Synthesis of F-18 labeled resazurin by direct electrophilic fluorination.
We present the synthesis and characterization of F18-labeled fluorinated derivatives of resazurin, a probe for cell viability. The compounds were prepared by direct fluorination of resazurin with diluted [F18]-F2gas under acidic conditions. The fluorination occurs into theortho-positions to the hydroxyl group producing various mono-, di-, and trifluorinated derivatives. The properties of the fluorinated resazurins are similar to the parent compound with the addition of fluorine leading to decreasedpKavalues and a bathochromic shift of the absorption maxima. The fluorinated resazurin derivatives can be used as probes for observation of cell viability in various cells, tissues and organs using a combination of positron emission tomography and direct optical imaging of Cerenkov luminescence.
Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia, PA 19104, USA ; Department of Chemistry and Biochemistry, Misher College of Arts and Sciences, University of the Sciences, Philadelphia, PA 19104.
Alexander V
AV
Kachur
Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia, PA 19104, USA.
Alejandro D
AD
Arroyo
Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia, PA 19104, USA.
Anatoliy V
AV
Popov
Department of Chemistry and Biochemistry, Misher College of Arts and Sciences, University of the Sciences, Philadelphia, PA 19104.
Sarah J
SJ
Saylor
Department of Radiology, Perelman School of Medicine, University of Pennsylvania, Philadelphia, PA 19104, USA.
E James
EJ
Delikatny
Cerenkov luminescence; F-18; electrophilic fluorination; resazurin; resorufin