Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer.

Abstract

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).

• Authors: Min Wang, Mingzhang Gao, Kathy D Miller, George W Sledge, Gary D Hutchins, Qi-Huang Zheng
• Journal: Steroids (Steroids) Vol. 75 Issue 12 Pg. 967-73 (Dec 2010) ISSN: 1878-5867 [Electronic] United States
• PMID: 20558190 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S.)
• Copyright: Copyright 2010 Elsevier Inc. All rights reserved.

Chemical References

• Aromatase Inhibitors
• Benzodioxoles
• Carbon Radioisotopes
• Quinolones
• Radioactive Tracers
• 6-methoxy-9-methyl-(1,3)dioxolo(4,5-h)quinolin-8(9H)-one
• Aromatase
• NAD(P)H Dehydrogenase (Quinone)

Topics

• Aromatase (metabolism)
• Aromatase Inhibitors (pharmacology)
• Benzodioxoles (pharmacology)
• Breast Neoplasms (diagnostic imaging, enzymology, genetics)
• Carbon Radioisotopes
• Gene Expression Regulation, Neoplastic
• Inhibitory Concentration 50
• NAD(P)H Dehydrogenase (Quinone) (antagonists & inhibitors, metabolism)
• Positron-Emission Tomography (methods)
• Quinolones (pharmacology)
• Radioactive Tracers
• Radiochemistry