New synthesis of 6â³-[18 F]fluoromaltotriose for positron emission tomography imaging of bacterial infection.
J Labelled Comp Radiopharm
; 63(11): 466-475, 2020 09.
Article
en En
| MEDLINE
| ID: mdl-32602175
ABSTRACT
6â³-[18 F]fluoromaltotriose is a positron emission tomography tracer that can differentiate between bacterial infection and inflammation in vivo. Bacteria-specific uptake of 6â³-[18 F]fluoromaltotriose is attributed to the targeting of maltodextrin transporter in bacteria that is absent in mammalian cells. Herein, we report a new synthesis of 6â³-[18 F]fluoromaltotriose as a key step for its clinical translation. In comparison with the previously reported synthesis, the new synthesis features unambiguous assignment of the fluorine-18 position on the maltotriose unit. The new method utilizes direct fluorination of 2â³,3â³,4â³-tri-O-acetyl-6â³-O-trifyl-α-D-glucopyranosyl-(1-4)-O-2',3',6'-tri-O-acetyl-α-D-glucopyranosyl-(1-4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose followed by basic hydrolysis. Radiolabeling of the new maltotriose triflate precursor proceeds using a single HPLC purification step, which results in shorter reaction time in comparison with the previously reported synthesis. Successful synthesis of 6â³-[18 F]fluoromaltotriose has been achieved in 3.5 ± 0.3% radiochemical yield (decay corrected, n = 7) and radiochemical purity above 95%. The efficient radiosynthesis of 6â³-[18 F]fluoromaltotriose would be critical in advancing this positron emission tomography tracer into clinical trials for imaging bacterial infections.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Infecciones Bacterianas
/
Trisacáridos
/
Radioisótopos de Flúor
/
Tomografía de Emisión de Positrones
Límite:
Animals
/
Humans
Idioma:
En
Revista:
J Labelled Comp Radiopharm
Año:
2020
Tipo del documento:
Article
País de afiliación:
Estados Unidos