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  1. Article ; Online: Persistent guaiazulene arylmethylium ions as electrophilic traps for metal enolates.

    Kisszékelyi, Péter / Mudráková, Brigita / Cigáň, Marek / Šebesta, Radovan

    Chemical communications (Cambridge, England)

    2024  Volume 60, Issue 24, Page(s) 3339–3342

    Abstract: Guaiazulene-stabilized cations reacted with metal enolates affording carbonyl compounds with an azulene moiety. Metal enolates generated by asymmetric conjugate addition of organometallic reagents led to enantioenriched products. Additionally, ... ...

    Abstract Guaiazulene-stabilized cations reacted with metal enolates affording carbonyl compounds with an azulene moiety. Metal enolates generated by asymmetric conjugate addition of organometallic reagents led to enantioenriched products. Additionally, guaiazulene-substituted cations efficiently react with silyl enol ethers. DFT calculations allowed estimation of the electrophilicities of the carbocations. Reaction progress was monitored by a decrease in the reactant's Vis-light absorption and an increase in the product's anti-Kasha emission.
    Language English
    Publishing date 2024-03-19
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d4cc00208c
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  2. Article ; Online: Rigidized 3-aminocoumarins as fluorescent probes for strongly acidic environments and rapid yeast vacuolar lumen staining: mechanism and application.

    Joniak, Jakub / Stankovičová, Henrieta / Budzák, Šimon / Sýkora, Milan / Gaplovská-Kyselá, Katarína / Filo, Juraj / Cigáň, Marek

    Physical chemistry chemical physics : PCCP

    2023  Volume 25, Issue 30, Page(s) 20212–20217

    Abstract: Coumarins remain one of the most important groups of fluorescent bio-probes, thanks to their high quantum yields, moderate photostability, efficient cell permeation and low (cyto)toxicity. Herein, we introduce new 3-aminocoumarins as turn-on pH probes ... ...

    Abstract Coumarins remain one of the most important groups of fluorescent bio-probes, thanks to their high quantum yields, moderate photostability, efficient cell permeation and low (cyto)toxicity. Herein, we introduce new 3-aminocoumarins as turn-on pH probes under strongly acidic conditions and for indicators capable of significantly improving yeast vacuolar lumen staining compared to the commercial CMAC derivatives. We present the details of the on-off switching mechanism revealed by the TD-DFT and
    MeSH term(s) Fluorescent Dyes ; Aminocoumarins ; Saccharomyces cerevisiae ; Acids ; Coumarins
    Chemical Substances Fluorescent Dyes ; Aminocoumarins ; Acids ; Coumarins
    Language English
    Publishing date 2023-08-02
    Publishing country England
    Document type Journal Article
    ZDB-ID 1476244-4
    ISSN 1463-9084 ; 1463-9076
    ISSN (online) 1463-9084
    ISSN 1463-9076
    DOI 10.1039/d3cp01090b
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Phosphate linkers with traceable cyclic intermediates for self-immolation detection and monitoring

    Procházková, Eliška / Šimon, Petr / Straka, Michal / Filo, Juraj / Májek, Michal / Cigáň, Marek / Baszczyňski, Ondřej

    Chemical communications. 2021 Jan. 7, v. 57, no. 2

    2021  

    Abstract: Self-immolation (SI) is the key principle of ProTide nucleotide prodrugs such as remdesivir, which is currently used to treat COVID-19 patients. Developing novel tailor-made SI systems requires new analytical methods for the detection and monitoring of ... ...

    Abstract Self-immolation (SI) is the key principle of ProTide nucleotide prodrugs such as remdesivir, which is currently used to treat COVID-19 patients. Developing novel tailor-made SI systems requires new analytical methods for the detection and monitoring of SI. We developed a robust method for SI analysis using novel phosphate-based SI linkers with NMR traceable cyclic intermediates to distinguish SI from alternative fragmentation pathways and to monitor cargo release in real time.
    Keywords COVID-19 infection ; analytical methods ; chemical communication ; monitoring ; patients ; phosphates
    Language English
    Dates of publication 2021-0107
    Size p. 211-214.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d0cc06928k
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  4. Article ; Online: Enhancing the Potential of Fused Heterocycle-Based Triarylhydrazone Photoswitches.

    Hegedüsová, Lea / Blaise, Nadine / Pašteka, Lukáš F / Budzák, Šimon / Medveď, Miroslav / Filo, Juraj / Mravec, Bernard / Slavov, Chavdar / Wachtveitl, Josef / Grabarz, Anna M / Cigáň, Marek

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  Volume 30, Issue 8, Page(s) e202303509

    Abstract: Triarylhydrazones represent an attractive class of photochromic compounds offering many interesting features including high molar absorptivity, good addressability, and extraordinary thermal stability. In addition, unlike most other hydrazone-based ... ...

    Abstract Triarylhydrazones represent an attractive class of photochromic compounds offering many interesting features including high molar absorptivity, good addressability, and extraordinary thermal stability. In addition, unlike most other hydrazone-based photoswitches, they effectively absorb light above 365 nm. However, previously prepared triaryhydrazones suffer from low quantum yields of the Z→E photoisomerization. Here, we have designed a new subclass of naphthoyl-benzothiazole hydrazones that balance the most beneficial features of previously reported naphthoyl-quinoline and benzoyl-pyridine triarylhydrazones. These preserve the attractive absorption characteristics, exhibit higher thermal stability of the metastable form than the former and enhance the rate of the Z→E photoisomerization compared to the later, as a result of the weakening of the intramolecular hydrogen bonding between the hydrazone hydrogen and the benzothiazole moiety. Introducing the benzothiazole motif extends the tunability of the photochromic behaviour of hydrazone-based switches.
    Language English
    Publishing date 2024-01-11
    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.202303509
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  5. Article ; Online: Enhancing the Potential of Fused Heterocycle-Based Triarylhydrazone Photoswitches.

    Hegedüsová, Lea / Blaise, Nadine / Pašteka, Lukáš F / Budzák, Šimon / Medved', Miroslav / Filo, Juraj / Mravec, Bernard / Slavov, Chavdar / Wachtveitl, Josef / Grabarz, Anna M / Cigáň, Marek

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  Volume 30, Issue 8, Page(s) e202400141

    Abstract: Invited for the cover of this issue are Marek Cigáň, Anna M. Grabarz and co-workers. The image depicts how a non-expert might imagine a "molecular photoswitch". Read the full text of the article at 10.1002/chem.202303509. ...

    Abstract Invited for the cover of this issue are Marek Cigáň, Anna M. Grabarz and co-workers. The image depicts how a non-expert might imagine a "molecular photoswitch". Read the full text of the article at 10.1002/chem.202303509.
    Language English
    Publishing date 2024-01-23
    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.202400141
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  6. Article ; Online: Unsymmetrical benzothiazole-based dithienylethene photoswitches.

    Bovoloni, Michelangelo / Filo, Juraj / Sigmundová, Ivica / Magdolen, Peter / Budzák, Šimon / Procházková, Eliška / Tommasini, Matteo / Cigáň, Marek / Bianco, Andrea

    Physical chemistry chemical physics : PCCP

    2022  Volume 24, Issue 38, Page(s) 23758–23768

    Abstract: Herein, we investigate the structure-property relationships in a new series of benzothiazole based unsymmetrical hexafluorocyclopentene dithienylethenes (DTEs) and compare the results with the known facts for symmetric diarylethenes (DAEs). We reveal ... ...

    Abstract Herein, we investigate the structure-property relationships in a new series of benzothiazole based unsymmetrical hexafluorocyclopentene dithienylethenes (DTEs) and compare the results with the known facts for symmetric diarylethenes (DAEs). We reveal high photocyclization efficiency resulting from a significant shift of ground state equilibrium to the antiparallel conformation and a barrierless excited state pathway to conical intersection, which remains unperturbed even in polar solvents for most of the prepared DTEs. Furthermore, we uncover that the rate of back thermal cycloreversion correlates clearly more with the central C-C bond-length in the transition state than with the central C-C bond-length in the ground state of the cyclic form. Finally, our detailed vibrational spectral analysis of studied DTEs points out significant changes in Raman and infrared spectra during photoswitching cycles which pave the way for a non-destructive readout of stored information.
    Language English
    Publishing date 2022-10-05
    Publishing country England
    Document type Journal Article
    ZDB-ID 1476244-4
    ISSN 1463-9084 ; 1463-9076
    ISSN (online) 1463-9084
    ISSN 1463-9076
    DOI 10.1039/d2cp02325c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Phosphate linkers with traceable cyclic intermediates for self-immolation detection and monitoring.

    Procházková, Eliška / Šimon, Petr / Straka, Michal / Filo, Juraj / Májek, Michal / Cigáň, Marek / Baszczyňski, Ondřej

    Chemical communications (Cambridge, England)

    2020  Volume 57, Issue 2, Page(s) 211–214

    Abstract: Self-immolation (SI) is the key principle of ProTide nucleotide prodrugs such as remdesivir, which is currently used to treat COVID-19 patients. Developing novel tailor-made SI systems requires new analytical methods for the detection and monitoring of ... ...

    Abstract Self-immolation (SI) is the key principle of ProTide nucleotide prodrugs such as remdesivir, which is currently used to treat COVID-19 patients. Developing novel tailor-made SI systems requires new analytical methods for the detection and monitoring of SI. We developed a robust method for SI analysis using novel phosphate-based SI linkers with NMR traceable cyclic intermediates to distinguish SI from alternative fragmentation pathways and to monitor cargo release in real time.
    Language English
    Publishing date 2020-12-10
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d0cc06928k
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: Tautomeric photoswitches: anion-assisted azo/azine-to-hydrazone photochromism

    Filo, Juraj / Tisovský, Pavol / Csicsai, Klaudia / Donovalová, Jana / Gáplovský, Martin / Gáplovský, Anton / Cigáň, Marek

    RSC advances. 2019 May 21, v. 9, no. 28

    2019  

    Abstract: The photoswitching properties of two easily synthesized isatin 4-nitrophenylhydrazones were investigated. Although the parent isatin 4-nitrophenylhydrazones exhibit low addressability which hampers their photochromic applications, the addition of ... ...

    Abstract The photoswitching properties of two easily synthesized isatin 4-nitrophenylhydrazones were investigated. Although the parent isatin 4-nitrophenylhydrazones exhibit low addressability which hampers their photochromic applications, the addition of strongly basic anions to phenylhydrazone solutions creates a new Vis–Vis photochromic system with the unusual azo/azine-to-hydrazone photo-tautomerization process as the photoswitching mechanism. To the best of our knowledge, this is the first report related to the anion-assisted azo/azine-to-hydrazone photo-tautomerism.
    Keywords anions
    Language English
    Dates of publication 2019-0521
    Size p. 15910-15916.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ISSN 2046-2069
    DOI 10.1039/c9ra02906k
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  9. Article ; Online: Structural and Spectroscopic Properties of Benzoylpyridine-Based Hydrazones.

    Mravec, Bernard / Marini, Anna / Tommasini, Matteo / Filo, Juraj / Cigáň, Marek / Mantero, Mariachiara / Tosi, Silvano / Canepa, Maurizio / Bianco, Andrea

    Chemphyschem : a European journal of chemical physics and physical chemistry

    2021  Volume 22, Issue 6, Page(s) 533–541

    Abstract: Photochromic hydrazones are attracting the attention in the field of photochromic systems especially due to their P-type character. To understand the structural features and their correlation with the spectroscopic data, UV-Vis, vibrational and ... ...

    Abstract Photochromic hydrazones are attracting the attention in the field of photochromic systems especially due to their P-type character. To understand the structural features and their correlation with the spectroscopic data, UV-Vis, vibrational and ellipsometry spectroscopic techniques are employed with the support of density functional theory (DFT) calculations to three hydrazone derivatives based on benzoylpyridine. Interestingly, analysis of the structure shows the presence of two distinct rotamers around the pyridine ring with different energy and the well-defined conjugation path that changes due to E to Z isomerization especially in the hydrazone -C=N-NH part of the skeleton. IR and Raman spectra are analyzed, showing a higher selectivity in the Z form; moreover, the comparison with the normal modes proves the effect of the reaction on the backbone structure. The experimental results are in good agreement with the theoretical predictions, especially in the case of the Raman spectrum. The molecular polarization also changes from E to Z forms as predicted by DFT calculations. Spectroscopic ellipsometry on thin films of TOPAS doped with 10 %wt of the dimethylamino hydrazone derivative is used to prove such change at the molecular level. A modulation of the refractive index is observed, and it is correlated with the concentration of the active moiety and the calculated electronic polarizabilities.
    Language English
    Publishing date 2021-02-17
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2025223-7
    ISSN 1439-7641 ; 1439-4235
    ISSN (online) 1439-7641
    ISSN 1439-4235
    DOI 10.1002/cphc.202000941
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article: Design of High-Performance Pyridine/Quinoline Hydrazone Photoswitches

    Mravec, Bernard / Budzák, Šimon / Medved’, Miroslav / Pašteka, Lukáš F. / Slavov, Chavdar / Saßmannshausen, Torben / Wachtveitl, Josef / Kožíšek, Jozef / Hegedüsová, Lea / Filo, Juraj / Cigáň, Marek

    Journal of organic chemistry. 2021 July 29, v. 86, no. 17

    2021  

    Abstract: The design of P-type photoswitches with thermal stability of the metastable form of hundreds of years that would efficiently transform using excitation wavelengths above 350 nm remains a challenge in the field of photochromism. In this regard, we ... ...

    Abstract The design of P-type photoswitches with thermal stability of the metastable form of hundreds of years that would efficiently transform using excitation wavelengths above 350 nm remains a challenge in the field of photochromism. In this regard, we designed and synthesized an extended set of 13 pyridine/quinoline hydrazones and systematically investigated the structure–property relationships, defining their kinetic and photoswitching parameters. We show that the operational wavelengths of the pyridine hydrazone structural motif can be effectively shifted toward the visible region without simultaneous loss of their high thermal stability. Furthermore, we characterized the ground-state and excited-state potential energy surfaces with quantum-chemical calculations and ultrafast transient absorption spectroscopy, which allowed us to rationalize both the thermal and photochemical reaction mechanisms of the designed hydrazones. Whereas introducing an electron-withdrawing pyridyl moiety in benzoylpyridine hydrazones leads to thermal stabilities exceeding 200 years, extended π-conjugation in naphthoylquinoline hydrazones pushes the absorption maxima toward the visible spectral region. In either case, the compounds retain highly efficient photoswitching characteristics. Our findings open a route to the rational design of a new family of hydrazone-based P-type photoswitches with high application potential in photonics or photopharmacology.
    Keywords absorption ; hydrazones ; moieties ; new family ; organic chemistry ; photochemical reactions ; photonics ; potential energy ; pyridines ; quinoline ; spectroscopy ; thermal stability
    Language English
    Dates of publication 2021-0729
    Size p. 11633-11646.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c01174
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