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Synthesis of radiolabeled O 6 ‐benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O 6 ‐alkylguanine‐DNA alkyltransferase
Author(s) -
Zheng QiHuang,
Liu Xuan,
Fei Xiangshu,
Wang JiQuan,
Ohannesian David W.,
Erickson Leonard C.,
Stone K. Lee,
Martinez Tanya D.,
Miller Kathy D.,
Hutchins Gary D.
Publication year - 2002
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.636
Subject(s) - chemistry , dna , hydroxymethyl , trifluoromethanesulfonate , chemical synthesis , positron emission tomography , purine metabolism , stereochemistry , biochemistry , enzyme , nuclear medicine , medicine , in vitro , catalysis
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.