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Ratiometric fluorescence sensing of phenylalanine derivatives by synthetic macrocyclic receptors

Paper ID Volume ID Publish Year Pages File Format Full-Text
27703 44038 2010 7 PDF Available
Title
Ratiometric fluorescence sensing of phenylalanine derivatives by synthetic macrocyclic receptors
Abstract

The supramolecular analytical behavior of eight pseudopeptidic fluorescent receptors (1a–c, 2a–c, 3, 4) has been studied. The receptors are either macrocyclic or open chain derivatives based on the naphthalene chromophore. The ability of 1–4 for the molecular recognition of amino acids (as Z-protected derivatives) has been evaluated in dichloromethane. The signal observed corresponds to a fluorescence emission of turn-on type. The preferential binding of all the receptors for phenylalanine (Phe) over aliphatic amino acids (Ala, Val) by a factor of 3–4 has been found. Among the family of studied fluorescent molecules, two macrocyclic receptors (1a and 1b) display high exciplex emissions and great fluorescence changes both at long (fluorescence quenching at 390 nm) and short wavelengths (fluorescence enhancement at 340 nm). This feature makes the macrocycles 1a and 1b potentially practical as fluorescent ratiometric sensors for Phe. As a proof of concept, 1a and 1b have been assayed as analytical tools for the identification of model samples enriched with Phe, mimicking the concentrations found in the pathology phenylketonuria (PKU). This result opens the door to the development of new Phe-sensing sensors based on the exciplex signaling mechanism as a new strategy for the analysis of aminoacidemias.

Keywords
32.50.+d; 81.16.FgFluorescence; Analysis; Ratiometric; Amino acids; Aminoacidemias; Phenylketonuria
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Ratiometric fluorescence sensing of phenylalanine derivatives by synthetic macrocyclic receptors
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 209, Issue 1, 1 January 2010, Pages 61–67
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
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