Integration of DOTA as a bridging unit during solid-phase peptide synthesis

A method for the introduction of bifunctionalized 1,4,7,10-tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid (DOTA) into the bridging unit of peptide-based radiopharmaceuticals has been developed. The method is executed in the context of Fmoc-based solid-phase peptide synthesis (SPPS) using stand...

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Bibliographic Details
Published in:Results in Chemistry
Main Authors: Lennard Wendlinger, Mara Parzinger, Margret Schottelius, Hans-Jürgen Wester
Format: Article
Language:English
Published: Elsevier 2023-12-01
Subjects:
Chelator
Bridging Unit
Radiopharmaceuticals
Solid-Phase Peptide Synthesis
Radiohybrid Tracers
Online Access:http://www.sciencedirect.com/science/article/pii/S2211715623003156
Description
Summary:A method for the introduction of bifunctionalized 1,4,7,10-tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid (DOTA) into the bridging unit of peptide-based radiopharmaceuticals has been developed. The method is executed in the context of Fmoc-based solid-phase peptide synthesis (SPPS) using standard coupling reagents (HOAt, TBTU, DIPEA) and was optimized to maximize yields (>99% conversion) and suppress the formation of side products (<25%). The bifunctionalized DOTA chelator can be used to integrate radioactive or non-radioactive Ga3+-isotopes. This facilitates novel and structurally simple PET tracer designs and the combination of other functional moieties, such as dyes, with Ga-DOTA-chelates in one hybrid tracer.
ISSN:2211-7156

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