The syntheses of 1-[11C]-D-glucose and related compounds for the measurement of brain glucose metabolism

✍ Scribed by Chyng-Yann Shiue; Alfred P. Wolf

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: French
• Weight: 431 KB
• Volume: 22
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580220210

✦ Synopsis

The Syntheses of 1-[ llC]-D-Clucose and R e l a t e d Compounds f o r t h e Yeasurement of Rrain Glucose Metabolism Chyng-Yann Shiue and A l f r e d P. Wolf Department OE Chemistry, Brookhaven N a t i o n a l L a b o r a t o r y Upton, New York 11973 USA SUMART A new s y n t h e s i s of l-[llC]-D-glucose (3 and r e l a t e d com ounds g i v e s l -[ l l C ] -a l d o n o n i t r i l e s (A). Reduction of w?th Raney a l l o y in 30% formic a c i d g i v e s l-[llC]-D-glucose (3 and l-[IZC]-D7pannose (3 tn r a d i ochemical y i e l d s of -40-50% (EOB) i n a s y n t h e s i s time of 50 min from EOB. The y i e l d and r a t i o of 2 and s e p a r a t e d by HPLC. The radiochemical y i e l d of 3~ is -15% (EOB) and t h e €rom H 1 k N is d e s c r i b e d . Reaction of D-arabinose ( 1 ) w i t h Na P l C N a t pH 8 is pH dependent. ' Compounds 2 and A a r e t o t a l s y n t h e s i s time ( i n c l u d i n g HPLC p u r i f i c a t i % ) same method has also been a p p l i e d t o s y n t h e s i z e 1radiochemical y i e l d s of -30% (EOB) in a s y n t h e s i s The advantages and d i s a d v a n t a g e s of t h i s s y n t h e t i c Key Words: 1-[ llC]-D-Glucose; 1-[ llC]-D-Hannose, K i l i a n i -F i s c h e r cyanohydrin s y n t h e s i s ; is 70 min from EOB. The llC]-D-galactose (2) w i t h time of 70 min from EOB. method are d i s c u s s e d . -[ l l C ] -D-Galac t o s e ; molybdate ion c a t a l y s i s . 171 The r a p i d development i n t h e technology of p o s i t r o n e m i s s i o n tomography (PET) has made i t p o s s i b l e to s t u d y t h e dynamic p r o p e r t i e s of radiopharmac e u t i c a l s in v i v o non-invasively and q u a n t i t a t i v e l y . For example, s e v e r a l g l u c o s e a n a l o g s l a b e l e d w i t h p o s i t r o n e m i t t i n g n u c l e i have been used t o s t u d y r e g i o n a l b r a i n g l u c o s e metabolism non-invasively i n humans (1-3). Among t h e s e , 2-deoxy-2-[ 18F]fluoro-D-glucose (4-13) and 1-[ 11C]-2-deoxy-D-glucose (14-17) have

been used as tracers for q u a n t i t a t i v e l y mapping t h e f i r s t s t e p of g l y c o l y s i s i n t h e b r a i n and t h e h e a r t .

h a s a l s o been suggested f o r u t i l i z a t i o n .

h a s been prepared and e v a l u a t e d as a tracer f o r g l u c o s e t r a n s p o r t (20,21