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Issue 12, 2014
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Synthesis of tripeptide derivatized cyclopentadienyl complexes of technetium and rhenium as radiopharmaceutical probes

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Abstract

We describe the syntheses of half-sandwich complexes of the type [(η5-Cp(CONH-R))M(CO)3] with M = Re or 99mTc. The R group represents different tri-peptides (tpe) which display high binding affinities for oligopeptide transporters PEPT2. The 99mTc complexes were prepared directly from [99mTc(OH2)3(CO)3]+ and Diels–Alder dimerized, cyclopentadienyl derivatized peptides in water. This approach corroborates the feasibility of metal-mediated retro Diels–Alder reactions for the preparation of not only small molecules but also peptides carrying a [(η5-Cp)99mTc(CO)3] tag. We synthesized the Diels–Alder product [(HCpCONH-tpe)2] from Thiele's acid [(η5-HCpCOOH)2] via double peptide coupling. The Re-complexes [(η5-CpCONH-tpe)Re(CO)3] were obtained by attaching [(Cp-COOH)Re(CO)3] directly to the N-terminus of peptides as received from SPPS. The authenticity of the 99mTc-complexes is confirmed by chromatographic comparison with the corresponding rhenium complexes, fully characterized by spectroscopic techniques.

Graphical abstract: Synthesis of tripeptide derivatized cyclopentadienyl complexes of technetium and rhenium as radiopharmaceutical probes

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Supplementary files

Article information


Submitted
12 Sep 2013
Accepted
23 Jan 2014
First published
23 Jan 2014

This article is Open Access

Org. Biomol. Chem., 2014,12, 1966-1974
Article type
Paper

Synthesis of tripeptide derivatized cyclopentadienyl complexes of technetium and rhenium as radiopharmaceutical probes

Q. Nadeem, D. Can, Y. Shen, M. Felber, Z. Mahmood and R. Alberto, Org. Biomol. Chem., 2014, 12, 1966
DOI: 10.1039/C3OB41866A

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