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Synthesis and Fluorescence Properties of Six Fluorescein-Nitroxide Radical Hybrid-Compounds

Synthesis and Fluorescence Properties of Six Fluorescein-Nitroxide Radical Hybrid-Compounds

Shingo Sato, Susumu Endo, Yusuke Kurokawa, Masaki Yamaguchi, Akio Nagai, Tomohiro Ito, Tateaki Ogata

Spectrochim Acta A Mol Biomol Spectrosc. 2016 Dec 5;169:66-71.

PMID: 27337053

Abstract:

Six fluorescein-nitroxide radical hybrid-compounds (2ab, 3ab, 4, and 5) were synthesized by the condensation of 5- or 6-carboxy-fluorescein and 4-amino-TEMPO (2ab), 5- or 6-aminofluorescein and 4-carboxy-TEMPO (3ab), and fluorescein and 4-carboxy-TEMPO (4), or by reaction of the 3-hydroxyl group of fluorescein with DPROXYL-3-ylmethyl methanesulfonate (5). Fluorescence intensities (around 520nm) after reduction of the radical increased to 1.43-, 1.38-, and 1.61-folds for 2a, 2b and 3b respectively; 3a alone exhibited a decrease in intensity on reduction. Since 4 was readily solvolyzed in PBS or even methanol to afford fluorescein and 4-carboxy-TEMPO, its fluorescence change could not be measured. Hybrid compound 5 containing an ether-linkage between the fluorescein phenol and 3-hydroxymethyl-DPROXYL hydroxyl centers, was stable and on reduction, showed a maximum increase (3.21-fold) in relative fluorescence intensity in PBS (pH5.0), despite its remarkably low absolute fluorescence intensity.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP51649833	6-Aminofluorescein		51649-83-3	Price

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