Synthesis and evaluation of [123I] labeled iodovinyl amino acids syn-, anti-1-amino-3-[2-iodoethenyl]-cyclobutane-1-carboxylic acid, and 1-amino-3-iodomethylene-cyclobutane-1-carboxylic acid as potential SPECT brain tumor imaging agents.

Abstract

syn- and anti-1-amino-3-[2-iodoethenyl]-cyclobutane-1-carboxylic acid (syn-, anti-IVACBC 16, 17) and their analogue 1-amino-3-iodomethylene-cyclobutane-1-carboxylic acid (gem-IVACBC 18) were synthesized and radioiodoinated with [(123)I] in 34-43% delay-corrected yield. All these amino acids entered 9L gliosarcoma cells primarily via L-type transport in vitro with high uptake of 8-10% ID/1 x 10(6) cells. Biodistribution studies of [(123)I]16, 17 and 18 in rats with 9L gliosarcoma brain tumors demonstrated high tumor to brain ratios (4.7-7.3:1 at 60 min post-injection). In this model, syn-, anti-, and gem-[(123)I]IVACBC are promising radiotracers for SPECT brain tumor imaging.

• Authors: Weiping Yu, Larry Williams, Eugene Malveaux, Vernon M Camp, Jeffrey J Olson, Mark M Goodman
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 18 Issue 4 Pg. 1264-8 (Feb 15 2008) ISSN: 1464-3405 [Electronic] England
• PMID: 18258425 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 1-amino-3-(2-iodoethenyl)cyclobutane-1-carboxylic acid
• 1-amino-3-iodomethylene-cyclobutane-1-carboxylic acid
• Carboxylic Acids
• Cyclobutanes
• Iodine Radioisotopes
• Radiopharmaceuticals

Topics

• Animals
• Brain (diagnostic imaging, metabolism)
• Brain Neoplasms (diagnostic imaging, metabolism)
• Carboxylic Acids (chemical synthesis, pharmacokinetics)
• Cyclobutanes (chemical synthesis, pharmacokinetics)
• Gliosarcoma (diagnostic imaging, metabolism)
• Iodine Radioisotopes (chemistry, pharmacokinetics)
• Radiopharmaceuticals (chemical synthesis, pharmacokinetics)
• Rats
• Rats, Inbred F344
• Stereoisomerism
• Tissue Distribution
• Tomography, Emission-Computed, Single-Photon (methods)