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

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

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

Novel radiolabeled O6-benzylguanine derivatives, 2-amino-6-O-[11C]-[(methoxymethyl)benzyloxy]-9-benzyl purines ([11C]p-O6AMBP, 1a; [11C]m-O6-AMBP, 1b; [11C]o-O6-AMBP, 1c), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging agents for the DNA repair protein, O6-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-[11C]methylation of hydroxymethyl precursors using [11C]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 20-25 min.

Original languageEnglish (US)
Pages (from-to)1239-1252
Number of pages14
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume45
Issue number14
DOIs
StatePublished - Dec 1 2002

Keywords

  • 2-amino-6-O-[C]- [(methoxymethyl)benzyloxy]-9-benzyl purines
  • Carbon-11
  • DNA repair protein
  • O-alkylguanine-DNA alkyltransferase
  • Positron emission tomography
  • Radiolabeled O-benzylguanine derivatives

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Clinical Biochemistry
  • Molecular Medicine
  • Pharmacology

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