Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer.
Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [(11)C]casimiroin (6-[(11)C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [(11)C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[(11)C]methyl-4-methylquinolin-2(1H)-one ([(11)C]17), 8-methoxy-1-[(11)C]methyl-4-methylquinolin-2(1H)-one ([(11)C]21a), 6,8-dimethoxy-1-[(11)C]methyl-4-methylquinolin-2(1H)-one ([(11)C]21b), and 5,8-dimethoxy-1-[(11)C]methyl-4-methylquinolin-2(1H)-one ([(11)C]21c), were prepared from their corresponding precursors with [(11)C]methyl triflate ([(11)C]CH(3)OTf) under basic conditions (NaH) through either O- or N-[(11)C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [(11)C]CO(2), and 111-185GBq/mumol specific activity at the end of synthesis (EOS).
Wang
Min
M
Department of Radiology and Imaging Sciences, Indiana University School of Medicine, 1345 West 16th Street, L3-208, Indianapolis, IN 46202, USA.
Gao
Mingzhang
M
Miller
Kathy D
KD
Sledge
George W
GW
Hutchins
Gary D
GD
Zheng
Qi-Huang
QH
D001141:Aromatase / Q000378:metabolism*; D047072:Aromatase Inhibitors / Q000494:pharmacology; D052117:Benzodioxoles / Q000494:pharmacology; D001943:Breast Neoplasms / Q000000981:diagnostic imaging* / Q000201:enzymology / Q000235:genetics*; D002250:Carbon Radioisotopes; D015972:Gene Expression Regulation, Neoplastic; D020128:Inhibitory Concentration 50; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000037:antagonists & inhibitors / Q000378:metabolism*; D049268:Positron-Emission Tomography / Q000379:methods*; D015363:Quinolones / Q000494:pharmacology; D011849:Radioactive Tracers; D011854:Radiochemistry
D047072:Aromatase Inhibitors; D052117:Benzodioxoles; D002250:Carbon Radioisotopes; D015363:Quinolones; D011849:Radioactive Tracers; C540179:6-methoxy-9-methyl-(1,3)dioxolo(4,5-h)quinolin-8(9H)-one; D001141:Aromatase; D016660:NAD(P)H Dehydrogenase (Quinone)