Fluorescent transmembrane anion transporters: shedding light on anionophoric activity in cells

Chemical Science
Stuart N BerryPhilip A Gale

Abstract

A series of fluorescent anion transporters consisting of a urea or thiourea group linked to a naphthalimide fluorophore have been synthesised and their anion transport properties studied. The compounds possess similar anion transport properties to (thio)urea-based anionophores that have previously been reported. Fluorescence studies in cells show all anionophores cross the plasma membrane and localise within the interior of cells. The most lipophilic, aromatic substituted transporters localise homogeneously throughout the cell and are toxic towards cancer cells with the highly fluorinated compound 6 being the most effective. The least lipophilic, alkyl substituted transporters localise in specific vesicles and are non-toxic to cells. This work provides new insight to the actions of anionophores in cells and may be useful in the design of novel antineoplastic agents.

References

Sep 1, 1985·Journal of Medicinal Chemistry·R K Zee-Cheng, C C Cheng
Jan 1, 1980·Cancer Chemotherapy and Pharmacology·M F BrañaA Jiménez
Jul 1, 1980·Physiological Reviews·S G McLaughlin, J P Dilger
Aug 15, 1998·The Journal of Biological Chemistry·T SatoS Ohkuma
Jul 17, 2001·Current Opinion in Cell Biology·S P YuD W Choi
Dec 17, 2004·Journal of the American Chemical Society·Massimo BoiocchiEnrico Monzani
Apr 14, 2005·Organic & Biomolecular Chemistry·David Esteban GómezEnrico Monzani
Jul 2, 2005·The Journal of Organic Chemistry·David Esteban-GómezMaurizio Licchelli
Aug 23, 2005·Angewandte Chemie·Jonathan L SesslerDarren J Magda
Oct 19, 2005·Journal of Computer-aided Molecular Design·Igor V TetkoVolodymyr V Prokopenko
Nov 25, 2005·Chemical Communications : Chem Comm·Jennifer L Seganish, Jeffery T Davis
Dec 17, 2005·The Journal of Organic Chemistry·Thorfinnur GunnlaugssonGillian M Hussey
May 11, 2006·The Journal of Membrane Biology·Y OkadaN Takahashi
Sep 19, 2008·The Journal of Organic Chemistry·Emma B Veale, Thorfinnur Gunnlaugsson
Oct 1, 2008·Biochimica Et Biophysica Acta·Tomasz RógMikko Karttunen
Oct 16, 2008·Chemistry : a European Journal·Claudia CaltagironePhilip A Gale
Sep 8, 2010·Chemical Society Reviews·Jeffery T DavisRoberto Quesada
Mar 11, 2011·Chemical Society Reviews·Stefan MatileAndrea Fin
May 10, 2011·European Journal of Medicinal Chemistry·Hong YinJianwen Liu
Aug 19, 2011·Journal of the American Chemical Society·Nathalie BusschaertPhilip A Gale
Mar 31, 2012·Angewandte Chemie·Nathalie BusschaertPhilip A Gale
Apr 26, 2012·Chemical Communications : Chem Comm·Vittorio SaggiomoRoberto Quesada
Jan 4, 2013·Angewandte Chemie·Nathalie Busschaert, Philip A Gale
Sep 24, 2013·Organic & Biomolecular Chemistry·Cally J E HaynesPhilip A Gale
Jan 31, 2015·Organic & Biomolecular Chemistry·Stuart N BerryPhilip A Gale
May 23, 2015·Chemical Reviews·Nathalie BusschaertPhilip A Gale
Dec 18, 2015·Nature Chemistry·Hongyu LiAnthony P Davis
Feb 26, 2016·Organic & Biomolecular Chemistry·Wim Van RossomPhilip A Gale

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Citations

Oct 20, 2018·Organic & Biomolecular Chemistry·Xiao-Qiao HongWen-Hua Chen
Aug 22, 2020·Angewandte Chemie·Shao-Ping ZhengMihail Barboiu
Mar 27, 2020·Angewandte Chemie·Shao-Ping ZhengMihail Barboiu
Jul 8, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Martina OlivariClaudia Caltagirone
Jan 23, 2018·Chemical Communications : Chem Comm·Xiaoping BaoPhilip A Gale
Oct 12, 2017·Chemical Society Reviews·Di WuTony D James
Feb 3, 2018·Angewandte Chemie·Mathieu DenisStephen M Goldup
May 16, 2017·Chemistry : a European Journal·Aleksandr S OshchepkovEvgeny A Kataev
Aug 26, 2017·Scientific Reports·Laura A JowettPhilip A Gale
Nov 7, 2017·Coordination Chemistry Reviews·Gabriela I Vargas-Zúñiga, Jonathan L Sessler
Jan 29, 2020·Chemical Science·Javid Ahmad MallaPinaki Talukdar
May 28, 2021·Chembiochem : a European Journal of Chemical Biology·Arundhati Roy, Pinaki Talukdar
Aug 6, 2021·ChemPlusChem·Lokesh K KumawatRobert B P Elmes
Oct 29, 2021·Organic & Biomolecular Chemistry·Daniel A McNaughtonPhilip A Gale

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Methods Mentioned

BETA
fluorescence microscopy
X-ray
NMR

Software Mentioned

Origin

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