6533b86ffe1ef96bd12cd34f

RESEARCH PRODUCT

Isomerism of [64Cu-NOTA-Bn]-labeled radiotracers: separation of two complex isomers and determination of their interconversion energy barrier using ion pair chromatography.

Veronica FagerholmPatrik EklundJoern SchlesingerOlof SolinPirjo NuutilaDinesh RameshJohan RajanderJohan RajanderJanne A. Ihalainen

subject

Ion pair chromatographyAnalytical chemistryMolecular Conformationchemistry.chemical_elementAcetatesChemical Fractionation010402 general chemistry01 natural sciencesMolecular conformationIonInorganic Chemistrychemistry.chemical_compoundHeterocyclic Compounds 1-RingDrug StabilityIsomerismCoordination ComplexesHeterocyclic CompoundsAmmoniumPhysical and Theoretical ChemistryRadioactive TracersChromatography010405 organic chemistryChemistryChemical fractionationTemperatureWaterHydrogen-Ion ConcentrationCopper0104 chemical sciencesSolutionsPositron-Emission TomographyPhysical chemistryThermodynamicsAmmonium acetateCopper

description

The model complex [(64)Cu((S)-p-NH(2)-Bn-NOTA)](-) ([(64)Cu]1) was used to study the isomerism of [(64)Cu-NOTA-Bn]-labeled radiotracers. Two complex isomers [(64)Cu]1a and [(64)Cu]1b, which were formed at a ratio of 1:9 during the complexation of [(64)Cu]Cu(2+) with (S)-p-NH(2)-Bn-NOTA, were separated using ion pair chromatography. To study the interconversion, the nonradioactive complex isomers Cu1a and Cu1b were separated and thermally treated at 90 °C in both ammonium acetate solution and deionized water. A faster interconversion rate was observed for both isomers with lower concentrations of ammonium ions. At the end of reaction, the thermodynamic Cu1a to Cu1b equilibrium ratio was 6:94. The particular energy barriers of the interconversion for Cu1a and Cu1b were 130 kJ mol(-1) and 140 kJ mol(-1). Spectrophotometric measurements with Cu1a and Cu1b revealed two isomers adopting different geometrical configurations.

10.1021/ic101775qhttps://pubmed.ncbi.nlm.nih.gov/21488661