Synthesis of carbon-11-labeled 4-aryl-4H-chromens as new PET agents for imaging of apoptosis in cancer.
Carbon-11-labeled 4-aryl-4H-chromenes, 2-amino-7-(dimethylamino)-4-(3-[(11)C]methoxy-5-methoxyphenyl)-4H-chromene-3-carbonitrile ([(11)C]6a), 2-amino-4-(3-bromo-4-[(11)C]methoxy-5-methoxyphenyl)-7-(dimethylamino)-4H-chromene-3-carbonitrile ([(11)C]6c), 2-amino-4-(3-[(11)C]methoxy-5-methoxyphenyl)-4,7-dihydropyrano[2,3-e]indole-3-carbonitrile ([(11)C]6d), 2-amino-4-(3-bromo-4-[(11)C]methoxy-5-methoxyphenyl)-4,7-dihydropyrano[2,3-e]indole-3-carbonitrile ([(11)C]6f), 2-amino-4-(3-[(11)C]methoxy-5-methoxyphenyl)-4,9-dihydropyrano[3,2-g]indole-3-carbonitrile ([(11)C]6g), 2-amino-4-(3-bromo-4-[(11)C]methoxy-5-methoxyphenyl)-4,9-dihydropyrano[3,2-g]indole-3-carbonitrile ([(11)C]6i), 2-amino-4-(3-[(11)C]methoxy-5-methoxyphenyl)-7-methyl-4,7-dihydropyrano[2,3-e]indole-3-carbonitrile ([(11)C]6j) and 2-amino-4-(3-bromo-4-[(11)C]methoxy-5-methoxyphenyl)-7-methyl-4,7-dihydropyrano[2,3-e]indole-3-carbonitrile ([(11)C]6l), were prepared by O-[(11)C]methylation of their corresponding precursors using [(11)C]CH(3)OTf under basic conditions and isolated by a simplified solid-phase extraction (SPE) method in 30-50% radiochemical yields based on [(11)C]CO(2) and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 15-20min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 111-185GBq/micromol.
Gao
Mingzhang
M
Department of Radiology, Indiana University School of Medicine, 1345 West 16th Street, L3-208, Indianapolis, IN 46202, USA.
Wang
Min
M
Miller
Kathy D
KD
Hutchins
Gary D
GD
Zheng
Qi-Huang
QH
D017209:Apoptosis; D001578:Benzopyrans / Q000138:chemical synthesis*; D001943:Breast Neoplasms / Q000378:metabolism / Q000473:pathology; D002250:Carbon Radioisotopes; D002289:Carcinoma, Non-Small-Cell Lung / Q000378:metabolism / Q000473:pathology; D020169:Caspases / Q000378:metabolism; D045744:Cell Line, Tumor; D004789:Enzyme Activation; D006801:Humans; D009369:Neoplasms / Q000000981:diagnostic imaging*; D049268:Positron-Emission Tomography / Q000379:methods
D001578:Benzopyrans; D002250:Carbon Radioisotopes; D020169:Caspases