydrin.  J Heterocycl Chem. 54, 1077-1083, (2017) DOI: 10.1002/jhet.2677

The reaction of indoles with ninhydrin has been reported to provide only 1:1 condensation products (cf. A or 8) that show good antioxidant and anti-inflammatory activity. In the present work, our synthetic challenge for the synthesis of innovative, highly substituted tetra-indole indanes of type 1 via a 4:1 condensation reaction in acetic acid gave two unexpected new products, the diazatruxene derivatives 3 and 4. The novel structures have been characterized by their analytical and spectral data including 1D- and 2D-NMR. With 5-chloroindole, only the known 1:1 reaction.
Publikation

Farag, M. A. Ali., S. E., Hodaya, R. H., El-Seedi, H. R., Sultani, H. N., Laub, A., Eissa, T. F., Abou-Zaid, F. O. F. & Wessjohann, L. A. Molecules 22, 761, (2017) DOI: 10.3390/molecules22050761

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Publikation

Stojković, D. L., Jevtić, V. V., Vuković, N., Vukić, M., Potočňák, I., Zelen, I. R., Zarić, M. M., Mišić, M. M., Baskić, D., Kaluđerović, G. N. & Trifunović, S. R. Crystal and molecular structure of a new palladium(II) complex with a coumarin-valine derivate. J. Struct. Chem 58, 550-557, (2017) DOI: 10.1134/S0022476617030179

The new coumarine derivate with methyl ester of 2-((Z)-1(2,4-dioxochroman-3-ylidene)ethylamino)-3-methylbutanoic acid and the corresponding palladium(II) complex are synthesized and characterized by microanalysis, infrared, 1H and 13C NMR spectroscopy. The proposed structure of the ligand was confirmed based on the X-ray structural study.
Publikation

Farag, M. A., Al-Mahdy, D. A., Meyer, A., Westphal, H. & Wessjohann, L. A. Metabolomics reveals biotic and abiotic elicitor effects on the soft coral Sarcophyton ehrenbergi terpenoid content. Scientific Reports 7, 648, (2017) DOI: 10.1038/s41598-017-00527-8

The effects of six biotic and abiotic elicitors, i.e. MeJA (methyl jasmonate), SA (salicylic acid), ZnCl2, glutathione and β-glucan BG (fungal elicitor), and wounding, on the secondary metabolite accumulation in the soft coral Sarcophyton ehrenbergi were assessed. Upon elicitation, metabolites were extracted and analysed by ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). Except for MeJA, no differences in photosynthetic efficiency were observed after treatments, suggesting the absence of a remarkable stress on primary production. Chemometric analyses of UPLC-MS data showed clear segregation of SA and ZnCl2 elicited samples at 24 and 48 h post elicitation. Levels of acetylated diterpene and sterol viz., sarcophytonolide I and cholesteryl acetate, was increased in ZnCl2 and SA groups, respectively, suggesting an activation of specific acetyl transferases. Post elicitation, sarcophytonolide I level increased 132 and 17-folds at 48 h in 0.1 mM SA and 1 mM ZnCl2 groups, respectively. Interestingly, decrease in sarcophine, a major diterpene was observed only in response to ZnCl2, whereas no change was observed in sesquiterpene content following treatments. To the best of our knowledge, this study provides the first documentation for elicitation effects on a soft corals secondary metabolome and suggests that SA could be applied to increase diterpenoid levels in corals.
Publikation

Otto, A., Laub, A., Wendt, L., Porzel, A., Schmidt, J., Palfner, G., Becerra, J., Krüger, D., Stadler, M., Wessjohann, L., Westermann, B. & Arnold, N. Chilenopeptins A and B, Peptaibols from the Chilean Sepedonium aff. chalcipori KSH 883 J. Nat. Prod. 79, 929-938, (2016) DOI: 10.1021/acs.jnatprod.5b01018

The Chilean Sepedonium aff. chalcipori strain KSH 883, isolated from the endemic Boletus loyo Philippi, was studied in a polythetic approach based on chemical, molecular, and biological data. A taxonomic study of the strain using molecular data of the ITS, EF1-α, and RPB2 barcoding genes confirmed the position of the isolated strain within the S. chalcipori clade, but also suggested the separation of this clade into three different species. Two new linear 15-residue peptaibols, named chilenopeptins A (1) and B (2), together with the known peptaibols tylopeptins A (3) and B (4) were isolated from the semisolid culture of strain KSH 883. The structures of 1 and 2 were elucidated on the basis of HRESIMSn experiments in conjunction with comprehensive 1D and 2D NMR analysis. Thus, the sequence of chilenopeptin A (1) was identified as Ac-Aib1-Ser2-Trp3-Aib4-Pro5-Leu6-Aib7-Aib8-Gln9-Aib10-Aib11-Gln12-Aib13-Leu14-Pheol15, while chilenopeptin B (2) differs from 1 by the replacement of Trp3 by Phe3. Additionally, the total synthesis of 1 and 2 was accomplished by a solid-phase approach, confirming the absolute configuration of all chiral amino acids as l. Both the chilenopeptins (1 and 2) and tylopeptins (3 and 4) were evaluated for their potential to inhibit the growth of phytopathogenic organisms.

Publikation

Farag, M.A., Otify, A., Porzel, A., Michel, C. G., Elsayed, A. & Wessjohann, L. A. Comparative metabolite profiling and fingerprinting of genus Passiflora leaves using a multiplex approach of UPLC-MS and NMR analyzed by chemometric tools. Anal Bioanal Chem 408, 3125–3143, (2016) DOI: 10.1007/s00216-016-9376-4

Passiflora incarnata as well as some other Passiflora species are reported to possess anxiolytic and sedative activity and to treat various CNS disorders. The medicinal use of only a few Passiflora species has been scientifically verified. There are over 400 species in the Passiflora genus worldwide, most of which have been little characterized in terms of phytochemical or pharmacological properties. Herein, large-scale multi-targeted metabolic profiling and fingerprinting techniques were utilized to help gain a broader insight into Passiflora species leaves’ chemical composition. Nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS) spectra of extracted components derived from 17 Passiflora accessions and from different geographical origins were analyzed using multivariate data analyses. A total of 78 metabolites were tentatively identified, that is, 20 C-flavonoids, 8 O-flavonoids, 21 C, O-flavonoids, 2 cyanogenic glycosides, and 23 fatty acid conjugates, of which several flavonoid conjugates are for the first time to be reported in Passiflora spp. To the best of our knowledge, this study provides the most complete map for secondary metabolite distribution within that genus. Major signals in 1H-NMR and MS spectra contributing to species discrimination were assigned to those of C-flavonoids including isovitexin-2″-O-xyloside, luteolin-C-deoxyhexoside-O-hexoside, schaftoside, isovitexin, and isoorientin. P. incarnata was found most enriched in C-flavonoids, justifying its use as an official drug within that genus. Compared to NMR, LC-MS was found more effective in sample classification based on genetic and/ or geographical origin as revealed from derived multivariate data analyses. Novel insight on metabolite candidates to mediate for Passiflora CNS sedative effects is also presented.

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