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Issue 8, 2012
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Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate

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Abstract

A new rhenium tricarbonyl complex of a bis(quinoline)-derived ligand (2-azido-N,N-bis((quinolin-2-yl)methyl)ethanamine, L–N3), namely [Re(CO)3(L–N3)]Br was synthesized and characterized in-depth, including by X-ray crystallography. [Re(CO)3(L–N3)]Br exhibits a strong UV absorbance in the range 300–400 nm with a maximum at 322 nm, and upon photoexcitation, shows two distinct emission bands at about 430 and 560 nm in various solvents (water, ethylene glycol). [Re(CO)3(L–N3)]Br could be conjugated, on a solid phase, to a peptide nucleic acid (PNA) oligomer using the copper(I)-catalyzed azidealkyne cycloaddition reaction (Cu–AAC, “click” chemistry) and an alkyne-containing PNA building block to give RePNA. It was demonstrated that upon hybridisation with a complementary DNA strand (DNA), the position of the maxima and emission intensity for the hybrid Re–PNA·DNA remained mainly unchanged compared to those of the single strand RePNA. The rhenium-containing PNA oligomer RePNA could be then mediated in living cells where they have been shown to be non-toxic contrary to the general notion that organometallic compounds are usually unstable under physiological conditions and/or cytotoxic. Furthermore, RePNA could be detected in living cells using fluorescent microscopy.

Graphical abstract: Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate

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Supplementary files

Article information


Submitted
04 Nov 2011
Accepted
23 Nov 2011
First published
20 Dec 2011

Dalton Trans., 2012,41, 2304-2313
Article type
Paper

Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate

G. Gasser, A. Pinto, S. Neumann, A. M. Sosniak, M. Seitz, K. Merz, R. Heumann and N. Metzler-Nolte, Dalton Trans., 2012, 41, 2304
DOI: 10.1039/C2DT12114J

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