School of Chemistry - Research Publications

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    Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes
    Xiao, Z ; Bonnard, T ; Shakouri-Motlagh, A ; Wylie, RAL ; Collins, J ; White, J ; Heath, DE ; Hagemeyer, CE ; Connal, LA (WILEY-V C H VERLAG GMBH, 2017-08-22)
    Hydrogen sulfide (H2 S) has been identified as an important cell-signaling mediator and has a number of biological functions, such as vascular smooth muscle relaxation, neurotransmission, and regulation of inflammation. A facile and versatile approach for H2 S production initiated by light irradiation and controlled by reaction with an amine or an amino acid was developed. The donor was synthesized in a one-pot reaction, and simple crystallization led to a yield of approximately 90 %. The synthetic strategy is scalable and versatile, and the H2 S donors can be expressed ina number of different molecular and macromolecular forms, including crystalline small-molecule compounds, water-soluble polymers, polystyrene films, and hydrogels. The H2 S donors based on polystyrene film and hydrogel were used as cell-culture scaffolds. The H2 S donor based on water-soluble polymer was applied in photocontrolled inhibition of P-selectin expression on human platelets and subsequent regulation of platelet aggregation. This study provides the simplest controllable H2 S source to study its biological functions. The developed materials are also new therapeutic platforms to deliver H2 S, as there is no accumulation of toxic byproducts, and the donor materials from polystyrene films and hydrogels can be readily removed after releasing H2 S.
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    Guest‐induced Assembly of Bis(thiosemicarbazonato) Zinc(II) Coordination Nanotubes
    Paterson, BM ; White, KF ; White, JM ; Abrahams, BF ; Donnelly, PS (Wiley, 2017-07-10)
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    Guest-induced Assembly of Bis(thiosemicarbazonato) Zinc(II) Coordination Nanotubes
    Paterson, BM ; White, KF ; White, JM ; Abrahams, BF ; Donnelly, PS (Wiley, 2017-07-10)
    A ZnII complex of the dianionic tetradentate ligand formed by deprotonation of glyoxal‐bis(4‐phenyl‐3‐thiosemicarbazone) (H2gtsp) is a [3+3] trinuclear triangular prism. Recrystallization of this complex in the presence of either CO2, CS2, or CH3CN leads to the formation of [4+4] open‐ended charge‐neutral tetranuclear coordination nanotubes, approximately 2 nm in length and with internal dimensions large enough to accommodate linear guest molecules, which serve to template their formation. Upon removal of the templating molecules the nanotubes demonstrated reversible sorption of CO2 with an isosteric enthalpy of sorption of 28 kJ mol−1 at low loading.
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    Dihydro-beta-agarofurans from the Australian Endemic Rainforest Plant Denhamia pittosporoides Inhibit Leucine Transport in Prostate Cancer Cells
    Wibowo, M ; Wang, Q ; Holst, J ; White, JM ; Hofmann, A ; Davis, RA (WILEY-V C H VERLAG GMBH, 2016-12-01)
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    Fluorine-18 radiolabeling of a nitrophenyl sulfoxide and its evaluation in an SK-RC-52 model of tumor hypoxia
    Laurens, E ; Yeoh, SD ; Rigopoulos, A ; O'Keefe, GJ ; Tochon-Danguy, HJ ; Chong, LW ; White, JM ; Scott, AM ; Ackermann, U (WILEY-BLACKWELL, 2016-08-01)
    The significance of imaging hypoxia with the positron emission tomography ligand [(18) F]FMISO has been demonstrated in a variety of cancers. However, the slow kinetics of [(18) F]FMISO require a 2-h delay between tracer administration and patient scanning. Labeled chloroethyl sulfoxides have shown faster kinetics and higher contrast than [(18) F]FMISO in a rat model of ischemic stroke. However, these nitrogen mustard analogues are unsuitable for routine production and use in humans. Here, we report on the synthesis and in vitro and in vivo evaluation of a novel sulfoxide, which contains an ester moiety for hydrolysis and subsequent trapping in hypoxic cells. Non-decay corrected yields of radioactivity were 1.18 ± 0.24% (n = 27, 2.5 ± 0.5% decay corrected radiochemical yield) based on K[(18) F]F. The radiotracer did not show any defluorination and did not undergo metabolism in an in vitro assay using S9 liver fractions. Imaging studies using an SK-RC-52 tumor model in BALB/c nude mice have revealed that [(18) F]1 is retained in hypoxic tumors and has similar hypoxia selectivity to [(18) F]FMISO. Because of a three times faster clearance rate than [(18) F]FMISO from normoxic tissue, [(18) F]1 has emerged as a promising new radiotracer for hypoxia imaging.
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    Synthesis of Homochiral Co-III- and Mn-IV-[2.2]Paracyclophane Schiff Base Complexes with Predetermined Chirality at the Metal Centre
    Loits, D ; Braese, S ; North, AJ ; White, JM ; Donnelly, PS ; Rizzacasa, MA (WILEY-V C H VERLAG GMBH, 2016-08-01)
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    Tetraphenylethene 9,10-Diphenylanthracene Derivatives - Synthesis and Photophysical Properties
    Gao, C ; Seow, JY ; Zhang, B ; Hall, CR ; Tilley, AJ ; White, JM ; Smith, TA ; Wong, WWH (WILEY-V C H VERLAG GMBH, 2019-06-01)
    A series of tetraphenylethene 9,10-diphenylanthracene (TPE-DPA) derivatives have been synthesized, and their photophysical properties studied. Photoluminescence measurements in PMMA, neat films and nanoparticle dispersions reveal that different aggregation states are formed, which leads to different photophysical behavior. The triplet excited state properties were studied using Pt(II) octaethylporphyrin (PtOEP) as triplet sensitizer. Upconverted emission from the DPA moiety is observed in nanoparticle dispersions of each derivative. A higher upconverted emission intensity is observed in aerated (compared to deaerated) solutions of the derivatives following irradiation, which is attributed to oxidation of the TPE moiety. These results provide valuable insight for the design of AIE luminogens for triplet-triplet annihilation upconversion (TTA-UC).
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    A new potassium-based coordination polymer with hydrogen bonding and zigzag metallophilic interactions
    Moghadam, Z ; Akhbari, K ; White, J ; Phuruangrat, A (WILEY, 2018-12-01)
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