BF2-Azadipyrromethene Fluorophores for Intraoperative Vital Structure Identification

A series of mono- and bis-polyethylene glycol (PEG)-substituted BF2-azadipyrromethene fluorophores have been synthesized with emissions in the near-infrared region (700–800 nm) for the purpose of fluorescence guided intraoperative imaging; chiefly ureter imaging. The Bis-PEGylation of fluorophores r...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-02, Vol.28 (5), p.2167
Main Authors: Caulfield, Cathal, Wu, Dan, Miller, Ian S., Byrne, Annette T., Mac Aonghusa, Pól, Zhuk, Sergiy, Cinelli, Lorenzo, Bannone, Elisa, Marescaux, Jacques, Gioux, Sylvain, Diana, Michele, March, Taryn L., Vahrmeijer, Alexander L., Cahill, Ronan, O’Shea, Donal F.
Format: Article
Language:English
Subjects:
Animal models
Aqueous solutions
BF2-azadipyrromethene
Chemical compounds
Chromatography
Clinical outcomes
Color coding
Emissions
Fluorescence
fluorescence guided surgery
Fluorophores
Imaging
Kidneys
Mass spectrometry
Molecular weight
NIR-fluorescence
pegylation
Phenols
Polyethylene glycol
Renal function
Scientific imaging
Surgery
Ureter
ureter identification
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Summary:A series of mono- and bis-polyethylene glycol (PEG)-substituted BF2-azadipyrromethene fluorophores have been synthesized with emissions in the near-infrared region (700–800 nm) for the purpose of fluorescence guided intraoperative imaging; chiefly ureter imaging. The Bis-PEGylation of fluorophores resulted in higher aqueous fluorescence quantum yields, with PEG chain lengths of 2.9 to 4.6 kDa being optimal. Fluorescence ureter identification was possible in a rodent model with the preference for renal excretion notable through comparative fluorescence intensities from the ureters, kidneys and liver. Ureteral identification was also successfully performed in a larger animal porcine model under abdominal surgical conditions. Three tested doses of 0.5, 0.25 and 0.1 mg/kg all successfully identified fluorescent ureters within 20 min of administration which was sustained up to 120 min. 3-D emission heat map imaging allowed the spatial and temporal changes in intensity due to the distinctive peristaltic waves of urine being transferred from the kidneys to the bladder to be identified. As the emission of these fluorophores could be spectrally distinguished from the clinically-used perfusion dye indocyanine green, it is envisaged that their combined use could be a step towards intraoperative colour coding of different tissues.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28052167