製備與評估氟-18芬布芬衍生物4-硼頻那醇甲基[18F]氟芬布芬於正子照影和硼中子捕獲治療之應用

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製備與評估氟-18芬布芬衍生物4-硼頻那醇甲基[18F]氟芬布芬於正子照影和硼中子捕獲治療之應用

Preparation and biological assessment of 4-boron pinacol methyl [18F] fluorofenbufen for potential application in positron emission tomography and boron neutron capture therapy

田世維 , Masters　　Advisor：俞鐘山　　

繁體中文

氟十八；硼中子捕獲治療；非類固醇抗發炎藥物

Abstract │ Reference (59) │ Altmetrics

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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.

Reference ( 59 ) 〈TOP〉

1. Husain, A.; Ahmad, A.; Alam, M. M.; Ajmal, M.; Ahuja, P., Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1 -(biphenyl-4-yl) propan-1-ones as safer antiinflammatory and analgesic agents. European Journal of Medicinal Chemistry 2009, 44 (9), 3798-804.
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2. Smith, W. L.; Urade, Y.; Jakobsson, P. J., Enzymes of the Cyclooxygenase Pathways of Prostanoid Biosynthesis. Chem Rev 2011, 111 (10), 5821-5865.
連結：
3. Liu, J. K.; Patel, S. K.; Gillespie, D. L.; Whang, K.; Couldwell, W. T., R-flurbiprofen, a novel nonsteroidal anti-inflammatory drug, decreases cell proliferation and induces apoptosis in pituitary adenoma cells in vitro. J Neuro-Oncol 2012, 106 (3), 561-569.
連結：
4. Johannesdottir, S. A.; Chang, E. T.; Mehnert, F.; Schmidt, M.; Olesen, A. B.; Sorensen, H. T., Nonsteroidal anti-inflammatory drugs and the risk of skin cancer. Cancer-Am Cancer Soc 2012, 118 (19), 4768-4776.
連結：
7. Cunha, L.; Szigeti, K.; Mathe, D.; Metello, L. F., The role of molecular imaging in modern drug development. Drug Discov Today 2014, 19 (7), 936-948.
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