Evaluation of Dermal Irritancy Potential of Benzanthrone-Derived Dye Analogs: Structure Activity Relationship

Abstract

The twelve structural analogs of benzanthrone-derived dyes of commercial use were screened for their dermal irritation potential response using the Draize occlusive patch test. The test dyes, dissolved in DMSO as vehicle, were topically applied on the skin of the male Druckery rats (160 ± 10 g) according to the OECD protocol. The potential dermal hazard was assessed in terms of the primary cutaneous irritation (PCI) index and irritancy. Irritancy was evaluated according to the AFNOR scale. In terms of irritancy, the twelve benzanthrone dyes qualified as moderately irritant (3.0–5.0) according to the above scale. In decreasing order, PCI index of the various dyes was: Navy Blue R (4.5); Jade Green XBN (4.25); 16, 17-dihydroxydibenzanthrone (3.84); Black NB (3.75), Jade Green 2G (3.75); 3-bromobenzanthrone (3.58); Brilliant Purple 4R (3.58); Olive D (3.50); Dark Blue 2R (3.41); Olive Green B (3.33); isodibenzanthrone (3.33), and benzanthrone (3.16). These results indicate that benzanthrone-derived dyes/dye intermediates caused dermal toxicity which appears to be influenced by the number of carbonyl and amino-anthraquinone groups as well as by the presence of functional groups like halogen, nitro, hydroxy and methoxy in the parent molecule, benzanthrone.

Comparative effect of benzanthrone and 3-bromobenzanthrone on hepatic xenobiotic metabolism and anti-oxidative defense system in guinea pigs

“…It has been speculated that 3-BBA may have more hazardous effects than BA (Volodchenko et al 1977). Our recent studies have shown that 3-BBA has greater skin irritancy potential than BA (Singh et al 2000). However, it is not known whether continuous exposure to 3-BBA causes any malfunctioning of liver and other vital organs.…”

Allergic contact dermatitis caused by benzanthrone in a pair of trousers

“…Benzanthrone has been reported to cause systemic symptoms from the gastrointestinal tract, liver malfunction, and skin lesions (15)(16)(17). Regarding skin lesions, benzanthrone has been reported to cause dermal toxicity (18), phototoxicity, and, possibly, photoallergic reactions (8,19,20). There is very little evidence in the literature for benzanthrone being a contact allergen.…”

“…These are often used in the colouring process for cellulose fibres such as cotton . Benzanthrone is already known to be irritating to the skin and to cause phototoxic and, perhaps, photoallergic reactions .…”

“…These are often used in the colouring process for cellulose fibres such as cotton (7). Benzanthrone is already known to be irritating to the skin (8) and to cause phototoxic and, perhaps, photoallergic reactions (9). Environmental Dermatology after having experienced a rash on her lower abdomen that she ascribed to the use of a newly purchased pair of trousers.…”