Abstract
By using 4-bromobiphenyl as starting material, via three steps synthesis, we obtain methyl 4-oxo-4-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)butanoate (6) with chemical yield 81.6%. After radio-labeling by [18F] F2, 4-boron pinacol methyl [18F] fluorofenbufen (FFBpin) was prepared with a radiochemical yield 3.3% and the specific activity was 12.3 MBq/ μmole. To figure out the structure of FFBpin, we compared FFBpin’s NMR and mass spectrometry with precursor’s. The 1H-NMR signal of precursor at δ 7.80 and δ 7.85 disappeared, and three new signals raised at δ 7.51, 7.56 and 7.65. The 19F-NMR showed that there were two signals at δ -119.07 and δ -119.6. Calculated by the Hesse Meier Zeeh equation, we deduced the fluorine atom locating on the ortho and meta site of boron atom. The result showed that [18F] FFBpin preferentially interacts with COX-1 and the IC50 is 3.16 μM comparing with that of COX-2 in 11.22 μM. [18F] fluorocelecoxib binds COX-2 with IC50 0.13 nM and that of COX-1 with IC50 12.59 nM. Besides, increasing accumulation of [18F] FFBpin from 1% to 1.5% in HuCCT1 was observed during 2 hrs-study, in contradictory to a plain accumulation by fibroblast cell.