Published In
Journal of Fluorescence
Document Type
Citation
Publication Date
1-1-2016
Subjects
Fluorescein, Aldehydes, Homocysteine
Abstract
Elevated homocysteine levels are a well-known independent risk factor for cardiovascular disease. To date, relatively few selective fluorescent probes for homocysteine detection have been reported. The lack of sensing reagents and remaining challenges largely derive from issues of sensitivity and/or selectivity. For example, homocysteine is a structural homologue of the more abundant (ca, 20-25 fold) aminothiol cysteine, differing only by an additional methylene group side chain. Fluorescein tri-aldehyde, described herein, has been designed and synthesized as a sensitive and selective fluorophore for the detection of homocysteine in human plasma samples. It responds to analytes selectively via a photoinduced electron transfer (PET) inhibition process that is modulated by predictable analyte-dye product hybridization and ionization states. Mulliken population analysis of fluorescein tri-aldehyde and its reaction products reveals that the characteristic formation of multiple cationic of homocysteine-derived heterocycles leads to enhanced relative negative charge build up on the proximal phenolate oxygen of the fluorophore as a contributing factor to selective emission enhancement.
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DOI
10.1007/s10895-015-1762-3
Persistent Identifier
http://archives.pdx.edu/ds/psu/18827
Citation Details
Barve, A., Lowry, M., Escobedo, J.O. et al. (2016). Fluorescein Tri-Aldehyde Promotes the Selective Detection of Homocysteine. Journal of Fluorescence 26: 731.