MO tripeptide diastereomers (M=99/99mTc, Re): models to identify the structure of 99mTc peptide targeted radiopharmaceuticals

Inorganic Chemistry
Melchor V CantoriasLynn C Francesconi

Abstract

Biologically active molecules, such as many peptides, serve as targeting vectors for radiopharmaceuticals based on 99mTc. Tripeptides can be suitable chelates and are easily and conveniently synthesized and linked to peptide targeting vectors through solid-phase peptide synthesis and form stable TcVO complexes. Upon complexation with [TcO]3+, two products form; these are syn and anti diastereomers, and they often have different biological behavior. This is the case with the approved radiopharmaceutical [99mTcO]depreotide ([99mTcO]P829, NeoTect) that is used to image lung cancer. [99mTcO]depreotide indeed exhibits two product peaks in its HPLC profile, but assignment of the product peaks to the diastereomers has proven to be difficult because the metal peptide complex is difficult to crystallize for structural analysis. In this study, we isolated diastereomers of [99TcO] and [ReO] complexes of several tripeptide ligands that model the metal chelator region of [99mTcO]depreotide. Using X-ray crystallography, we observed that the early eluting peak (A) corresponds to the anti diastereomer, where the Tc=O group is on the opposite side of the plane formed by the ligand backbone relative to the pendant groups of the tripeptide ligand...Continue Reading

References

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Citations

Oct 29, 2008·Chemical Communications : Chem Comm·Meryn L Bowen, Chris Orvig
Aug 1, 2012·Radiochimica acta·Valerie CarrollSilvia S Jurisson
Aug 24, 2011·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Baikuntha P AryalChuan He
Jun 13, 2009·Journal of Receptor and Signal Transduction Research·Alex N Eberle, Gabriele Mild
Jun 16, 2017·Journal of Labelled Compounds & Radiopharmaceuticals·Dionysia Papagiannopoulou
Jun 16, 2009·Journal of Medicinal Chemistry·Eleni GourniAlexandra D Varvarigou

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