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Download fileSynthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores
journal contribution
posted on 2021-11-15, 17:06 authored by Dan WuDan Wu, Gonzalo Durán-Sampedro, Donal O'SheaDonal O'SheaBis-alkylsulfonic acid and polyethylene glycol (PEG)-substituted BF2 azadipyrromethenes have been synthesized by an adaptable and versatile route. Only four synthetic stages were required to produce the penultimate fluorophore compounds, containing either two alcohol or two terminal alkyne substituents. The final synthetic step introduced either sulfonic acid or polyethylene glycol groups to impart aqueous solubility. Sulfonic acid groups were introduced by reaction of the bis-alcohol-substituted fluorophore with sulfur trioxide, and a double Cu(I)-catalyzed cycloaddition reaction between the bis-alkyne fluorophore and methoxypolyethylene glycol azide yielded a neutral bis-pegylated derivative. Both fluorophores exhibited excellent near-infrared (NIR) photophysical properties in methanol and aqueous solutions. Live cell microscopy imaging revealed efficient uptake and intracellular labelling of cells for both fluorophores. Their simple synthesis, with potential for last-step structural modifications, makes the present NIR-active azadipyrromethene derivatives potentially useful as NIR fluorescence imaging probes for live cells.
Funding
European Union’s Horizon 2020 research and innovation program, under the Marie Sklodowska-Curie grant agreement No. 707618
History
Comments
This is a post-peer-review, pre-copyedit version of an article published in Frontiers of Chemical Science and Engineering. The final authenticated version is available online at: https://doi.org/10.1007/s11705-019-1828-xPublished Citation
Wu D, Durán-Sampedro G, O’Shea DF. Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores. Front. Chem. Sci. Eng. 2020;14:97–104Publication Date
26 October 2019External DOI
Department/Unit
- Chemistry
Research Area
- Cancer
- Surgical Science and Practice
- Chemistry and Pharmaceutical Sciences
Publisher
Springer Nature Switzerland AGVersion
- Accepted Version (Postprint)