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  1. Article ; Online: Divergent Synthesis of Six Recent Berkeleylactones.

    Schriefer, Manuel G / Schobert, Rainer

    Journal of natural products

    2023  Volume 86, Issue 2, Page(s) 423–428

    Abstract: The six recently isolated berkeleylactones E, J, K, M, N, and O were synthesized for the first time by a divergent strategy starting from a common intermediate in our synthesis of berkeleylactone A. Key features were the stereoselective formation of the ... ...

    Abstract The six recently isolated berkeleylactones E, J, K, M, N, and O were synthesized for the first time by a divergent strategy starting from a common intermediate in our synthesis of berkeleylactone A. Key features were the stereoselective formation of the γ,δ-dihydroxy-α,β-unsaturated ester moiety and the development of a general protection group strategy. Along the way we also established a short high-yielding formal synthesis of the often-synthesized antibiotic A26771B.
    MeSH term(s) Stereoisomerism ; Anti-Bacterial Agents ; Esters
    Chemical Substances Anti-Bacterial Agents ; Esters
    Language English
    Publishing date 2023-02-13
    Publishing country United States
    Document type Journal Article
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.3c00053
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Analogues of the fungal macrocidin Z, derived from different amino acids: Syntheses and antibiofilm activity

    Röder, Moritz / Karau, Annika / Schobert, Rainer / Schrey, Hedda

    Tetrahedron. 2023 May, v. 137 p.133377-

    2023  

    Abstract: Three new analogues of the fungal metabolite macrocidin Z, derived from homoserine, o-tyrosine and 5-hydroxytryptophan, rather than l-tyrosine were synthesised and tested for efficacy against selected pathogenic biofilms. They exhibited significant ... ...

    Abstract Three new analogues of the fungal metabolite macrocidin Z, derived from homoserine, o-tyrosine and 5-hydroxytryptophan, rather than l-tyrosine were synthesised and tested for efficacy against selected pathogenic biofilms. They exhibited significant growth inhibitory and dispersal effects against S. aureus biofilms, comparable to those of the natural lead macrocidin Z, and even superior to those of non-natural normacrocidin Z, which they resemble more closely. Their low level of toxicity to human cells and bacteria warrants a more detailed assessment.
    Keywords 5-hydroxytryptophan ; antimicrobial properties ; biofilm ; fungi ; homoserine ; humans ; lead ; metabolites ; toxicity ; tyrosine ; Macrocidins ; Tetramic acids ; Macrolactams ; Biofilm activity
    Language English
    Dates of publication 2023-05
    Publishing place Elsevier Ltd
    Document type Article ; Online
    ZDB-ID 204285-x
    ISSN 1464-5416 ; 0040-4020 ; 0563-2064
    ISSN (online) 1464-5416
    ISSN 0040-4020 ; 0563-2064
    DOI 10.1016/j.tet.2023.133377
    Database NAL-Catalogue (AGRICOLA)

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  3. Article: Formal synthesis of kibdelomycin and derivatisation of amycolose glycosides.

    Schriefer, Manuel G / Treiber, Laura / Schobert, Rainer

    Chemical science

    2023  Volume 14, Issue 13, Page(s) 3562–3568

    Abstract: A convergent total synthesis of bacterial gyrase B/topoisomerase IV inhibitor kibdelomycin (a.k.a. amycolamicin) (1) was devised starting from inexpensive d-mannose and l-rhamnose, which were converted in new efficient ways to ... ...

    Abstract A convergent total synthesis of bacterial gyrase B/topoisomerase IV inhibitor kibdelomycin (a.k.a. amycolamicin) (1) was devised starting from inexpensive d-mannose and l-rhamnose, which were converted in new efficient ways to an
    Language English
    Publishing date 2023-03-03
    Publishing country England
    Document type Journal Article
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/d3sc00595j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Syntheses and Antibacterial Evaluation of New Penicillium Metabolites Gregatins G and Thiocarboxylics C.

    Gillsch, Franziska / Mbui, Fredrick / Bilitewski, Ursula / Schobert, Rainer

    Chemistry & biodiversity

    2023  Volume 20, Issue 4, Page(s) e202300181

    Abstract: Two pairs of side-chain epimeric 3-methoxycarbonyl-dihydrofuran-4-ones with structures purported for thiocarboxylics ... ...

    Abstract Two pairs of side-chain epimeric 3-methoxycarbonyl-dihydrofuran-4-ones with structures purported for thiocarboxylics C
    MeSH term(s) Anti-Bacterial Agents/chemistry ; Escherichia coli/drug effects ; Furans/chemistry ; Furans/pharmacology ; Microbial Sensitivity Tests ; Molecular Structure ; Penicillium/chemistry ; Staphylococcus aureus/drug effects
    Chemical Substances Anti-Bacterial Agents ; Furans ; gregatin G
    Language English
    Publishing date 2023-03-22
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2139001-0
    ISSN 1612-1880 ; 1612-1872
    ISSN (online) 1612-1880
    ISSN 1612-1872
    DOI 10.1002/cbdv.202300181
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Syntheses and Biofilm Reducing Effects of l-Dopa-Derived Analogues of the Fungal Macrocidins A and Z.

    Pezolt, Christine / Karau, Annika / Schobert, Rainer / Schrey, Hedda

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2023  Volume 29, Issue 21, Page(s) e202203647

    Abstract: Four analogues of the fungal metabolites macrocidin A and Z, featuring [13]para- or [13]metacyclophanes, were synthesised from fully and orthogonally protected l-dopa instead of l-tyrosine. They were tested for antibiotic activities and for effects on ... ...

    Abstract Four analogues of the fungal metabolites macrocidin A and Z, featuring [13]para- or [13]metacyclophanes, were synthesised from fully and orthogonally protected l-dopa instead of l-tyrosine. They were tested for antibiotic activities and for effects on the growth and persistence of microbial biofilms. Tentative structure-activity relationships and distinct differences when compared with the natural lead compounds were identified.
    MeSH term(s) Levodopa ; Biofilms ; Structure-Activity Relationship ; Anti-Bacterial Agents/pharmacology ; Tyrosine
    Chemical Substances Levodopa (46627O600J) ; Anti-Bacterial Agents ; Tyrosine (42HK56048U)
    Language English
    Publishing date 2023-03-10
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202203647
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Fluorinated and

    Ghosh, Hindole / Bhattacharyya, Sangita / Schobert, Rainer / Dandawate, Prasad / Biersack, Bernhard

    Pharmaceutics

    2023  Volume 15, Issue 7

    Abstract: Pancreatic carcinoma is a cancer disease with high mortality. Thus, new and efficient treatments for this disease are badly needed. Curcumin has previously shown promising effects in pancreatic cancer patients; however, this natural compound suffers from ...

    Abstract Pancreatic carcinoma is a cancer disease with high mortality. Thus, new and efficient treatments for this disease are badly needed. Curcumin has previously shown promising effects in pancreatic cancer patients; however, this natural compound suffers from inadequate efficacy and bioavailability, preventing its clinical approval. The synthetic curcuminoid EF24 was developed with activities superior to curcumin against various cancer types. In this study, a series of analogs of EF24 were investigated for anticancer effects on pancreatic carcinoma models. A distinct activity boost was achieved by straightforward
    Language English
    Publishing date 2023-07-11
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2527217-2
    ISSN 1999-4923
    ISSN 1999-4923
    DOI 10.3390/pharmaceutics15071921
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Syntheses and biological effects of natural Morinda lactone and derivatives.

    Güttlein, Patricia / Schrey, Hedda / Zeng, Haoxuan / Schobert, Rainer

    Organic & biomolecular chemistry

    2022  Volume 20, Issue 23, Page(s) 4794–4802

    Abstract: 2-Caffeoyl-3-ketohexulofuranosonic acid γ-lactone (morinda lactone; 1a), a natural constituent ... ...

    Abstract 2-Caffeoyl-3-ketohexulofuranosonic acid γ-lactone (morinda lactone; 1a), a natural constituent of
    MeSH term(s) Animals ; Anti-Bacterial Agents/pharmacology ; Candida albicans ; Lactones/pharmacology ; Mammals ; Morinda/chemistry ; Plant Extracts/chemistry ; Staphylococcus aureus
    Chemical Substances Anti-Bacterial Agents ; Lactones ; Plant Extracts
    Language English
    Publishing date 2022-06-15
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d2ob00511e
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article ; Online: Synthesis and Bioactivity of Thiocarboxylic A and Derivatives.

    Gillsch, Franziska / Mbui, Fredrick / Bilitewski, Ursula / Schobert, Rainer

    Journal of natural products

    2022  

    Abstract: ... ...

    Abstract The
    Language English
    Publishing date 2022-11-23
    Publishing country United States
    Document type Journal Article
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.2c00870
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: 3D cell cultures, as a surrogate for animal models, enhance the diagnostic value of preclinical in vitro investigations by adding information on the tumour microenvironment: a comparative study of new dual-mode HDAC inhibitors.

    Bär, Sofia I / Biersack, Bernhard / Schobert, Rainer

    Investigational new drugs

    2022  Volume 40, Issue 5, Page(s) 953–961

    Abstract: Anchorage-independent 3D-cultures of multicellular tumour spheroids (MCTS) and in vitro microtumours of cancer cells can provide upfront information on the effects of anticancer drug candidates, tantamount to that obtained from animal xenograft studies. ... ...

    Abstract Anchorage-independent 3D-cultures of multicellular tumour spheroids (MCTS) and in vitro microtumours of cancer cells can provide upfront information on the effects of anticancer drug candidates, tantamount to that obtained from animal xenograft studies. Unlike 2D cancer cell cultures, 3D-models take into account the influence of the tumour microenvironment and the location dependence of drug effects and accumulation. We exemplified this by comparison of the effects of two new dual-mode anticancer agents, Troxbam and Troxham, and their monomodal congeners SAHA (suberoylanilide hydroxamic acid) and CA-4 (combretastatin A-4). We assessed the growth of MCTS of HCT116<sup>wt</sup> human colon carcinoma cells exposed to these compounds, as well as the spatial distribution of dead HCT116<sup>wt</sup> cells in these MCTS. Also, fluorescence imaging of live and fixed MCTS was used to assess the type of cellular death induced by test compounds. Furthermore, an innovative perfusion bioreactor system was used to grow microtumours in the presence or absence of test compounds. Both new investigational compounds led to significant reductions of the size of such MCTS and also of corresponding in vitro microtumours by inducing caspase-9 dependent apoptosis and elevated levels of reactive oxygen species. 3D multicellular tumour spheroids are easy to grow and employ for compound tests in the familiar well-plate set-up. Together with 3D microtumours grown at scaffolds in continuously perfused bioreactors they allow to study, early on in the course of drug evaluations, the communication of tumour cells with their microenvironment to an extent hitherto available only in animal experiments.
    MeSH term(s) Animals ; Antineoplastic Agents/pharmacology ; Cell Culture Techniques, Three Dimensional ; Cell Line, Tumor ; Colonic Neoplasms/drug therapy ; Histone Deacetylase Inhibitors/pharmacology ; Humans ; Models, Animal ; Spheroids, Cellular ; Tumor Microenvironment ; Vorinostat/pharmacology
    Chemical Substances Antineoplastic Agents ; Histone Deacetylase Inhibitors ; Vorinostat (58IFB293JI)
    Language English
    Publishing date 2022-07-07
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 604895-x
    ISSN 1573-0646 ; 0167-6997
    ISSN (online) 1573-0646
    ISSN 0167-6997
    DOI 10.1007/s10637-022-01280-0
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Book ; Online ; Thesis: Präklinische Studien neuer multimodaler, antitumoraler Hybridwirkstoffe mittels klassischer 2D- und realitätsnäherer 3D-Tumorzellkulturassays

    Bär, Sofia I. [Verfasser] / Schobert, Rainer [Akademischer Betreuer]

    2023  

    Author's details Sofia I. Bär ; Betreuer: Rainer Schobert
    Keywords Naturwissenschaften ; Science
    Subject code sg500
    Language German
    Publisher Universität Bayreuth
    Publishing place Bayreuth
    Document type Book ; Online ; Thesis
    Database Digital theses on the web

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