The University of Southampton
University of Southampton Institutional Repository

Fluorescent rhenium-naphthalimide conjugates as cellular imaging agents

Fluorescent rhenium-naphthalimide conjugates as cellular imaging agents
Fluorescent rhenium-naphthalimide conjugates as cellular imaging agents
A range of biologically compatible, fluorescent rhenium-naphthalimide conjugates, based upon the rhenium fac-tricarbonyl core, has been synthesized. The fluorescent ligands are based upon a N-functionalized, 4-amino-derived 1,8-naphthalimide core and incorporate a dipicolyl amine binding unit to chelate Re(I); the structural variations accord to the nature of the alkylated imide with ethyl ester glycine (L-1), 3-propanol (L-2), diethylene glycol (L-3), and benzyl alcohol (L-4) variants. The species are fluorescent in the visible region between 505 and 537 nm through a naphthalimide-localized intramolecular charge transfer, with corresponding fluorescent lifetimes of up to 9.8 ns. The ligands and complexes were investigated for their potential as imaging agents for human osteoarthritic cells and protistan fish parasite Spironucleus vortens using confocal fluorescence microscopy. The results show that the specific nature of the naphthalimide structure serves to control the uptake and intracellular localization of these imaging agents. Significant differences were noted between the free ligands and complexes, with the Re(I) complex of L-2 showing hydrogenosomal localization in S. vortens.
0020-1669
3788-3797
Langdon-Jones, Emily E.
b11f5d82-87fa-4206-9169-8f70826f2070
Symonds, Nadine O.
da4536c8-26c7-4e8f-a5ac-2f7344d9b540
Yates, Sara E.
7744be62-53f6-4c34-ba67-4819fc822c38
Hayes, Anthony J.
1e4d30da-155d-47d1-8ebc-733efe6ea2f8
Lloyd, David
e7a912a2-f666-43d7-aa88-e1d97bb4e77f
Williams, Rebecca
c8d08cdd-67bb-4322-acf4-055a81de875c
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Pope, Simon J.A.
db9a489c-29ba-41cd-a96a-623bace0889d
Langdon-Jones, Emily E.
b11f5d82-87fa-4206-9169-8f70826f2070
Symonds, Nadine O.
da4536c8-26c7-4e8f-a5ac-2f7344d9b540
Yates, Sara E.
7744be62-53f6-4c34-ba67-4819fc822c38
Hayes, Anthony J.
1e4d30da-155d-47d1-8ebc-733efe6ea2f8
Lloyd, David
e7a912a2-f666-43d7-aa88-e1d97bb4e77f
Williams, Rebecca
c8d08cdd-67bb-4322-acf4-055a81de875c
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Pope, Simon J.A.
db9a489c-29ba-41cd-a96a-623bace0889d

Langdon-Jones, Emily E., Symonds, Nadine O., Yates, Sara E., Hayes, Anthony J., Lloyd, David, Williams, Rebecca, Coles, Simon J., Horton, Peter N. and Pope, Simon J.A. (2014) Fluorescent rhenium-naphthalimide conjugates as cellular imaging agents. Inorganic Chemistry, 53 (7), 3788-3797. (doi:10.1021/ic500142z).

Record type: Article

Abstract

A range of biologically compatible, fluorescent rhenium-naphthalimide conjugates, based upon the rhenium fac-tricarbonyl core, has been synthesized. The fluorescent ligands are based upon a N-functionalized, 4-amino-derived 1,8-naphthalimide core and incorporate a dipicolyl amine binding unit to chelate Re(I); the structural variations accord to the nature of the alkylated imide with ethyl ester glycine (L-1), 3-propanol (L-2), diethylene glycol (L-3), and benzyl alcohol (L-4) variants. The species are fluorescent in the visible region between 505 and 537 nm through a naphthalimide-localized intramolecular charge transfer, with corresponding fluorescent lifetimes of up to 9.8 ns. The ligands and complexes were investigated for their potential as imaging agents for human osteoarthritic cells and protistan fish parasite Spironucleus vortens using confocal fluorescence microscopy. The results show that the specific nature of the naphthalimide structure serves to control the uptake and intracellular localization of these imaging agents. Significant differences were noted between the free ligands and complexes, with the Re(I) complex of L-2 showing hydrogenosomal localization in S. vortens.

Full text not available from this repository.

More information

Published date: 7 April 2014
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 369250
URI: http://eprints.soton.ac.uk/id/eprint/369250
ISSN: 0020-1669
PURE UUID: 4026f258-6f16-47ad-b2cd-8f223a446723
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 30 Sep 2014 11:16
Last modified: 18 Feb 2021 16:54

Export record

Altmetrics

Contributors

Author: Emily E. Langdon-Jones
Author: Nadine O. Symonds
Author: Sara E. Yates
Author: Anthony J. Hayes
Author: David Lloyd
Author: Rebecca Williams
Author: Simon J. Coles ORCID iD
Author: Peter N. Horton ORCID iD
Author: Simon J.A. Pope

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×