Journal
CHEMBIOCHEM
Volume 14, Issue 2, Pages 224-229Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201200637
Keywords
avidin; biotin; click chemistry; fluorescence; scorpionand complexes
Funding
- National Breast Cancer Fund for a Novel Concept Grant [NC-10-69]
- Australian Research Council [DP120104035]
- University of Sydney International Scholarship (USydIS)
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We describe a new class of fluorescent reporter and its employment to visualize the biotin/avidin binding interaction. Derivatives of the azamacrocycle cyclam that contain a pendant naphthalimide dye are inherently fluorescent when zinc(II) is coordinated. Introducing a second pendant groupbiotinaffords an unsymmetrical bis-triazole-scorpionand ligand that interacts specifically with avidin. This ligand has been assembled by using a one-pot double-click strategy and complexed with copper(II) and zinc(II). The zinc(II) complex is fluorescent, and its fluorescence output changes in the presence of avidin. Upon avidin binding, the fluorescence output is diminished by interaction with the protein, at [complex]/[avidin] ratios of up to 4:1. The observed change might arise from a specific quenching effect in the biotin binding pocket or from a binding-induced change in the coordination geometry of the complex.
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