Title
Straightforward Synthesis of DFO* ‐ An Octadentate Chelator for Zirconium‐89
... show all
Abstract
DFO* is an octadentate chelator able to form highly stable chelates with Zirconium-89 (89Zr) for nuclear medicinal applications in Positron Emission Tomography (PET).[1,2] The synthesis of DFO* and its scale-up remains challenging by reported synthetic protocols. For this reason, we set out to develop a de novo synthesis of a hydroxamate-containing building block suitable for the coupling to the commercially available DFO (desferrioxamine B, mesylate salt) yielding, after deprotection, the desired chelator DFO* in a more efficient procedure. Highlights of the new synthesis of DFO* reported herein are less synthetic steps and the isolation of the desired product DFO* by using solid phase extraction (SPE), thus avoiding tedious HPLC purification. DFO* is obtained in excellent purity (92-98 %) and an overall yield of approximately 29 %. In addition, the isolated trifluoroacetic acid (TFA)-salt of DFO* displays an improved solubility in organic solvents (DMSO, DMF, methanol), which will facilitate its use for the preparation of structurally diverse derivatives suitable for bioconjugation chemistry and the development of 89Zr-labeled radiotracers.
Keywords
SynthesisChelatorDFO*Positron Emission Tomography (PET)Zirconium-89 (89Zr)
Object type
Language
English [eng]
Persistent identifier
https://phaidra.univie.ac.at/o:2045048
Appeared in
Title
ChemMedChem
Volume
19
Issue
3
ISSN
1860-7179
Issued
2024
Publisher
Wiley
Date issued
2024
Access rights
Rights statement
© 2023 The Authors
University of Vienna | Universitätsring 1 | 1010 Vienna | T +43-1-4277-0