Design and Characterization of Dicyanovinyl Reactive Dyes for the Colorimetric Detection of Thiols and Biogenic Amines.

Tinkara Mastnak,Gerhard Mohr,Aleksandra Lobnik,Matejka Turel

doi:10.3390/s18030814

Abstract

The synthesis of two new azobenzene dyes, namely CR-528 and CR-555, and their spectral properties in ethanol solution are described. The recognition of sulfur-containing analytes (2-mercaptoethanol (2-ME), sodium hydrosulfide (NaHS)), and biogenic amines (spermine, spermidine, ethanolamine) bestowed significant spectral changes with color changes from pink/purple to pale yellow/orange-yellow. The nitro acceptor group in the dicyanovinyl reactive dye contributes to higher sensitivity and lower detected analyte concentrations. The absorption maxima of both the dyes are at wavelengths compatible with low-cost light sources and detectors, making them excellent candidates for optical probes that are economic, simple to use, and do not require well-trained personnel.

Highlights

Derived thiols are important antioxidants that protect cells from oxidative damage
42800 M−1 cm absorptioncoefficient is due to (ε) theofpronounced donor and acceptor strengths of the substituents that were absorption is due to the pronounced donor and acceptor strengths of the substituents that were attached attached to the azobenzene structure (Figure 1)
Due to the presence of the NO2 group on CR-555, the reactivity of this chromoreactand is higher when compared to CR-528 without nitro group

Summary

Introduction

Derived thiols (biothiols) are important antioxidants that protect cells from oxidative damage. They are involved in signal transduction, apoptosis, and protein structure. Biogenic amines are nitrogen-containing low molecular weight organic compounds that are naturally synthesized in animals, plants, and microorganisms—generally by decarboxylation of free amino acids or by amination or transamination of aldehydes and ketones [5]. Like spermine and spermidine, are among the most abundant organic polycations that are found in the human body, involved in protein synthesis, conformational stabilization of nucleic acids, and cytoskeleton structures, and they play multiple roles in cell growth, proliferation, and survival [6,7]

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