Tyrian Purple: 6,6’-Dibromoindigo and Related Compounds

Molecules 01/2001; 6(9):736-769. DOI: 10.3390/60900736
Source: DOAJ

ABSTRACT The genesis of the purple dye from shellfish, its composition, origin, intermediates, analysis and synthesis of the components, 6,6'-dibromoindigo, 6- bromoindigo and 6,6'-dibromoindirubin are reviewed

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    ABSTRACT: Objective: Indigo and indigoid dyes are natural dyes and have been known since Bronze Age (B.C. 2000). Nowadays, indigoid dyes are widely used in the industry of textile, cosmetic, food and medicine. The aim of this study was to estimate the DNA damage of indigotin, 6-bromo indigotin, indirubin and 6-bromo indirubin by in vitro alkaline single-cell gel electrophoresis (SCGE-Comet) in the peripheral lymphocytes. Methods: The cytotoxic effects of indigo and indigoid dyes were assessed by trypan blue exclusion. The cells were incubated with 10, 25, 50 μg/mL of the test substances for 30 min at 37°C. Comet assay was used to evaluate the genotoxic effect of test substances on human peripheral lymphocytes. Results: Our results revealed that indigotin and 6-bromo indigotin increased the DNA migration in a dose-dependent manner. DNA damage was higher in cells that had been incubated with 50 μg/mL indigotin and 6-bromo indigotin (p<0.05). Conclusion: Our results indicate that indigo and indigoid dyes would be genotoxic at higher concentrations. It is probable that a genotoxic effect might occur due to the fact that the individuals who have worked with these dyestuffs, both in the past and today, used highly concentrated dyes. Key words: Indigotin, 6-bromo indigotin, indirubin, 6-bromo indirubin, comet assay, DNA damage
    Journal of Marmara University Institute of Health Sciences. 07/2012; 2(3):108-112.
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    Medecine sciences: M/S 06/2004; 20(5):516-8. · 0.56 Impact Factor
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    ABSTRACT: Abstract Anthranilic acid (2-aminobenzoic acid, Aa) is the biochemical precursor to the amino acid tryptophan, as well as a catabolic product of tryptophan in animals. It is also integrated into many,alkaloids isolated from plants. Aa is produced industrially for production of dyestuffs and pharmaceuticals. The dissertation gives a historical background,and a short review on the reactivityof Aa. The synthesis of several types of nitrogen heterocycles from Aa is discussed. Treatment of anthranilonitrile (2-aminobenzonitrile, a derivative of Aa) with organomagnesium,compounds,gave deprotonation and addition to the nitrile triple bond to form amine-imine complexed,dianions. Capture of these intermediate with acyl halides normally gave aromatic quinazolines, a type of heterocyclic compounds that is considered to be highly interesting as scaffolds for development,of new drugs. When the acyl halide was a tertiary 2-haloacylhalide, the reaction instead gave 1,4- benzodiazepine-3-ones via rearrangement. These compounds,are isomeric to the common benzodiazepine drugs (such asdiazepam, Valium®) which are 1,4- benzodiazepine-2-ones. Capture of the dianionswith aldehydes or ketones, led to 1,2- dihydroquinazolines. Unsubstituted imine anions could be formed by treatment of anthranilonitrile with diisobutylaluminium hydride. Also in this case capture with aldehydes gave 1,2-dihydroquinazolines.


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