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Copper, Nickel, and Zinc Cyclam–Amino Acid and Cyclam–Peptide Complexes May Be Synthesized with “Click” Chemistry and Are Noncytotoxic

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Mingfeng Yu†, Jason R. Price‡, Paul Jensen‡, Carrie J. Lovitt§, Todd Shelper§, Sandra Duffy§, Louisa C. Windus§, Vicky M. Avery§, Peter J. Rutledge†, and Matthew H. Todd*†

School of Chemistry, The University of Sydney, NSW 2006, Australia

Crystal Structure Analysis Facility, School of Chemistry, The University of Sydney, NSW 2006, Australia

Discovery Biology, Eskitis Institute for Cell and Molecular Therapies, Griffith University, Nathan, QLD 4111, Australia

Inorg. Chem., 2011, 50 (24), pp 12823–12835

DOI: 10.1021/ic2020012

Publication Date (Web): November 23, 2011

E-mail: matthew.todd@sydney.edu.au.

Section:

Inorganic Chemicals and Reactions

Abstract

We describe the synthesis of cyclam metal complexes derivatized with amino acids or a tripeptide using a copper(I)-catalyzed Huisgen “click” reaction. The linker triazole formed during the synthesis plays an active coordinating role in the complexes. The reaction conditions do not racemize the amino acid stereocenters. However, a methylene group adjacent to the triazole is susceptible to H/D exchange under ambient conditions, an observation which has potentially important implications for structures involving stereocenters adjacent to triazoles in click-derived structures. The successful incorporation of several amino acids is described, including reactive tryptophan and cysteine side chains. All complexes are formed rapidly upon introduction of the relevant metal salt, including synthetically convenient cases where trifluoroacetate salts of cyclam derivatives are used directly in the metalation. None of the metal complexes displayed any cytotoxicity to mammalian cells, suggesting that the attachment of such complexes to amino acids and peptides does not induce toxicity, further supporting their potential suitability for labeling/imaging studies. One Cu(II)–cyclam–triazole–cysteine disulfide complex displayed moderate activity against MCF-10A breast nontumorigenic epithelial cells.

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History

Published In Issue December 19, 2011
Article ASAPNovember 23, 2011
Received: September 13, 2011

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Copper, Nickel, and Zinc Cyclam–Amino Acid and Cyclam–Peptide Complexes May Be Synthesized with “Click” Chemistry and Are Noncytotoxic