Perfluorinated analogues of poison ivy allergens. Synthesis and skin tolerogenic activity in mice.
3-(Tridecafluoroundecyl)catechol (8) and 3-(nonafluoropentadecyl)catechol (9), perfluorinated analogues of pentadecylcatechol (PDC), a constituent of poison ivy, have been synthesized. These compounds were nonsensitizers in mice. Compounds 8 and 9, however, were elicitors of allergic contact dermatitis in PDC-sensitized animals. Moreover, compound 9 exhibited tolerogenic properties to sensitization by poison ivy allergens, i.e. mice pretreated with perfluorinated compounds could not be sensitized to PDC.
Fraginals
R
R
Laboratoire de Dermatochimie, Université Louis Pasteur, CHU, Strasbourg, France.
Schaeffer
M
M
Stampf
J L
JL
Benezra
C
C
D000485:Allergens / Q000276:immunology*; D000818:Animals; D002396:Catechols / Q000138:chemical synthesis / Q000276:immunology*; D055598:Chemical Phenomena; D002621:Chemistry; D003877:Dermatitis, Contact / Q000276:immunology; D005260:Female; D005466:Fluorocarbons / Q000138:chemical synthesis / Q000276:immunology*; D007108:Immune Tolerance / Q000276:immunology*; D007114:Immunization; D051379:Mice; D008807:Mice, Inbred BALB C; D015394:Molecular Structure; D010947:Plants, Toxic; D012251:Toxicodendron
D000485:Allergens; D002396:Catechols; D005466:Fluorocarbons; C067825:3-(tridecafluoroundecyl)catechol; C067826:3-(nonafluoropentadecyl)catechol; C005297:3-pentadecacatechol