Photochemical reactions of quindoxin, olaquindox, carbadox and cyadox with protein, indicating photoallergic properties.
Quindoxin (quinoxaline-1,4-dioxide), a former 'growth promoter' used in animal husbandry, has been taken from the market because of its photoallergic properties. Nowadays its derivatives olaquindox, carbadox and cyadox are frequently applied for the same purpose. Recent reports show that olaquindox too, can induce photoallergic skin reactions in stockmen. From the present investigation it appeared that all compounds mentioned, form a reactive oxaziridine upon exposure to light, just like many other imino-N-oxides. Photoreactivity with protein, which is considered as an important condition for a compound to be a potential photoallergen, was also studied. Quindoxin and olaquindox proved to meet this condition, as was expected. But carbadox and cyadox also react and were shown to be even more reactive towards human serum albumin.
de Vries
H
H
Center for Bio-Pharmaceutical Sciences, State University of Leiden, The Netherlands.
Bojarski
J
J
Donker
A A
AA
Bakri
A
A
Beyersbergen van Henegouwen
G M
GM
D000818:Animals; D000900:Anti-Bacterial Agents / Q000378:metabolism / Q000528:radiation effects; D002218:Carbadox / Q000378:metabolism* / Q000528:radiation effects / Q000633:toxicity; D055598:Chemical Phenomena; D002621:Chemistry; D006801:Humans; D009943:Organophosphorus Compounds / Q000494:pharmacology; D010777:Photochemistry; D010787:Photosensitivity Disorders / Q000209:etiology*; D011506:Proteins / Q000378:metabolism*; D011810:Quinoxalines / Q000378:metabolism* / Q000528:radiation effects / Q000633:toxicity; D012709:Serum Albumin / Q000378:metabolism; D014466:Ultraviolet Rays
D000900:Anti-Bacterial Agents; D009943:Organophosphorus Compounds; D011506:Proteins; D011810:Quinoxalines; D012709:Serum Albumin; C061896:triphenylphosphine; C020728:cyadox; C003282:quindoxin; C013168:olaquindox; D002218:Carbadox