Radiosynthesis of three [11C]ureido-substituted benzenesulfonamides as PET probes for carbonic anhydrase IX in tumors.
Three ureido-substituted benzenesulfonamides 1a-c have been developed as potent inhibitors for carbonic anhydrase IX, which is overexpressed in hypoxic tumors. In this study, we labeled these unsymmetrical ureas 1a-c using [(11)C]phosgene ([(11)C]COCl(2)) as a labeling agent with the expectation that [(11)C]1a-c could become promising positron tomography probes for imaging carbonic anhydrase IX in tumors. The strategy for radiosynthesis of [(11)C]1a-c was to react hydrochloride of anilines 2a-c with [(11)C]COCl(2) to give isocyanate [(11)C]4a-c, followed by a reaction with 4-aminobenzenesulfonamide (3).
Department of Molecular Probes, Molecular Imaging Center, National Institute of Radiological Sciences, Inage-ku, Chiba, Japan.
Chiharu
C
Asakawa
Masanao
M
Ogawa
Katsushi
K
Kumata
Masayuki
M
Fujinaga
Tomoteru
T
Yamasaki
Lin
L
Xie
Joji
J
Yui
Kazunori
K
Kawamura
Toshimitsu
T
Fukumura
Ming-Rong
MR
Zhang
D000951:Antigens, Neoplasm / Q000032:analysis* / Q000378:metabolism; D002250:Carbon Radioisotopes; D000071231:Carbonic Anhydrase IX; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis; D002256:Carbonic Anhydrases / Q000032:analysis* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003952:Diagnostic Imaging; D006801:Humans; D000860:Hypoxia; D015394:Molecular Structure; D009369:Neoplasms / Q000175:diagnosis*; D049268:Positron-Emission Tomography; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry; D014508:Urea / Q000138:chemical synthesis* / Q000737:chemistry; D000096926:Benzenesulfonamides
D000951:Antigens, Neoplasm; D002250:Carbon Radioisotopes; D000071231:Carbonic Anhydrase IX; D002257:Carbonic Anhydrase Inhibitors; D002256:Carbonic Anhydrases; D019275:Radiopharmaceuticals; D013449:Sulfonamides; D014508:Urea; D000096926:Benzenesulfonamides; C089226:CA9 protein, human