Rapid aqueous [18F]-labeling of a bodipy dye for positron emission tomography/fluorescence dual modality imaging

Zibo Li, Tzu-Pin Lin, Shuanglong Liu, Chiun-Wei Huang, Todd W. Hudnall, François P. Gabbaï, Peter S. Conti
2011 Chemical Communications  
This document includes: Materials and Methods NMR study of [2-OH] + with KHF 2 (Figure S1) UV-vis and fluorescence measurements of [2-OH] + and [2-F] + (Figure S2) PBS stability (Figure S3) MicroPET imaging Fluorescence Imaging Results of the carrier-free radiofluorination reactions Electronic Supplementary Material (ESI) for Chemical Communications This journal is General considerations. 4-dimethylaminobenzaldehyde, p-chloranil, and phenylboron dichloride were purchased from Aldrich.
more » ... Aldrich. 2,4-dimethylpyrrole was purchased from TCI. All preparations were carried out under an atmosphere of dry N 2 employing either a glove box or standard Schlenk techniques. Solvents were dried by passing through an alumina column (CH 2 Cl 2 ) or refluxing under N 2 over Na/K (Et 3 N). NMR spectra were recorded on a Varian Unity Inova 400 NMR and an Inova 500 NMR spectrometer at ambient temperature. Chemical shifts are given in ppm, and are referenced to residual 1 H and 13 C solvent signals and external neat BF 3 -Et 2 O for 11 B and 19 F. Electrospray mass spectra were acquired on a MDS Sciex API QStar Pulsar. The spray voltage was 4.5 kV. All spectra were obtained in positive mode from CH 3 CN. HPLC analyses were carried out on a analytical reversed-phase high performance liquid chromatography (HPLC) system equipped with a dual UV absorbance detector (Waters 2487) using a phenomenex C18 RP (250 x 4.6 mm 5 micron ). The flow was 1 mL/min, with the mobile phase starting from 95% solvent A (0.1% TFA in water) and 5% solvent B (0.1% TFA in acetonitrile) (0-2 min), followed by a gradient mobile phase to 5% solvent A and 95% solvent B at 22 min. The radioactivity was detected by a model of Ludlum 2200 single-channel radiation detector. The stability study was performed using the same HPLC condition. Synthesis of 10-dimethyl-aminophenyl-5-hydroxyl-5-phenyl-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2c:1',2'-f][1,3,2]diazaborinin-4-ium-5-uide (A-OH)
doi:10.1039/c1cc13089g pmid:21779546 fatcat:bza34dejkzajxkisieqlrjxppe