Fluorescent rhenium-naphthalimide conjugates as cellular imaging agents

Langdon-Jones, Emily E., Symonds, Nadine O., Yates, Sara E., Hayes, Anthony J., Lloyd, David ORCID: https://orcid.org/0000-0002-5656-0571, Williams, Rebecca ORCID: https://orcid.org/0000-0003-2168-7369, Coles, Simon J., Horton, Peter N. and Pope, Simon J. A. ORCID: https://orcid.org/0000-0001-9110-9711 2014. Fluorescent rhenium-naphthalimide conjugates as cellular imaging agents. Inorganic Chemistry 53 (7) , pp. 3788-3797. 10.1021/ic500142z

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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 (L1), 3-propanol (L2), diethylene glycol (L3), and benzyl alcohol (L4) 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 L2 showing hydrogenosomal localization in S. vortens.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Biosciences Chemistry
Subjects:	Q Science > QD Chemistry
Additional Information:	Online publication date: 13 March 2014.
Publisher:	American Chemical Society
ISSN:	0020-1669
Date of Acceptance:	13 March 2014
Last Modified:	05 Jul 2023 01:05
URI:	https://orca.cardiff.ac.uk/id/eprint/58394

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