title: Perfluorinated analogues of poison ivy allergens. Synthesis and skin tolerogenic activity in mice.
abstract: 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.
authors.affiliation: Laboratoire de Dermatochimie, Université Louis Pasteur, CHU, Strasbourg, France.
authors.forename: R
authors.initials: R
authors.lastname: Fraginals
authors.forename: M
authors.initials: M
authors.lastname: Schaeffer
authors.forename: J L
authors.initials: JL
authors.lastname: Stampf
authors.forename: C
authors.initials: C
authors.lastname: Benezra
mesh_terms: 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
chemical_list: D000485:Allergens; D002396:Catechols; D005466:Fluorocarbons; C067825:3-(tridecafluoroundecyl)catechol; C067826:3-(nonafluoropentadecyl)catechol; C005297:3-pentadecacatechol