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

Fluorescent transmembrane anion transporters: shedding light on anionophoric activity in cells
Fluorescent transmembrane anion transporters: shedding light on anionophoric activity in cells
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 of (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.
1478-6524
1-9
Berry, Stuart N.
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Soto-Cerrato, Vanessa
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Howe, Ethan N.W.
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Clarke, Harriet J.
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Mistry, Ishna
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Tavassoli, Ali
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Chang, Young-Tae
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Pérez-Tomás, Ricardo
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Gale, Philip A.
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Berry, Stuart N.
c7287fbf-5845-4f28-b3ab-bf3a35e3fd9f
Soto-Cerrato, Vanessa
d14f15d9-a8f6-4a9a-9be8-f27417482712
Howe, Ethan N.W.
be05ae9a-02e0-443b-97b2-d65cc387af40
Clarke, Harriet J.
f5c240ce-625a-47b4-a835-8b7cb44681d2
Mistry, Ishna
70e94cae-a95e-44f8-b1f3-3218d6d278cf
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Chang, Young-Tae
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Pérez-Tomás, Ricardo
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Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

Berry, Stuart N., Soto-Cerrato, Vanessa, Howe, Ethan N.W., Clarke, Harriet J., Mistry, Ishna, Tavassoli, Ali, Chang, Young-Tae, Pérez-Tomás, Ricardo and Gale, Philip A. (2016) Fluorescent transmembrane anion transporters: shedding light on anionophoric activity in cells. Chemical Science, 1-9. (doi:10.1039/c6sc01643j).

Record type: Article

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 of (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.

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Accepted/In Press date: 15 April 2016
e-pub ahead of print date: 26 April 2016
Organisations: Organic Chemistry: SCF

Identifiers

Local EPrints ID: 393447
URI: http://eprints.soton.ac.uk/id/eprint/393447
ISSN: 1478-6524
PURE UUID: ae6b3e80-e92e-4340-aaf3-05ad572fe920
ORCID for Ali Tavassoli: ORCID iD orcid.org/0000-0002-7420-5063
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

Catalogue record

Date deposited: 27 Apr 2016 09:36
Last modified: 17 Dec 2019 06:50

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Contributors

Author: Stuart N. Berry
Author: Vanessa Soto-Cerrato
Author: Ethan N.W. Howe
Author: Harriet J. Clarke
Author: Ishna Mistry
Author: Ali Tavassoli ORCID iD
Author: Young-Tae Chang
Author: Ricardo Pérez-Tomás
Author: Philip A. Gale ORCID iD

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