Copper, Nickel, and Zinc Cyclam−Amino Acid and Cyclam−Peptide Complexes May Be Synthesized with 'Click' Chemistry and Are Noncytotoxic

Article


Yu, Mingfeng, Price, Jason, Jensen, Paul D., Lovitt, Carrie J., Shelper, Todd, Duffy, Sandra, Windus, Louisa C., Avery, Vicky, Rutledge, Peter and Todd, Matthew. 2011. "Copper, Nickel, and Zinc Cyclam−Amino Acid and Cyclam−Peptide Complexes May Be Synthesized with 'Click' Chemistry and Are Noncytotoxic." Inorganic Chemistry: including bioinorganic chemistry. 50, pp. 12823-12835. https://doi.org/10.1021/ic2020012
Article Title

Copper, Nickel, and Zinc Cyclam−Amino Acid and Cyclam−Peptide Complexes May Be Synthesized with 'Click' Chemistry and Are Noncytotoxic

ERA Journal ID1525
Article CategoryArticle
AuthorsYu, Mingfeng (Author), Price, Jason (Author), Jensen, Paul D. (Author), Lovitt, Carrie J. (Author), Shelper, Todd (Author), Duffy, Sandra (Author), Windus, Louisa C. (Author), Avery, Vicky (Author), Rutledge, Peter (Author) and Todd, Matthew (Author)
Journal TitleInorganic Chemistry: including bioinorganic chemistry
Journal Citation50, pp. 12823-12835
Article Number24
Number of Pages13
Year2011
Place of PublicationUnited States
ISSN0020-1669
1520-510X
Digital Object Identifier (DOI)https://doi.org/10.1021/ic2020012
Web Address (URL)https://pubs.acs.org/doi/10.1021/ic2020012
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.

Keywordssolid-phase synthesis; metal-complexes; biomedical applications; scorpionate complex; agents; cytotoxicity; stability; cells; probe
ANZSRC Field of Research 2020340208. Non-metal chemistry
Open access urlhttps://pubs.acs.org/doi/10.1021/ic2020012
Institution of OriginUniversity of Southern Queensland
Byline AffiliationsUniversity of Sydney
Griffith University
Griffith University
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