Dyes, structures

N. Tyutyulkov and co-workers, Polymethine Dyes Structure and Properties, St. Kliment Ohtidski University Press, Sofia, Bulgaria, 1991. 

Numerous dyes structurally related to the safranines, such as the eurodines, e.g. (141), the indulines, e.g. (142), the nigrosines (143) and aniline black, a pigment of unknown structure used in the printing industry, are well known and a detailed account of their chemistry and applications has been presented (57HC(ll)l). 

Dye structures of passive tracers placed in time-periodic chaotic flows evolve in an iterative fashion an entire structure is mapped into a new structure with persistent large-scale features, but finer and finer scale features are revealed at each period of the flow. After a few periods, strategically placed blobs of passive tracer reveal patterns that serve as templates for subsequent stretching and folding. Repeated action by the flow generates a lamellar structure consisting of stretched and folded striations, with thicknesses s(r), characterized by a probability density function, f(s,t), whose... 

Reference [33] describes recent progress on cyanine probes that bind noncova-lently to DNA, with a special emphasis on the relationship between the dye structure and the DNA binding mode. Some of the featured dyes form well-defined helical aggregates using DNA as a template. This reference also includes spectroscopic data for characterizing these supramolecular assemblies as well as the monomeric complexes. 

Squaraine dyes 10b, 39a, 39b, 41a, 41c, 41d, and 41e were used to measure different proteins such as BSA, HSA, ovalbumin, avidin from hen egg white, lysozyme, and trypsin (Fig. 12) [58]. It is difficult to predict correlations between the dyes structures and the affinity or sensitivity of the dyes for different proteins. All squaraine probes exhibit considerable fluorescence increases in the presence of BSA. Dicyanomethylene-squaraine 41c is the brightest fluorescent probe and demonstrates the most pronounced intensity increase (up to 190 times) in presence of BSA. At the same time, the fluorescent response of the dyes 10b, 39a, 39b, 41a, 41c, 41d, and 41e in presence of other albumins (HSA and ovalbumin) is, in general, significantly lower (intensity increases up to 24 times). Dicyanomethylene-squaraine 41a and amino-squaraines 39a and 39b are the most sensitive probes for ovalbumin. Dyes 41d, 10b, and 41e containing an A-carboxyalky I -group demonstrate sufficient enhancement (up to 16 times) in the presence of avidin. Nevertheless, the presence of hydrolases like lysozyme or trypsin has only minor effects on the fluorescence intensity of squaraine dyes. 

Cyanine dyes also are used as labels for oligonucleotide probes. Unlike the hydrophilic cyanine dyes valuable for protein labeling, the use of dye-phosphoramidite compounds to synthesize DNA or RNA probes typically requires the use of more hydrophobic dye structures to make them compatible with the solvents and reactions of oligonucleotide synthesis. Thus, indol cyanines containing few or no sulfonates are used in these applications to label oligos for applications such as array detection, hybridization assays, and RT-PCR. 

Chung KT, Cemiglia CE (1992) Mutagenicity of azo dyes structure-activity relationships. Mut Res 277 201-220... 

The azo reductases in aerobic bacteria were found to be existent when azoreductases from obligate aerobic bacteria were isolated and characterized from strains K22 and KF46 and were shown to be flavin-free after purification, characterization, and comparison 364, 362,363. These intracellular azoreductases showed high specificity to dye structures. Furthermore, Blumel and Stolz cloned and characterized the genetic code of the aerobic azo reductase from Pagmentiphaga... 

Though extensive research has been recently reported in the open literature concerning biodegradation of azo-dyes, there is still a need for additional research. The close link between dye structure and reaction pathways and rates makes it difficult to extrapolate results obtained with one dye to that with others, even belonging to the same class. Dye-specific assessment of process rates and yields is therefore required. Also, the degradation potential of several bacteria or consortia active toward xenobiotics in dye degradation is far from being fully assessed. 

To reach the reductive step of the azo bond cleavage, due to the reaction between reduced electron carriers (flavins or hydroquinones) and azo dyes, either the reduced electron carrier or the azo compound should pass the cell plasma membrane barrier. Highly polar azo dyes, such as sulfonated compounds, cannot pass the plasma membrane barrier, as sulfonic acid substitution of the azo dye structure apparently blocks effective dye permeation [28], The removal of the block to the dye permeation by treatment with toluene of Bacillus cereus cells induced a significant increase of the uptake of sulfonated azo dyes and of their reduction rate [29]. Moreover, cell extracts usually show to be more active in anaerobic reduction of azo dyes than whole cells. Therefore, intracellular reductases activities are not the best way to reach sulfonated azo dyes reduction the biological systems in which the transport of redox mediators or of azo dye through the plasma membrane is not required are preferable to achieve their degradation [13]. 

There is as yet no agreed international list of permitted food colours. Thus a food dye that is permitted in one country may be considered unacceptable in another. The synthetic food colorants permitted in the European Union are listed in Table 1.8 [60]. All were originally introduced as acid dyes for wool many years ago. Furthermore, more than thirty colorants of natural origin are permitted in most countries. The natural carotenoid dyes are of outstanding importance for colouring edible fats and oils. These yellow to red methine dye structures occur in many families of plants and animals, including vegetables, berries,... 

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