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Cellular localisation of structurally diverse diphenylacetylene fluorophores.
Chisholm, David R; Hughes, Joshua G; Blacker, Thomas S; Humann, Rachel; Adams, Candace; Callaghan, Daniel; Pujol, Alba; Lembicz, Nicola K; Bain, Angus J; Girkin, John M; Ambler, Carrie A; Whiting, Andrew.
Afiliación
  • Chisholm DR; LightOx Limited, 65 Westgate Road, Newcastle upon Tyne, NE1 1SG, UK. david.chisholm@lightox.co.uk and Department of Chemistry, Durham University, Science Laboratories, South Road, Durham, DH1 3LE, UK.
  • Hughes JG; LightOx Limited, 65 Westgate Road, Newcastle upon Tyne, NE1 1SG, UK. david.chisholm@lightox.co.uk and Department of Biosciences, Durham University, South Road, Durham, DH1 3LE, UK and Centre for Advanced Instrumentation, Department of Physics, Durham University, South Road, Durham, DH1 3LE, UK.
  • Blacker TS; Department of Physics & Astronomy, University College London, Gower Street, London, WC1E 6BT, UK.
  • Humann R; Department of Chemistry, Durham University, Science Laboratories, South Road, Durham, DH1 3LE, UK and High Force Research Limited, Bowburn North Industrial Estate, Bowburn, Durham DH6 5PF, UK.
  • Adams C; LightOx Limited, 65 Westgate Road, Newcastle upon Tyne, NE1 1SG, UK. david.chisholm@lightox.co.uk.
  • Callaghan D; LightOx Limited, 65 Westgate Road, Newcastle upon Tyne, NE1 1SG, UK. david.chisholm@lightox.co.uk.
  • Pujol A; LightOx Limited, 65 Westgate Road, Newcastle upon Tyne, NE1 1SG, UK. david.chisholm@lightox.co.uk.
  • Lembicz NK; High Force Research Limited, Bowburn North Industrial Estate, Bowburn, Durham DH6 5PF, UK.
  • Bain AJ; Department of Physics & Astronomy, University College London, Gower Street, London, WC1E 6BT, UK.
  • Girkin JM; Centre for Advanced Instrumentation, Department of Physics, Durham University, South Road, Durham, DH1 3LE, UK.
  • Ambler CA; LightOx Limited, 65 Westgate Road, Newcastle upon Tyne, NE1 1SG, UK. david.chisholm@lightox.co.uk and Department of Biosciences, Durham University, South Road, Durham, DH1 3LE, UK.
  • Whiting A; LightOx Limited, 65 Westgate Road, Newcastle upon Tyne, NE1 1SG, UK. david.chisholm@lightox.co.uk and Department of Chemistry, Durham University, Science Laboratories, South Road, Durham, DH1 3LE, UK.
Org Biomol Chem ; 18(45): 9231-9245, 2020 11 25.
Article en En | MEDLINE | ID: mdl-32966518
Fluorescent probes are increasingly used as reporter molecules in a wide variety of biophysical experiments, but when designing new compounds it can often be difficult to anticipate the effect that changing chemical structure can have on cellular localisation and fluorescence behaviour. To provide further chemical rationale for probe design, a series of donor-acceptor diphenylacetylene fluorophores with varying lipophilicities and structures were synthesised and analysed in human epidermal cells using a range of cellular imaging techniques. These experiments showed that, within this family, the greatest determinants of cellular localisation were overall lipophilicity and the presence of ionisable groups. Indeed, compounds with high log D values (>5) were found to localise in lipid droplets, but conversion of their ester acceptor groups to the corresponding carboxylic acids caused a pronounced shift to localisation in the endoplasmic reticulum. Mildly lipophilic compounds (log D = 2-3) with strongly basic amine groups were shown to be confined to lysosomes i.e. an acidic cellular compartment, but sequestering this positively charged motif as an amide resulted in a significant change to cytoplasmic and membrane localisation. Finally, specific organelles including the mitochondria could be targeted by incorporating groups such as a triphenylphosphonium moiety. Taken together, this account illustrates a range of guiding principles that can inform the design of other fluorescent molecules but, moreover, has demonstrated that many of these diphenylacetylenes have significant utility as probes in a range of cellular imaging studies.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Colorantes Fluorescentes Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2020 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Colorantes Fluorescentes Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2020 Tipo del documento: Article Pais de publicación: Reino Unido