Synthesis of radiolabeled O6-benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O6-alkylguanine-DNA alkyltransferase

✍ Scribed by Qi-Huang Zheng; Xuan Liu; Xiangshu Fei; Ji-Quan Wang; David W. Ohannesian; Leonard C. Erickson; K. Lee Stone; Tanya D. Martinez; Kathy D. Miller; Gary D. Hutchins

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: French
• Weight: 121 KB
• Volume: 45
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.636

✦ Synopsis

Abstract

Novel radiolabeled O^6^‐benzylguanine derivatives, 2‐amino‐6‐O‐[^11^C]‐[(methoxymethyl)benzyloxy]‐9‐benzyl purines ([^11^C]p‐O^6^‐AMBP, 1a; [^11^C]m‐O^6^‐AMBP, 1b; [^11^C]o‐O^6^‐AMBP, 1c), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging agents for the DNA repair protein, O^6^‐alkylguanine‐DNA alkyltransferase (AGT). The appropriate precursors for radiolabeling were obtained in three steps from starting material 2‐amino‐6‐chloropurine with moderate to excellent chemical yields. Tracers were prepared by O‐[^11^C]methylation of hydroxymethyl precursors using [^11^C]methyl triflate. Pure target compounds were isolated by solid‐phase extraction (SPE) purification procedure in 45–60% radiochemical yields (decay corrected to the end of bombardment), and a synthesis time of 20–25min. Copyright © 2002 John Wiley & Sons, Ltd.