Conjugation of Some Phenolic Compounds With Amino Groups and Related Sensitization Potency

Abstract

The conjugation of some phenolic compounds with ten dansyl amino acids was examined and the results indicated the importance of conjugation with the lysine residue. The conjugation of phenolic compounds with monodansyl cadaverine and cadaverine was also studied. The results obtained by these in vitro tests correlated well with those of animal sensitization tests and patch tests on patients with contact dermatitis.

FACTORS INFLUENCING CONJUGATION OF PHENOLIC COMPOUNDS WITH THE ɛ‐AMINO GROUP

“…MIE and ME are not sensitizers. Osamura et al (7) found that the conjugation of phenolic compounds with the e-amino group of lysine residues played an important role in producing allergenicity and their in vitro test results agreed well with animal sensitization test results. They also reported that as the methoxy group at the C-l position of ME and MIE is chemically very stable, conjugation of these compounds with amino groups does not occur readily.…”

“…The phenolic compounds tested included the purest samples available of eugenol (E), isoeugenol (IE), methyl isoeugenol (MIE), and acetyl isoeugenol (AlE) (Shiono Perfume Company, Osaka). For the amine donor with an s-amino group such as lysine, s-aminccaproic acid (e-ACA) ( [1][2][3][4][5][6][7][8][9][10][11][12][13][14] CJe-ACA e-ACA has a chemical structure similar to that of lysine and is used as the amine donor. (Table 1).…”

“…the -SH group of cysteine, and the imidazole group of histidine in carrier proteins (5,6). Osamura et al (7) investigated the conjugation of isoeugenol with ten different dansyl amino acids and determined that lysine residues play an important role in conjugation. They also developed a semi -quantitative in vitro test using monodansyl cadaverine and cadaverine, which both have a chemical structure similar to that of lysine.…”