(R,S)-anti-1-amino-2-[18F]fluorocyclopentyl-1-carboxylic acid: synthesis from racemic 2-benzyloxycyclopentanone and biological evaluation for brain tumor imaging with positron emission tomography.
(R,S)-anti-1-amino-2-fluorocyclopentyl-1-carboxylic acid (2-FACPC, 4b) was radiolabeled in 39% yield starting from cyclic sulfamidate 12. The 9L gliosarcoma cells assays showed that 4b is mainly a substrate for the L-type amino acid transport with some affinity to the A-type. In rats bearing 9L gliosarcoma tumors, 4b displayed high tumor to brain ratio (10:1) at 120 min after injection. FACPC is an attractive candidate for imaging brain tumors with PET, and its isolated enantiomers are under investigation.
Jarkas
Nachwa
N
Department of Radiology, Emory University CSI, Wesley Woods Health Center, 1841 Clifton Road, NE, Atlanta, Georgia 30329, USA.
Voll
Ronald J
RJ
Williams
Larry
L
Camp
Vernon M
VM
Goodman
Mark M
MM
D027241:Amino Acid Transport System y+L / Q000378:metabolism; D000818:Animals; D001921:Brain / Q000000981:diagnostic imaging / Q000378:metabolism; D001932:Brain Neoplasms / Q000000981:diagnostic imaging*; D045744:Cell Line, Tumor; D003515:Cycloleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D005462:Fluorine Radioisotopes; D008297:Male; D049268:Positron-Emission Tomography; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D051381:Rats; D011916:Rats, Inbred F344; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014018:Tissue Distribution
C552703:1-amino-2-fluorocyclopentyl-1-carboxylic acid; D027241:Amino Acid Transport System y+L; D003517:Cyclopentanes; D005462:Fluorine Radioisotopes; D019275:Radiopharmaceuticals; D003515:Cycloleucine