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  1. Article ; Online: Recent advances in photorelease complexes for therapeutic applications.

    Benniston, Andrew C / Zeng, Lingli

    Dalton transactions (Cambridge, England : 2003)

    2022  Volume 51, Issue 11, Page(s) 4202–4212

    Abstract: Photorelease complexes represent a class of agents for which UV-visible light triggers the expulsion of a specfic molecule that is intrinsically part of the inner coordination sphere or held in close proximity to the metal centre. The reaction does not ... ...

    Abstract Photorelease complexes represent a class of agents for which UV-visible light triggers the expulsion of a specfic molecule that is intrinsically part of the inner coordination sphere or held in close proximity to the metal centre. The reaction does not occur in the ground-state complex and requires a photon, but an additional agent may be present that facilitates the release process. In this context, the perspective article covers recent papers from the past five years (2017-2021) on metal-based complexes containing ligands that are expelled under light activation. In addition, the examples primarily focus on ligands with potential biological activity and have specfic therapeutic applications. Some examples include NO, CO, Cl
    MeSH term(s) Coordination Complexes/chemistry ; Ligands ; Oxidation-Reduction ; Photochemical Processes ; Ultraviolet Rays
    Chemical Substances Coordination Complexes ; Ligands
    Language English
    Publishing date 2022-03-15
    Publishing country England
    Document type Journal Article ; Review
    ZDB-ID 1472887-4
    ISSN 1477-9234 ; 1364-5447 ; 0300-9246 ; 1477-9226
    ISSN (online) 1477-9234 ; 1364-5447
    ISSN 0300-9246 ; 1477-9226
    DOI 10.1039/d2dt00254j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Deducing the conformational space for an octa-proline helix.

    Waly, Sara M A / Benniston, Andrew C / Harriman, Anthony

    Chemical science

    2023  Volume 15, Issue 5, Page(s) 1657–1671

    Abstract: A molecular dyad, PY- ... ...

    Abstract A molecular dyad, PY-P
    Language English
    Publishing date 2023-12-21
    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/d3sc05287g
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Light-Harvesting Crystals Formed from BODIPY-Proline Biohybrid Conjugates: Antenna Effects and Excitonic Coupling.

    Waly, Sara M / Karlsson, Joshua K G / Waddell, Paul G / Benniston, Andrew C / Harriman, Anthony

    The journal of physical chemistry. A

    2022  Volume 126, Issue 9, Page(s) 1530–1541

    Abstract: A boron dipyrromethene (BODIPY) derivative bearing ... ...

    Abstract A boron dipyrromethene (BODIPY) derivative bearing a
    MeSH term(s) Boron/chemistry ; Boron Compounds ; Porphobilinogen/analogs & derivatives ; Porphobilinogen/chemistry ; Proline
    Chemical Substances 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene ; Boron Compounds ; dipyrromethene ; Porphobilinogen (74KHC72QXK) ; Proline (9DLQ4CIU6V) ; Boron (N9E3X5056Q)
    Language English
    Publishing date 2022-03-01
    Publishing country United States
    Document type Journal Article
    ISSN 1520-5215
    ISSN (online) 1520-5215
    DOI 10.1021/acs.jpca.2c00035
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Stereochemical Control of Secondary Benzamide-based BODIPY Emitters.

    Waly, Sara M A / Benniston, Andrew C / Karlsson, Joshua K G / Dixon, Casey M / Wills, Corinne / Waddell, Paul G / Harriman, Anthony

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2023  Volume 29, Issue 31, Page(s) e202300383

    Abstract: ... The primary concern with acyl amides is rotation around the C-N bond, leading to cis and trans isomers. Using ... an important structural feature. Indeed, rotation around the C(sp ...

    Abstract Aromatic amides can be used to construct light-harvesting materials with valuable optical properties. The amide bond is formed using well-known coupling agents in near quantitative yield, as illustrated here through the synthesis of two boron dipyrromethene derivatives bearing an amide linkage. The primary concern with acyl amides is rotation around the C-N bond, leading to cis and trans isomers. Using NMR spectroscopy, quantum chemical calculations and critical comparison to simpler benzamides, the stereochemistry of the target compounds has been addressed. The N-cyclohexyl derivative gave diffraction quality crystals that established a trans geometry for the amide bond. Quantum chemical calculations support the trans geometry as being the lowest-energy structure in solution but indicate that inversion of the aryl ring is an important structural feature. Indeed, rotation around the C(sp
    Language English
    Publishing date 2023-04-24
    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.202300383
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Autocatalytic photodegradation of [Ru(II)(2,2'-bipyridine)

    Zeng, Lingli / Sirbu, Dumitru / Tkachenko, Nikolai V / Benniston, Andrew C

    Dalton transactions (Cambridge, England : 2003)

    2021  Volume 50, Issue 22, Page(s) 7640–7646

    Abstract: As part of a continuing effort to identify ruthenium agents capable of the photorelease of anthraquinone-based ligands the complexes Δ/Λ-[Ru(bpy)2DAD]+ (bpy = 2,2'-bipyridine) were produced by the reaction of 1,2-dihydroxyanthracene-9,10-dione (DADH) ... ...

    Abstract As part of a continuing effort to identify ruthenium agents capable of the photorelease of anthraquinone-based ligands the complexes Δ/Λ-[Ru(bpy)2DAD]+ (bpy = 2,2'-bipyridine) were produced by the reaction of 1,2-dihydroxyanthracene-9,10-dione (DADH) with chirally pure Δ/Λ-[Ru(bpy)2(py)2][(+)-O,O'-dibenzoyl-d-tartrate]·12H2O (py = pyridine). A very subtle difference in the chemical shift of the hydroxyl proton in their high-field 1H NMR spectra was observed, supporting that the OH proton is susceptible to a small change in environment at the metal centre. The excited state lifetime of the complexes, as measured by femtosecond pump-probe spectroscopy, was 7.1 (±0.8) ps in water (pH 2) and 13 (±1) ps in MeCN. Illumination of a sample of Λ-[Ru(bpy)2DAD]+ in water (pH 2) in the presence of hydrogen peroxide resulted in decomposition of the complex. The decay profile, as monitored at several wavelengths, was sigmoidal indicating the reaction was autocatalytic, in which the product formed catalysed decomposition of the starting complex. A mechanism is proposed that relies on participation of the uncoordinated hydroxyl group on the anthraquinone ligand in promoting water loss and radical formation in the excited state. The radical is oxidised by peroxide to generate the ruthenium(iii) complex, which behaves as an oxidant in the autocatalytic process.
    Language English
    Publishing date 2021-05-10
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472887-4
    ISSN 1477-9234 ; 1364-5447 ; 0300-9246 ; 1477-9226
    ISSN (online) 1477-9234 ; 1364-5447
    ISSN 0300-9246 ; 1477-9226
    DOI 10.1039/d1dt00952d
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Voltage-induced fluorescence lifetime imaging of a BODIPY derivative in giant unilamellar vesicles as potential neuron membrane mimics.

    Sirbu, Dumitru / Zeng, Lingli / Waddell, Paul G / Tkachenko, Nikolai V / Botchway, Stanley W / Benniston, Andrew C

    Chemical communications (Cambridge, England)

    2021  Volume 57, Issue 94, Page(s) 12631–12634

    Abstract: Fluorescence lifetime imaging (FLIM) was used to study the behaviour of a BODIPY dye in a giant unilamellar vesicle (GUV) in the presence of an electric field. The modulation of the electric field resulted in distinctive fluorescence lifetime changes in ... ...

    Abstract Fluorescence lifetime imaging (FLIM) was used to study the behaviour of a BODIPY dye in a giant unilamellar vesicle (GUV) in the presence of an electric field. The modulation of the electric field resulted in distinctive fluorescence lifetime changes in line with environment alterations within the membrane mimic.
    Language English
    Publishing date 2021-11-25
    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/d1cc03756k
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Correction: Functionalized fluorescent terephthalate monomers and their attempted polyester formation.

    Choo, Yvonne S L / Giamberini, Marta / Reina, José Antonio / Waddell, Paul G / Benniston, Andrew C

    Organic & biomolecular chemistry

    2020  Volume 18, Issue 45, Page(s) 9316

    Abstract: Correction for 'Functionalized fluorescent terephthalate monomers and their attempted polyester formation' by Yvonne S. L. Choo et al., Org. Biomol. Chem., 2020, 18, 8735-8745, DOI: 10.1039/D0OB01533D. ...

    Abstract Correction for 'Functionalized fluorescent terephthalate monomers and their attempted polyester formation' by Yvonne S. L. Choo et al., Org. Biomol. Chem., 2020, 18, 8735-8745, DOI: 10.1039/D0OB01533D.
    Language English
    Publishing date 2020-11-23
    Publishing country England
    Document type Published Erratum
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d0ob90154g
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: Porphyrin linked poly(pyridyl)-based conjugates as artificial photosynthetic reaction centre models.

    Benniston, Andrew C

    Physical chemistry chemical physics : PCCP

    2009  Volume 9, Issue 43, Page(s) 5739–5747

    Abstract: This short review covers some of the advances made in artificial photosynthetic models using porphyrin-spacer-poly(pyridyl) cation conjugates. ...

    Abstract This short review covers some of the advances made in artificial photosynthetic models using porphyrin-spacer-poly(pyridyl) cation conjugates.
    MeSH term(s) Electrochemistry ; Electrons ; Energy Transfer ; Models, Chemical ; Photosynthetic Reaction Center Complex Proteins/chemistry ; Porphyrins/chemistry ; Pyridines/chemistry
    Chemical Substances Photosynthetic Reaction Center Complex Proteins ; Porphyrins ; Pyridines ; pyridine (NH9L3PP67S)
    Language English
    Publishing date 2009-02-03
    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/b708166a
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: One-Pot Synthesis of a Mono-O,B,N-strapped BODIPY Derivative Displaying Bright Fluorescence in the Solid State.

    Sirbu, Dumitru / Benniston, Andrew C / Harriman, Anthony

    Organic letters

    2017  Volume 19, Issue 7, Page(s) 1626–1629

    Abstract: Tin(IV) catalysis allows isolation of a boron dipyrromethene derivative bearing a solitary strap around the boron center. The conditions favor internal cyclization without contamination by side products and provide high yields of product in good purity. ... ...

    Abstract Tin(IV) catalysis allows isolation of a boron dipyrromethene derivative bearing a solitary strap around the boron center. The conditions favor internal cyclization without contamination by side products and provide high yields of product in good purity. A phenolate-based strap imposes chirality and causes geometrical distortion of the dipyrrin. Relatively strong fluorescence is observed for single crystals, evaporated films, and adsorbed layers. Single-crystal absorption and emission spectra resemble those observed from solution with contributions from a dimer.
    Language English
    Publishing date 2017-04-07
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.7b00435
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: Functionalized fluorescent terephthalate monomers and their attempted polyester formation.

    Choo, Yvonne S L / Giamberini, Marta / Antonio, José / Waddell, Paul G / Benniston, Andrew C

    Organic & biomolecular chemistry

    2020  Volume 18, Issue 42, Page(s) 8735–8745

    Abstract: The reaction of diethyl 2,5-bis(tert-butyl)phenoxy-3,6-dihydroxyterephthalate (1) with tetraethylene glycol di(p-toluenesulfonate) under high-dilution conditions afforded several isolated products. Two products were identified as macrocycles with one ... ...

    Abstract The reaction of diethyl 2,5-bis(tert-butyl)phenoxy-3,6-dihydroxyterephthalate (1) with tetraethylene glycol di(p-toluenesulfonate) under high-dilution conditions afforded several isolated products. Two products were identified as macrocycles with one being the 1 + 1 crown ether derivative 3 (10% yield), and the second being the 2 + 2 crown ether compound D3 (19% yield). The X-ray structure for 3 was determined with the asymmetric unit observed to comprise half of the molecule. The small crown ether ring of 3 interacts with K+ or H+ ions in MeOH, but binding is weak and the macrocyclic cavity is too small to fully encapsulate the K+ ion. Transesterification of compounds 1, its methylated version 2 and 3 with diols such as ethylene glycol or 1,4-butandiol produced monomers (M1-M3) which were reacted with terephthaloyl chloride. Short oligomers were produced (PolyM1-PolyM3) rather than extensive polymeric materials and all displayed solid state fluorescence. The absorption and fluorescence properties of M1-M2 and their polymers can be related to subtle structural changes. The Stokes shift for M2 of 15 627 cm-1 in DCM is one of the largest observed for a simple organic chromophore in fluid solution.
    Language English
    Publishing date 2020-10-23
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d0ob01533d
    Database MEDical Literature Analysis and Retrieval System OnLINE

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