Simple synthesis of carbon-11 labeled styryl dyes as new potential PET RNA-specific, living cell imaging probes.
A new type of styryl dyes have been developed as RNA-specific, live cell imaging probes for fluorescent microscopy technology to study nuclear structure and function. This study was designed to develop carbon-11 labeled styryl dyes as new probes for biomedical imaging technique positron emission tomography (PET) imaging of RNA in living cells. Precursors (E)-2-(2-(1-(triisopropylsilyl)-1H-indol-3-yl)vinyl)quinoline (2), (E)-2-(2,4,6-trimethoxystyryl)quinoline (3) and (E)-4-(2-(6-methoxyquinolin-2-yl)vinyl)-N,N-diemthylaniline (4), and standards styryl dyes E36 (6), E144 (7) and F22 (9) were synthesized in multiple steps with moderate to high chemical yields. Precursor 2 was labeled by [(11)C]CH(3)OTf, trapped on a cation-exchange CM Sep-Pak cartridge following a quick deprotecting reaction by addition of (n-Bu)(4)NF in THF, and isolated by solid-phase extraction (SPE) purification to provide target tracer [(11)C]E36 ([(11)C]6) in 40-50% radiochemical yields, decay corrected to end of bombardment (EOB), based on [(11)C]CO(2). The target tracers [(11)C]E144 ([(11)C]7) and [(11)C]F22 ([(11)C]9) were prepared by N-[(11)C]methylation of the precursors 3 and 4, respectively, using [(11)C]CH(3)OTf and isolated by SPE method in 50-70% radiochemical yields at EOB. The specific activity of the target tracers [(11)C]6, [(11)C]7 and [(11)C]9 was in a range of 74-111GBq/mumol at the end of synthesis (EOS).
Wang
Min
M
Department of Radiology, Indiana University School of Medicine, 1345 West 16th Street, L3-208, Indianapolis, IN 46202-2111, USA.
Gao
Mingzhang
M
Miller
Kathy D
KD
Sledge
George W
GW
Hutchins
Gary D
GD
Zheng
Qi-Huang
QH
D000814:Aniline Compounds / Q000138:chemical synthesis; D002250:Carbon Radioisotopes; D004396:Coloring Agents; D007553:Isotope Labeling / Q000379:methods*; D008856:Microscopy, Fluorescence; D015336:Molecular Probe Techniques; D049268:Positron-Emission Tomography / Q000379:methods*; D011804:Quinolines; D012313:RNA / Q000032:analysis*
D000814:Aniline Compounds; D002250:Carbon Radioisotopes; D004396:Coloring Agents; D011804:Quinolines; D012313:RNA