Evaluation of fluorine-18-labeled alkylating agents as potential synthons for the labeling of oligonucleotides.
Six fluorine-18-labeled alkylating agents were selected as potentially suitable synthons for the labeling of antisense oligonucleotides. The selected synthons were evaluated in a model reaction with the monomer adenosine 5'-O-thiomonophosphate. Of these synthons, alpha-bromo-alpha'-[18F]fluoro-m-xylene and N-(4-[18F]fluorobenzyl)-2-bromoacetamide were found to be the most promising. Labeling with the former synthon was less complicated and time consuming and gave higher uncorrected overall yields. The latter synthon required smaller amounts of the costly precursor to achieve acceptable labeling yields.
de Vries
Erik F J
EF
PET Center, Groningen University Hospital, P.O. Box 30.001, 9700 RB, Groningen, The Netherlands. e.f.j.de.vries@pet.azg.nl
Vroegh
Joke
J
Elsinga
Philip H
PH
Vaalburg
Willem
W
D000249:Adenosine Monophosphate / Q000031:analogs & derivatives; D000477:Alkylating Agents / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods*; D016376:Oligonucleotides, Antisense / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D019275:Radiopharmaceuticals / Q000737:chemistry*; D013873:Thionucleotides / Q000737:chemistry
D000477:Alkylating Agents; D001965:Bromides; D005462:Fluorine Radioisotopes; D016376:Oligonucleotides, Antisense; D010710:Phosphates; D019275:Radiopharmaceuticals; D013873:Thionucleotides; D000249:Adenosine Monophosphate