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Contents Vol 64(3)

Towards the Preparation of Novel Re/99mTc Tricarbonyl-Containing Peptide Nucleic Acid Bioconjugates

Gilles Gasser A C , Anna M. Sosniak B , Anna Leonidova A , Henrik Braband A and Nils Metzler-Nolte B C
+ Author Affiliations
- Author Affiliations

A Institute of Inorganic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.

B Ruhr-University Bochum, Faculty of Chemistry and Biochemistry, Bioinorganic Chemistry Department I, Universitätsstrasse 150, D-44801 Bochum, Germany.

C Corresponding authors. Email: gilles.gasser@aci.uzh.ch; nils.metzler-nolte@rub.de

Australian Journal of Chemistry 64(3) 265-272 https://doi.org/10.1071/CH11010
Submitted: 6 January 2011  Accepted: 20 February 2011   Published: 11 March 2011

Abstract

A novel azido derivative of the di-(2-picolyl)amide (Dpam) ligand, namely 3-azido-N,N-bis-pyridin-2-ylmethyl-propionamide (3), was prepared from 3-bromo-N,N-bis(pyridin-2-ylmethyl)propanamide (2) with an excess of sodium azide in DMSO. 3 was then reacted, by CuI-catalyzed [3 + 2] cycloaddition (often referred to as ‘Click Chemistry’), with the previously reported alkyne-containing peptide nucleic acid (PNA) monomer Fmoc-1-OtBu to give the Dpam-containing PNA monomer (Fmoc-4-OtBu) in 44% yield. It was also demonstrated that 3 could be reacted by Click Chemistry, on the solid phase, to an alkyne-containing PNA oligomer (Alkyne-PNA) to yield Dpam-PNA. Our attempts to complex Dpam-PNA with [NEt4]2[ReBr3(CO)3] and [99mTc(CO)3(H2O)3]+ are also discussed in detail.


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