Development of fluorinated naphthofluoresceins for Cerenkov imaging.

Autor: Arroyo AD; Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia PA 19104., Guzmán AE; Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia PA 19104., Kachur AV; Department of Chemistry and Biochemistry, Misher College of Arts and Sciences, University of the Sciences, Philadelphia, PA 19104., Saylor SJ; Department of Chemistry and Biochemistry, Misher College of Arts and Sciences, University of the Sciences, Philadelphia, PA 19104., Popov AV; Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia PA 19104., Delikatny EJ; Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia PA 19104.
Jazyk: angličtina
Zdroj: Journal of fluorine chemistry [J Fluor Chem] 2019 Sep; Vol. 225, pp. 27-34. Date of Electronic Publication: 2019 May 24.
DOI: 10.1016/j.jfluchem.2019.05.010
Abstrakt: In this paper, we report the synthesis and characterization of fluorinated derivatives of naphthofluorescein (NF), a fluorescent pH-sensitive probe that can be used for functional Cerenkov imaging. The compounds were prepared using electrophilic fluorination with dilute fluorine gas under acidic conditions. The fluorination of the NF molecule occurred in the ortho positions to the hydroxyl moiety, producing mono-, di-, and tri-substituted derivatives. The properties of the fluorinated naphthofluoresceins were similar to the parent compound, retaining pH sensitivity and fluorescence capability, but showed a more acidic pK a with increasing fluorination degree and a bathochromic shift in both absorbance and fluorescence. NF and its two major fluorinated derivatives were shown to attenuate Cerenkov radiation in the basic form; the greatest attenuation was observed at wavelengths coinciding with the absorption maxima. NF also showed potential as a Cerenkov Radiation Energy Transfer (CRET) probe. Fluorinated naphthofluoresceins provide a new family of molecular imaging probes for the detection of pH in tissue and organs by using a combination of PET and Cerenkov imaging.
Competing Interests: Financial disclosure The authors have no financial conflicts to disclose.
Databáze: MEDLINE
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