title: Design, synthesis and 64Cu labeling of fatty acid analogs containing dithiosemicarbazone chelate.
abstract: For the development of 62Cu labeled fatty acid analogs, two fatty acid analogs, containing dithiosemicarbazone (DTS) molecule as the 62Cu coordinating site, were designed and synthesized: a fatty acid analog containing DTS molecule at the omega-position, (a) the 12,13-dioxotetradecanoic acid di(N-methyl-thiosemicarbazone) (FA-DTS), and an omega-phenyl fatty acid analog containing DTS molecule at the para-position, (b) the p-carboxyundecylphenylglyoxal-di (N-methylthiosemicarbazone] (PFA-DTS). FA-DTS was synthesized by the reaction of ethyl diethoxyacetate with ethyl 11-bromonundecanate by successive decarboxylation and hydrolysis and final condensation with N-methylthiosemicarbazide. PFA-DTS was synthesized by the Friedel-Craft acylation of ethyl 11-phenylundecanate, selenium oxidation of the acetophenone derivative, followed by the condensation with N-methylthiosemicarbazide. Radiolabeling of FA-DTS and PFA-DTS with [64Cu]copper acetate was simple, rapid and quantitative. When injected into mice, both compounds were distributed and retained in the myocardium. These results offer a good basis for further development of 62Cu labeled fatty acid analogs.
authors.affiliation: Department of Radiopharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Arano
authors.forename: Y
authors.initials: Y
authors.lastname: Magata
authors.forename: K
authors.initials: K
authors.lastname: Horiuchi
authors.forename: K
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Y
authors.initials: Y
authors.lastname: Fujibayashi
authors.forename: Y
authors.initials: Y
authors.lastname: Ohmomo
authors.forename: C
authors.initials: C
authors.lastname: Tanaka
authors.forename: H
authors.initials: H
authors.lastname: Saji
authors.forename: A
authors.initials: A
authors.lastname: Yokoyama
mesh_terms: D000818:Animals; D002614:Chelating Agents; D003301:Copper Radioisotopes; D015195:Drug Design; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D008297:Male; D051379:Mice; D011854:Radiochemistry; D013882:Thiosemicarbazones; D014018:Tissue Distribution
chemical_list: D002614:Chelating Agents; D003301:Copper Radioisotopes; D005227:Fatty Acids; D013882:Thiosemicarbazones; C015848:dithiosemicarbazone