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  1. Article ; Online: Increasing Complexity in Adamantyl Thioethers Characterized by Rotational Spectroscopy.

    Pinacho, Pablo / Loru, Donatella / Šumanovac, Tatjana / Šekutor, Marina / Schnell, Melanie

    Chemphyschem : a European journal of chemical physics and physical chemistry

    2023  Volume 24, Issue 23, Page(s) e202300561

    Abstract: We report on the synthesis and characterization using high-resolution rotational spectroscopy of three bulky thioethers that feature an adamantyl group connected to a sulfur atom. Detailed experimental and theoretical structures are provided and compared ...

    Abstract We report on the synthesis and characterization using high-resolution rotational spectroscopy of three bulky thioethers that feature an adamantyl group connected to a sulfur atom. Detailed experimental and theoretical structures are provided and compared with the 1,1'-diadamantyl ether. In addition, we expand on previous findings concerning microsolvation of adamantyl derivatives by investigating the cluster formation between these thioethers and a water molecule. The investigation of such clusters provides valuable insights into the sulfur-centered hydrogen bonding in thioethers with increasing size and steric repulsion.
    Language English
    Publishing date 2023-10-09
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2025223-7
    ISSN 1439-7641 ; 1439-4235
    ISSN (online) 1439-7641
    ISSN 1439-4235
    DOI 10.1002/cphc.202300561
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  2. Article ; Online: Interaction of crown ethers with the ABCG2 transporter and their implication for multidrug resistance reversal.

    Mioč, Marija / Telbisz, Ágnes / Radman, Katarina / Bertoša, Branimir / Šumanovac, Tatjana / Sarkadi, Balázs / Kralj, Marijeta

    Histochemistry and cell biology

    2022  Volume 158, Issue 3, Page(s) 261–277

    Abstract: Overexpression of ABC transporters, such as ABCB1 and ABCG2, plays an important role in mediating multidrug resistance (MDR) in cancer. This feature is also attributed to a subpopulation of cancer stem cells (CSCs), having enhanced tumourigenic potential. ...

    Abstract Overexpression of ABC transporters, such as ABCB1 and ABCG2, plays an important role in mediating multidrug resistance (MDR) in cancer. This feature is also attributed to a subpopulation of cancer stem cells (CSCs), having enhanced tumourigenic potential. ABCG2 is specifically associated with the CSC phenotype, making it a valuable target for eliminating aggressive and resistant cells. Several natural and synthetic ionophores have been discovered as CSC-selective drugs that may also have MDR-reversing ability, whereas their interaction with ABCG2 has not yet been explored. We previously reported the biological activities, including ABCB1 inhibition, of a group of adamantane-substituted diaza-18-crown-6 (DAC) compounds that possess ionophore capabilities. In this study, we investigated the mechanism of ABCG2-inhibitory activity of DAC compounds and the natural ionophores salinomycin, monensin and nigericin. We used a series of functional assays, including real-time microscopic analysis of ABCG2-mediated fluorescent substrate transport in cells, and docking studies to provide comparative aspects for the transporter-compound interactions and their role in restoring chemosensitivity. We found that natural ionophores did not inhibit ABCG2, suggesting that their CSC selectivity is likely mediated by other mechanisms. In contrast, DACs with amide linkage in the side arms demonstrated noteworthy ABCG2-inhibitory activity, with DAC-3Amide proving to be the most potent. This compound induced conformational changes of the transporter and likely binds to both Cavity 1 and the NBD-TMD interface. DAC-3Amide reversed ABCG2-mediated MDR in model cells, without affecting ABCG2 expression or localization. These results pave the way for the development of new crown ether compounds with improved ABCG2-inhibitory properties.
    MeSH term(s) ATP Binding Cassette Transporter, Subfamily G, Member 2/metabolism ; Antineoplastic Agents/pharmacology ; Cell Line, Tumor ; Crown Ethers/pharmacology ; Drug Resistance, Multiple ; Drug Resistance, Neoplasm ; Ionophores/pharmacology
    Chemical Substances ATP Binding Cassette Transporter, Subfamily G, Member 2 ; Antineoplastic Agents ; Crown Ethers ; Ionophores
    Language English
    Publishing date 2022-06-01
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1222930-1
    ISSN 1432-119X ; 0301-5564 ; 0948-6143
    ISSN (online) 1432-119X
    ISSN 0301-5564 ; 0948-6143
    DOI 10.1007/s00418-022-02106-z
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  3. Article ; Online: Photoelimination of nitrogen from adamantane and pentacycloundecane (PCU) diazirines: a spectroscopic study and supramolecular control.

    Šumanovac, Tatjana / Alešković, Marija / Šekutor, Marina / Matković, Marija / Baron, Thibaut / Mlinarić-Majerski, Kata / Bohne, Cornelia / Basarić, Nikola

    Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

    2019  Volume 18, Issue 7, Page(s) 1806–1822

    Abstract: Photochemical reactivity of pentacycloundecane (PCU) and adamantane diazirines was investigated by preparative irradiation in different solvents, laser flash photolysis (LFP) and quantum chemical computations. In addition, formation of inclusion ... ...

    Abstract Photochemical reactivity of pentacycloundecane (PCU) and adamantane diazirines was investigated by preparative irradiation in different solvents, laser flash photolysis (LFP) and quantum chemical computations. In addition, formation of inclusion complexes for diazirines with cucurbit[7]uril, β- and γ-cyclodextrin (β- and γ-CD) was investigated by 1H NMR spectroscopy, isothermal microcalorimetry and circular dichroism spectroscopy, followed by the investigation of photochemical reactivity of the formed complexes. Diazirines undergo efficient photochemical elimination of nitrogen (ΦR > 0.5) and deliver the corresponding singlet carbenes. Singlet carbenes react in intra- and intermolecular reactions and we found a rare singlet carbene pathway in CH3OH involving protonation and formation of a carbocation, detected due to the specific rearrangement of the pentacycloundecane skeleton. Singlet diazirines undergo intersystem crossing and deliver triplet carbenes that react with oxygen to form ketones which were isolated after irradiation. Our main finding is that the formation of diazirine inclusion complexes with β-CD and γ-CD changes the relative ratio of singlet vs. triplet pathways, with singlet carbene products being dominant from the chemistry of the irradiated complexes. Our combined theoretical and experimental studies provide new insights into the supramolecular control of carbene reactivity which has possible applications for the control of product distribution by solvent effects and the choice of constrained media.
    Language English
    Publishing date 2019-06-04
    Publishing country England
    Document type Journal Article
    ZDB-ID 2072584-X
    ISSN 1474-9092 ; 1474-905X
    ISSN (online) 1474-9092
    ISSN 1474-905X
    DOI 10.1039/c9pp00124g
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