Relationship Between Azo Dye Structure and Rat Hepatic Azoreductase Activity

The rate of reduction was determined for a variety of azo dyes using the rat hepatic azoreductase enzyme system. In decreasing order, the rates of reduction for the azo dyes expressed as nmol of arylamine product formed/min/0.25g of liver were amaranth (33.2), azosulfamide (32.5), orange G (12.4), 1...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1984-02, Vol.73 (2), p.161-164
Main Authors: Shargel, Leon, Banijamali, Ali R., Kuttab, Simon H.
Format: Article
Language:English
Subjects:
2-dimethyl-4-p-(carboxyphenylazo)-5-hydroxybenzene
amaranth
Animals
Azo Compounds - metabolism
Azo dyes-relationship between structure and rat hepatic azoreductase activity
Azo dyes—relationship between structure and rat hepatic azoreductase activity, amaranth, azosulfamide, orange G, 1,2‐dimethyl‐4‐p‐(carboxyphenylazo)‐5‐hydroxybenzene, brilliant crystal scarlet, sulfachrysoidine, Sudan I
Azoreductase-rat hepatic activity
Azoreductase—rat hepatic activity, relationship to azo dye structure, amaranth, azosulfamide, orange G, 1,2‐dimethyl‐4‐p‐(carboxyphenylazo)‐5‐hydroxybenzene, brilliant crystal scarlet, sulfachrysoidine, Sudan I
azosulfamide
Biological and medical sciences
brilliant crystal scarlet
Chemical and industrial products toxicology. Toxic occupational diseases
Coloring Agents - metabolism
In Vitro Techniques
Liver - enzymology
Male
Medical sciences
NADH, NADPH Oxidoreductases - metabolism
orange G
Rats
relationship to azo dye structure
Solubility
Sudan I
sulfachrysoidine
Time Factors
Toxicology
Various organic compounds
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Summary:The rate of reduction was determined for a variety of azo dyes using the rat hepatic azoreductase enzyme system. In decreasing order, the rates of reduction for the azo dyes expressed as nmol of arylamine product formed/min/0.25g of liver were amaranth (33.2), azosulfamide (32.5), orange G (12.4), 1,2‐dimethyl‐4‐p‐(carboxyphenylazo)‐5‐hydroxybenzene (CPA) (9.27), brilliant crystal scarlet (8.00), sulfachrysoidine (7.27), and Sudan I (1.03). A comparison of the partition coefficient with its rate of reduction indicated that the water‐soluble azo dyes were reduced more rapidly than the lipid‐soluble ones. Furthermore, higher rates of reduction were observed for those dyes containing electron‐withdrawing groups on the aromatic rings.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600730206