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Published on: August 20, 2012
Induced-Fit Recognition by a Calixarene-Pyrene Conjugate for Single- and Dual-Wavelength Fluorescence Sensing in
Joana N Martins1, Márcia Pessêgo2, Luis Garcia-Rio2
1Laboratório Associado para a Química Verde (LAQV), Rede De Química e Tecnologia (REQUIMTE), Departamento De Química, Faculdade De Ciências e Tecnologia, Universidade NOVA De Lisboa, Caparica, Portugal.
None:
The discovery of fluorescence receptors that selectively bind small molecules with high affinity in aqueous media is critical for the development of new sensing and bioimaging assays. We herein report a new fluorescence receptor-dye chemosensor based on the monofunctionalization of p-sulfonatocalix[4]arene (SC4) receptor with pyrene (SC4-4Py). The SC4-4Py conjugate was found to retain the exceptional binding properties of SC4, allowing the high-affinity recognition of neurotransmitters, amino acids, and biogenic amines in aqueous solution and their optical detection. The SC4-4Py chemosensor operates through a photoinduced electron transfer (PET) mechanism triggered by conformational changes in the calixarene structure upon binding, allowing single-wavelength fluorescence detection of target analytes and its expansion into a dual-wavelength ratiometric indicator displacement assay (IDA) that relies on competitive PET between the pyrene and non-covalently bound lucigenin dye.
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